stavudine
Trade name: zerit
Approved
Jun 24, 1994
Stavudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Stavudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated. Stavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. Stavudine is used for the treatment of human immunovirus (HIV) infections. Stavudine is sold under the brand name Zerit among others. — NCATS
Clinical trial activity
141 trials · 89 clinical orgs · 12 marketing orgs
Earliest trial started Jan 1, 1995 (NCT00002349)
Timeline
1990s
- Jun 24, 1994
Bristol-Myers Squibb — Earliest FDA Approval
- Jun 24, 1994
Bristol-Myers — Marketing Organization
- Jun 24, 1994
Bristol-Myers Squibb — NDA Organization
- Jan 1, 1996
Bristol-Myers Squibb — Earliest Phase 3 Sponsor(trial)
- Jan 1, 1997
Earliest Phase 1 Sponsor(trial)
- Jan 1, 1998
Earliest Phase 2 Sponsor(trial)
2000s
- Aug 28, 2006
Strides Pharma Science — Marketing Organization
- Nov 17, 2006
Cipla — Marketing Organization
- Nov 17, 2006
Cipla — NDA Secondary Org
- Mar 13, 2007
Strides Pharma Science — NDA Secondary Org
- Nov 2, 2007
Matrix Laboratories Limited — Marketing Organization
- Nov 2, 2007
Mylan — NDA Secondary Org
- Dec 12, 2007
Emcure — Marketing Organization
- Dec 29, 2008
Aurobindo Pharma — Marketing Organization
- Dec 29, 2008
Mylan — Marketing Organization
- Dec 29, 2008
PHARMOBEDIENT — Marketing Organization
- Feb 27, 2009
Pharmacare PLC, Palestine — Marketing Organization
- Feb 27, 2009
Pharmacare PLC, Palestine — NDA Secondary Org
- Jul 16, 2009
Emcure — NDA Secondary Org
2010s
- May 17, 2010
Hetero Labs Ltd — Marketing Organization
- May 17, 2010
Hetero Labs Ltd — NDA Secondary Org
- Aug 5, 2010
Macleods Pharmaceuticals, Ltd — Marketing Organization
- Aug 5, 2010
Macleods Pharmaceuticals, Ltd — NDA Secondary Org
Indications
Approved for
Studied for
- Acidosis, Lactic · Phase 2/Phase 3
- Acquired Immunodeficiency Syndrome · Phase 4
- AIDS-Associated Nephropathy · Phase 3
- AIDS Dementia Complex · Phase 3
- AIDS-Related Opportunistic Infections · Phase 4
- Cardiovascular Diseases · Phase 4
- Drug-Related Side Effects and Adverse Reactions · Phase 4
- Drugs, Investigational · Phase 4
- Hemophilia A · Phase 4
- Herpesvirus 8, Human · Phase 4
- HIV · Phase 4
- HIV-Associated Lipodystrophy Syndrome · Phase 4
- HIV Seropositivity · Phase 2
- Lipodystrophy · Phase 4
- Liver Diseases · Phase 4
- Metabolic Diseases · Phase 4
- Pregnancy · Phase 1
- Sarcoma, Kaposi · Phase 4
- Tuberculosis · Phase 1
Mechanism of action
Q72547 inhibitor
Approval history
- approvedPriority reviewAcceleratedJun 24, 1994
Chemistry & pharmacology
SMILES
CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O- Mol. weight
- 224.2133 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Discontinued
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaStavudine ↗
- NCATSBO9LE4QFZF ↗
- ChEMBLCHEMBL991 ↗
Also known as
- 1-(2,3-dideoxy-beta-d-glycero-pent-2-enofuranosyl)thymine
- 1-(2,3-dideoxy-beta-d-glycero-pent-2-enofuranosyl)thymine
- 2',3'-didehydro-3'-deoxythimidine
- 2',3'-didehydro-3'-deoxythimidine
- 3'-deoxy-2'-thymidinene
- 3'-deoxy-2'-thymidinene
- bmy-27857
- bmy-27857
- d4t
- d4t
- d4t
- d4t
- estavudina
- estavudina
- sanilvudine
- sanilvudine
- sanilvudine
- staduvine
- stavudin
- stavudin
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine
- stavudine (d4t)
- stavudinum
- stavudinum
- stv
- stv
- triomune
- triomune
- zerit
- zerit
- zerit
- zerit
- zerit
- zerit
- zerit
- zerit
- zerit, stavudine
- zerit xr
- zerit xr
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01817283 | Phase 1/Phase 2 (Phase 2) | Jan 1, 2013 | Peking University, Tsinghua University |
| NCT02670772 | Phase 3 | Jul 1, 2012 | Bill and Melinda Gates Foundation, University of the Witwatersrand, Willem Daniel Francois Venter, Wits University |
| NCT01516970 | Phase 3 | Nov 1, 2011 | Johnson and Johnson |
| NCT01440569 | Phase 3 | Sep 1, 2011 | Gilead Sciences, Johnson and Johnson |
| NCT02002286 | N/A | Aug 1, 2011 | Peking University, Tsinghua University |
| NCT01252940 | Phase 3 | Nov 1, 2010 | Gilead Sciences |
| NCT01146873 | Phase 3 | Jul 1, 2010 | Columbia University, National Institutes of Health (NIH), University of the Witwatersrand |
| NCT00986063 | Phase 4 | Jul 1, 2009 | Chulalongkorn University, Mahidol University, National Institutes of Health (NIH), RIKEN, Srinakharinwirot University, Thammasat University |
| NCT00872417 | Phase 4 | Mar 1, 2009 | Government of China, Tsinghua University |
| NCT01601899 | Phase 4 | Oct 1, 2008 | University of the Witwatersrand |
| NCT00669487 | Phase 3 | Apr 1, 2008 | Queen Savang Vadhana Memorial Hospital, Thailand, SEARCH Thailand, South East Asia Research Collaboration with Hawaii, Thai Red Cross AIDS Research Centre, Bangkok, Thailand, University of Hawaii |
| NCT01174914 | Phase 2 | Mar 1, 2008 | Bamako University, The Ojai Foundation |
| NCT00427297 | Phase 3 | Sep 1, 2007 | National Institutes of Health (NIH), University of Nairobi, University of Washington |
| NCT00100646 | N/A | Mar 1, 2007 | The Wistar Institute, University of the Witwatersrand |
| NCT00455585 | Phase 4 | Jan 1, 2007 | Department of Foreign Affairs, Ireland, Makerere University, Trinity College Dublin |
| NCT00312091 | Phase 1/Phase 2 (Phase 2) | Dec 1, 2006 | Mahidol University, National Institute of Allergy and Infectious Diseases (NIAID), National Institute of Child Health and Human Development (NICHD), National Institutes of Health (NIH) |
| NCT00528957 | Phase 3 | Dec 1, 2006 | Gilead Sciences |
| NCT00830856 | N/A | Oct 1, 2006 | AIDS Care Research in Africa, University of Zimbabwe |
| NCT00255840 | N/A | Jul 1, 2006 | Cipra, National Institute of Allergy and Infectious Diseases (NIAID), University of Cape Town, University of the Witwatersrand |
| NCT01025830 | Phase 4 | Feb 1, 2006 | Harvard University, Makerere University, University of California, San Francisco |
Organizations
Research & Development (89)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 55 | 53 | 5 | 1999 |
| Bristol-Myers Squibb | For profit | 30 | 21 | 5 | 1995 |
| National Institutes of Health (NIH) | Government | 11 | 1 | 4 | 1999 |
| Merck | For profit | 8 | 8 | 4 | 1999 |
| Gilead Sciences | For profit | 6 | 6 | 2 | 1999 |
| Triangle Pharmaceuticals | For profit | 6 | 4 | 2 | 1999 |
| University of the Witwatersrand | Academic/Hospital | 5 | 1 | 3 | 2006 |
| Boehringer Ingelheim | For profit | 4 | 2 | 3 | 1999 |
| Glaxo Wellcome | For profit | 4 | 3 | 2 | 1999 |
| Roche | For profit | 4 | 4 | 2 | 1999 |
| Tsinghua University | Academic/Hospital | 4 | 2 | 3 | 2005 |
| Abbott | For profit | 2 | 2 | 2 | 1997 |
| AIDS Care Research in Africa | Academic/Hospital | 2 | 0 | 2 | 2003 |
| Duke University | Academic/Hospital | 2 | 0 | 2 | 1999 |
| DuPont Merck | For profit | 2 | 2 | 1 | 1999 |
| GlaxoSmithKline | For profit | 2 | 0 | 2 | 2001 |
| Government of China | Government | 2 | 0 | 1 | 2005 |
| Harvard University | Academic/Hospital | 2 | 1 | 2 | 2002 |
| Johnson and Johnson | For profit | 2 | 1 | 1 | 2011 |
| Mahidol University | Academic/Hospital | 2 | 1 | 2 | 2006 |
Marketing (25)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Aurobindo Pharma | For profit | MKTG | Dec 29, 2008 |
| Bristol-Myers | For profit | MKTG | Jun 24, 1994 |
| Bristol-Myers Squibb | For profit | SYN | Jun 24, 1994 |
| Bristol-Myers Squibb | For profit | SYN | Sep 6, 1996 |
| Bristol-Myers Squibb | For profit | NDA | Jun 24, 1994 |
| Cipla | For profit | MKTG | Nov 17, 2006 |
| Cipla | For profit | SYN | Mar 20, 2009 |
| Cipla | For profit | NDA2 | Nov 17, 2006 |
| Emcure | For profit | MKTG | Dec 12, 2007 |
| Emcure | For profit | NDA2 | Jul 16, 2009 |
| Hetero Labs Ltd | For profit | MKTG | May 17, 2010 |
| Hetero Labs Ltd | For profit | SYN | Dec 29, 2008 |
| Hetero Labs Ltd | For profit | NDA2 | May 17, 2010 |
| Macleods Pharmaceuticals, Ltd | For profit | MKTG | Aug 5, 2010 |
| Macleods Pharmaceuticals, Ltd | For profit | NDA2 | Aug 5, 2010 |
| Matrix Laboratories Limited | For profit | MKTG | Nov 2, 2007 |
| Mylan | For profit | MKTG | Dec 29, 2008 |
| Mylan | For profit | SYN | Jan 5, 2009 |
| Mylan | For profit | NDA2 | Nov 2, 2007 |
| PHARMOBEDIENT | For profit | MKTG | Dec 29, 2008 |
| Pharmacare PLC, Palestine | For profit | MKTG | Feb 27, 2009 |
| Pharmacare PLC, Palestine | For profit | NDA2 | Feb 27, 2009 |
| Strides Pharma Science | For profit | MKTG | Aug 28, 2006 |
| Strides Pharma Science | For profit | SYN | Mar 20, 2008 |
| Strides Pharma Science | For profit | NDA2 | Mar 13, 2007 |