5,6-dihydro-5-azacytidine profile

5,6-dihydro-5-azacytidine, a nucleoside analog, is a potent inhibitor of DNA methyltransferases (DNMTs). It acts as a mechanism-based inhibitor of DNMTs, forming a covalent adduct with the enzyme. This inhibition leads to global hypomethylation of DNA, which can reactivate silenced genes and promote differentiation of cancer cells. It is being investigated in clinical trials as a potential treatment for various types of cancer, including hematological malignancies and solid tumors. The compound's unique ability to induce demethylation and its potential to modulate gene expression makes it a promising therapeutic agent. Its mechanism of action, therapeutic potential, and safety profile are actively studied.'

5,6-dihydro-5-azacytidine: NSC-264880 refers to 5,6-dihydro-5-azacytidine hydrochloride [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	99681
CHEMBL ID	3278060
SCHEMBL ID	14196
MeSH ID	M0062111

Synonym
dhac
dihydro-5-azacytidine
nsc-265483
62488-57-7
nsc265483
5,6-dihydro-5-azacytidine
6-amino-3-beta-d-ribofuranosyl-3,4-dihydro-1,3,5-triazin-2(1h)-one
1,3,5-triazin-2(1h)-one,4-amino-3,6-dihydro-1-.beta.-d-ribofuranosyl-
6-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,2-dihydro-1,3,5-triazin-4-one
ccris 6743
4-amino-5,6-dihydro-1-beta-d-ribofuranosyl-s-triazin-2(1h)-one
4-amino-5,6-dihydro-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1h)-one
5,6-dihydro-4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-one
1,3,5-triazin-2(1h)-one, 4-amino-3,6-dihydro-1-beta-d-ribofuranosyl-
s-triazin-2(1h)-one, 5,6-dihydro-4-amino-1-beta-d-ribofuranosyl-
6-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydro-1,3,5-triazin-2-one
nsc 265483
unii-0627d8vg1c
0627d8vg1c ,
1,3,5-triazin-2(1h)-one, 4-amino-5,6-dihydro-1-.beta.-d-ribofuranosyl-
CHEMBL3278060
4-amino-1-((2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5,6-dihydro-1,3,5-triazin-2(1h)-one
LJIRBXZDQGQUOO-KVTDHHQDSA-N
SCHEMBL14196
DTXSID7020471
6-amino-3-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,4-dihydro-1,3,5-triazin-2(1h)-one
dihydro-5-azacytidine; nsc 264-880; nsc 26480; nsc 265483
Q27236168
A848797
HY-106689
CS-0026355
AKOS040758243

Excerpt	Relevance	Reference
" The plasma concentration time data for the first 12 h after dosing was computer fitted to a two compartment open model."	( Pharmacokinetics of 5,6-dihydro-5-azacytidine (NSC-264880) in the foxhound. Cheng, H; Malspeis, L; Staubus, AE, 1983)	0.59

Assay ID	Title	Year	Journal	Article
AID1148525	Antitumor activity against mouse L1210 cells allografted in ip dosed mouse assessed as increase in life span at MNTD administered qd from day 1 to day 9 post tumor implantation relative to control	1977	Journal of medicinal chemistry, Jun, Volume: 20, Issue:6	Synthesis and antitumor activity of dihydro-5-azacytidine, a hydrolytically stable analogue of 5-azacytidine.
AID1148527	Antitumor activity against mouse L1210 cells allografted in ip dosed mouse assessed as change in body weight at MNTD administered qd from day 1 to day 9 post tumor implantation measured on day 5 relative to control	1977	Journal of medicinal chemistry, Jun, Volume: 20, Issue:6	Synthesis and antitumor activity of dihydro-5-azacytidine, a hydrolytically stable analogue of 5-azacytidine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	19 (67.86)	18.7374
1990's	6 (21.43)	18.2507
2000's	2 (7.14)	29.6817
2010's	1 (3.57)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	4 (13.33%)	5.53%
Reviews	2 (6.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (80.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
cytosine [no description available]	3.17	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymidine [no description available]	1.95	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
uridine [no description available]	2.36	2	0	uridines	drug metabolite; fundamental metabolite; human metabolite
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	1.95	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
cytidine [no description available]	8.46	2	0	cytidines	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytarabine [no description available]	1.97	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	8.82	28	4	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
deoxycytidine [no description available]	2.37	2	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
5-azacytosine 5-azacytosine: structure given in first source. 5-azacytosine : A monoamino-1,3,5-triazine that is cytosine in which the aromatic CH at position 5 is replaced by a nitrogen.	3.17	1	0	monoamino-1,3,5-triazine
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	1.95	1	0	dihydrogen
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.02	1	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
fazarabine fazarabine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-arabinofuranosyl residue via an N-glycosidic linkage. A synthetic analogue of cytosine arabinoside and 5-azacytidine that incorporates structural features of both compounds, it shows good activity against a variety of transplanted tumors.	3.76	3	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.36	2	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
6-azacytidine 6-azacytidine: MH AZACITIDINE refers to 5-azacytidine	1.98	1	0
pseudoisocytidine pseudoisocytidine: RN given refers to parent cpd; structure	3.06	1	0
decitabine [no description available]	2.37	2	0	2'-deoxyribonucleoside
5-fluoro-2'-deoxycytidine 5-fluoro-2'-deoxycytidine: structure	1.98	1	0
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	1.95	1	0	carbon group element atom; metalloid atom; nonmetal atom
tetrahydrouridine Tetrahydrouridine: An inhibitor of nucleotide metabolism.	1.95	1	0
kp 1461 KP 1461: an anti-HIV agent and prodrug of KP-1212	2.02	1	0

Condition	Relationship Strength	Studies	Trials
Leukemia L 1210 [description not available]	3.46	8	0
Experimental Leukemia [description not available]	3.28	2	0
Malignant Melanoma [description not available]	8.75	2	1
Experimental Neoplasms [description not available]	1.95	1	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	8.75	2	1
Benign Neoplasms [description not available]	3.32	2	0
HIV Coinfection [description not available]	3.36	2	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	2.99	1	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.32	2	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	3.36	2	0
Mesothelioma A tumor derived from mesothelial tissue (peritoneum, pleura, pericardium). It appears as broad sheets of cells, with some regions containing spindle-shaped, sarcoma-like cells and other regions showing adenomatous patterns. Pleural mesotheliomas have been linked to exposure to asbestos. (Dorland, 27th ed)	10.21	4	3
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	1.96	1	0
Leucocythaemia [description not available]	2.38	2	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	7.38	2	0
Leukemia L5178 An experimental lymphocytic leukemia of mice.	1.98	1	0
Chromosome-Defective Micronuclei [description not available]	1.98	1	0
Precordial Catch [description not available]	4.98	3	3
Emesis [description not available]	3.37	1	1
Chest Pain Pressure, burning, or numbness in the chest.	4.98	3	3
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	3.37	1	1
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	3.37	1	1
Arrhythmia [description not available]	3.38	1	1
Neoplasms, Pleural [description not available]	4.98	3	3
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	3.38	1	1
Leukocytopenia [description not available]	3.38	1	1
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	3.38	1	1
Carcinoma, Non-Small Cell Lung [description not available]	2.37	2	0
Cardiac Diseases [description not available]	1.97	1	0
Cancer of Lung [description not available]	2.37	2	0
Ache [description not available]	1.97	1	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.37	2	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	1.97	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.37	2	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	1.97	1	0

5,6-dihydro-5-azacytidine

Description

Cross-References

Synonyms (32)

Research Excerpts

Dosage Studied

Bioassays (2)

Research

Studies (28)

Market Indicators

Research Demand Index: 15.69

Study Types