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]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 329.4
  Topological Polar Surface Area (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
  DrugBank ID: DB08639
  TTD ID: D0DC6U
  INTEDE ID: DR1822

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]

References

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• [2] Metabolism Of Antiretroviral Drugs Used In Hiv Preexposure Prophylaxis
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• [15] Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72.
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• [20] Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
• [21] Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
• [22] Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
• [23] HIV-1 reverse transcriptase complex with DNA and nevirapine reveals non-nucleoside inhibition mechanism.Nat Struct Mol Biol.2012 Jan 22;19(2):253-9.
• [24] A peptide inhibitor of HIV-1 reverse transcriptase using alpha,beta-dehydro residues: a structure-based computer model. J Biomol Struct Dyn. 1998 Oct;16(2):347-54.
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• [26] Quadruple nucleos(t)ide reverse transcriptase inhibitors-only regimen of tenofovir plus zidovudine/lamivudine/abacavir in heavily pre-treated HIV-1 infected patients: salvage therapy or backbone only Curr HIV Res. 2009 May;7(3):320-6.
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