Zidovudine
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MedKoo CAT#: 318994

CAS#: 30516-87-1

Description: Zidovudine, also known as azidothymidine, is an antiretroviral medication used to prevent and treat HIV/AIDS. It is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class. Zidovudine inhibits the enzyme (reverse transcriptase) that HIV uses to synthesize DNA, thus preventing viral DNA from forming. Zidovudine was the first breakthrough in AIDS therapy, significantly reducing the replication of the virus and leading to clinical and immunologic improvements. It can also be used to prevent HIV transmission, such as from mother to child during the period of birth or after a needle stick injury. Used by itself in HIV-infected patients, AZT slows HIV replication in patients, but does not stop it entirely.


Chemical Structure

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Zidovudine
CAS# 30516-87-1

Theoretical Analysis

MedKoo Cat#: 318994
Name: Zidovudine
CAS#: 30516-87-1
Chemical Formula: C10H13N5O4
Exact Mass: 267.09675
Molecular Weight: 267.245
Elemental Analysis: C, 44.94; H, 4.90; N, 26.21; O, 23.95

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 2 Weeks
2.0g USD 250.0 2 Weeks
5.0g USD 450.0 2 Weeks
10.0g USD 750.0 2 Weeks
20.0g USD 1050.0 2 Weeks
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Synonym: BW A509U; BWA 509U; BWA-509U; BWA509U; ZDV; AZT; azidothymidine; Zidovudine; brand name Retrovir.

IUPAC/Chemical Name: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

InChi Key: HBOMLICNUCNMMY-XLPZGREQSA-N

InChi Code: InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

SMILES Code: O=C1NC(C(C)=CN1[C@@H]2O[C@H](CO)[C@@H](N=[N+]=[N-])C2)=O

Appearance: Solid powder

Purity: >98% (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, not in 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

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 267.245 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.

Recalculate based on batch purity %
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

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1: Soares KC, Rediguieri CF, Souza J, Serra CH, Abrahamsson B, Groot DW, Kopp S, Langguth P, Polli JE, Shah VP, Dressman J. Biowaiver monographs for immediate-release solid oral dosage forms: Zidovudine (azidothymidine). J Pharm Sci. 2013 Aug;102(8):2409-23. doi: 10.1002/jps.23624. Epub 2013 Jun 10. Review. PubMed PMID: 23754446.

2: Shey MS, Kongnyuy EJ, Alobwede SM, Wiysonge CS. Co-formulated abacavir-lamivudine-zidovudine for initial treatment of HIV infection and AIDS. Cochrane Database Syst Rev. 2013 Mar 28;3:CD005481. doi: 10.1002/14651858.CD005481.pub3. Review. PubMed PMID: 23543540.

3: Teixeira C, Gomes JR, Gomes P, Maurel F, Barbault F. Viral surface glycoproteins, gp120 and gp41, as potential drug targets against HIV-1: brief overview one quarter of a century past the approval of zidovudine, the first anti-retroviral drug. Eur J Med Chem. 2011 Apr;46(4):979-92. doi: 10.1016/j.ejmech.2011.01.046. Epub 2011 Feb 3. Review. Erratum in: Eur J Med Chem. 2011 Aug;46(8):3541. Barbault, Florent [added]. PubMed PMID: 21345545.

4: Spaulding A, Rutherford GW, Siegfried N. Tenofovir or zidovudine in three-drug combination therapy with one nucleoside reverse transcriptase inhibitor and one non-nucleoside reverse transcriptase inhibitor for initial treatment of HIV infection in antiretroviral-naïve individuals. Cochrane Database Syst Rev. 2010 Oct 6;(10):CD008740. doi: 10.1002/14651858.CD008740. Review. PubMed PMID: 20927777.

5: 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.

6: Cihlar T, Ray AS. Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. Review. PubMed PMID: 19887088.

7: Shey M, Kongnyuy EJ, Shang J, Wiysonge CS. A combination drug of abacavir-lamivudine-zidovudine (Trizivir) for treating HIV infection and AIDS. Cochrane Database Syst Rev. 2009 Jul 8;(3):CD005481. doi: 10.1002/14651858.CD005481.pub2. Review. Update in: Cochrane Database Syst Rev. 2013;3:CD005481. PubMed PMID: 19588374.

8: Foster C, Lyall H, Olmscheid B, Pearce G, Zhang S, Gibb DM. Tenofovir disoproxil fumarate in pregnancy and prevention of mother-to-child transmission of HIV-1: is it time to move on from zidovudine? HIV Med. 2009 Aug;10(7):397-406. doi: 10.1111/j.1468-1293.2009.00709.x. Epub 2009 May 12. Review. PubMed PMID: 19459986.

9: Scruggs ER, Dirks Naylor AJ. Mechanisms of zidovudine-induced mitochondrial toxicity and myopathy. Pharmacology. 2008;82(2):83-8. doi: 10.1159/000134943. Epub 2008 May 27. Review. PubMed PMID: 18504416.

10: Stürmer M, Staszewski S, Doerr HW. Quadruple nucleoside therapy with zidovudine, lamivudine, abacavir and tenofovir in the treatment of HIV. Antivir Ther. 2007;12(5):695-703. Review. PubMed PMID: 17713153.

11: Keiser P, Nassar N. Abacavir sulfate/lamivudine/zidovudine fixed combination in the treatment of HIV infection. Expert Opin Pharmacother. 2007 Mar;8(4):477-83. Review. PubMed PMID: 17309342.

12: Piscitelli SC, Polis MA. An update on drug interactions with zidovudine. AIDS Patient Care STDS. 1998 Sep;12(9):687-90. Review. PubMed PMID: 15468442.

13: Ibbotson T, Perry CM. Lamivudine/zidovudine/abacavir: triple combination tablet. Drugs. 2003;63(11):1089-98; discussion 1099-1100. Review. PubMed PMID: 12749741.

14: Bhana N, Ormrod D, Perry CM, Figgitt DP. Zidovudine: a review of its use in the management of vertically-acquired pediatric HIV infection. Paediatr Drugs. 2002;4(8):515-53. Review. PubMed PMID: 12126455.

15: Kuritzkes DR. A fossil record of zidovudine resistance in transmitted isolates of HIV-1. Proc Natl Acad Sci U S A. 2001 Nov 20;98(24):13485-7. Review. PubMed PMID: 11717419; PubMed Central PMCID: PMC61066.

16: Darbyshire J, Foulkes M, Peto R, Duncan W, Babiker A, Collins R, Hughes M, Peto T, Walker A. Immediate versus deferred zidovudine (AZT) in asymptomatic or mildly symptomatic HIV infected adults. Cochrane Database Syst Rev. 2000;(3):CD002039. Review. PubMed PMID: 10908524.

17: Darbyshire J, Foulkes M, Peto R, Duncan W, Babiker A, Collins R, Hughes M, Peto T, Walker A. Zidovudine (AZT) versus AZT plus didanosine (ddI) versus AZT plus zalcitabine (ddC) in HIV infected adults. Cochrane Database Syst Rev. 2000;(3):CD002038. Review. PubMed PMID: 10908523.

18: Darbyshire J, Foulkes M, Peto R, Duncan W, Babiker A, Collins R, Hughes M, Peto T, Walker A. Immediate versus deferred zidovudine (AZT) in asymptomatic or mildly symptomatic HIV infected adults. Cochrane Database Syst Rev. 2000;(2):CD002039. Review. Update in: Cochrane Database Syst Rev. 2000;(3):CD002039. PubMed PMID: 10796852.

19: Darbyshire J, Foulkes M, Peto R, Duncan W, Babiker A, Collins R, Hughes M, Peto T, Walker A. Zidovudine (AZT) versus AZT plus didanosine (ddI) versus AZT plus zalcitabine (ddC) in HIV infected adults. Cochrane Database Syst Rev. 2000;(2):CD002038. Review. Update in: Cochrane Database Syst Rev. 2000;(3):CD002038. PubMed PMID: 10796851.

20: Simpson DM. Human immunodeficiency virus-associated dementia: review of pathogenesis, prophylaxis, and treatment studies of zidovudine therapy. Clin Infect Dis. 1999 Jul;29(1):19-34. Review. PubMed PMID: 10433561.