5,6-DIHYDRO-5-AZACYTIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H14N4O5
Molecular Weight	246.2206
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(CN1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

InChI

InChIKey=LJIRBXZDQGQUOO-KVTDHHQDSA-N

InChI=1S/C8H14N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h3-6,13-15H,1-2H2,(H3,9,10,11,16)/t3-,4-,5-,6-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C8H14N4O5
Molecular Weight	246.2206
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/dihydro-5-azacytidine |https://www.ncbi.nlm.nih.gov/pubmed/7687819 | https://www.ncbi.nlm.nih.gov/pubmed/2450689 | https://www.ncbi.nlm.nih.gov/pubmed/7540895 | https://www.ncbi.nlm.nih.gov/pubmed/9554537 | https://www.ncbi.nlm.nih.gov/pubmed/9179072 | https://www.ncbi.nlm.nih.gov/pubmed/67884

5,6-dihydro-5-azacytidine (DHAC) is a hydrolytically stable congener of 5-azacytidine. It exerts cytostatic action in vitro. DHAC induces DNA hypomethylation. DHAC inhibits DNA methyltransferase, thereby interfering with abnormal DNA methylation patterns that are associated with genetic instability in some tumor cells. Inhibition of this enzyme may restore expression of tumor-suppressor genes and result in antitumor activity. It was in phase II studies for the treatment of several cancers such as malignant melanoma, mesothelioma and others.

Approval Year

PubMed

Title	Date	PubMed
Identification of active antiviral compounds against a New York isolate of West Nile virus.	2002 Jul	12076755
Characterization of decomposition products and preclinical and low dose clinical pharmacokinetics of decitabine (5-aza-2'-deoxycytidine) by a new liquid chromatography/tandem mass spectrometry quantification method.	2006	16523529
Melanoma: Stem cells, sun exposure and hallmarks for carcinogenesis, molecular concepts and future clinical implications.	2010 Apr 1	20442802

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:59:32 GMT 2023` Edited by `admin` on `Fri Dec 15 17:59:32 GMT 2023`
Record UNII	0627D8VG1C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5,6-DIHYDRO-5-AZACYTIDINE

Systematic Name

English

NSC-265483

Code

English

1,3,5-TRIAZIN-2(1H)-ONE, 4-AMINO-5,6-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-

Common Name

English

NSC-26480

Code

English

DHAC

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

67292