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zidovudine

Trade name: retrovir

Small moleculeapprovedOrphan Drug FDA

Approved

Mar 19, 1987

Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Zidovudine 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. Zidovudine, a structural analog of thymidine, is a prodrug that must be phosphorylated to its active 5′-triphosphate metabolite, zidovudine triphosphate (ZDV-TP). It inhibits the activity of HIV-1 reverse transcriptase (RT) via DNA chain termination after incorporation of the nucleotide analogue. It competes with the natural substrate dGTP and incorporates itself into viral DNA. It is also a weak inhibitor of cellular DNA polymerase α and γ. Zidovudine is used in combination with other antiretroviral agents for the treatment of human immunovirus (HIV) infections. Zidovudine is marketed as Retrovir. — NCATS

Clinical trial activity

426 trials · 220 clinical orgs · 30 marketing orgs

Phase 1
83
Phase 2
191
Phase 3
95
Phase 4
53

Earliest trial started Oct 1, 1990 (NCT00001267)

Timeline

1980s

  1. Jul 1, 1985

    Burroughs Wellcome — IND Organization

  2. Jul 1, 1985

    Burroughs Wellcome — IND Organization

  3. Jul 17, 1985

    Orphan Drug Designation

  4. Mar 19, 1987

    Earliest FDA Approval

  5. Mar 19, 1987

    ViiV Healthcare — NDA Secondary Org

1990s

  1. Jan 1, 1990

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 1991

    Earliest Phase 2 Sponsor(trial)

  3. Feb 24, 1995

    Barr Laboratories — Marketing Organization

  4. Jan 1, 1997

    Earliest Phase 1 Sponsor(trial)

2000s

  1. Jan 24, 2005

    Pharmacare PLC, Palestine — NDA Secondary Org

  2. Sep 19, 2005

    Aurobindo Pharma — Marketing Organization

  3. Sep 19, 2005

    West-Ward Pharmaceutical — Marketing Organization

  4. Sep 19, 2005

    Hikma — Marketing Organization

  5. Jan 31, 2007

    Cipla — NDA Secondary Org

  6. Mar 2, 2007

    Strides Pharma Science — Marketing Organization

  7. Mar 2, 2007

    Strides Pharma Science — NDA Secondary Org

  8. Aug 8, 2007

    Emcure — Marketing Organization

  9. Nov 29, 2007

    Matrix Laboratories Limited — Marketing Organization

  10. Feb 14, 2008

    PHARMOBEDIENT — Marketing Organization

  11. Oct 21, 2008

    Mylan — NDA Secondary Org

  12. May 7, 2009

    Hetero Labs Ltd — Marketing Organization

  13. May 7, 2009

    Hetero Labs Ltd — NDA Secondary Org

  14. Jul 23, 2009

    Aurobindo Pharma — NDA Secondary Org

2010s

  1. May 6, 2010

    Lutipold — Marketing Organization

  2. May 6, 2010

    Sankyo — Marketing Organization

  3. May 6, 2010

    Daiichi Sankyo — Marketing Organization

  4. Oct 27, 2010

    Cipla — Marketing Organization

  5. Jan 5, 2011

    Matrix Laboratories Limited — NDA Secondary Org

  6. May 25, 2011

    Teva — Marketing Organization

  7. May 25, 2011

    Chartwell Pharmaceuticals — Marketing Organization

  8. Oct 7, 2011

    Sunshine Lake Pharma Co., Ltd. — Marketing Organization

  9. Feb 8, 2012

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  10. Feb 8, 2012

    Macleods Pharmaceuticals, Ltd — NDA Secondary Org

  11. May 15, 2012

    Lupin — Marketing Organization

  12. Nov 26, 2013

    Liaoning Chengda — Marketing Organization

  13. Feb 4, 2014

    Mylan — Marketing Organization

  14. Aug 28, 2014

    Natco Pharma — Marketing Organization

  15. Mar 17, 2017

    Pharmacare PLC, Palestine — Marketing Organization

  16. Apr 10, 2018

    Shanghai Acebright Pharmaceuticals Co., Ltd. — Marketing Organization

  17. Apr 10, 2018

    ANDA Repository — Marketing Organization

  18. Apr 10, 2018

    Epic Pharma Llc — Marketing Organization

  19. Aug 13, 2018

    Micro Labs Ltd India — Marketing Organization

  20. Aug 13, 2018

    Micro Labs Ltd India — NDA Secondary Org

  21. Aug 29, 2018

    Neogen — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • combivir

    with lamivudine

  • lamivudine; zidovudine

    with efavirenz, lamivudine

  • lamivudine/zidovudine 150 mg/300 mg tablets co-packaged with nevirapine 200 mg tablets

    with lamivudine, nevirapine

    Also known as lamivudine/nevirapine/zidovudine tablets, lamivudine, zidovudine tabs 150mg/300mg co-packaged with nevirapine tabs 200mg

  • trizivir

    with abacavir, lamivudine

    Also known as abacavir sulfate; lamivudine; zidovudine

Approval history

  • approvedPriority reviewMar 19, 1987

Chemistry & pharmacology

Loading structure…

SMILES

CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O
Mol. weight
267.2413 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Black box warningProdrug

Sources

Also known as

  • abacavir (as sulfate) / lamivudine / zidovudine
  • azidothimidine
  • azidothymidine
  • azidothymidine
  • azidothymidine
  • azidothymidine
  • azitidin
  • azt
  • azt
  • azt
  • azt
  • azt
  • bwa509u
  • bwa509u
  • bw-a509u
  • bw-a509u
  • bw-a-509u
  • bw-a-509u
  • combivir
  • combivir
  • combivir
  • compound s
  • compound s
  • lamivudine / zidovudine
  • lamivudine / zidovudine / abacavir sulfate
  • lamivudine, zidovudine drug combination
  • retrovir
  • retrovir
  • retrovir
  • zdv
  • zdv
  • zidovudin
  • zidovudin
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudine
  • zidovudinum
  • zidovudinum

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT04802707Phase 2Oct 18, 2021McGill University
NCT04731103Phase 2Jun 30, 2021Medical Research Council, NHS Lothian, University of Edinburgh
NCT04581733Phase 3Dec 31, 2020Modis Therapeutics, Inc., Zogenix, Inc.
NCT03845712Phase 2Jul 1, 2019Modis Therapeutics, Inc.
NCT03991013Phase 4Jun 20, 2019Medecins Sans Frontieres, University of Cape Town
NCT03988452Phase 3Jun 20, 2019Infectious Disease Institute, Kampala, Uganda, Makerere University, National University of Singapore
NCT03394196N/AJul 4, 2018Centre de Sante de Ziguinchor, Casamance, Senegal, CHU Fann Dakar, Janssen Pharmaceutica NV, Merck, National Institute of Allergy and Infectious Diseases (NIAID), University of Washington
NCT03642704Phase 4Feb 22, 2017CHU Donka, Government of France
NCT02737046Phase 2Dec 12, 2016University of Miami
NCT02832778Phase 1Nov 21, 2016Infectious Disease Institute, Kampala, Uganda, Mylan, St Stephens Aids Trust, United States Agency for International Development
NCT02712801Phase 4Apr 1, 2016Government of China, Guangdong Provincial Maternal and Child Health Hospital, Guangxi Medical University, Maternal and Child Health Hospital of Yunan Province, Sichuan University, Xinjiang Medical University
NCT03088410Phase 4Apr 1, 2016Icahn School of Medicine at Mount Sinai, National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)
NCT02655471Early Phase 1 (Phase 1)Mar 1, 2016Cayetano Heredia University, Instituto de Medicina Tropical Alexander von Humboldt, Merck
NCT02150993Phase 2/Phase 3 (Phase 3)Jan 26, 2016French National Agency for Research on AIDS and Viral Hepatitis
NCT01818258Phase 4Oct 26, 2015National Institute of Allergy and Infectious Diseases (NIAID), National Institute of Child Health and Human Development (NICHD), National Institute of Mental Health (NIMH), National Institutes of Health (NIH)
NCT02363452Phase 2Sep 1, 2015University of Paris
NCT02346487Phase 3Sep 1, 2015Drugs for Neglected Diseases Initiative, French Development Agency, UNITAID, University of Nairobi
NCT02431975Phase 4Aug 1, 2015Columbia University, National Institutes of Health (NIH), University of the Witwatersrand
NCT02499874Phase 1Aug 1, 2015Mylan, St Stephens Aids Trust
NCT02437110Phase 1Apr 23, 2015National Institute of Neurological Disorders and Stroke (NINDS)
Showing 20 of 426 trials
Page 1 / 22

Organizations

Research & Development (220)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Institute of Allergy and Infectious Diseases (NIAID)Government19618251991
Glaxo WellcomeFor profit683451999
National Institutes of Health (NIH)Government34351997
Bristol-Myers SquibbFor profit28941996
Gilead SciencesFor profit211341999
RocheFor profit191041999
AbbottFor profit13441999
Boehringer IngelheimFor profit131051999
GlaxoSmithKlineFor profit13542001
MerckFor profit11741999
National Cancer Institute (NCI)Government11631990
Harvard UniversityAcademic/Hospital8331997
University of WashingtonAcademic/Hospital8332002
French National Agency for Research on AIDS and Viral HepatitisGovernment7722002
University of MiamiAcademic/Hospital7431999
Government of FranceGovernment6531997
PfizerFor profit6431999
Pharmacia & UpjohnFor profit6631999
AgouronFor profit5441999
Government of ChinaGovernment5122005
220 organizations
Page 1 / 11

Marketing (54)

OrganizationOrg typeRelationshipDate
ANDA RepositoryFor profitMKTGApr 10, 2018
Aurobindo PharmaFor profitNDA2Jul 23, 2009
Aurobindo PharmaFor profitMKTGSep 19, 2005
Aurobindo PharmaFor profitSYNMar 6, 2006
Barr LaboratoriesFor profitMKTGFeb 24, 1995
Burroughs WellcomeFor profitNDA—
Burroughs WellcomeFor profitINDJul 1, 1985
Chartwell PharmaceuticalsFor profitMKTGMay 25, 2011
CiplaFor profitMKTGOct 27, 2010
CiplaFor profitSYNJan 31, 2007
CiplaFor profitSYNMay 23, 2007
CiplaFor profitNDA2Jan 31, 2007
Daiichi SankyoFor profitMKTGMay 6, 2010
EmcureFor profitMKTGAug 8, 2007
Epic Pharma LlcFor profitMKTGApr 10, 2018
Hetero Labs LtdFor profitMKTGMay 7, 2009
Hetero Labs LtdFor profitSYNApr 25, 2008
Hetero Labs LtdFor profitSYNFeb 3, 2014
Hetero Labs LtdFor profitSYNNov 18, 2011
Hetero Labs LtdFor profitNDA2May 7, 2009
HikmaFor profitMKTGSep 19, 2005
HikmaFor profitSYNSep 19, 2005
Liaoning ChengdaGovernmentMKTGNov 26, 2013
LupinFor profitMKTGMay 15, 2012
LupinFor profitSYNDec 5, 2013
LutipoldFor profitMKTGMay 6, 2010
Macleods Pharmaceuticals, LtdFor profitMKTGFeb 8, 2012
Macleods Pharmaceuticals, LtdFor profitNDA2Feb 8, 2012
Matrix Laboratories LimitedFor profitNDA2Jan 5, 2011
Matrix Laboratories LimitedFor profitMKTGNov 29, 2007
Micro Labs Ltd IndiaFor profitMKTGAug 13, 2018
Micro Labs Ltd IndiaFor profitNDA2Aug 13, 2018
MylanFor profitMKTGFeb 4, 2014
MylanFor profitSYNSep 4, 2014
MylanFor profitSYNJul 15, 2009
MylanFor profitSYNFeb 14, 2008
MylanFor profitSYNAug 28, 2014
MylanFor profitNDA2Oct 21, 2008
Natco PharmaFor profitMKTGAug 28, 2014
NeogenFor profitMKTGAug 29, 2018
PHARMOBEDIENTFor profitMKTGFeb 14, 2008
Pharmacare PLC, PalestineFor profitMKTGMar 17, 2017
Pharmacare PLC, PalestineFor profitNDA2Jan 24, 2005
RanbaxyFor profitMKTG—
SankyoFor profitMKTGMay 6, 2010
Shanghai Acebright Pharmaceuticals Co., Ltd.For profitMKTGApr 10, 2018
Strides Pharma ScienceFor profitMKTGMar 2, 2007
Strides Pharma ScienceFor profitSYNDec 22, 2009
Strides Pharma ScienceFor profitSYNMay 13, 2015
Strides Pharma ScienceFor profitNDA2Mar 2, 2007
Sunshine Lake Pharma Co., Ltd.For profitMKTGOct 7, 2011
TevaFor profitMKTGMay 25, 2011
ViiV HealthcareFor profitNDA2Mar 19, 1987
West-Ward PharmaceuticalFor profitMKTGSep 19, 2005