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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014552

Secondary Accession Numbers

HMDB14552

Metabolite Identification

Common Name

Loxapine

Description

Loxapine, also known as cloxazepine or loxapinum, belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring. Several researchers have argued that loxapine may behave as an atypical antipsychotic. Loxapine is a drug which is used for the management of the manifestations of psychotic disorders such as schizophrenia. Loxapine is a very strong basic compound (based on its pKa). Loxapine is a potentially toxic compound. Loxapine (several trade names worldwide) is a typical antipsychotic medication used primarily in the treatment of schizophrenia. The US Food and Drug Administration (FDA) has approved loxapine inhalation powder for the acute treatment of agitation associated with schizophrenia or bipolar I disorder in adults. A brief review of loxapine found no conclusive evidence that it was particularly effective in patients with paranoid schizophrenia. At lower dosages its propensity for causing extrapyramidal side effects appears to be similar to that of atypical antipsychoticsBlurred visionUrinary retentionSomnolence (which appears to be moderate in severity compared to other antipsychotic drugs)DyspnoeaNasal congestionRare side effects includeParalytic ileusAgranulocytosisLeukopeniaThrombocytopeniaHepatocellular liver damageNeuroleptic malignant syndromeSeizureTardive dyskinesiaStrokeTransient ischaemic attackDeathThe data in the table to the right was obtained from the PDSP Ki database and they are for binding towards human cloned proteins (receptor and transporter) unless otherwise specified. Loxapine may be metabolized by N-demethylation to amoxapine, a tricyclic antidepressant. This drug is unrelated to the habit-forming benzodiazepines, and misuse is rare. Note: Percentages given after possible adverse effects refer to the incidence of said adverse effects, according to DrugPoint.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014552
     RDKit          3D
Loxapine
 41 44  0  0  0  0  0  0  0  0999 V2000
    3.5793   -1.7879    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041   -0.6292   -0.4831 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.5892    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    0.8495    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    0.5000   -0.2736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846    0.2620   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772   -0.9836    0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -1.5753    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281   -2.9067   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -3.6499    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021   -2.9974    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0444   -1.6694    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.9522    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0426    0.3591    1.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    1.4294    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9427    2.6252    0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    3.7779    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    3.7527   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    5.2248   -0.6694 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    2.5611   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677    1.4075    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837    0.3853   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.6939   -1.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -1.9199    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.7131   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2649   -1.6544    1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421    1.4284   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369    0.5275    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    0.1940    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    1.8887    1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480   -3.3870   -0.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0402   -4.6955   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328   -3.5187    0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -1.1976    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    2.7044    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8428    4.7258    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    2.5367   -0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2415    1.3151   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9809    0.1129   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -0.5236   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.7017   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END

408
  Mrv0541 02231214392D          

 23 26  0  0  0  0            999 V2000
    1.5841   -1.1304    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6238   -2.1816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8841    0.2673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    1.6946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0198   -0.4464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    0.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0943    0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9866    1.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2277   -0.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338   -1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5136   -1.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -1.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5237   -2.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2983   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9335   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9074   -1.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237   -2.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 11  1  0  0  0  0
  5 10  2  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 16  1  0  0  0  0
 14 20  2  0  0  0  0
 15 18  2  0  0  0  0
 16 21  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014552

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC2=CC=CC=C2OC2=C1C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18ClN3O/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3

> <INCHI_KEY>
XJGVXQDUIWGIRW-UHFFFAOYSA-N

> <FORMULA>
C18H18ClN3O

> <MOLECULAR_WEIGHT>
327.808

> <EXACT_MASS>
327.11383992

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.985659606226186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.4606024319999995

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.175142290157757

> <JCHEM_POLAR_SURFACE_AREA>
28.07

> <JCHEM_REFRACTIVITY>
95.11110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
loxapine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014552
     RDKit          3D
Loxapine
 41 44  0  0  0  0  0  0  0  0999 V2000
    3.5793   -1.7879    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041   -0.6292   -0.4831 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.5892    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    0.8495    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    0.5000   -0.2736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846    0.2620   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772   -0.9836    0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -1.5753    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281   -2.9067   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -3.6499    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021   -2.9974    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0444   -1.6694    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.9522    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0426    0.3591    1.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    1.4294    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9427    2.6252    0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    3.7779    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    3.7527   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    5.2248   -0.6694 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    2.5611   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677    1.4075    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837    0.3853   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.6939   -1.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -1.9199    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.7131   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2649   -1.6544    1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421    1.4284   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369    0.5275    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    0.1940    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    1.8887    1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480   -3.3870   -0.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0402   -4.6955   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328   -3.5187    0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -1.1976    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    2.7044    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8428    4.7258    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    2.5367   -0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2415    1.3151   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9809    0.1129   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -0.5236   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.7017   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 408                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       2.957  -2.110   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       8.631  -4.072   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.250   0.499   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.967   3.163   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.370  -0.833   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.083   1.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.776   0.609   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.442   3.053   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.134   1.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.892  -0.833   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.326   4.495   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.970  -1.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.299  -3.431   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.292  -1.989   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.505  -1.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.963  -3.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.186  -4.495   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.368  -2.551   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.711  -4.053   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.757  -1.513   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.076  -4.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.894  -2.552   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.551  -4.053   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   13   16                                                       
CONECT    3    6    7   10                                                  
CONECT    4    8    9   11                                                  
CONECT    5   10   14                                                       
CONECT    6    3    8                                                       
CONECT    7    3    9                                                       
CONECT    8    4    6                                                       
CONECT    9    4    7                                                       
CONECT   10    3    5   12                                                  
CONECT   11    4                                                            
CONECT   12   10   13   15                                                  
CONECT   13    2   12   17                                                  
CONECT   14    5   16   20                                                  
CONECT   15   12   18                                                       
CONECT   16    2   14   21                                                  
CONECT   17   13   19                                                       
CONECT   18    1   15   19                                                  
CONECT   19   17   18                                                       
CONECT   20   14   22                                                       
CONECT   21   16   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0014552
HETATM    1  C1  UNL     1       3.579  -1.788   0.384  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.704  -0.629  -0.483  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.627   0.589   0.259  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.209   0.849   0.776  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.288   0.500  -0.274  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.085   0.262  -0.034  1.00  0.00           C  
HETATM    7  N3  UNL     1      -0.477  -0.984   0.001  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.749  -1.575   0.213  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.828  -2.907  -0.134  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.003  -3.650   0.007  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.102  -2.997   0.515  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.044  -1.669   0.867  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.889  -0.952   0.724  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.043   0.359   1.134  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.258   1.429   0.672  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.943   2.625   0.778  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.307   3.778   0.363  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.027   3.753  -0.145  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -0.230   5.225  -0.669  1.00  0.00          CL  
HETATM   20  C15 UNL     1      -0.326   2.561  -0.259  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.968   1.408   0.159  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.784   0.385  -1.622  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.846  -0.694  -1.622  1.00  0.00           C  
HETATM   24  H1  UNL     1       2.537  -1.920   0.761  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.906  -2.713  -0.135  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.265  -1.654   1.240  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.942   1.428  -0.373  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.337   0.527   1.102  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.036   0.194   1.656  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.177   1.889   1.100  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.948  -3.387  -0.529  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.040  -4.696  -0.273  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.033  -3.519   0.646  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.930  -1.198   1.261  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.942   2.704   1.167  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.843   4.726   0.445  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.687   2.537  -0.661  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.241   1.315  -2.012  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.981   0.113  -2.337  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.465  -0.524  -2.545  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.404  -1.702  -1.720  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   22
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   20
CONECT   20   21   21   37
CONECT   22   23   38   39
CONECT   23   40   41
END

HMDB0014552
     RDKit          3D
Loxapine
 41 44  0  0  0  0  0  0  0  0999 V2000
    3.5793   -1.7879    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041   -0.6292   -0.4831 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273    0.5892    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    0.8495    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    0.5000   -0.2736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846    0.2620   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772   -0.9836    0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -1.5753    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281   -2.9067   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -3.6499    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021   -2.9974    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0444   -1.6694    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.9522    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0426    0.3591    1.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    1.4294    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9427    2.6252    0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    3.7779    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270    3.7527   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    5.2248   -0.6694 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    2.5611   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677    1.4075    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837    0.3853   -1.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.6939   -1.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -1.9199    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.7131   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2649   -1.6544    1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421    1.4284   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369    0.5275    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    0.1940    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    1.8887    1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480   -3.3870   -0.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0402   -4.6955   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328   -3.5187    0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9302   -1.1976    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    2.7044    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8428    4.7258    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    2.5367   -0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2415    1.3151   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9809    0.1129   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647   -0.5236   -2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.7017   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 13  8  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Chloro-11-(4-methyl-1-piperazinyl)dibenz[b,F][1,4]oxazepine	ChEBI
Cloxazepine	ChEBI
Loxapina	ChEBI
Loxapinum	ChEBI
Oxilapine	ChEBI
Adasuve	Kegg
Loxapine hydrochloride	HMDB
Loxapine succinate	HMDB
Loxipine maleate	HMDB
Loxapine monohydrochloride	HMDB
Loxapinsuccinate	HMDB
Succinate, loxapine	HMDB
Hydrochloride, loxapine	HMDB
Loxipine succinate	HMDB
Loxitane	HMDB
2-Chloro-11-(4-methyl-1-piperazinyl)-dibenz(b,F)(1,4)oxazepine	HMDB
Maleate, loxipine	HMDB

Chemical Formula

C₁₈H₁₈ClN₃O

Average Molecular Weight

327.808

Monoisotopic Molecular Weight

327.11383992

IUPAC Name

13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene

Traditional Name

loxapine

CAS Registry Number

1977-10-2

SMILES

CN1CCN(CC1)C1=NC2=CC=CC=C2OC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C18H18ClN3O/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3

InChI Key

XJGVXQDUIWGIRW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazepines

Sub Class

Dibenzoxazepines

Direct Parent

Dibenzoxazepines

Alternative Parents

Substituents

Dibenzoxazepine
Diaryl ether
N-methylpiperazine
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Benzenoid
Imidolactam
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Carboxylic acid amidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Amidine
Amine
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzoxazepine (CHEBI:50841 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014552)

Source

Exogenous

Exogenous (HMDB: HMDB0014552)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antipsychotic (HMDB: HMDB0014552)

Dopamine uptake inhibitor (HMDB: HMDB0014552)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	109 - 110 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.1 g/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	175.7	30932474
[M+H]+	Not Available	176.383	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001100

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.46	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	7.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	28.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	95.11 m³·mol⁻¹	ChemAxon
Polarizability	34.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.617	30932474
DeepCCS	[M-H]-	169.259	30932474
DeepCCS	[M-2H]-	202.144	30932474
DeepCCS	[M+Na]+	177.71	30932474
AllCCS	[M+H]+	175.1	32859911
AllCCS	[M+H-H2O]+	171.8	32859911
AllCCS	[M+NH4]+	178.0	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	177.3	32859911
AllCCS	[M+HCOO]-	176.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.0 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4009 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	83.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1047.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	234.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	378.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	421.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	841.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	292.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	877.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	308.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	50.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loxapine	CN1CCN(CC1)C1=NC2=CC=CC=C2OC2=C1C=C(Cl)C=C2	3867.7	Standard polar	33892256
Loxapine	CN1CCN(CC1)C1=NC2=CC=CC=C2OC2=C1C=C(Cl)C=C2	2630.0	Standard non polar	33892256
Loxapine	CN1CCN(CC1)C1=NC2=CC=CC=C2OC2=C1C=C(Cl)C=C2	2622.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Loxapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r5-8094000000-3f11548f145e2cd0d2a5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loxapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-7590000000-118f30ca0699bf2b3d2e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Loxapine LC-ESI-qTof , Positive-QTOF	splash10-00ai-0149000000-d463f8ddf4248264d132	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Loxapine LC-ESI-qTof , Positive-QTOF	splash10-01r6-0930000000-4798aec046d747300d80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Loxapine , positive-QTOF	splash10-00ai-0149000000-d463f8ddf4248264d132	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Loxapine , positive-QTOF	splash10-01r6-0930000000-4798aec046d747300d80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Loxapine 35V, Positive-QTOF	splash10-00di-0092000000-d36334adec23dfc827b7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 10V, Positive-QTOF	splash10-004i-0009000000-13c7c5980fa375485ea6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 20V, Positive-QTOF	splash10-004i-0029000000-ee11b761132aadb447f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 40V, Positive-QTOF	splash10-0596-9250000000-cdb8e78cf5fd1fd059b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 10V, Negative-QTOF	splash10-004i-0009000000-71d4c9395b89ad9fc22a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 20V, Negative-QTOF	splash10-004i-0039000000-ca6576c997e0e1af0ab2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 40V, Negative-QTOF	splash10-006y-3491000000-40caba03e0caacbf4b76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 10V, Positive-QTOF	splash10-004i-0009000000-1f57d14978e5410155ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 20V, Positive-QTOF	splash10-004i-0019000000-171a44896a8b8aa67151	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 40V, Positive-QTOF	splash10-00di-0090000000-8f9b474f4d539ce49d69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 10V, Negative-QTOF	splash10-004i-0009000000-f859e2aff8bfc6f7a27b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 20V, Negative-QTOF	splash10-004i-0039000000-568c941d47f67e7c6c41	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxapine 40V, Negative-QTOF	splash10-001i-5091000000-1f13f155778e72cff118	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00408	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00408	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00408

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3827

KEGG Compound ID

C07104

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loxapine

METLIN ID

Not Available

PubChem Compound

3964

PDB ID

Not Available

ChEBI ID

50841

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Cheung SW, Tang SW, Remington G: Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):213-21. [PubMed:1860915 ]
Glazer WM: Does loxapine have "atypical" properties? Clinical evidence. J Clin Psychiatry. 1999;60 Suppl 10:42-6. [PubMed:10340686 ]

Enzymes

Enzyme Details

1. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Lee T, Tang SW: Loxapine and clozapine decrease serotonin (S2) but do not elevate dopamine (D2) receptor numbers in the rat brain. Psychiatry Res. 1984 Aug;12(4):277-85. [PubMed:6239298 ]
Hjerde E, Dahl SG, Sylte I: Atypical and typical antipsychotic drug interactions with the dopamine D2 receptor. Eur J Med Chem. 2005 Feb;40(2):185-94. [PubMed:15694653 ]
Kalkman HO, Neumann V, Nozulak J, Tricklebank MD: Cataleptogenic effect of subtype selective 5-HT receptor antagonists in the rat. Eur J Pharmacol. 1998 Feb 19;343(2-3):201-7. [PubMed:9570468 ]
Froimowitz M, Cody V: Biologically active conformers of phenothiazines and thioxanthenes. Further evidence for a ligand model of dopamine D2 receptor antagonists. J Med Chem. 1993 Jul 23;36(15):2219-27. [PubMed:8101879 ]
Froimowitz M, Cody V: The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists. Drug Des Discov. 1997 Aug;15(2):63-81. [PubMed:9342550 ]
Lang AE, Sandor P, Duff J: Remoxipride in Parkinson's disease: differential response in patients with dyskinesias fluctuations versus psychosis. Clin Neuropharmacol. 1995 Feb;18(1):39-45. [PubMed:8665533 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Li Z, Ichikawa J, Meltzer HY: A comparison of the effects of loxapine with ziprasidone and thioridazine on the release of dopamine and acetylcholine in the prefrontal cortex and nucleus accumbens. Psychopharmacology (Berl). 2003 May;167(3):315-23. Epub 2003 Mar 28. [PubMed:12664192 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Herrick-Davis K, Grinde E, Teitler M: Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. J Pharmacol Exp Ther. 2000 Oct;295(1):226-32. [PubMed:10991983 ]

Enzyme Details

4. D(1A) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Loxapine (HMDB0014552)

MOL for HMDB0014552 (Loxapine)

3D MOL for HMDB0014552 (Loxapine)

3D SDF for HMDB0014552 (Loxapine)

3D-SDF for HMDB0014552 (Loxapine)

PDB for HMDB0014552 (Loxapine)

3D PDB for HMDB0014552 (Loxapine)

SMILES for HMDB0014552 (Loxapine)

INCHI for HMDB0014552 (Loxapine)

Structure for HMDB0014552 (Loxapine)

3D Structure for HMDB0014552 (Loxapine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References