Details of the Drug

General Information of Drug (ID: DMJPSIL)

Drug Name
Dapivirine
Synonyms
Dapivirinum; R 147681; R147681; TMC 120; TMC120; GEL-002; R-147681; TMC-120; TMC120-R147681; TMC-120/R-147681; 4-((4-((2,4,6-Trimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile; 4-({4-[(2,4,6-Trimethylphenyl)amino]pyrimidin-2-yl}amino)benzenecarbonitrile; 4-[4-(2,4,6-TRIMETHYL-PHENYLAMINO)-PYRIMIDIN-2-YLAMINO]-BENZONITRILE; 4-[[4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Phase 1/2 [1]
ATC Code
G01AX17: Dapivirine
G01AX: Other antiinfectives and antiseptics
G01A: ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
G01: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 329.4
Logarithm of the Partition Coefficient (xlogp) 4.8
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C20H19N5
IUPAC Name
4-[[4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile
Canonical SMILES
CC1=CC(=C(C(=C1)C)NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C
InChI
InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)
InChIKey
ILAYIAGXTHKHNT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
214347
CAS Number
244767-67-7
UNII
TCN4MG2VXS
DrugBank ID
DB08639
TTD ID
D0DC6U
INTEDE ID
DR1822
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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 [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [2]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
2 Metabolism Of Antiretroviral Drugs Used In Hiv Preexposure Prophylaxis