[CAS NO. 3056-17-5] Stavudine
PRODUCTS SPECIFICATIONS [3056-17-5]
DESCRIPTION [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 |
3 Publications Citing Use of MCE
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
DMSO : 125 mg/mL ( 557.51 mM ; Need ultrasonic)
H 2 O : 16.67 mg/mL ( 74.35 mM ; Need ultrasonic)
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 |
-
1.
Add each solvent one by one: PBS
Solubility: 120 mg/mL (535.21 mM); Clear solution; Need ultrasonic
-
2.
-
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
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
