Decitabine

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Names

[ CAS No. ]:
2353-33-5

[ Name ]:
Decitabine

[Synonym ]:
4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
s-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-
MFCD00043011
5-AZA-CDR
DAC
5-AZA-DC
Decitabine
5-DEOXY-2'-AZACYTIDINE
EINECS 219-089-4
1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-
4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one
5-Aza-1-(2-deoxy-β-D-ribofuranosyl)cytosine
4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one
2'-deoxy-5-azacytidine
5-Aza-2'-deoxycytidine
Dacogen
2-Desoxy-5-azacytidine
5-azadeoxycytidine
5-Aza-2′-deoxycytidine
5-Aza-2‘-deoxycytidine
4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-on
4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,3,5-triazin-2(1H)-one
4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-s-triazin-2(1H)-one

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
485.8±55.0 °C at 760 mmHg

[ Melting Point ]:
~200 °C (dec.)

[ Molecular Formula ]:
C8H12N4O4

[ Molecular Weight ]:
228.205

[ Flash Point ]:
247.6±31.5 °C

[ Exact Mass ]:
228.085861

[ PSA ]:
123.49000

[ LogP ]:
-1.93

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.780

[ Stability ]:
Stable. May be light or air sensitive. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
acetic acid/water (1:1): 50 mg/mL

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XZ3012000
CHEMICAL NAME :
s-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-
CAS REGISTRY NUMBER :
2353-33-5
LAST UPDATED :
199709
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C8-H12-N4-O4
MOLECULAR WEIGHT :
228.24
WISWESSER LINE NOTATION :
T6NVN ENJ DZ A- ET5OTJ B1Q CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Blood - leukopenia Blood - thrombocytopenia Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 8-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
300 ug/kg
SEX/DURATION :
female 10-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
300 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
DNA inhibition

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
5 umol/L
REFERENCE :
EJCAEL European Journal of Cancer. (Pergamon Press, c/o Elsevier Science, 660 White Plains Rd., Tarrytown, NY 10591) V.26-28(2/3), 1990-92. For publisher information, see EJCTEA Volume(issue)/page/year: 28,362,1992

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H319-H335-H341-H360

[ Precautionary Statements ]:
P201-P261-P281-P305 + P351 + P338-P308 + P313

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
XZ3012000

Synthetic Route

Precursor & DownStream

Precursor

  • 5-Azacytosine
  • 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose
  • 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose
  • 1-O-Acetyl-3,5-bis-(4-chlorobenzoyl)-2-deoxy-D-ribose
  • N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-1,3,5-triazin-2-amine
  • 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine
  • 4-amino-1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
  • 3',5'-di-O-Acetyl-2-deoxy-5-azacytosine

DownStream

  • 5-Azacytosine
  • 2-deoxy-D-ribofuranose

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Related Compounds

  • Decitabine
  • decitabine mesylate
  • 3-Toluoyl Decitabine
  • Decitabine iMpurity 7
  • Decitabine iMpurity 6
  • decitabine monohydrate
  • Methyl 2-amino-4-[(pentan-3-yl)amino]butanoate
  • 5-amino-1-(1-ethyl-1H-pyrazol-4-yl)piperidin-2-one
  • 3-(3-Methylpiperidin-4-yl)aniline
  • 4-(aminomethyl)-4-methyl-N-(2-methylpropyl)cyclohexan-1-amine
  • 4-(aminomethyl)-4-methyl-N-propylcyclohexan-1-amine
  • 3,6-Diethylpyridazine-4-carbaldehyde
  • 3-Chloro-2-(thiophen-2-yl)phenol
  • 1-(pentan-2-yl)-1H-indol-6-amine
  • 3-amino-2,3-dihydro-1H-indene-1-thiol
  • N-(3,4-dihydroxybutyl)-2-methylpentanamide
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