Product Name

Zidovudine

Name: Zidovudine - LGM Pharma
SKU: 30516-87-1

CAS Number

30516-87-1

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Product Name:

Zidovudine

CAS Number:

30516-87-1

Indication:

For the treatment of human immunovirus (HIV) infections.

Mode of Action:

Zidovudine, a structural analog of thymidine, inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.

Pharmacodynamics:

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.

Metabolism:

Hepatic. Metabolized by glucuronide conjugation to major, inactive metabolite, 3_-azido-3_-deoxy-5_- O-beta-D-glucopyranuronosylthymidine (GZDV).

Toxicity:

Symptoms of overdose include fatigue, headache, nausea, and vomiting. LD₅₀ is 3084 mg/kg (orally in mice).

IUPAC:

1-[(2R, 4S, 5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1, 2, 3, 4-tetrahydropyrimidine-2, 4-dione

ATC:

J05AF01

PubChem:

35370

DrugBank:

DB00495 (APRD00449)

Formula:

C₁₀H₁₃N₅O₄

Molecular Mass:

267.2413

SMILES:

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

AHFS Code:

08:18.08.20

InChi:

HBOMLICNUCNMMY-XLPZGREQSA-N

General Reference:

De Clercq E: HIV resistance to reverse transcriptase inhibitors. Biochem Pharmacol. 1994 Jan 20;47(2):155-69. Pubmed
Yarchoan R, Mitsuya H, Broder S: AIDS therapies. Sci Am. 1988 Oct;259(4):110-9. Pubmed
Connor EM, Sperling RS, Gelber R, Kiselev P, Scott G, OêSullivan MJ, VanDyke R, Bey M, Shearer W, Jacobson RL, et al.: Reduction of maternal-infant transmission of human immunodeficiency virus type 1 with zidovudine treatment. Pediatric AIDS Clinical Trials Group Protocol 076 Study Group. N Engl J Med. 1994 Nov 3;331(18):1173-80. Pubmed
Mitsuya H, Yarchoan R, Broder S: Molecular targets for AIDS therapy. Science. 1990 Sep 28;249(4976):1533-44. Pubmed
Mitsuya H, Weinhold KJ, Furman PA, St Clair MH, Lehrman SN, Gallo RC, Bolognesi D, Barry DW, Broder S: 3ê-Azido-3ê-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci U S A. 1985 Oct;82(20):7096-100. Pubmed

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Zidovudine

30516-87-1

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