Zidovudine

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Cat Number

API0232228

CAS Number

30516-87-1

For research use only. We do not supply to patients.

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Product Detail Description Scientific Support Customer Q&A

CAS Number

30516-87-1

EINECS

623-849-4

Storage

Store at room temperature

Synonyms

Azidothymidine; 3'-Azido-3'-deoxythymidine; Retrovir; Thymidine, 3'-azido-3'-deoxy-; Zidovudinum; Zidovudina

Molecular Formula

C10H13N5O4

Molecular Weight

267.24

Smiles

CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]

Appearance

Off-white crystalline powder

Melting Point

113-115°C (lit.)

Boiling Point

410.43°C (Estimate)

Relative Density

1.3382 (Estimated)

General Description

Zidovudine (AZT) is a synthetic thymidine analogue with an azido group substituting the 3'-hydroxyl group, making it a chain terminator of DNA synthesis. Its chemical structure is 3'-azido-3'-deoxythymidine, with a molecular weight of 267.2 Da. Zidovudine was the first antiretroviral agent approved for the treatment of HIV.

Mechanism of Action

Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI) that, after intracellular phosphorylation to the active triphosphate, competes with the natural substrate thymidine triphosphate for incorporation into the viral DNA. Once incorporated, it terminates the DNA chain elongation because it lacks the 3'-hydroxyl group required for the addition of the next nucleotide.

Application

Zidovudine is indicated for the treatment of HIV-1 infection in combination with other antiretroviral agents. It is also used for the prevention of mother-to-child transmission of HIV during pregnancy and delivery.

Zidovudine (AZT), a nucleoside reverse transcriptase inhibitor, inhibited P2RX7 functions via the same allosteric site as other antagonists. In DMDmdx mice, short-term AZT treatment at disease peak reduced sarcolemma permeability (lower creatine kinase, IgG influx), decreased inflammation, and improved muscle strength without mitochondrial toxicity.

Fig. 1 AZT binds to the same allosteric site as canonical P2RX7 antagonists. (Al-Khalidi R, et al., 2018)

References

Al-Khalidi R, et al. Zidovudine ameliorates pathology in the mouse model of Duchenne muscular dystrophy via P2RX7 purinoceptor antagonism. Acta Neuropathol Commun. 2018;6(1):27.

Does Zidovudine require protection from light during storage?

Yes, it is photosensitive. Light exposure can cause photodegradation and discoloration of the thymidine analog. Store in light-resistant containers, preferably amber glass.