Stavudine

Base Information

• Chemical Name: Stavudine
• CAS No.: 3056-17-5
• Deprecated CAS: 132425-31-1
• Molecular Formula: C10H12N2O4
• Molecular Weight: 224.216
• Hs Code.: 29349990
• European Community (EC) Number: 641-374-0
• NSC Number: 759897
• UNII: BO9LE4QFZF
• DSSTox Substance ID: DTXSID1023819
• Nikkaji Number: J83.276F
• Wikipedia: Stavudine
• Wikidata: Q423984
• NCI Thesaurus Code: C1428
• RXCUI: 59763
• Metabolomics Workbench ID: 42969
• ChEMBL ID: CHEMBL991
• Mol file: 3056-17-5.mol

Synonyms:2',3' Didehydro 3' deoxythymidine;2',3'-Didehydro-2',3'-dideoxythmidine;2',3'-Didehydro-3'-deoxythymidine;BMY 27857;BMY-27857;BMY27857;D4T;Stavudine;Stavudine, Monosodium Salt;Zerit

Chemical Property of Stavudine

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 159-160 °C
• Refractive Index: -46 ° (C=0.69, H2O)
• PKA: 9.47±0.10(Predicted)
• PSA: 84.32000
• Density: 1.374 g/cm³
• LogP: -0.70910
• Storage Temp.: −20°C
• Solubility.: Soluble in water, sparingly soluble in ethanol (96 per cent), slightly soluble in methylene chloride. It shows polymorphism (5.9).
• Water Solubility.: 5-10 g/100 mL at 21 ºC
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 224.07970687
• Heavy Atom Count: 16
• Complexity: 388

Purity/Quality:

98%, ^*data from raw suppliers

Stavudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C=CC(O2)CO
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
• Recent ClinicalTrials: Preventing Sexual Transmission of HIV With Anti-HIV Drugs
• Recent EU Clinical Trials: Randomized,multicenter,open-label, study of monoterapy with darunavir/ritonavir or lopinavir/ritonavir vs standard of care in virologically suppressed HIV-infected patients.
• Description: Stavudine, a dideoxynucleoside analog of thymidine, has been introduced in the U.S.A. for the treatment of late-stage AIDS patients who are refractory to other AIDS treatments. Similar as other currently available agents for AIDS treatment such as zidovudine (AZT), didanosine, and zalcitabine, the anti-HIV activity of these 2'3'- dideoxynucleosides is ascribed to the inhibitory effect of their corresponding 5'- triphosphates against the HlVsncoded RNAdependent DNA polymerase (reverse transcriptase). While some of these drugs have rapid development of drug resistance, stavudine is active against AZT-resistant HIV strains. It has a favorable pharmacokinetic profile with more complete and less variable oral absorption than AZT and didanosine and has a bioavailability of 80-90%.
• Uses: Used as an antiviral. A reverse transcriptase inhibitor angiotensin 1 receptor antagonist Stavudine (Zidovudine EP Impurity A) is used as an antiviral. A reverse transcriptase inhibitor.
• Indications: Stavudine (d4T, Zerit) is a thymidine nucleoside analogue that is active against HIV-1 and HIV-2. It is approved for the therapy of HIV infection as part of a multidrug regimen and is also used for postexposure prophylaxis.
• Therapeutic Function: Antiviral
• Clinical Use: Treatment of HIV infection in adults and children
• Drug interactions: Potentially hazardous interactions with other drugs Antivirals: zidovudine may inhibit intracellular activation - avoid; increased risk of side effects with didanosine - avoid; increased risk of toxicity with ribavirin. Cytotoxics: effects possibly inhibited by doxorubicin; increased risk of toxicity with hydroxycarbamide - avoid. Orlistat: absorption of stavudine possibly reduced

Technology Process of Stavudine

There total 164 articles about Stavudine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine (125440-17-7) → stavudin (3056-17-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1246/bcsj.68.2327

Reference yield: 94.0%

5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine (122567-97-9) → stavudin (3056-17-5)

Guidance literature:

With sodium methylate; In methanol; N,N-dimethyl-formamide; at 120 ℃; for 0.0333333h;

DOI:10.1021/acs.joc.1c01013

Reference yield: 87.0%

1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine (77421-68-2) → stavudin (3056-17-5)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00281a017

upstream raw materials:

2,3'-anhydrothymidine

5′-benzoyl-2′,3′-didehydro-3′-deoxythymidine

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine

1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine

Downstream raw materials:

2',3'-dideoxy-2'-cytidinene

5-Methyluridine

5'-O-p-tolylsulfonyl-2',3'-didehydro-3'-deoxythymidine

2',3'-didehydro-3'-deoxythymidine 5'-(phenyl methoxyalaninyl phosphate)

Refernces

• 1、 Girard, Frederic,Leonce, Stephane,Agrofoglio, Luigi A.. "Synthesis of some 5'-thiopentofuranosylpyrimidines as potential anti-tumor agents.". . p. 7535 - 7538. Retrieved 1997.
• 2、 D'yakova,Shastina,Shvets. "Lymphotropic prodrugs based on 2′,3′-Didehydro-3′- deoxythymidine. Synthesis and sensitivity to hydrolysis". . p. 1588 - 1593. Retrieved 2011.
• 3、 Ruman, Tomasz,Dlugopolska, Karolina,Jurkiewicz, Agata,Rydel, Katarzyna,Les, Andrzej,Rode, Wojciech. "The synthesis and NMR investigation on novel boron derivatives of stavudine". . p. 87 - 91. Retrieved 2010.
• 4、 Mansuri,Starrett Jr.,Ghazzouli,Hitchcock,Sterzycki,Brankovan,Lin,August,Prusoff,Sommadossi,Martin. "1 (2,3 Dideoxy β-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent". . p. 461 - 466. Retrieved 1989.
• 5、 Sagandira, Cloudius R.,Akwi, Faith M.,Sagandira, Mellisa B.,Watts, Paul. "Multistep Continuous Flow Synthesis of Stavudine". . p. 13934 - 13942. Retrieved 2021/06/28.
• 6、 -. "Methyl ketone derivative, and preparation method and applications thereof". Paragraph 0043; 0044. . Retrieved 2017/08/28.