3056-17-5 Stavudine AKSci J10003
 
 
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  J10003    AKSci Reference Standard
Stavudine
, 99% (HPLC)
 
2′,3′-Didehydro-3′-deoxythymidine




IDENTITY
CAS Number:3056-17-5
MDL Number:MFCD00132921
MF:C10H12N2O4
MW:224.21
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:99% (HPLC)
Spectra:NMR, LCMS, FT-IR, HPLC, Polarimetry
Physical Form:White to off-white powder
Melting Point:162-169°C
Optical Rotation:-48° to -40° (c=0.7, H2O)
Long-Term Storage:Store long-term at -20°C
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:DMSO: 45mg/mL; H2O: 45mg/mL; EtOH: 20mg/mL
Application(s):Nucleoside analog reverse transcriptase inhibitor
Form:Free Base

REVIEW

 Stavudine is a dideoxynucleoside analog reverse transcriptase inhibitor active against HIV. It is phosphorylated by cellular kinases into active triphosphate, which inhibits the activity of HIV-1 reverse transcriptase, both by competing with the natural substrate thymidine triphosphate and by its incorporation into viral DNA, resulting in termination of DNA replication.

REFERENCES
[1]Herdewijn, Piet; Balzarini, Jan; De Clercq, Erik; Pauwels, Rudi; Baba, Masanori; Broder, Samuel; Vanderhaeghe, Hubert 3'-Substituted 2',3'-dideoxynucleoside analogs as potential anti-HIV (HTLV-III/LAV) agents Journal of Medicinal Chemistry (1987), 30(8), 1270-8.
[2] Lin, Taishun; Prusoff, William H Preparation of and pharmaceutical composition comprising 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) in treating patients infected with retrovirus Eur. Pat. Appl. (1988), EP 273277 A2 19880706.
[3] Skonezny, Paul M.; Eisenreich, Emerich; Stark, Derron R.; Boyhan, Brenda T.; Baker, Stephen R. Process for bulk-scale preparation of 2',3'-didehydro-3'-dideoxythymidine U.S. (1996), US 5539099 A 19960723.
[4] Martin JC, Hitchcock MJ, Fridland A, Ghazzouli I, Kaul S, Dunkle LM, Sterzycki RZ, Mansuri MM. Comparative studies of 2',3'-didehydro-2',3'-dideoxythymidine (D4T) with other pyrimidine nucleoside analogues. Ann N Y Acad Sci. 1990;616:22-8.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501


Current as of December 1, 2021

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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CATEGORIES

 APIs and Bioactives > Antivirals, Antiretrovirals, NRTIs


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