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AzddMeC

Names

[ CAS No. ]:
87190-79-2

[ Name ]:
AzddMeC

[Synonym ]:
CS-92
AZMC
3'-Azido-2',3'-dideoxy-5-methylcytidine
Az-Dcme
Azddmec
AZ-5MeC
Cytidine, 3'-azido-2',3'-dideoxy-5-methyl-

Biological Activity

[Description]:

AzddMeC (CS-92) is an antiviral nucleoside analogue and a potent potent, selective and orally active HIV-1 reverse transcriptase and HIV-1 replication inhibitor. In HIV-1-infected human PBM cells and HIV-1-infected human macrophages, the EC50 values of AzddMeC are 9 nM and 6 nM, respectively[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV
Research Areas >> Infection
Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog
Signaling Pathways >> Anti-infection >> Reverse Transcriptase

[Target]

HIV-1:9 nM (EC50, Human PBM cells)

HIV-1:6 nM (EC50, Human macrophages)


[In Vitro]

AzddMeC (CS-92) is also effective against HIV-2 in lymphocytes. The replication of Friend murine virus is only weakly inhibited, and no effect is observed against HSV type 1 and type 2 and coxsackievirus B4. The interaction of the 5'-triphosphate of AzddMeC with HIV-1 reverse transcriptase indicated competitive inhibition (the inhibition constant, Kis, is 9.3 nM)[1].

[In Vivo]

The pharmacokinetics of AzddMeC are characterized following intravenous and oral administration of 60 mg/kg of the compound to male rhesus monkeys. 3'-azido-3'-deoxythymidine (AZT) is a major metabolite of AzddMeC in monkeys. AzddMeC concentrations in serum declined rapidly in a biexponential fashion with the terminal half-life ranging from 0.5 to 1.3 hr. Renal excretion of unchanged nucleoside and metabolic deamination yielding AZT are the primary routes of AzddMeC clearance. The oral bioavailability is 26%[2].

[References]

[1]. R F Schinazi, et al. Antiretroviral Activity, Biochemistry, and Pharmacokinetics of 3'-azido-2',3'-dideoxy-5-methylcytidine. Ann N Y Acad Sci. 1990;616:385-97.

[2]. Boudinot FD, et al. Pharmacokinetics and metabolism of 3'-azido-2',3'-dideoxy-5-methylcytidine in rhesus monkeys. Drug Metab Dispos. 1993;21(5):855‐860.

Chemical & Physical Properties

[ Molecular Formula ]:
C10H14N6O3

[ Molecular Weight ]:
266.257

[ Exact Mass ]:
266.112732

[ PSA ]:
141.11000

[ LogP ]:
-0.47

Precursor & DownStream

Precursor

DownStream