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MedKoo Cat#: 328057 | Name: Capravirine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Capravirine, also known as AG-1549; AG 549; S-1153, is a non-nucleoside reverse transcriptase inhibitor potentially for the treatment of HIV infection.

Chemical Structure

Capravirine
Capravirine
CAS#178979-85-6

Theoretical Analysis

MedKoo Cat#: 328057

Name: Capravirine

CAS#: 178979-85-6

Chemical Formula: C20H20Cl2N4O2S

Exact Mass: 450.0684

Molecular Weight: 451.37

Elemental Analysis: C, 53.22; H, 4.47; Cl, 15.71; N, 12.41; O, 7.09; S, 7.10

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Capravirine; AG-1549; AG 1549; AG1549; AG 549; AG-549; AG549; S-1153; S 1153; S1153;
IUPAC/Chemical Name
(5-((3,5-dichlorophenyl)thio)-4-isopropyl-1-(pyridin-4-ylmethyl)-1H-imidazol-2-yl)methyl carbamate
InChi Key
YQXCVAGCMNFUMQ-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CC(C1=C(SC2=CC(Cl)=CC(Cl)=C2)N(CC3=CC=NC=C3)C(COC(N)=O)=N1)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 451.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Li X, Zhan P, De Clercq E, Liu X. The HIV-1 non-nucleoside reverse transcriptase inhibitors (part V): capravirine and its analogues. Curr Med Chem. 2012;19(36):6138-49. Review. PubMed PMID: 22934811. 2: Bu HZ, Zhao P, Kang P, Pool WF, Wu EY, Shetty BV. Evaluation of capravirine as a CYP3A probe substrate: in vitro and in vivo metabolism of capravirine in rats and dogs. Drug Metab Dispos. 2007 Sep;35(9):1593-602. PubMed PMID: 17567732. 3: Bu HZ, Pool WF, Wu EY, Shetty BV. A unique example of drug metabolism: tetra- and penta-oxygenation reactions of capravirine in rats, dogs and humans. Drug Metab Lett. 2007 Jan;1(1):61-5. PubMed PMID: 19356020. 4: 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. PubMed PMID: 16914510. 5: Sato A, Hammond J, Alexander TN, Graham JP, Binford S, Sugita K, Sugimoto H, Fujiwara T, Patick AK. In vitro selection of mutations in human immunodeficiency virus type 1 reverse transcriptase that confer resistance to capravirine, a novel nonnucleoside reverse transcriptase inhibitor. Antiviral Res. 2006 Jun;70(2):66-74. PubMed PMID: 16472877. 6: Bu HZ, Kang P, Zhao P, Pool WF, Wu EY. A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans. Drug Metab Dispos. 2005 Oct;33(10):1438-45. PubMed PMID: 16006566. 7: Loksha YM, el-Barbary AA, el-Badawi MA, Nielsen C, Pedersen EB. Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues. Bioorg Med Chem. 2005 Jul 1;13(13):4209-20. PubMed PMID: 15896963. 8: Gewurz BE, Jacobs M, Proper JA, Dahl TA, Fujiwara T, Dezube BJ. Capravirine, a nonnucleoside reverse-transcriptase inhibitor in patients infected with HIV-1: a phase 1 study. J Infect Dis. 2004 Dec 1;190(11):1957-61. PubMed PMID: 15529260. 9: 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 PMID: 15205383. 10: Capravirine trials stopped. AIDS Patient Care STDS. 2001 Apr;15(4):225. PubMed PMID: 11359665.