Censavudine

Censavudine
Clinical data
Other names	4'-ethynylstavudine, festinavir
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name 1-[(2R,5R)-5-ethynyl-5-(hydroxymethyl)-2H-furan-2-yl]-5-methylpyrimidine-2,4-dione;
CAS Number	634907-30-5;
PubChem CID	3008897;
ChemSpider	2278330;
UNII	6IE83O6NGA;
KEGG	D10550;
ChEMBL	ChEMBL124363;
NIAID ChemDB	209894;
CompTox Dashboard (EPA)	DTXSID50212893 ;
ECHA InfoCard	100.225.812
Chemical and physical data
Formula	C12H12N2O4
Molar mass	248.238 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@](O2)(CO)C#C;
	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; Key:OSYWBJSVKUFFSU-SKDRFNHKSA-N;

Censavudine (INN)[1] (BMS-986001) is an investigational new drug being developed by Bristol Myers-Squibb for the treatment of HIV infection.[2][3] It was originally developed at Yale University.[4]It is still in an investigational phase of development as of 2023.[5]

Renaming

Until 2013, censavudine has been known as festinavir, but the name was changed to avoid confusion with HIV protease inhibitors which all bear class suffix "–navir" (e.g. tipranavir, lopinavir, saquinavir etc.).[6]

References

"International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed International Nonproprietary Names: List 110" (PDF). World Health Organization. pp. 409–410.
Wu VH, Smith RA, Masoum S, Raugi DN, Ba S, Seydi M, et al. (August 2017). "MK-8591 (4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine) Exhibits Potent Activity against HIV-2 Isolates and Drug-Resistant HIV-2 Mutants in Culture". Antimicrobial Agents and Chemotherapy. 61 (8). doi:10.1128/AAC.00744-17. PMC 5527656. PMID 28559249.
Gupta SK, McComsey GA, Lombaard J, Echevarría J, Orrell C, Avihingsanon A, et al. (January 2016). "Efficacy, safety, bone and metabolic effects of HIV nucleoside reverse transcriptase inhibitor BMS-986001 (AI467003): a phase 2b randomised, controlled, partly blinded trial". The Lancet. HIV. 3 (1): e13-22. doi:10.1016/S2352-3018(15)00231-3. hdl:1805/10552. PMID 26762988.
Alcorn K (21 December 2010). "Bristol-Myers Squibb buys festinavir, new NRTI active against MDR HIV". aidsmap.com. aidsmap. Retrieved 24 June 2011.
PubChem. "Censavudine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-24.
PubChem. "Censavudine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-24.

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[1] "International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed International Nonproprietary Names: List 110" (PDF). World Health Organization. pp. 409–410.

[pmid28559249-2] Wu VH, Smith RA, Masoum S, Raugi DN, Ba S, Seydi M, et al. (August 2017). "MK-8591 (4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine) Exhibits Potent Activity against HIV-2 Isolates and Drug-Resistant HIV-2 Mutants in Culture". Antimicrobial Agents and Chemotherapy. 61 (8). doi:10.1128/AAC.00744-17. PMC 5527656. PMID 28559249.

[pmid26762988-3] Gupta SK, McComsey GA, Lombaard J, Echevarría J, Orrell C, Avihingsanon A, et al. (January 2016). "Efficacy, safety, bone and metabolic effects of HIV nucleoside reverse transcriptase inhibitor BMS-986001 (AI467003): a phase 2b randomised, controlled, partly blinded trial". The Lancet. HIV. 3 (1): e13-22. doi:10.1016/S2352-3018(15)00231-3. hdl:1805/10552. PMID 26762988.

[4] Alcorn K (21 December 2010). "Bristol-Myers Squibb buys festinavir, new NRTI active against MDR HIV". aidsmap.com. aidsmap. Retrieved 24 June 2011.

[5] PubChem. "Censavudine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-24.

[6] PubChem. "Censavudine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-24.