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CAS 84472-85-5

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3'-azido-2',3'-dideoxyuridine

Description:
3'-Azido-2',3'-dideoxyuridine (commonly known as AZT or zidovudine) is a nucleoside analog that is primarily used as an antiretroviral medication for the treatment of HIV/AIDS. It is characterized by the presence of an azido group at the 3' position and lacks the hydroxyl group at the 2' and 3' positions of the sugar moiety, which is crucial for its mechanism of action. This structural modification allows AZT to inhibit reverse transcriptase, an enzyme critical for viral replication, thereby preventing the synthesis of viral DNA from RNA. AZT is typically administered in its phosphate form, which is activated within the body to exert its therapeutic effects. The compound is soluble in water and exhibits moderate stability under physiological conditions. Its pharmacokinetics involve rapid absorption and distribution, with metabolism primarily occurring in the liver. While effective, AZT can have side effects, including bone marrow suppression and gastrointestinal disturbances, necessitating careful monitoring during treatment. Overall, 3'-azido-2',3'-dideoxyuridine represents a significant advancement in antiviral therapy.
Formula:C9H11N5O4
InChI:InChI=1/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)/t5-,6+,8+/m0/s1
InChI key:ZSNNBSPEFVIUDS-SHYZEUOFSA-N
SMILES:C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)N=[N+]=[N-]
Synonyms:
  • 1-(2,3-dideoxy-3-triaza-1,2-dien-2-ium-1-ylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione
  • NSC 380882
  • 3'-Azido-2',3'-dideoxy-1-beta-D-erythro-pentofuranosyluracil
  • 3'-N3-ddU
  • Navuridine
  • 3'-AZIDO-2',3'-DIDEOXYURIDINE
  • 3’-Azido-2’,3’-dideoxyuridine, 3’-Azido-ddU, AZDU, AzddU, CS-87
  • AzddU
  • 3’-Azido-2’,3’-dideoxy uridine v 3’-Azido-ddU, AZDU, AzddU, CS-87, HIV drug
  • CS-87
  • See more synonyms
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