87190-79-2

87190-79-2 structure

Name: AzddMeC
Chemical Name: 4-amino-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
CAS Number: 87190-79-2
Molecular Formula: C₁₀H₁₄N₆O₃
Molecular Weight: 266.257
Catalog: Signaling Pathways Anti-infection HIV
Create Date: 2017-03-09 17:07:11
Modify Date: 2023-01-15 12:09:44
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].

Name	4-amino-1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
Synonyms	CS-92 AZMC 3'-Azido-2',3'-dideoxy-5-methylcytidine Az-Dcme Azddmec AZ-5MeC Cytidine, 3'-azido-2',3'-dideoxy-5-methyl-

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.

Molecular Formula	C₁₀H₁₄N₆O₃
Molecular Weight	266.257
Exact Mass	266.112732
PSA	141.11000
LogP	-0.47

Precursor 0
DownStream 1
87190-81-6

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