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Dihydro-5-azacytidine

Names

[ CAS No. ]:
62488-57-7

[ Name ]:
Dihydro-5-azacytidine

[Synonym ]:
1,3,5-triazin-2(1H)-one, 4-amino-5,6-dihydro-1-β-D-ribofuranosyl-
4-Amino-1-(β-D-ribofuranosyl)-5,6-dihydro-1,3,5-triazin-2(1H)-one
5,6 dihydro-5-azacytidine
1,3,5-Triazin-2(1H)-one, 4-amino-3,6-dihydro-1-β-D-ribofuranosyl-
6-Amino-3-(β-D-ribofuranosyl)-3,4-dihydro-1,3,5-triazin-2(1H)-one

Biological Activity

[Description]:

Dihydro-5-azacytidine (DHAC), the nucleoside analog, is incorporated into DNA and inhibits DNA methylation. Dihydro-5-azacytidine has an antitumor activity[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog
Signaling Pathways >> Epigenetics >> DNA Methyltransferase

[In Vitro]

Methylation studies show that an LD10 dose of [3H]DHAC results in a 25.06% hypomethylation of DNA in L1210/0 cells and a 46.32% hypomethylation in a deoxycytidine kinase mutant cell line L1210/dCK(-), compared with their respective controls[2]. Dihydro-5-azacytidine (DHAC) competes with cytidine triphosphate for incorporation into RNA, leading to ribosomal degradation and defective protein synthesis[1].

[In Vivo]

In tumor-bearing mice (injected with L1210/0 cells), after an LD10 dose of Dihydro-5-azacytidine (DHAC; 1500 mg/kg), the plasma peak concentration achieved is 317 μM and is eliminated biexponentially, with a t1/2 α of 1.03 h and a t1/2 β of 5 h[2].

[References]

[1]. Robert A Kratzke, et al. Response to the methylation inhibitor dihydro-5-azacytidine in mesothelioma is not associated with methylation of p16INK4a: results of cancer and leukemia group B 159904. J Thorac Oncol. 2008 Apr;3(4):417-21.

[2]. W C Powell, et al. Biochemical pharmacology of 5,6-dihydro-5-azacytidine (DHAC) and DNA hypomethylation in tumor (L1210)-bearing mice. Cancer Chemother Pharmacol. 1988;21(2):117-21.

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Boiling Point ]:
529.1ºC at 760 mmHg

[ Molecular Formula ]:
C8H14N4O5

[ Molecular Weight ]:
246.221

[ Flash Point ]:
273.8ºC

[ Exact Mass ]:
246.096420

[ PSA ]:
140.64000

[ LogP ]:
-2.20

[ Index of Refraction ]:
1.823

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XZ3018500
CHEMICAL NAME :
s-Triazin-2(1H)-one, 5,6-dihydro-4-amino-1-beta-D-ribofuranosyl-
CAS REGISTRY NUMBER :
62488-57-7
LAST UPDATED :
199709
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C8-H14-N4-O5
MOLECULAR WEIGHT :
246.26
WISWESSER LINE NOTATION :
T6NVN EN DHJ EZ C- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - mouse Embryo
DOSE/DURATION :
30 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 42,817,1982

Related Compounds