Capravirine
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Identification
- Generic Name
- Capravirine
- DrugBank Accession Number
- DB08502
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- 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.
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AGag-Pol polyprotein inhibitorUGag-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
- Not Available
Interactions
- Drug Interactions
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 4 somestatus stop reason just information to hide 2 Suspended Treatment Human Immunodeficiency Virus (HIV) Infections 2 somestatus stop reason just information to hide 1 Completed Treatment Healthy Volunteers (HV) / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide 1 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 2 somestatus stop reason just information to hide
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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1. DetailsGag-Pol polyprotein
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Gag-Pol polyprotein Mediates, with Gag polyprotein, 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 the binding genomic RNA in the 5'-UTR. At low concentration, the polyprotein would promote translation, whereas at high concentration, the polyprotein would encapsidate genomic RNA and then shut off translation.
- Specific Function
- aspartic-type endopeptidase activity
- Gene Name
- gag-pol
- Uniprot ID
- P03366
- Uniprot Name
- Gag-Pol polyprotein
- Molecular Weight
- 163287.51 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsGag-Pol polyprotein
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Unknown
- General Function
- Gag-Pol polyprotein Mediates, with Gag polyprotein, 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 the binding genomic RNA in the 5'-UTR. At low concentration, the polyprotein would promote translation, whereas at high concentration, the polyprotein would encapsidate genomic RNA and then shut off translation.
- Specific Function
- aspartic-type endopeptidase activity
- 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]
3. DetailsReverse transcriptase/RNaseH
- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- aspartic-type endopeptidase activity
- 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
1. DetailsCytochrome P450 2C8
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- 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]
2. DetailsCytochrome P450 2C9
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- 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]
3. DetailsCytochrome P450 2C19
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 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]
4. DetailsCytochrome P450 3A4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- 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 August 26, 2024 19:22