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CAS 29706-85-2

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3'-azido-3'-deoxythymidine phosphate

Description:
3'-Azido-3'-deoxythymidine phosphate, commonly known as AZT phosphate, is a nucleotide analog that plays a significant role in antiviral therapy, particularly in the treatment of HIV. This compound is characterized by the presence of an azido group at the 3' position of the thymidine base, which replaces the hydroxyl group typically found in natural nucleotides. The phosphate group enhances its solubility and facilitates incorporation into nucleic acids. AZT phosphate acts as a competitive inhibitor of reverse transcriptase, an enzyme critical for viral replication, thereby disrupting the synthesis of viral DNA from RNA. Its structure allows it to mimic natural nucleotides, leading to chain termination during DNA synthesis. The compound is generally administered in its triphosphate form, which is the active form that exerts its pharmacological effects. Due to its mechanism of action, AZT phosphate has been pivotal in antiretroviral therapy, contributing to the management of HIV infection and improving patient outcomes. However, its use can be associated with side effects, necessitating careful monitoring during treatment.
Formula:C10H16N5O8P
InChI:InChI=1/C10H13N5O4.H3O4P/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8;1-5(2,3)4/h3,6-8,16H,2,4H2,1H3,(H,12,17,18);(H3,1,2,3,4)/t6-,7+,8+;/m0./s1
Synonyms:
  • 3'-Azido-3'-Deoxythymidine Phosphate (1:1)
  • Thymidine, 3'-Azido-3'-Deoxy-, Phosphate (1:1)
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