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Stavudine
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WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H318756

CAS#: 3056-17-5

Description: Stavudine is an antiretroviral medication used to prevent and treat HIV/AIDS. It is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class.

Chemical Structure

Stavudine

CAS# 3056-17-5

Instruction

Theoretical Analysis

Hodoodo Cat#: H318756
Name: Stavudine
CAS#: 3056-17-5
Chemical Formula: C10H12N2O4
Exact Mass: 224.08
Molecular Weight: 224.216
Elemental Analysis: C, 53.57; H, 5.39; N, 12.49; O, 28.54

Price and Availability

Size	Price	Availability
1g	USD 150	Ready to ship
2g	USD 200	Ready to ship
5g	USD 350	2 weeks
10g	USD 550	2 weeks
25g	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. Hodoodo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: NSC-163661; NSC163661; NSC 163661; Stavudine; Stavudinum; Zerit

IUPAC/Chemical Name: 1-((2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

InChi Key: XNKLLVCARDGLGL-JGVFFNPUSA-N

InChi Code: 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

SMILES Code: OC[C@@H]1C=C[C@H](N2C(NC(C(C)=C2)=O)=O)O1

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

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.

Storage Condition: 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 and water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:	Stavudine is a nucleoside analog reverse transcriptase inhibitor (NARTI).
In vitro activity:	In an in vitro model reproducing the Aβ-driven inflammation seen in AD, stavudine reduced NLRP3 inflammasome-associated inflammation and stimulates Aβ autophagy by macrophages. Stavudine reduced NLRP3 assembly and IL-18 and caspase-1 production but did not affect IL-1β production and TREM2 expression. Stavudine reduced Aβ phagocytosis and stimulated Aβ autophagy, evidenced by the down-modulation of ERK1/2 and AKT phosphorylation and the upregulation of beclin, LAMP, and p70-S6K. Reference: J Alzheimers Dis. 2019;72(2):401-412. https://pubmed.ncbi.nlm.nih.gov/31594217/
In vivo activity:	Results from this study suggest that stavudine exposure disturbs the embryonic development, and its use in pregnant mothers should be re-examined. In cultured mouse embryos, stavudine exposure reduced somite numbers, yolk sac diameter, crown-rump length, and increased the rate of embryonic degeneration compared with the control. Stavudine produced DNA damage, increased phospho-CHK1 and cleaved-caspase-3 levels, and decreased the expression level of proliferating cell nuclear antigen. Reference: Toxicology. 2020 Jun;439:152443. https://pubmed.ncbi.nlm.nih.gov/32278789/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	45.0	200.70
	Water	16.7	74.35

Preparing Stock Solutions

The following data is based on the product molecular weight 224.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. La Rosa F, Saresella M, Marventano I, Piancone F, Ripamonti E, Al-Daghri N, Bazzini C, Zoia CP, Conti E, Ferrarese C, Clerici M. Stavudine Reduces NLRP3 Inflammasome Activation and Modulates Amyloid-β Autophagy. J Alzheimers Dis. 2019;72(2):401-412. doi: 10.3233/JAD-181259. PMID: 31594217. 2. Velsor LW, Kovacevic M, Goldstein M, Leitner HM, Lewis W, Day BJ. Mitochondrial oxidative stress in human hepatoma cells exposed to stavudine. Toxicol Appl Pharmacol. 2004 Aug 15;199(1):10-9. doi: 10.1016/j.taap.2004.03.005. PMID: 15289086. 3. Ao RF, Liang YX, Liu XQ, Tan K, Wang X, Liu D, Zhang T, Sun G, Xie J. Stavudine exposure results in developmental abnormalities by causing DNA damage, inhibiting cell proliferation and inducing apoptosis in mouse embryos. Toxicology. 2020 Jun;439:152443. doi: 10.1016/j.tox.2020.152443. Epub 2020 Apr 9. PMID: 32278789. 4. Gaou I, Malliti M, Guimont MC, Lettéron P, Demeilliers C, Peytavin G, Degott C, Pessayre D, Fromenty B. Effect of stavudine on mitochondrial genome and fatty acid oxidation in lean and obese mice. J Pharmacol Exp Ther. 2001 May;297(2):516-23. PMID: 11303038.
In vitro protocol:	1. La Rosa F, Saresella M, Marventano I, Piancone F, Ripamonti E, Al-Daghri N, Bazzini C, Zoia CP, Conti E, Ferrarese C, Clerici M. Stavudine Reduces NLRP3 Inflammasome Activation and Modulates Amyloid-β Autophagy. J Alzheimers Dis. 2019;72(2):401-412. doi: 10.3233/JAD-181259. PMID: 31594217. 2. Velsor LW, Kovacevic M, Goldstein M, Leitner HM, Lewis W, Day BJ. Mitochondrial oxidative stress in human hepatoma cells exposed to stavudine. Toxicol Appl Pharmacol. 2004 Aug 15;199(1):10-9. doi: 10.1016/j.taap.2004.03.005. PMID: 15289086.
In vivo protocol:	1. Ao RF, Liang YX, Liu XQ, Tan K, Wang X, Liu D, Zhang T, Sun G, Xie J. Stavudine exposure results in developmental abnormalities by causing DNA damage, inhibiting cell proliferation and inducing apoptosis in mouse embryos. Toxicology. 2020 Jun;439:152443. doi: 10.1016/j.tox.2020.152443. Epub 2020 Apr 9. PMID: 32278789. 2. Gaou I, Malliti M, Guimont MC, Lettéron P, Demeilliers C, Peytavin G, Degott C, Pessayre D, Fromenty B. Effect of stavudine on mitochondrial genome and fatty acid oxidation in lean and obese mice. J Pharmacol Exp Ther. 2001 May;297(2):516-23. PMID: 11303038.

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1: Magula N, Dedicoat M. Low dose versus high dose stavudine for treating people with HIV infection. Cochrane Database Syst Rev. 2015 Jan 28;1:CD007497. doi: 10.1002/14651858.CD007497.pub2. Review. PubMed PMID: 25627012.

2: Mateo MG, Gutierrez Mdel M, Vidal F, Domingo P. Stavudine extended release (once-daily, Bristol-Myers Squibb) for the treatment of HIV/AIDS. Expert Opin Pharmacother. 2013 Jun;14(8):1055-64. doi: 10.1517/14656566.2013.782285. Epub 2013 Mar 20. Review. PubMed PMID: 23510448.

3: Spaulding A, Rutherford GW, Siegfried N. Stavudine or zidovudine in three-drug combination therapy for initial treatment of HIV infection in antiretroviral-naïve individuals. Cochrane Database Syst Rev. 2010 Aug 4;(8):CD008651. doi: 10.1002/14651858.CD008651. Review. PubMed PMID: 20687097.

4: Guimarães NN, de Andrade HH, Lehmann M, Dihl RR, Cunha KS. The genetic toxicity effects of lamivudine and stavudine antiretroviral agents. Expert Opin Drug Saf. 2010 Sep;9(5):771-81. doi: 10.1517/14740331003702384. Review. PubMed PMID: 20377473.

5: Martin JC, Hitchcock MJ, De Clercq E, Prusoff WH. Early nucleoside reverse transcriptase inhibitors for the treatment of HIV: a brief history of stavudine (D4T) and its comparison with other dideoxynucleosides. Antiviral Res. 2010 Jan;85(1):34-8. doi: 10.1016/j.antiviral.2009.10.006. Epub 2009 Oct 23. Review. PubMed PMID: 19854224.

6: Makinson A, Moing VL, Kouanfack C, Laurent C, Delaporte E. Safety of stavudine in the treatment of HIV infection with a special focus on resource-limited settings. Expert Opin Drug Saf. 2008 May;7(3):283-93. doi: 10.1517/14740338.7.3.283 . Review. PubMed PMID: 18462186.

7: Hill A, Ruxrungtham K, Hanvanich M, Katlama C, Wolf E, Soriano V, Milinkovic A, Gatell J, Ribera E. Systematic review of clinical trials evaluating low doses of stavudine as part of antiretroviral treatment. Expert Opin Pharmacother. 2007 Apr;8(5):679-88. Review. PubMed PMID: 17376022.

8: Siegfried NL, Van Deventer PJ, Mahomed FA, Rutherford GW. Stavudine, lamivudine and nevirapine combination therapy for treatment of HIV infection and AIDS in adults. Cochrane Database Syst Rev. 2006 Apr 19;(2):CD004535. Review. PubMed PMID: 16625606.

9: Lafeuillade A, Tardy JC. Stavudine in the face of cross-resistance between HIV-1 nucleoside reverse transcriptase inhibitors: a review. AIDS Rev. 2003 Apr-Jun;5(2):80-6. Review. PubMed PMID: 12876897.

10: Cheer SM, Goa KL. Stavudine once daily. Drugs. 2002;62(18):2667-74; discussion 2675-6. Review. PubMed PMID: 12466009.

11: Moyle GJ, Gazzard BG. The role of stavudine in the management of adults with HIV infection. Antivir Ther. 1997 Dec;2(4):207-18. Review. PubMed PMID: 11327440.

12: Murphy RL. Stavudine-based multiple agent combinations: initial studies and ongoing comparative trials. Antivir Ther. 1998;3 Suppl 4:69-73. Review. PubMed PMID: 10723516.

13: Clumeck N. Stavudine plus a non-thymidine nucleoside reverse transcriptase inhibitor as a backbone for highly active antiretroviral therapy. Antivir Ther. 1998;3 Suppl 4:39-43. Review. PubMed PMID: 10723508.

14: Hurst M, Noble S. Stavudine: an update of its use in the treatment of HIV infection. Drugs. 1999 Nov;58(5):919-49. Review. PubMed PMID: 10595868.

15: Rana KZ, Dudley MN. Clinical pharmacokinetics of stavudine. Clin Pharmacokinet. 1997 Oct;33(4):276-84. Review. PubMed PMID: 9342503.

16: Lea AP, Faulds D. Stavudine: a review of its pharmacodynamic and pharmacokinetic properties and clinical potential in HIV infection. Drugs. 1996 May;51(5):846-64. Review. PubMed PMID: 8861550.

17: Katlama C, Havlir DV. Newer nucleosides: lamivudine and stavudine. AIDS. 1996;10 Suppl A:S135-43. Review. PubMed PMID: 8883621.

18: Friedland G, Dunkle LW, Cross AP. Stavudine (d4T, Zerit). Adv Exp Med Biol. 1996;394:271-7. Review. PubMed PMID: 8815691.

19: Riddler SA, Anderson RE, Mellors JW. Antiretroviral activity of stavudine (2',3'-didehydro-3'-deoxythymidine, D4T). Antiviral Res. 1995 Jun;27(3):189-203. Review. PubMed PMID: 8540743.

20: Sommadossi JP. Comparison of metabolism and in vitro antiviral activity of stavudine versus other 2',3'-dideoxynucleoside analogues. J Infect Dis. 1995 Mar;171 Suppl 2:S88-92. Review. PubMed PMID: 7861023.