Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1785)
Drug Name
RS-8359
Synonyms
RS 8359; RS-8359; RS-8359 [WHO-DD]; 105365-76-2; 119670-32-5; 4-((7-hydroxy-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)benzonitrile; 4-(4-Cyanoanilino)-5,6-dihydro-7-hydroxy-7H-cyclopenta[d]pyrimidine; 4-(7-hydroxy-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)benzonitrile; 4-[(7-hydroxy-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl)amino]benzonitrile; Benzonitrile, 4-[(6,7-dihydro-7-hydroxy-5H-cyclopentapyrimidin-4-yl)amino]-;Benzonitrile, 4-[(6,7-dihydro-7-hydroxy-5H-cyclopentapyrimidin-4-yl)amino]-
Indication Depression [ICD11: 6A71] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 252.27 Topological Polar Surface Area 81.8
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
164116
CAS Number
105365-76-2
TTD Drug ID
D06QOJ
Formula
C14H12N4O
Canonical SMILES
C1CC2=C(C1O)N=CN=C2NC3=CC=C(C=C3)C#N
InChI
1S/C14H12N4O/c15-7-9-1-3-10(4-2-9)18-14-11-5-6-12(19)13(11)16-8-17-14/h1-4,8,12,19H,5-6H2,(H,16,17,18)
InChIKey
YKTSVZRWKHWINV-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
RS-8359 M1 PDM007678 N. A. Oxidation - Oxidation of pyrimidine 1 Human
RS-8359 M2 PDM007679 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
RS-8359 M3 PDM007680 N. A. Conjugation - Sulfation of secondary alcohol 1 Human
RS-8359 M4 PDM007681 N. A. Other reaction - Degradation of nitrile to carboxamide 1 Gut microbial environment
RS-8359 M5 PDM007682
20136476
Other reaction - Degradation of aromatic nitrile to carboxylic acid 1 Gut microbial environment
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800000633)
2 Stereoselective pharmacokinetics of RS-8359, a selective and reversible MAO-A inhibitor, by species-dependent drug-metabolizing enzymes. Chirality. 2005 Mar;17(3):135-41.

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