Product Name

Zidovudine

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:
General Reference:

  1. De Clercq E: HIV resistance to reverse transcriptase inhibitors. Biochem Pharmacol. 1994 Jan 20;47(2):155-69. Pubmed
  2. Yarchoan R, Mitsuya H, Broder S: AIDS therapies. Sci Am. 1988 Oct;259(4):110-9. Pubmed
  3. 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
  4. Mitsuya H, Yarchoan R, Broder S: Molecular targets for AIDS therapy. Science. 1990 Sep 28;249(4976):1533-44. Pubmed
  5. 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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