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Showing metabocard for N-Methylhydantoin (HMDB0003646)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 02:29:33 UTC
Update Date2023-02-21 17:16:46 UTC
HMDB IDHMDB0003646
Secondary Accession Numbers
  • HMDB03646
Metabolite Identification
Common NameN-Methylhydantoin
DescriptionN-methylhydantoin is a imidazolidine-2,4-dione that is the N-methyl-derivative of hydantoin. It has a role as a bacterial metabolite. It derives from a hydantoin. N-Methylhydantoin is a small molecular weight polar substance, the product of degradation of creatinine by bacteria (hydrolyzed by creatinine iminohydrolase, EC 3.5.4.21 to ammonia and N-methylhydantoin). In mammals, the metabolism of 1-methylhydantoin occurs via 5-hydroxy-1-methylhydantoin. In a reported human case, 1-Methylhydantoin was found as an unexpected metabolite of the intelligence-affecting substance dupracetam (PMID:15533691 , 8287520 , 3196760 , 7294979 ).
Structure
Data?1676999806
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003646 (N-Methylhydantoin)


  Mrv1652305271900232D          

  8  8  0  0  0  0            999 V2000
   24.4142  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5099  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3746  -14.7269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9621  -15.9965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8596  -14.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5495  -14.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6295  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2946  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0003646 (N-Methylhydantoin)

HMDB0003646
     RDKit          3D
N-Methylhydantoin
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9188    0.2379   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.1783    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.9700    0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -0.8488   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458   -1.7687   -0.4183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883    0.5411   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025    1.1714   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    2.3979   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    1.0001   -0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -0.7508   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.4931    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3277   -0.7825    1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026   -1.9181    0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.0191   -0.3685 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
Download

3D SDF for HMDB0003646 (N-Methylhydantoin)


  Mrv1652305271900232D          

  8  8  0  0  0  0            999 V2000
   24.4142  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5099  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3746  -14.7269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9621  -15.9965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8596  -14.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5495  -14.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6295  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2946  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003646

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N2O2/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8)

> <INCHI_KEY>
RHYBFKMFHLPQPH-UHFFFAOYSA-N

> <FORMULA>
C4H6N2O2

> <MOLECULAR_WEIGHT>
114.1026

> <EXACT_MASS>
114.042927446

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.248660447524124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
-1.20

> <JCHEM_LOGP>
-1.2265444019999998

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109753519841874

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.940479971810053

> <JCHEM_PKA_STRONGEST_BASIC>
-8.478788567664584

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
25.9428

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methylhydantoin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003646 (N-Methylhydantoin)

HMDB0003646
     RDKit          3D
N-Methylhydantoin
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9188    0.2379   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.1783    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.9700    0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -0.8488   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458   -1.7687   -0.4183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883    0.5411   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025    1.1714   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    2.3979   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    1.0001   -0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -0.7508   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.4931    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3277   -0.7825    1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026   -1.9181    0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.0191   -0.3685 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
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PDB for HMDB0003646 (N-Methylhydantoin)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      45.573 -29.431   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      40.152 -29.431   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      43.633 -27.490   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      42.863 -29.860   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      44.538 -26.244   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.092 -27.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      44.108 -28.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.617 -28.955   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    5    6    7                                                  
CONECT    4    7    8                                                       
CONECT    5    3                                                            
CONECT    6    3    8                                                       
CONECT    7    1    3    4                                                  
CONECT    8    2    4    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0003646 (N-Methylhydantoin)

COMPND    HMDB0003646
HETATM    1  C1  UNL     1      -1.919   0.238  -0.219  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.498   0.178   0.033  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.215  -0.970   0.568  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.535  -0.849  -0.063  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.346  -1.769  -0.418  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.788   0.541  -0.229  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.502   1.171  -0.166  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.229   2.398  -0.263  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.192   1.000  -0.969  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.241  -0.751  -0.635  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.501   0.493   0.702  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.328  -0.782   1.673  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.303  -1.918   0.357  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.709   1.019  -0.369  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    7
CONECT    3    4   12   13
CONECT    4    5    5    6
CONECT    6    7   14
CONECT    7    8    8
END
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SMILES for HMDB0003646 (N-Methylhydantoin)

CN1CC(=O)NC1=O
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INCHI for HMDB0003646 (N-Methylhydantoin)

InChI=1S/C4H6N2O2/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-MethylhydantoinChEBI
Dioxy-creatinineChEBI
N-Methylimidazolidine-2,4-dioneChEBI
1-Methyl-2,4-imidazolidinedioneHMDB
1-Methyl-hydantoinHMDB
1-Methyldiazolidine-2,4-dioneHMDB
1-Methylimidazolidine-2,4-dioneHMDB
N-MethylhydantoinMeSH
Chemical FormulaC4H6N2O2
Average Molecular Weight114.1026
Monoisotopic Molecular Weight114.042927446
IUPAC Name1-methylimidazolidine-2,4-dione
Traditional Name1-methylhydantoin
CAS Registry Number616-04-6
SMILES
CN1CC(=O)NC1=O
InChI Identifier
InChI=1S/C4H6N2O2/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8)
InChI KeyRHYBFKMFHLPQPH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazolines. These are organic compounds containing an imidazoline ring, which is an unsaturated ring (derived from imidazole) with two nitrogen atoms at positions 1 and 3 respectively, and containing only one CN double bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolines
Sub ClassImidazolines
Direct ParentImidazolines
Alternative Parents
Substituents
  • 3-imidazoline
  • Carbonic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.148Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility265 g/LALOGPS
logP-1.2ALOGPS
logP-1.2ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
pKa (Strongest Basic)-8.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.94 m³·mol⁻¹ChemAxon
Polarizability10.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.49931661259
DarkChem[M-H]-117.39531661259
DeepCCS[M+H]+122.26730932474
DeepCCS[M-H]-119.40530932474
DeepCCS[M-2H]-155.60630932474
DeepCCS[M+Na]+130.69130932474
AllCCS[M+H]+124.332859911
AllCCS[M+H-H2O]+119.532859911
AllCCS[M+NH4]+128.832859911
AllCCS[M+Na]+130.132859911
AllCCS[M-H]-119.332859911
AllCCS[M+Na-2H]-122.032859911
AllCCS[M+HCOO]-125.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.1.99 minutes32390414
Predicted by Siyang on May 30, 20229.5866 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.83 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1128.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid342.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid92.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid221.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid72.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid265.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid404.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)219.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid694.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid160.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1033.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid221.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid250.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate584.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA236.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water187.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-MethylhydantoinCN1CC(=O)NC1=O2271.8Standard polar33892256
N-MethylhydantoinCN1CC(=O)NC1=O1104.8Standard non polar33892256
N-MethylhydantoinCN1CC(=O)NC1=O1242.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methylhydantoin,1TMS,isomer #1CN1CC(=O)N([Si](C)(C)C)C1=O1384.3Semi standard non polar33892256
N-Methylhydantoin,1TMS,isomer #1CN1CC(=O)N([Si](C)(C)C)C1=O1339.5Standard non polar33892256
N-Methylhydantoin,1TMS,isomer #1CN1CC(=O)N([Si](C)(C)C)C1=O1994.7Standard polar33892256
N-Methylhydantoin,1TBDMS,isomer #1CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=O1582.2Semi standard non polar33892256
N-Methylhydantoin,1TBDMS,isomer #1CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=O1599.9Standard non polar33892256
N-Methylhydantoin,1TBDMS,isomer #1CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=O2031.9Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.9 (1.0-11.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified8.947 +/- 7.774 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified10.022 +/- 8.701 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023209
KNApSAcK IDNot Available
Chemspider ID62430
KEGG Compound IDC02565
BioCyc IDN-METHYLHYDANTOIN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69217
PDB IDNot Available
ChEBI ID16354
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hollosi L, Kettrup A, Schramm KW: MMSPE-RP-HPLC method for the simultaneous determination of methimazole and selected metabolites in fish homogenates. J Pharm Biomed Anal. 2004 Nov 19;36(4):921-4. [PubMed:15533691 ]
  2. Fossati P, Ponti M, Passoni G, Tarenghi G, Melzi d'Eril GV, Prencipe L: A step forward in enzymatic measurement of creatinine. Clin Chem. 1994 Jan;40(1):130-7. [PubMed:8287520 ]
  3. Ienaga K, Nakamura K, Naka F, Goto T: The metabolism of 1-methylhydantoin via 5-hydroxy-1-methylhydantoin in mammals. Biochim Biophys Acta. 1988 Dec 15;967(3):441-3. [PubMed:3196760 ]
  4. Dell HD, Jacobi H, Kamp R, Kurz J, Wunsche C: [1-Methylhydantoin, an unexpected metabolite of the intelligence-affecting substance dupracetam (author's transl)]. Arch Pharm (Weinheim). 1981 Aug;314(8):697-702. [PubMed:7294979 ]