Identification
- Generic Name
- Capravirine
- DrugBank Accession Number
- DB08502
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Capravirine (DB08502)
- Weight
- Average: 451.369
Monoisotopic: 450.068402008 - Chemical Formula
- C20H20Cl2N4O2S
- Synonyms
- Capravirina
- Capravirine
- Capravirinum
- External IDs
- AG 1549
- AG 549
- S 1153
- S-1153
Pharmacology
- Indication
Investigated for use/treatment in acquired immune deficiency syndrome (AIDS) and aids-related infections and HIV infection.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGag-Pol polyprotein Not Available UReverse transcriptase/RNaseH inhibitorHuman immunodeficiency virus 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Capravirine can be increased when combined with Abatacept. Abiraterone The metabolism of Capravirine can be decreased when combined with Abiraterone. Adalimumab The metabolism of Capravirine can be increased when combined with Adalimumab. Almotriptan The metabolism of Capravirine can be decreased when combined with Almotriptan. Alpelisib The metabolism of Capravirine can be decreased when combined with Alpelisib. - Food Interactions
- Not Available
Categories
- Drug Categories
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiviral Agents
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Non-Nucleoside Reverse Transcriptase Inhibitors
- Nucleic Acid Synthesis Inhibitors
- Reverse Transcriptase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2,4,5-tetrasubstituted imidazole / 1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Carbamic acid ester / Carbonic acid derivative show 21 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- VHC779598X
- CAS number
- 178979-85-6
- 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-yl)methyl]-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
References
- General References
- 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. [Article]
- External Links
- PubChem Compound
- 1783
- PubChem Substance
- 99444973
- ChemSpider
- 1717
- BindingDB
- 27579
- ChEMBL
- CHEMBL435128
- ZINC
- ZINC000000538635
- PDBe Ligand
- S11
- Wikipedia
- Capravirine
- PDB Entries
- 1ep4
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 4 2 Suspended Treatment Human Immunodeficiency Virus (HIV) Infections 2 1 Completed Treatment Healthy Subjects (HS) / Human Immunodeficiency Virus (HIV) Infections 1 1 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 2
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
Property Value Source Water Solubility 0.00387 mg/mL ALOGPS logP 4.76 ALOGPS logP 4.86 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 14.86 Chemaxon pKa (Strongest Basic) 5.47 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 83.03 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 115.68 m3·mol-1 Chemaxon Polarizability 45.43 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9879 Blood Brain Barrier + 0.8436 Caco-2 permeable - 0.5176 P-glycoprotein substrate Non-substrate 0.5163 P-glycoprotein inhibitor I Non-inhibitor 0.7484 P-glycoprotein inhibitor II Non-inhibitor 0.7797 Renal organic cation transporter Non-inhibitor 0.6271 CYP450 2C9 substrate Non-substrate 0.8336 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5505 CYP450 1A2 substrate Inhibitor 0.6755 CYP450 2C9 inhibitor Inhibitor 0.6173 CYP450 2D6 inhibitor Non-inhibitor 0.7287 CYP450 2C19 inhibitor Inhibitor 0.7363 CYP450 3A4 inhibitor Inhibitor 0.5184 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9061 Ames test Non AMES toxic 0.6911 Carcinogenicity Non-carcinogens 0.8857 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5551 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9799 hERG inhibition (predictor II) Inhibitor 0.6828
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0213900000-8b1da488c55b9805817e Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0010900000-01eb130bc77c1bf5e516 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f8c-0006900000-ac2c195b343859787fab Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-005a-1953200000-f5b2dd7270d213ba7244 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fal-3395200000-68a3da068dcada94cad7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001u-6790100000-5d057aad78f3020f64de Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.5754 predictedDeepCCS 1.0 (2019) [M+H]+ 198.9334 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.49211 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- P04585
- Uniprot Name
- Gag-Pol polyprotein
- Molecular Weight
- 162041.05 Da
References
- 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]
- 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. [Article]
- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Not Available
- Gene Name
- pol
- Uniprot ID
- Q72547
- Uniprot Name
- Reverse transcriptase/RNaseH
- Molecular Weight
- 65223.615 Da
References
- De Clercq E: Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid 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 oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid 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 oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
References
- 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. [Article]
Drug created at September 15, 2010 21:32 / Updated at June 28, 2022 02:25