Censavudine

Catalog No: 20632

CAS Number: 634907-30-5

Purity: 98% Min.

Censavudine, also known as OBP-601, BMS-986001 or festinavir, is a nucleoside reverse transcriptase inhibitor that is active against HIV resistant to both abacavir and tenofovir, making the drug a candidate for people with multi-drug resistant (MDR) strains of the virus. Censavudine is a derivative of stavudine (d4T), but is less toxic. Censavudine has demonstrated potent in vitro activity against HIV-2, including HIV-2 mutants containing the K65R and Q151M reverse transcriptase substitutions.

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Chemical Information

Name	Censavudine
Iupac Chemical Name	1-[(2R,5R)-5-ethynyl-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
Synonyms	OBP-601; OBP601; OBP 601; BMS-986001; BMS 986001; BMS986001; festinavir; 4′-Ed4T; Censavudine.
Molecular Formula	C12H12N2O4
Molecular Weight	248.23
Smile	O=C1NC(C(C)=CN1[C@@H]2O[C@@](CO)(C#C)C=C2)=O
InChiKey	OSYWBJSVKUFFSU-SKDRFNHKSA-N
InChi	InChI=1S/C12H12N2O4/c1-3-12(7-15)5-4-9(18-12)14-6-8(2)10(16)13-11(14)17/h1,4-6,9,15H,7H2,2H3,(H,13,16,17)/t9-,12+/m1/s1
CAS Number	634907-30-5
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Formulation	Solid powder
Purity	98% Min.
Storage	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
Handling
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.
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1: Gupta SK, McComsey GA, Lombaard J, Echevarría J, Orrell C, Avihingsanon A, Osiyemi O, Santoscoy M, Ray N, Stock DA, Joshi SR, Hanna GJ, Lataillade M. Efficacy, safety, bone and metabolic effects of HIV nucleoside reverse transcriptase inhibitor BMS-986001 (AI467003): a phase 2b randomised, controlled, partly blinded trial. Lancet HIV. 2016 Jan;3(1):e13-22. doi: 10.1016/S2352-3018(15)00231-3. Epub 2015 Dec 12. PubMed PMID: 26762988.

2: Smith RA, Raugi DN, Wu VH, Leong SS, Parker KM, Oakes MK, Sow PS, Ba S, Seydi M, Gottlieb GS. The Nucleoside Analog BMS-986001 Shows Greater In Vitro Activity against HIV-2 than against HIV-1. Antimicrob Agents Chemother. 2015 Dec;59(12):7437-46. doi: 10.1128/AAC.01326-15. Epub 2015 Sep 21. PubMed PMID: 26392486; PubMed Central PMCID: PMC4649195.

3: Yuan L, Schuster A, Shen JX, Garrison-Borowski P, Aubry AF. Dried blood spot analysis without dilution: Application to the LC-MS/MS determination of BMS-986001 in rat dried blood spot. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:201-9. doi: 10.1016/j.jchromb.2015.08.029. Epub 2015 Aug 28. PubMed PMID: 26340763.

4: Ortiz A, Benkovics T, Beutner GL, Shi Z, Bultman M, Nye J, Sfouggatakis C, Kronenthal DR. Scalable Synthesis of the Potent HIV Inhibitor BMS-986001 by Non-Enzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT). Angew Chem Int Ed Engl. 2015 Jun 8;54(24):7185-8. doi: 10.1002/anie.201502290. Epub 2015 Apr 29. PubMed PMID: 25925234.

5: Mausumee G, Frank S, Shawn C, Dara H, Zhao Y, Soleil PM, Sanderson TP, Michael G, Marc D. Nonclinical Safety Profile of BMS-986001, a Nucleoside Transcriptase Inhibitor for Combination Retroviral Therapy. Int J Toxicol. 2014 May 20;33(3):204-218. [Epub ahead of print] PubMed PMID: 24846376.

6: Urata Y, Paintsil E, Cheng YC, Matsuda T, Sevinsky H, Hawthorne D, Bertz R, Hanna GJ, Grasela D, Hwang C. Randomized, placebo-controlled single-ascending-dose study to evaluate the safety, tolerability and pharmacokinetics of the HIV nucleoside reverse transcriptase inhibitor, BMS-986001, in healthy subjects. J Clin Pharmacol. 2014 Jun;54(6):657-64. doi: 10.1002/jcph.252. Epub 2014 Jan 17. PubMed PMID: 24374821.

7: Maeda K, Desai DV, Aoki M, Nakata H, Kodama EN, Mitsuya H. Delayed emergence of HIV-1 variants resistant to 4'-ethynyl-2-fluoro-2'-deoxyadenosine: comparative sequential passage study with lamivudine, tenofovir, emtricitabine and BMS-986001. Antivir Ther. 2014;19(2):179-89. doi: 10.3851/IMP2697. Epub 2013 Oct 25. PubMed PMID: 24162098.

8: Flexner C, Saag M. The antiretroviral drug pipeline: prospects and implications for future treatment research. Curr Opin HIV AIDS. 2013 Nov;8(6):572-8. doi: 10.1097/COH.0000000000000011. Review. PubMed PMID: 24100879.

9: Wang F, Flint OP. BMS-986001, an HIV nucleoside reverse transcriptase inhibitor, does not degrade mitochondrial DNA in long-term primary cultures of cells isolated from human kidney, muscle, and adipose tissue. Antimicrob Agents Chemother. 2013 Dec;57(12):6205-12. doi: 10.1128/AAC.01206-13. Epub 2013 Sep 30. PubMed PMID: 24080659; PubMed Central PMCID: PMC3837843.

10: Li Z, Terry B, Olds W, Protack T, Deminie C, Minassian B, Nowicka-Sans B, Sun Y, Dicker I, Hwang C, Lataillade M, Hanna GJ, Krystal M. In vitro cross-resistance profile of nucleoside reverse transcriptase inhibitor (NRTI) BMS-986001 against known NRTI resistance mutations. Antimicrob Agents Chemother. 2013 Nov;57(11):5500-8. doi: 10.1128/AAC.01195-13. Epub 2013 Aug 26. PubMed PMID: 23979732; PubMed Central PMCID: PMC3811251.

11: Cotte L, Dellamonica P, Raffi F, Yazdanpanah Y, Molina JM, Boué F, Urata Y, Chan HP, Zhu L, Chang I, Bertz R, Hanna GJ, Grasela DM, Hwang C. Randomized placebo-controlled study of the safety, tolerability, antiviral activity, and pharmacokinetics of 10-day monotherapy with BMS-986001, a novel HIV NRTI, in treatment-experienced HIV-1-infected subjects. J Acquir Immune Defic Syndr. 2013 Jul 1;63(3):346-54. doi: 10.1097/QAI.0b013e3182965d12. PubMed PMID: 23771104.

12: Alexander AJ, Zhang L, Hooker TF, Tomasella FP. Comparison of supercritical fluid chromatography and reverse phase liquid chromatography for the impurity profiling of the antiretroviral drugs lamivudine/BMS-986001/efavirenz in a combination tablet. J Pharm Biomed Anal. 2013 May 5;78-79:243-51. doi: 10.1016/j.jpba.2013.02.019. Epub 2013 Feb 21. PubMed PMID: 23507686.

13: Zhao Y, Liu G, Liu Y, Yuan L, Hawthorne D, Shen JX, Guha M, Aubry A. Improved ruggedness of an ion-pairing liquid chromatography/tandem mass spectrometry assay for the quantitative analysis of the triphosphate metabolite of a nucleoside reverse transcriptase inhibitor in peripheral blood mononuclear cells. Rapid Commun Mass Spectrom. 2013 Feb 15;27(3):481-8. doi: 10.1002/rcm.6473. PubMed PMID: 23280981.

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Censavudine

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