Synonym
Az-Dcme; CS-92; AzddMeC; Azidodideoxymethylcytidine; 3'-Azido-2',3'-dideoxy-5-methylcytidine
IUPAC/Chemical Name
4-amino-1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1H)-one
InChi Key
GZSDAHQGNUAEBC-XLPZGREQSA-N
InChi Code
InChI=1S/C10H14N6O3/c1-5-3-16(10(18)13-9(5)11)8-2-6(14-15-12)7(4-17)19-8/h3,6-8,17H,2,4H2,1H3,(H2,11,13,18)/t6-,7+,8+/m0/s1
SMILES Code
OC[C@@H]1[C@@H](N=[N+]=[N-])C[C@H](N2C(N=C(C(C)=C2)N)=O)O1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
266.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Schinazi RF, Schlueter-Wirtz S, Stuyver L. Early detection of mixed mutations selected by antiretroviral agents in HIV-infected primary human lymphocytes. Antivir Chem Chemother. 2001;12 Suppl 1:61-5. PubMed PMID: 11594690.
2: Boudinot FD, Schinazi RF, Doshi KJ, McClure HM, Chu CK. Pharmacokinetics and metabolism of 3'-azido-2',3'-dideoxy-5-methylcytidine in rhesus monkeys. Drug Metab Dispos. 1993 Sep-Oct;21(5):855-60. PubMed PMID: 7902248.
3: Cretton EM, Xie MY, Goudgaon NM, Schinazi RF, Chu CK, Sommadossi JP. Catabolic disposition of 3'-azido-2',3'-dideoxyuridine in hepatocytes with evidence of azido reduction being a general catabolic pathway of 3'-azido-2',3'-dideoxynucleosides. Biochem Pharmacol. 1992 Sep 1;44(5):973-80. PubMed PMID: 1326966.
4: Matthes E, Reimer K, von Janta-Lipinski M, Meisel H, Lehmann C. Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerases by triphosphates of sugar-modified 5-methyldeoxycytidines and of other nucleoside analogs. Antimicrob Agents Chemother. 1991 Jun;35(6):1254-7. PubMed PMID: 1929276; PubMed Central PMCID: PMC284326.
5: Schinazi RF, Chu CK, Eriksson BF, Sommadossi JP, Doshi KJ, Boudinot FD, Oswald B, McClure HM. Antiretroviral activity, biochemistry, and pharmacokinetics of 3'-azido-2',3'-dideoxy-5-methylcytidine. Ann N Y Acad Sci. 1990;616:385-97. Review. PubMed PMID: 1706574.
6: Herdewijn P, Balzarini J, Baba M, Pauwels R, Van Aerschot A, Janssen G, De Clercq E. Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides. J Med Chem. 1988 Oct;31(10):2040-8. PubMed PMID: 3172142.
7: Galegov GA, Korneeva MN, Nosik DN, Kilesso TIu, Kraevskiĭ AA. [The effect of 3'-azido-3'-deoxynucleosides on the reproduction of AIDS virus in cell culture]. Mol Biol (Mosk). 1988 May-Jun;22(3):802-6. Russian. PubMed PMID: 2460737.