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
Melanoma: Stem cells, sun exposure and hallmarks for carcinogenesis, molecular concepts and future clinical implications.	2010-04-01	20442802
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.	2008-04	18379362
Tumor suppressor gene methylation in follicular lymphoma: a comprehensive review.	2006-10-06	17026765
Hydralazine target: from blood vessels to the epigenome.	2006-02-28	16507100
Antineoplastic effects of the DNA methylation inhibitor hydralazine and the histone deacetylase inhibitor valproic acid in cancer cell lines.	2006-01-31	16448574
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
Epigenetics of cervical cancer. An overview and therapeutic perspectives.	2005-10-25	16248899
Chemotherapy for malignant pleural mesothelioma: past results and recent developments.	2003-01-27	12610498
DNA methyltransferase inhibitors-state of the art.	2002-11	12419742
Inactivation of p16INK4a expression in malignant mesothelioma by methylation.	2002-11	12399123
Identification of active antiviral compounds against a New York isolate of West Nile virus.	2002-07	12076755
Dihydro-5-azacytidine and cisplatin in the treatment of malignant mesothelioma: a phase II study by the Cancer and Leukemia Group B.	1998-04-15	9554537
Dihydro-5-azacytidine in malignant mesothelioma. A phase II trial demonstrating activity accompanied by cardiac toxicity. Cancer and Leukemia Group B.	1997-06-01	9179072
A phase II study of 5,6-dihydro-5-azacytidine hydrochloride in disseminated malignant melanoma.	1993-06	7687819
Fetal hemoglobin gene activation in a phase II study of 5,6-dihydro-5-azacytidine for bronchogenic carcinoma.	1987-08-01	2440559

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:59:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:59:52 GMT 2025`
Record UNII	0627D8VG1C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-26480

Preferred Name

English

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

DHAC

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

67292