NAV

Dapivirine

Identification

Generic Name
Dapivirine
DrugBank Accession Number
DB08639
Background

Dapivirine has been investigated for the prevention of HIV-1 Infections and Topical Penile Exposures.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 329.3984
Monoisotopic: 329.164045633
Chemical Formula
C20H19N5
Synonyms
  • Dapivirine
External IDs
  • AIDS-105293
  • R-147681
  • TMC-120
  • TMC120
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGag-Pol polyproteinNot Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dapivirine hydrochloride55D48BY90H244768-47-6RHIYZDNOTUMYCA-UHFFFAOYSA-N

Categories

ATC Codes
G01AX17 — Dapivirine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzonitriles
Direct Parent
Benzonitriles
Alternative Parents
Aniline and substituted anilines / Aminopyrimidines and derivatives / Imidolactams / Heteroaromatic compounds / Secondary amines / Nitriles / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzonitrile / Carbonitrile / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aminopyrimidine, nitrile (CHEBI:46180)
Affected organisms
Not Available

Chemical Identifiers

UNII
TCN4MG2VXS
CAS number
244767-67-7
InChI Key
ILAYIAGXTHKHNT-UHFFFAOYSA-N
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)
IUPAC Name
4-({4-[(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl}amino)benzonitrile
SMILES
CC1=CC(C)=C(NC2=NC(NC3=CC=C(C=C3)C#N)=NC=C2)C(C)=C1

References

General References
Not Available
PubChem Compound
214347
PubChem Substance
99445110
ChemSpider
185837
ChEMBL
CHEMBL70663
ZINC
ZINC000000007761
PDBe Ligand
TPB
Wikipedia
Dapivirine
PDB Entries
1s6q

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionHIV, Prevention1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
3Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3WithdrawnPreventionHuman Immunodeficiency Virus (HIV) Infections2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 mg/mLALOGPS
logP4.12ALOGPS
logP5.6Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.43Chemaxon
pKa (Strongest Basic)4.45Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area73.63 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity100.8 m3·mol-1Chemaxon
Polarizability37.13 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.984
Blood Brain Barrier+0.8503
Caco-2 permeable+0.6773
P-glycoprotein substrateNon-substrate0.73
P-glycoprotein inhibitor INon-inhibitor0.7381
P-glycoprotein inhibitor IINon-inhibitor0.7798
Renal organic cation transporterNon-inhibitor0.84
CYP450 2C9 substrateNon-substrate0.8026
CYP450 2D6 substrateNon-substrate0.8019
CYP450 3A4 substrateNon-substrate0.6521
CYP450 1A2 substrateInhibitor0.7843
CYP450 2C9 inhibitorNon-inhibitor0.9177
CYP450 2D6 inhibitorNon-inhibitor0.8807
CYP450 2C19 inhibitorNon-inhibitor0.7548
CYP450 3A4 inhibitorNon-inhibitor0.8598
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5896
Ames testNon AMES toxic0.7603
CarcinogenicityNon-carcinogens0.907
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity2.8549 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9178
hERG inhibition (predictor II)Non-inhibitor0.7945
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-511fb5d47467b0e66a45
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-3cad48c286953d933325
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0019000000-cb29de96a71652046366
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0019000000-477d82e314898503bca5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0wmi-0669000000-170b75507e3402e30cee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-100u-3940000000-01ea1bf1ac2182eb30f7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-203.3487011
predicted
DarkChem Lite v0.1.0
[M-H]-188.62378
predicted
DeepCCS 1.0 (2019)
[M+H]+204.5905011
predicted
DarkChem Lite v0.1.0
[M+H]+191.12508
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.6652011
predicted
DarkChem Lite v0.1.0
[M+Na]+199.25244
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Gag-Pol polyprotein
Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
Gene Name
gag-pol
Uniprot ID
P03366
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
163287.51 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:33 / Updated at February 21, 2021 18:52