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  • Product Name: Decitabine
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Related CAS#:
2353-33-5 54199-94-9
879492-57-6 183016-21-9
20535-28-8 178671-74-4
135567-49-6 69304-65-0
78185-65-6 78185-66-7

2353-33-5

2353-33-5 structure
2353-33-5 structure
  • Name: Decitabine
  • Chemical Name: 5-aza-2'-deoxycytidine
  • CAS Number: 2353-33-5
  • Molecular Formula: C8H12N4O4
  • Molecular Weight: 228.205
  • Catalog: Biochemical Nucleoside drugs Deoxynucleotides and their analogues
  • Create Date: 2018-06-23 12:37:40
  • Modify Date: 2024-01-02 16:56:27
  • Decitabine (NSC 127716) is a DNA methyltransferase inhibitor commonly used to treat myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML).
Name 5-aza-2'-deoxycytidine
Synonyms 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
Description Decitabine (NSC 127716) is a DNA methyltransferase inhibitor commonly used to treat myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML).
Related Catalog
Target

DNMT1

DNMT3A

DNMT3B
In Vitro Decitabine treatment significantly inhibits cell growth of SNU719, NCC24 and KATOIII 96 hours after exposure to decitabine. Decitabine induces G2/M arrest and apoptosis in EBVaGC, inhibits invasion ability, and up-regulates E-cadherin expression for EBVaGC[1]. Tri-acetylation on the H4 N-terminal tail (H4K8acK12acK16ac) is reduced after DAC treatment in MDS-L sensitive cells[2]. Decitabine up-regulates DCTPP1 and dUTPase expression in HeLa cells[3].
In Vivo Decitabine (1.0 mg/kg, p.o.) in combination with tetrahydrouridine (THU) causes severe toxicity occurs in females, and results in an increased sensitivity to decitabine toxicity correlating with decitabine plasma levels[4].
Kinase Assay The pyrophosphohydrolase activity of DCTPP1 is determined using a continuous spectrophotometric assay. In a standard reaction (1 mL final volum), 10-250 μM of the nucleotide substrate is incubated in reaction buffer (20 mM MgCl2, 100 mM KCl, 0.75 mg/mL BSA and 4 mM DTT) with concentrations ranging from 0.1-1 μM of DCTTP1. All reactions are carried out at 25°C.
Cell Assay Cell viability is analyzed by cell count and MTS assay. SNU719, NCC24 and KATOIII are seeded at a density of 5×104 cells/mL and cultured with only RPMI-1640 supplemented with FBS for 24 hours. After 24 hours of incubation, cells are treated in the presence or absence of Decitabine (DAC) for 120 hours. Cells for cell counts are trypsinized and counted at 0, 24, 48, 72, 96 and 120 hours after DAC treatment. Viable cells are determined by trypan blue exclusion. For MTS assay, cells (SNU719 and NCC24: 1x104/well, KATOIII: 1x103/well) are eeded onto 96-well dishes. After seeding, MTS is added into the well at the indicated period. After incubation for 1 hour, the absorbance is measured at 490 nm.
Animal Admin Mice are assigned to four dose groups and a vehicle control group. Animals are gavaged with Decitabine (DAC) or its vehicle 1 hour ± 5 minutes after administration of tetrahydrouridine (THU) or its vehicle at a dose volume of 10 mL/kg. The DAC doses are selected based on the range finding study in which the mice tolerated six oral doses (2x/week) of 0.1, 0.2 and 0.4 mg/kg DAC in combination with a fixed dose of 167 mg/kg THU. A fixed THU dose (500 mg/m2) and the optimal timing between THU and DAC administration (60 min) are selected. Conversion of milligrams per body surface area dose in mice into milligrams per kilogram body weight dose estimation is based on Michaelis constant (Km) values for mice. In brief, the mouse dose in milligrams per body surface area (500 mg/m2) is divided by the Km of 3 to convert the dose to milligrams per kilogram body weight (167 mg/kg). The working body weight range of mice in the guideline is 11-34 gram; the body weight range of mice used in this study is 24-38 gram.
References

[1]. Nakamura M, et al. Decitabine inhibits tumor cell proliferation and up-regulates E-cadherin expression in Epstein-Barr virus-associated gastric cancer. J Med Virol. 2016 Jul 19.

[2]. Zhang C, et al. Quantitative proteomic analysis of histone modifications in decitabine sensitive and resistant leukemia cell lines. Clin Proteomics. 2016 Jul 5;13:14.

[3]. Requena CE, et al. The nucleotidohydrolases DCTPP1 and dUTPase are involved in the cellular response to decitabine. Biochem J. 2016 Jun 20.

[4]. Terse P, et al. Subchronic oral toxicity study of decitabine in combination with tetrahydrouridine in CD-1 mice. Int J Toxicol. 2014 Mar-Apr;33(2):75-85.

[5]. Yu J, et al. DNA methyltransferase expression in triple-negative breast cancer predicts sensitivity to decitabine. J Clin Invest. 2018 Jun 1;128(6):2376-2388.
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

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
Symbol GHS07 GHS08
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
931-86-2 structure

931-86-2
3601-89-6 structure

3601-89-6

~%

2353-33-5 structure

2353-33-5
Literature: EP2371825 A1, ; Page/Page column 9 ;
931-86-2 structure

931-86-2
21740-23-8 structure

21740-23-8

~%

2353-33-5 structure

2353-33-5
Literature: EP2048151 A1, ; Page/Page column 3 ;
1207459-15-1 structure

1207459-15-1
52523-35-0 structure

52523-35-0

~%

2353-33-5 structure

2353-33-5
Literature: US2010/36112 A1, ; Page/Page column 7-8 ;
1034301-08-0 structure

1034301-08-0

~98%

2353-33-5 structure

2353-33-5
Literature: Cilag AG Patent: EP2050757 A1, 2009 ; Location in patent: Page/Page column 4 ;
1034301-08-0 structure

1034301-08-0
1140891-02-6 structure

1140891-02-6

~%

2353-33-5 structure

2353-33-5
Literature: US2010/249394 A1, ; Page/Page column 6 ;
22432-93-5 structure

22432-93-5

~%

2353-33-5 structure

2353-33-5
Literature: WO2010/129211 A2, ; Page/Page column 28 ;
135567-49-6 structure

135567-49-6

~%

2353-33-5 structure

2353-33-5
Literature: US2006/14949 A1, ; Page/Page column 6; 15 ;
69304-64-9 structure

69304-64-9

~%

2353-33-5 structure

2353-33-5
Literature: Journal of Pharmaceutical Sciences, , vol. 70, # 11 p. 1228 - 1232

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title: CAS No. 2353-33-5 | Chemsrc address: https://www.chemsrc.com/en/baike/894713.html

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