Zidovudine | CAS#30516-87-1 | nucleoside analog reverse-transcriptase inhibitor

MedKoo Cat#: 318994 | Name: Zidovudine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Zidovudine

CAS#30516-87-1

Theoretical Analysis

MedKoo Cat#: 318994

Name: Zidovudine

CAS#: 30516-87-1

Chemical Formula: C10H13N5O4

Exact Mass: 267.0968

Molecular Weight: 267.25

Elemental Analysis: C, 44.94; H, 4.90; N, 26.21; O, 23.95

Price and Availability

Size	Price	Availability
1g	USD 150.00	2 weeks
2g	USD 250.00	2 weeks
5g	USD 450.00	2 weeks
10g	USD 750.00	2 weeks
20g	USD 1,050.00	2 weeks

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Related CAS #

30516-87-1 106060-89-3 (diphosphate) 92586-35-1 (triphosphate) 117675-21-5 (glucuronide)

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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T20C02I04

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	61.0	228.25

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 267.25 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.

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:

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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