5,6-DIHYDRO-5-AZACYTIDINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H14N4O5.ClH
Molecular Weight	282.682
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 5,6-DIHYDRO-5-AZACYTIDINE HYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=MRFRLYAOBSTHHU-MVNLRXSJSA-N

InChI=1S/C8H14N4O5.ClH/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);1H/t3-,4-,5-,6-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Fetal hemoglobin gene activation in a phase II study of 5,6-dihydro-5-azacytidine for bronchogenic carcinoma.	1987 Aug 1	2440559
A phase II study of 5,6-dihydro-5-azacytidine hydrochloride in disseminated malignant melanoma.	1993 Jun	7687819
Dihydro-5-azacytidine in malignant mesothelioma. A phase II trial demonstrating activity accompanied by cardiac toxicity. Cancer and Leukemia Group B.	1997 Jun 1	9179072
Dihydro-5-azacytidine and cisplatin in the treatment of malignant mesothelioma: a phase II study by the Cancer and Leukemia Group B.	1998 Apr 15	9554537
Identification of active antiviral compounds against a New York isolate of West Nile virus.	2002 Jul	12076755
DNA methyltransferase inhibitors-state of the art.	2002 Nov	12419742
Inactivation of p16INK4a expression in malignant mesothelioma by methylation.	2002 Nov	12399123
Epigenetics of cervical cancer. An overview and therapeutic perspectives.	2005 Oct 25	16248899
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
Tumor suppressor gene methylation in follicular lymphoma: a comprehensive review.	2006 Oct 6	17026765
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 15:05:11 GMT 2023` Edited by `admin` on `Fri Dec 15 15:05:11 GMT 2023`
Record UNII	TA5S1BS78J
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

5,6-DIHYDRO-5-AZACYTIDINE HYDROCHLORIDE

Systematic Name

English

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

Common Name

English

NSC-264880

Code

English

Code System Code Type Description

EPA CompTox

DTXSID20977982