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

General Information of Drug (ID: DR1791)
Drug Name
NSC-149027
Synonyms
Bropirimina [Spanish]; Bropirimine; Bropiriminum [Latin]; J57CTF25XJ; U-54461; 2-AMINO-5-BROMO-6-PHENYLPYRIMIDIN-4-OL; 2-Amino-5-bromo-4-hydroxy-6-phenylpyrimidine; 2-Amino-5-bromo-6-phenyl-4(1H)-pyrimidinone; 2-Amino-5-bromo-6-phenyl-4(3H)-pyrimidinone; 2-amino-5-bromo-6-phenyl-1H-pyrimidin-4-one; 2-amino-5-bromo-6-phenylpyrimidin-4(3H)-one; 4(1H)-Pyrimidinone, 2-amino-5-bromo-6-phenyl-; 5-Bromo-6-phenylisocytosine; 56741-95-8; ABPP; BRN 0651807; C10H8BrN3O; CCRIS 3730; CHEBI:31307; UNII-J57CTF25XJ
Indication Herpes simplex virus infection [ICD11: 1F00] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 266.09 Topological Polar Surface Area 67.5
Heavy Atom Count 15 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
135413497
ChEBI ID
CHEBI:55345
CAS Number
56741-95-8
TTD Drug ID
D07RPR
Formula
C10H8BrN3O
Canonical SMILES
C1=CC=C(C=C1)C2=C(C(=O)NC(=N2)N)Br
InChI
1S/C10H8BrN3O/c11-7-8(6-4-2-1-3-5-6)13-10(12)14-9(7)15/h1-5H,(H3,12,13,14,15)
InChIKey
CIUUIPMOFZIWIZ-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
NSC-149027 M4 DM007017 N. A. Oxidation - Oxidationn 1 [2]
Bropirimiedihydrodiol(M1) DM007018 N. A. Oxidation - Hydrolyzationn 2 [2]
m-hydroxybropirimine(M3) DM007019
135413497
Oxidation - Hydrolyzationn 2 [2]
p-hydroxyborpirimine(M2) DM007020
135435147
Oxidation - Hydrolyzationn 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007646 NSC-149027 NSC-149027 M4 Oxidation - Oxidationn CYP1A2 [2]
MR007647 NSC-149027 M4 Bropirimiedihydrodiol(M1) Oxidation - Hydrolyzationn Unclear [2]
MR007648 NSC-149027 M4 m-hydroxybropirimine(M3) Oxidation - Hydrolyzationn Unclear [2]
MR007649 NSC-149027 M4 p-hydroxyborpirimine(M2) Oxidation - Hydrolyzationn Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[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 800000744)
2 Human biotransformation of bropirimine. Characterization of the major bropirimine oxidative metabolites formed in vitro. Drug Metab Dispos. 1998 Oct;26(10):1048-51.

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