Identification
NameCapravirine
Accession NumberDB08502  (DB06456)
TypeSmall Molecule
GroupsInvestigational
DescriptionNot Available
Structure
Thumb
Synonyms
Capravirine
External IDs S-1153
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIVHC779598X
CAS numberNot Available
WeightAverage: 451.369
Monoisotopic: 450.068402008
Chemical FormulaC20H20Cl2N4O2S
InChI KeyYQXCVAGCMNFUMQ-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
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Gag-Pol polyproteinProteinunknownNot AvailableHIV-1P04585 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
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
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganosulfur compounds
Sub ClassThioethers
Direct ParentDiarylthioethers
Alternative Parents1,2,4,5-tetrasubstituted imidazoles / Thiophenol ethers / Dichlorobenzenes / Pyridines and derivatives / Aryl chlorides / N-substituted imidazoles / Carbamate esters / Heteroaromatic compounds / Sulfenyl compounds / Azacyclic compounds
SubstituentsDiarylthioether / 1,2,4,5-tetrasubstituted imidazole / 1,3-dichlorobenzene / Thiophenol ether / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot 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 spherical particles, recruiting the viral Env proteins, and packaging the genomic RNA via direct interactions with the RNA packaging sequence (Psi). Gag-Pol polyprotein may regulate its own translation, by...
Gene Name:
gag-pol
Uniprot ID:
P04585
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Drug created on September 15, 2010 15:32 / Updated on June 23, 2017 10:19