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

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI), widely used to treat HIV infection and increases CRISPR/Cas9mediated editing frequency.
In vitro activity: The effect of defective autophagy on total cellular mitochondrial abundance (MitoTracker Red [MTR Red] staining) and ROS production [5-(and-6)-chloromethyl-2′,7′-dichlorodihydrofluorescein diacetate, acetyl ester (CM-H2DCFDA)] in C2C12 cells incubated in the presence or absence of different concentrations of AZT (Zidovudine) (6, 30, 180 µM) for up to 8 days or with 3MA (5 mM) or nocodazole-vinblastine (50 µM) for 24 h was analyzed. Consistent with autophagy inhibition, incubation with AZT produced profound myocyte mitochondrial accumulation (Fig. 3A). AZT treatment was associated with mitochondrial membrane hyperpolarization, as revealed by an AZT-mediated increase in the ratio of potential-dependent MitoTracker Deep Red (MTR Deep Red) and potential-independent MitoTracker Green (MTR Green) staining (34) (see Fig. S1A and B in the supplemental material) as well as by increased mitochondrial potential-specific MitoProbe TMRM staining. At the same time, AZT had no major effect on the enzymatic activity of mitochondrial respiratory chain complexes (complexes I to V) (Fig. S2). Collectively, these data suggest that AZT-mediated autophagy inhibition prevents the removal of dysfunctional mitochondria produced in relation to its mitochondrial toxicity. Reference:Antimicrob Agents Chemother. 2019 Jan; 63(1): e01443-18. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6325205/
In vivo activity: AZT treatment resulted in significantly improved sarcolemma integrity: An analysis of membrane permeability using IgG influx into TA muscle revealed a significant reduction in IgG-positive fibers already after 2 weeks of treatment (IgG pixel intensity PBSmdx = 14.7 AU, AZT-mdx = 5.14 AU) (Fig. 7a). After 4 weeks of AZT treatment there was a significant, 60% reduction in serum CK level (Fig.7b), indicative of less sarcolemma damage and therefore less leakage of this intracellular muscle enzyme (serum CK levels: PBS-mdx = 864.37 UI/l, AZT-mdx = 351.72 UI/l; p = 0.004). The serum levels of miR-206, dystroMir, in mdx mice have been found to be less affected by movement compared to CK and therefore this dystroMir has been proposed as a stable molecular marker of muscle damage. Here, the serum levels of Mir-206 were significantly decreased in the AZT-treated mdx mice after 2 weeks of treatment (Fig.7c). The revertant fiber reduction was not statistically significant but no increase indicated that AZT treatment is not accelerating muscle damage (Additional file 5: Figure S4). Reference: Acta Neuropathol Commun. 2018; 6: 27. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5896059/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 61.0 228.25

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
Formulation protocol: 1. Carnicelli V, Di Giulio A, Bozzi A, Strom R, Oratore A. Zidovudine inhibits protein kinase C activity in human chronic myeloid (K562) cells. Basic Clin Pharmacol Toxicol. 2006 Oct;99(4):317-22. doi: 10.1111/j.1742-7843.2006.pto_486.x. PMID: 17040218. 2. Lin H, Stankov MV, Hegermann J, Budida R, Panayotova-Dimitrova D, Schmidt RE, Behrens GMN. Zidovudine-Mediated Autophagy Inhibition Enhances Mitochondrial Toxicity in Muscle Cells. Antimicrob Agents Chemother. 2018 Dec 21;63(1):e0144318. doi: 10.1128/AAC.01443-18. PMID: 30373793; PMCID: PMC6325205. 3. Drzazga Z, Ciszek W, Binek M. Prenatal Zidovudine Treatment Modifies Early Development of Rat Osteoid - Confocal Microspectroscopy Analysis. J Fluoresc. 2019 Sep;29(5):1257-1263. doi: 10.1007/s10895-019-02429-6. Epub 2019 Oct 16. PMID: 31620936; PMCID: PMC6853851. 4. Al-Khalidi R, Panicucci C, Cox P, Chira N, Róg J, Young CNJ, McGeehan RE, Ambati K, Ambati J, Zabłocki K, Gazzerro E, Arkle S, Bruno C, Górecki DC. Zidovudine ameliorates pathology in the mouse model of Duchenne muscular dystrophy via P2RX7 purinoceptor antagonism. Acta Neuropathol Commun. 2018 Apr 11;6(1):27. doi: 10.1186/s40478-018-0530-4. PMID: 29642926; PMCID: PMC5896059.
In vitro protocol: 1. Carnicelli V, Di Giulio A, Bozzi A, Strom R, Oratore A. Zidovudine inhibits protein kinase C activity in human chronic myeloid (K562) cells. Basic Clin Pharmacol Toxicol. 2006 Oct;99(4):317-22. doi: 10.1111/j.1742-7843.2006.pto_486.x. PMID: 17040218. 2. Lin H, Stankov MV, Hegermann J, Budida R, Panayotova-Dimitrova D, Schmidt RE, Behrens GMN. Zidovudine-Mediated Autophagy Inhibition Enhances Mitochondrial Toxicity in Muscle Cells. Antimicrob Agents Chemother. 2018 Dec 21;63(1):e0144318. doi: 10.1128/AAC.01443-18. PMID: 30373793; PMCID: PMC6325205.
In vivo protocol: 1. Drzazga Z, Ciszek W, Binek M. Prenatal Zidovudine Treatment Modifies Early Development of Rat Osteoid - Confocal Microspectroscopy Analysis. J Fluoresc. 2019 Sep;29(5):1257-1263. doi: 10.1007/s10895-019-02429-6. Epub 2019 Oct 16. PMID: 31620936; PMCID: PMC6853851. 2. Al-Khalidi R, Panicucci C, Cox P, Chira N, Róg J, Young CNJ, McGeehan RE, Ambati K, Ambati J, Zabłocki K, Gazzerro E, Arkle S, Bruno C, Górecki DC. Zidovudine ameliorates pathology in the mouse model of Duchenne muscular dystrophy via P2RX7 purinoceptor antagonism. Acta Neuropathol Commun. 2018 Apr 11;6(1):27. doi: 10.1186/s40478-018-0530-4. PMID: 29642926; PMCID: PMC5896059.

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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.