Identification

Name
Capravirine
Accession Number
DB08502  (DB06456)
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • Capravirine
External IDs
S-1153
Categories
UNII
VHC779598X
CAS number
Not Available
Weight
Average: 451.369
Monoisotopic: 450.068402008
Chemical Formula
C20H20Cl2N4O2S
InChI Key
YQXCVAGCMNFUMQ-UHFFFAOYSA-N
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)
IUPAC Name
{5-[(3,5-dichlorophenyl)sulfanyl]-4-(propan-2-yl)-1-(pyridin-4-ylmethyl)-1H-imidazol-2-yl}methyl carbamate
SMILES
CC(C)C1=C(SC2=CC(Cl)=CC(Cl)=C2)N(CC2=CC=NC=C2)C(COC(N)=O)=N1

Pharmacology

Indication

Investigated for use/treatment in acquired immune deficiency syndrome (AIDS) and aids-related infections and HIV infection.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGag-Pol polyproteinNot AvailableHIV-1
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Bu HZ, Zhao P, Kang P, Pool WF, Wu EY: 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. Epub 2006 Aug 16. [PubMed:16914510]
External Links
PubChem Compound
1783
PubChem Substance
99444973
ChemSpider
1717
BindingDB
27579
ChEMBL
CHEMBL435128
HET
S11
PDB Entries
1ep4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2SuspendedTreatmentHuman 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 Solubility0.00387 mg/mLALOGPS
logP4.76ALOGPS
logP4.86ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)14.18ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.03 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.68 m3·mol-1ChemAxon
Polarizability45.41 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9879
Blood Brain Barrier+0.8436
Caco-2 permeable-0.5176
P-glycoprotein substrateNon-substrate0.5163
P-glycoprotein inhibitor INon-inhibitor0.7484
P-glycoprotein inhibitor IINon-inhibitor0.7797
Renal organic cation transporterNon-inhibitor0.6271
CYP450 2C9 substrateNon-substrate0.8336
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5505
CYP450 1A2 substrateInhibitor0.6755
CYP450 2C9 inhibitorInhibitor0.6173
CYP450 2D6 inhibitorNon-inhibitor0.7287
CYP450 2C19 inhibitorInhibitor0.7363
CYP450 3A4 inhibitorInhibitor0.5184
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9061
Ames testNon AMES toxic0.6911
CarcinogenicityNon-carcinogens0.8857
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5551 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9799
hERG inhibition (predictor II)Inhibitor0.6828
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
Kingdom
Organic compounds
Super Class
Organosulfur compounds
Class
Thioethers
Sub Class
Aryl thioethers
Direct Parent
Diarylthioethers
Alternative Parents
1,2,4,5-tetrasubstituted imidazoles / Thiophenol ethers / Dichlorobenzenes / Pyridines and derivatives / Aryl chlorides / N-substituted imidazoles / Carbamate esters / Heteroaromatic compounds / Organic carbonic acids and derivatives / Sulfenyl compounds
show 7 more
Substituents
Diarylthioether / 1,2,4,5-tetrasubstituted imidazole / 1,3-dichlorobenzene / Thiophenol ether / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Benzenoid / Monocyclic benzene moiety
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
HIV-1
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
P04585
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
162041.05 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. [PubMed:10592235]
  2. Bu HZ, Pool WF, Wu EY, Raber SR, Amantea MA, Shetty BV: 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. [PubMed:15205383]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da

Drug created on September 15, 2010 15:32 / Updated on December 01, 2017 16:05