Details of the Drug

General Information of Drug (ID: DM9ERH1)

Drug Name
Capravirine
Synonyms AG-1549; S-1153; NNRTI (HIV infection), Pfizer
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Phase 1 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 451.4
Logarithm of the Partition Coefficient (xlogp) 4.5
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C20H20Cl2N4O2S
IUPAC Name
[5-(3,5-dichlorophenyl)sulfanyl-4-propan-2-yl-1-(pyridin-4-ylmethyl)imidazol-2-yl]methyl carbamate
Canonical SMILES
CC(C)C1=C(N(C(=N1)COC(=O)N)CC2=CC=NC=C2)SC3=CC(=CC(=C3)Cl)Cl
InChI
InChI=1S/C20H20Cl2N4O2S/c1-12(2)18-19(29-16-8-14(21)7-15(22)9-16)26(10-13-3-5-24-6-4-13)17(25-18)11-28-20(23)27/h3-9,12H,10-11H2,1-2H3,(H2,23,27)
InChIKey
YQXCVAGCMNFUMQ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1783
CAS Number
178979-85-6
UNII
VHC779598X
DrugBank ID
DB08502
TTD ID
D0KR5K
INTEDE ID
DR0267

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [4]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00002214) Phase I Trial of S-1153 in Patients With HIV Infection. U.S. National Institutes of Health.
2 Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers. Drug Metab Dispos. 2004 Jul;32(7):689-98.
3 Identification of enzymes responsible for primary and sequential oxygenation reactions of capravirine in human liver microsomes. Drug Metab Dispos. 2006 Nov;34(11):1798-802.
4 Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers. Drug Metab Dispos. 2004 Jul;32(7):689-98.