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3056-17-5-Stavudine Stavudine

Stavudine

For research use only. Not for therapeutic Use.

  • CAT Number: A000656
  • CAS Number: 3056-17-5
  • Molecular Formula: C10H12N2O4
  • Molecular Weight: 224.20
  • Purity: ≥95%
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Related Small Molecules: 5-Methyl-3-heptanone     p-Chlonixin     Carbazochrome sodium sulfonate (AC-17)    
Research Areas: Antiviral     Infection Disease Research     Viral Entry    

Stavudine（Cat No.:A000656）is a nucleoside reverse transcriptase inhibitor (NRTI) used in the treatment of HIV/AIDS. It works by inhibiting the reverse transcriptase enzyme, preventing viral replication. Stavudine is incorporated into the viral DNA, leading to premature chain termination, which effectively halts HIV replication. While it is often part of combination therapy, its use has been limited due to potential side effects, including peripheral neuropathy and lactic acidosis. Stavudine is typically used when other NRTIs are not suitable, but its safety profile requires careful monitoring.


Catalog Number A000656
CAS Number 3056-17-5
Synonyms

Sanilvudine; 3056-17-5; Zerit; 2/’,3/’-Didehydro-3/’-deoxythymidine; Estavudina

Molecular Formula C10H12N2O4
Purity ≥95%
Target Cell Cycle/DNA Damage
Solubility >8.4mg/mL in DMSO
Storage -20°C
IUPAC Name 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
InChI InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1
InChIKey XNKLLVCARDGLGL-JGVFFNPUSA-N
SMILES CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
Reference

1: Cassim H, Otwombe K, Lazarus E, Liberty A, Gray GE, Greeff OBW, Violari A. A
retrospective case-cohort study comparing treatment outcomes in abacavir versus
stavudine containing first line antiretroviral treatment regimens in children
<3yrs old, at a paediatric programme based in Soweto, South Africa. PLoS One.
2017 Jul 7;12(7):e0180645. doi: 10.1371/journal.pone.0180645. eCollection 2017.
PubMed PMID: 28686654; PubMed Central PMCID: PMC5501584.

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2: Conradie MM, van de Vyver M, Andrag E, Conradie M, Ferris WF. A Direct
Comparison of the Effects of the Antiretroviral Drugs Stavudine, Tenofovir and
the Combination Lopinavir/Ritonavir on Bone Metabolism in a Rat Model. Calcif
Tissue Int. 2017 May 20. doi: 10.1007/s00223-017-0290-3. [Epub ahead of print]
PubMed PMID: 28528404.
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3: Nayak D, Boxi A, Ashe S, Thathapudi NC, Nayak B. Stavudine loaded gelatin
liposomes for HIV therapy: Preparation, characterization and in vitro cytotoxic
evaluation. Mater Sci Eng C Mater Biol Appl. 2017 Apr 1;73:406-416. doi:
10.1016/j.msec.2016.12.073. Epub 2016 Dec 16. PubMed PMID: 28183626.

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4: Singh A, Hemal A, Agarwal S, Dubey NK, Buxi G. A prospective study of
haematological changes after switching from stavudine to zidovudine-based
antiretroviral treatment in HIV-infected children. Int J STD AIDS. 2016
Nov;27(13):1145-1152. Epub 2014 Feb 10. PubMed PMID: 24516076.

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5: Brennan AT, Davies MA, Bor J, Wandeler G, Stinson K, Wood R, Prozesky H,
Tanser F, Fatti G, Boulle A, Sikazwe I, Wool-Kaloustian K, Yuannoutsos C, Leroy
V, de Rekeneire N, Fox MP. Has the phasing out of stavudine in accordance with
changes in WHO guidelines led to a decrease in single-drug substitutions in
first-line antiretroviral therapy for HIV in sub-Saharan Africa? AIDS. 2017 Jan
2;31(1):147-157. PubMed PMID: 27776039; PubMed Central PMCID: PMC5137584.
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6: Marwaha L, Bansal Y, Singh R, Saroj P, Sodhi RK, Kuhad A. Niflumic acid, a
TRPV1 channel modulator, ameliorates stavudine-induced neuropathic pain.
Inflammopharmacology. 2016 Dec;24(6):319-334. Epub 2016 Oct 18. PubMed PMID:
27757590.

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7: Ghosh S, Mondal L, Chakraborty S, Mukherjee B. Early Stage HIV Management and
Reduction of Stavudine-Induced Hepatotoxicity in Rats by Experimentally Developed
Biodegradable Nanoparticles. AAPS PharmSciTech. 2017 Apr;18(3):697-709. doi:
10.1208/s12249-016-0539-6. Epub 2016 May 24. PubMed PMID: 27222026.

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8: van Zoest RA, Wit FW, Kooij KW, van der Valk M, Schouten J, Kootstra NA,
Wiersinga WJ, Prins M, van den Born BJ, Reiss P; AGEhIV Cohort Study Group.
Higher Prevalence of Hypertension in HIV-1-Infected Patients on Combination
Antiretroviral Therapy Is Associated With Changes in Body Composition and Prior
Stavudine Exposure. Clin Infect Dis. 2016 Jul 15;63(2):205-13. doi:
10.1093/cid/ciw285. Epub 2016 May 3. PubMed PMID: 27143668.

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9: Adebiyi OO, Adebiyi OA, Owira P. Naringin improves zidovudine- and
stavudine-induced skeletal muscle complications in rats. Hum Exp Toxicol. 2016
Mar 22. pii: 0960327116638726. [Epub ahead of print] PubMed PMID: 27005762.
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10: Vidyadhara S, Sasidhar RL, Balakrishna T, Balaji B, Amrutha R. Formulation
and Evaluation of Controlled Release Floating Microballoons of Stavudine. Sci
Pharm. 2015 Jun 9;83(4):671-82. doi: 10.3797/scipharm.1501-07. Print 2015
Oct-Dec. PubMed PMID: 26839847; PubMed Central PMCID: PMC4727757.

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