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[CAS NO. 3056-17-5] Stavudine

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Catalog:	HY-B0116
Brand:	MCE
CAS:	3056-17-5

Overview

MDL	MFCD00132921
Molecular Weight	224.21
Molecular Formula	C10H12N2O4
SMILES	OC[C@H]1O[C@@H](N2C=C(C)C(NC2=O)=O)C=C1

For research use only. We do not sell to patients.

3 Publications Citing Use of MCE

[1]Int J Antimicrob Agents. 2019 Dec;54(6):814-819.
[2]Biotechnol Bioeng. 2021 Sep 3.
[3]Toxicology. 2020 Jun;439:152443.

Summary

Stavudine (d4T) is an orally active nucleoside reverse transcriptase inhibitor (NRTI) . Stavudine has activity against HIV-1 and HIV-2 . Stavudine also inhibits the replication of mitochondrial DNA (mtDNA). Stavudine reduces NLRP3 inflammasome activation and modulates Amyloid-β autophagy. Stavudine induces apoptosis ^[1] ^[2] ^[3] ^[4] .

IC50 & Target

HIV-1

HIV-2

NLRP3

In Vitro

Stavudine (d4T) (50 μM) significantly reduces the expression of the NLRP3 inflammasome gene, IL-18 production and Aβ 42-stimulated cellular production of IL-1β in THP-1 derived macrophages ^[3] .
Stavudine (d4T) (50 μM) inhibits the assembly of the NLRP3 inflammasome complex and down-regulates the phagocytosis of Aβ 42 by macrophages ^[3] .
Stavudine (d4T) (10 μM, 7 or 14 days) significantly induced CEM cells apoptosis, especially after 14 days, and increases hydrogen peroxide levels ^[4] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Stavudine (d4T) (500 mg/kg, daily liquid, 2 weeks) can rapidly induce fat depletion and mild liver damage at high dose in male RjOrl Swiss mice ^[5] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Male RjOrl Swiss mice weighing 0.028-0.03 kg ^[1]
Dosage:	500 mg/kg
Administration:	Daily liquid; 2 weeks
Result:	Reduced fat weight gain by 58%, 5.7 g in the control group and 4.9 g in the d4T treated group. Significantly elevated plasma ALT and LDH levels. Reduced plasma acetoacetic acid and beta-hydroxybutyric acid levels. Reduced liver and muscle mtDNA levels at high dose concentration of 500 mg/kg.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT00002308	Bristol-Myers Squibb	HIV Infections		Not Applicable
NCT00002427	Research Institute for Genetic and Human Therapy\|NIH AIDS Clinical Trials Information Service	HIV Infections	May 1999	Phase 1
NCT00000838	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00255840	CIPRA SA\|National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections	July 2006	Not Applicable
NCT00050895	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 3
NCT00000922	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00000988	National Institute of Allergy and Infectious Diseases (NIAID)\|Bristol-Myers Squibb	HIV Infections		Phase 1
NCT00000916	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00002386	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections\|Hemophilia A		Phase 4
NCT00001084	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00002349	Bristol-Myers Squibb	HIV Infections	January 1995	Not Applicable
NCT00002230	Northwestern University\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 3
NCT00000686	National Institute of Allergy and Infectious Diseases (NIAID)\|Bristol-Myers Squibb	HIV Infections		Phase 1
NCT00013520	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 3
NCT00002397	Hoffmann-La Roche\|NIH AIDS Clinical Trials Information Service	HIV Infections\|AIDS-Associated Nephropathy		Phase 3
NCT00002354	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable
NCT00002442	Glaxo Wellcome\|NIH AIDS Clinical Trials Information Service	HIV Infections	June 1999	Phase 2
NCT00618176	Peking Union Medical College\|Ministry of Science and Technology of the People´s Republic of China	HIV Infections	January 2005	Phase 4
NCT00004583	Abbott	HIV Infections	March 1999	Phase 3
NCT00002411	Bristol-Myers Squibb	HIV Infections	March 1998	Not Applicable
NCT00002227	Dupont Merck\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00312091	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|International Maternal Pediatric Adolescent AIDS Clinical Trials Group	HIV Infections	December 2006	Phase 1\|Phase 2
NCT00002177	Bristol-Myers Squibb	HIV Infections	May 1997	Not Applicable
NCT00002369	Bristol-Myers Squibb	HIV Infections		Not Applicable
NCT00006190	National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)	HIV Infections\|Lipodystrophy	November 2000	Phase 4
NCT00002407	Weill Medical College of Cornell University\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable
NCT02670772	Willem Daniel Francois Venter\|Bill and Melinda Gates Foundation\|University of Witwatersrand, South Africa	Acquired Immune Deficiency Syndrome\|Human Immunodeficiency Virus	July 2012	Phase 3
NCT00158821	Gilead Sciences	HIV Infections	March 2000	Phase 3
NCT00143702	University of British Columbia\|GlaxoSmithKline\|CIHR Canadian HIV Trials Network	Acidosis, Lactic	August 2001	Phase 2\|Phase 3
NCT00005000	Agouron Pharmaceuticals\|NIH AIDS Clinical Trials Information Service	HIV Infections	December 1999	Phase 4
NCT00001067	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000896	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00000870	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00002412	Triangle Pharmaceuticals\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00002168	Bristol-Myers Squibb	HIV Infections		Not Applicable
NCT00002207	Bristol-Myers Squibb	HIV Infections	February 2004	Not Applicable
NCT00002424	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT01146873	Columbia University\|University of Witwatersrand, South Africa\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV+AIDS\|HIV Infections	July 2010	Phase 3
NCT00006144	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections	October 2000	Phase 2
NCT00002307	Bristol-Myers Squibb	HIV Infections		Not Applicable
NCT01601899	University of Witwatersrand, South Africa	Mitochondrial Toxicity\|Metabolic Complications	October 2008	Phase 4
NCT00055120	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|AIDS-Related Opportunistic Infections	March 2003	Phase 4
NCT00001087	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000872	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV Infections		Phase 2
NCT00192660	Kirby Institute\|St Vincent´s Hospital, Sydney\|National Heart, Lung, and Blood Institute (NHLBI)	HIV-Associated Lipodystrophy Syndrome\|Cardiovascular Disease	February 2003	Phase 4
NCT00002211	Pharmacia and Upjohn\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable
NCT00001083	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00034086	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00002371	Bristol-Myers Squibb	HIV Infections	June 1996	Phase 3
NCT00002418	Bristol-Myers Squibb\|Boehringer Ingelheim\|Triangle Pharmaceuticals	HIV Infections		Phase 2
NCT00002379	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00000831	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000891	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000822	National Institute of Allergy and Infectious Diseases (NIAID)\|Bristol-Myers Squibb\|Immuno-US	HIV Infections		Phase 1
NCT00000901	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 1
NCT00000841	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 3
NCT00002225	Dupont Merck\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00342355	National Institutes of Health Clinical Center (CC)	HIV	January 2004	Phase 4
NCT00002109	Immunobiology Research Institute\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 3
NCT00006443	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00004736	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|Tuberculosis		Phase 1
NCT00002362	Triangle Pharmaceuticals\|NIH AIDS Clinical Trials Information Service	HIV Infections	August 1999	Phase 3
NCT00004855	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00000899	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 1
NCT00001108	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV Infections		Phase 1
NCT00002240	Bristol-Myers Squibb	HIV Infections	March 1999	Phase 2
NCT00000851	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00080522	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections	February 2005	Not Applicable
NCT00000939	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000902	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 1
NCT00074581	National Institute of Allergy and Infectious Diseases (NIAID)\|HIV Prevention Trials Network	HIV Infections	February 2005	Phase 3
NCT00000924	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV Infections		Phase 2
NCT00002162	Hoffmann-La Roche\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00002420	Bristol-Myers Squibb\|Pharmacia and Upjohn\|Triangle Pharmaceuticals	HIV Infections		Phase 2
NCT00006154	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 3
NCT00006339	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00002451	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00006208	Triangle Pharmaceuticals\|NIH AIDS Clinical Trials Information Service	HIV Infections	August 2000	Phase 3
NCT00001688	National Cancer Institute (NCI)\|National Institutes of Health Clinical Center (CC)	HIV Infection	January 1998	Phase 2
NCT00000789	National Institute of Allergy and Infectious Diseases (NIAID)\|Glaxo Wellcome\|Bristol-Myers Squibb	HIV Infections		Phase 2
NCT02249130	Boehringer Ingelheim	HIV Infections	March 1999	Phase 2
NCT00004578	Abbott	HIV Infections	November 1997	Phase 1\|Phase 2
NCT00002430	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable
NCT00116116	Bristol-Myers Squibb	HIV Infections\|AIDS	March 2002	Phase 4
NCT00127972	International Antiviral Therapy Evaluation Center\|Boehringer Ingelheim	HIV Infections	February 2004	Phase 4
NCT00235222	Groupe Hospitalier Pitie-Salpetriere\|Bristol-Myers Squibb	HIV	June 2004	Phase 4
NCT00002208	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 3
NCT00135369	Bristol-Myers Squibb	HIV Infections	September 2002	Phase 3
NCT00005106	Glaxo Wellcome\|NIH AIDS Clinical Trials Information Service	HIV Infections	September 1999	Phase 4
NCT00002378	Hoffmann-La Roche\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 3
NCT00007202	National Institute of Allergy and Infectious Diseases (NIAID)\|Bristol-Myers Squibb	HIV Infections		Phase 2
NCT00000919	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00005918	Bristol-Myers Squibb	HIV Infections	June 2000	Phase 3
NCT00100646	The Wistar Institute	HIV Infections	March 2007	Not Applicable
NCT01344148	Shanghai Public Health Clinical Center	AIDS	February 2009	Not Applicable
NCT00002184	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00002381	Boehringer Ingelheim\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 1
NCT00002246	Bristol-Myers Squibb	AIDS Dementia Complex\|HIV Infections	October 1997	Phase 3
NCT00000940	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections	May 1999	Phase 2
NCT00005017	Glaxo Wellcome\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 4
NCT00001095	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00002176	Bristol-Myers Squibb	HIV Infections	May 1997	Not Applicable
NCT00001091	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV Infections		Phase 1
NCT00002374	Hoffmann-La Roche\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 3
NCT00000918	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000865	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 1
NCT00000882	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00014937	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00002224	Bristol-Myers Squibb	HIV Infections	March 1999	Phase 3
NCT00017992	Triangle Pharmaceuticals\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00006397	PPD\|NIH AIDS Clinical Trials Information Service	HIV Infections	August 2000	Phase 3
NCT00002241	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00002376	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 4
NCT00002429	Bristol-Myers Squibb	HIV Infections	July 1999	Phase 3
NCT00528957	Gilead Sciences	HIV Infections	December 28, 2006	Phase 3
NCT00036452	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000923	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00000878	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV Infections\|Pregnancy		Phase 1
NCT00001122	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00000885	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00001063	National Institute of Allergy and Infectious Diseases (NIAID)\|Bristol-Myers Squibb	HIV Infections		Phase 2

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 125 mg/mL ( 557.51 mM ; Need ultrasonic)

H ₂ O : 16.67 mg/mL ( 74.35 mM ; Need ultrasonic)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	4.4601 mL	22.3005 mL	44.6010 mL
5 mM	0.8920 mL	4.4601 mL	8.9202 mL
10 mM	0.4460 mL	2.2301 mL	4.4601 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: PBS

Solubility: 120 mg/mL (535.21 mM); Clear solution; Need ultrasonic
2.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 2.5 mg/mL (11.15 mM); Clear solution
3.

Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

Solubility: ≥ 2.5 mg/mL (11.15 mM); Clear solution
4.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 2.5 mg/mL (11.15 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Moyle GJ, et al. The role of stavudine in the management of adults with HIV infection. Antivir Ther. 1997;2(4):207-218.
[2] Riddler SA, et al. Antiretroviral activity of stavudine (2',3'-didehydro-3'-deoxythymidine, D4T). Antiviral Res. 1995;27(3):189-203.
[3] La Rosa F, et al. Stavudine Reduces NLRP3 Inflammasome Activation and Modulates Amyloid-β Autophagy. J Alzheimers Dis. 2019;72(2):401-412.
[4] Ferraresi R, et al. Protective effect of acetyl-L-carnitine against oxidative stress induced by antiretroviral drugs. FEBS Lett. 2006;580(28-29):6612-6616.
[5] Anissa Igoudjil, et al. High doses of stavudine induce fat wasting and mild liver damage without impairing mitochondrial respiration in mice. Antivir Ther. 2007;12(3):389-400.

Synonyms

Thymidine, 2′,3′-didehydro-3′-deoxy-

Thymine, 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-

2,4(1H,3H)-Pyrimidinedione, 1-[(2R,5S)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-

2′-Thymidinene, 3′-deoxy-

2′,3′-Didehydro-3′-deoxythymidine

d4T

3′-Deoxy-2′,3′-didehydrothymidine

BMY 27857

D 4T (nucleoside)

Stavudine

Sanilvudine

Zerit

NSC 163661

Stavir

Virostav

Stag

Avostav

Staduvine

Melxicap

2′,3′-Didehydro-2′,3′-dideoxythymidine

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