Decitabine
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MedKoo CAT#: 100250

CAS#: 2353-33-5

Description: Decitabine is a cytidine antimetabolite analogue with potential antineoplastic activity. Decitabine incorporates into DNA and inhibits DNA methyltransferase, resulting in hypomethylation of DNA and intra-S-phase arrest of DNA replication.


Chemical Structure

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Decitabine
CAS# 2353-33-5

Theoretical Analysis

MedKoo Cat#: 100250
Name: Decitabine
CAS#: 2353-33-5
Chemical Formula: C8H12N4O4
Exact Mass: 228.08585
Molecular Weight: 228.2
Elemental Analysis: C, 42.10; H, 5.30; N, 24.55; O, 28.04

Price and Availability

Size Price Availability Quantity
500.0mg USD 150.0 Ready to ship
1.0g USD 250.0 Ready to ship
2.0g USD 450.0 Ready to ship
5.0g USD 850.0 2 Weeks
10.0g USD 1450.0 2 Weeks
50.0g USD 3450.0 2 Weeks
Bulk inquiry

Synonym: 5-aza-dCyd; deoxyazacytidine; dezocitidine; US brand name: Dacogen. Abbreviations: 5AZA; DAC

IUPAC/Chemical Name: 4-amino-1-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one

InChi Key: XAUDJQYHKZQPEU-JKUQZMGJSA-N

InChi Code: InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6-/m0/s1

SMILES Code: O=C1N([C@H]2O[C@H](CO)[C@@H](O)C2)C=NC(N)=N1

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, and PBS

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO or water

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Decitabine (NSC 127716) is an orally active deoxycytidine analogue antimetabolite and a DNA methyltransferase inhibitor.
In vitro activity: Decitabine inhibited cell growth and induced G2/M arrest and apoptosis in EBVaGC cell lines. The expression of E-cadherin was up-regulated and cell motility was significantly inhibited in the cells treated with decitabine. The promoter regions of p73 and RUNX3 were demethylated, and their expression was up-regulated by decitabine. They enhanced the transcription of p21, which induced G2/M arrest and apoptosis through down-regulation of c-Myc. Decitabine also induced the expression of BZLF1 in SNU719. Induction of EBV lytic infection was an alternative way to cause apoptosis of the host cells. Reference: J Med Virol. 2017 Mar;89(3):508-517. https://onlinelibrary.wiley.com/doi/abs/10.1002/jmv.24634
In vivo activity: Decitabine (DAC), a DNA methylation inhibitor that is currently used for the treatment of myelodysplastic syndrome (MDS), acute myeloid leukemia (AML) and other malignant neoplasms, is capable of eliciting an anti-tumor cytotoxic T lymphocyte (CTL) response in mouse EL4 tumor model. C57BL/6 mice with established EL4 tumors were treated with DAC (1.0 mg/kg body weight) once daily for 5 days. DAC treatment resulted in infiltration of IFN-γ producing T lymphocytes into tumors and caused tumor rejection. Depletion of CD8(+), but not CD4(+) T cells resumed tumor growth. DAC-induced CTL response appeared to be elicited by the induction of CD80 expression on tumor cells. Epigenetic evidence suggests that DAC induces CD80 expression in EL4 cells via demethylation of CpG dinucleotide sites in the promoter of CD80 gene. In addition, we also showed that a transient, low-dose DAC treatment can induce CD80 gene expression in a variety of human cancer cells. Reference: PLoS One. 2013 May 9;8(5):e62924. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3650049/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 45.0 197.19
Water 18.0 78.87

Preparing Stock Solutions

The following data is based on the product molecular weight 228.2 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Nakamura M, Nishikawa J, Saito M, Sakai K, Sasaki S, Hashimoto S, Okamoto T, Suehiro Y, Yamasaki T, Sakaida I. Decitabine inhibits tumor cell proliferation and up-regulates e-cadherin expression in Epstein-Barr virus-associated gastric cancer. J Med Virol. 2017 Mar;89(3):508-517. doi: 10.1002/jmv.24634. Epub 2016 Nov 17. PMID: 27430892. 2. Hagemann S, Heil O, Lyko F, Brueckner B. Azacytidine and decitabine induce gene-specific and non-random DNA demethylation in human cancer cell lines. PLoS One. 2011 Mar 7;6(3):e17388. doi: 10.1371/journal.pone.0017388. PMID: 21408221; PMCID: PMC3049766. 3. Wang LX, Mei ZY, Zhou JH, Yao YS, Li YH, Xu YH, Li JX, Gao XN, Zhou MH, Jiang MM, Gao L, Ding Y, Lu XC, Shi JL, Luo XF, Wang J, Wang LL, Qu C, Bai XF, Yu L. Low dose decitabine treatment induces CD80 expression in cancer cells and stimulates tumor specific cytotoxic T lymphocyte responses. PLoS One. 2013 May 9;8(5):e62924. doi: 10.1371/journal.pone.0062924. PMID: 23671644; PMCID: PMC3650049.
In vitro protocol: 1. Nakamura M, Nishikawa J, Saito M, Sakai K, Sasaki S, Hashimoto S, Okamoto T, Suehiro Y, Yamasaki T, Sakaida I. Decitabine inhibits tumor cell proliferation and up-regulates e-cadherin expression in Epstein-Barr virus-associated gastric cancer. J Med Virol. 2017 Mar;89(3):508-517. doi: 10.1002/jmv.24634. Epub 2016 Nov 17. PMID: 27430892. 2. Hagemann S, Heil O, Lyko F, Brueckner B. Azacytidine and decitabine induce gene-specific and non-random DNA demethylation in human cancer cell lines. PLoS One. 2011 Mar 7;6(3):e17388. doi: 10.1371/journal.pone.0017388. PMID: 21408221; PMCID: PMC3049766.
In vivo protocol: 1. Wang LX, Mei ZY, Zhou JH, Yao YS, Li YH, Xu YH, Li JX, Gao XN, Zhou MH, Jiang MM, Gao L, Ding Y, Lu XC, Shi JL, Luo XF, Wang J, Wang LL, Qu C, Bai XF, Yu L. Low dose decitabine treatment induces CD80 expression in cancer cells and stimulates tumor specific cytotoxic T lymphocyte responses. PLoS One. 2013 May 9;8(5):e62924. doi: 10.1371/journal.pone.0062924. PMID: 23671644; PMCID: PMC3650049.

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1: Ganetsky A. The role of decitabine for the treatment of acute myeloid leukemia. Ann Pharmacother. 2012 Nov;46(11):1511-7. doi: 10.1345/aph.1R151. Epub 2012 Oct 31. Review. PubMed PMID: 23115225.

2: Joeckel TE, Lübbert M. Clinical results with the DNA hypomethylating agent 5-aza-2'-deoxycytidine (decitabine) in patients with myelodysplastic syndromes: an update. Semin Hematol. 2012 Oct;49(4):330-41. doi: 10.1053/j.seminhematol.2012.08.001. Review. PubMed PMID: 23079063.

3: Marks PW. Decitabine for acute myeloid leukemia. Expert Rev Anticancer Ther. 2012 Mar;12(3):299-305. doi: 10.1586/era.11.207. Review. PubMed PMID: 22369322.

4: Bryan J, Kantarjian H, Garcia-Manero G, Jabbour E. Pharmacokinetic evaluation of decitabine for the treatment of leukemia. Expert Opin Drug Metab Toxicol. 2011 May;7(5):661-72. doi: 10.1517/17425255.2011.575062. Review. PubMed PMID: 21500965.

5: Cowan LA, Talwar S, Yang AS. Will DNA methylation inhibitors work in solid tumors? A review of the clinical experience with azacitidine and decitabine in solid tumors. Epigenomics. 2010 Feb;2(1):71-86. doi: 10.2217/epi.09.44. Review. PubMed PMID: 22122748.

6: Daskalakis M, Blagitko-Dorfs N, Hackanson B. Decitabine. Recent Results Cancer Res. 2010;184:131-57. doi: 10.1007/978-3-642-01222-8_10. Review. PubMed PMID: 20072836.

7: Santos FP, Kantarjian H, Garcia-Manero G, Issa JP, Ravandi F. Decitabine in the treatment of myelodysplastic syndromes. Expert Rev Anticancer Ther. 2010 Jan;10(1):9-22. doi: 10.1586/era.09.164. Review. PubMed PMID: 20014881.

8: Stresemann C, Lyko F. Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. Int J Cancer. 2008 Jul 1;123(1):8-13. doi: 10.1002/ijc.23607. Review. PubMed PMID: 18425818.

9: Jabbour E, Issa JP, Garcia-Manero G, Kantarjian H. Evolution of decitabine development: accomplishments, ongoing investigations, and future strategies. Cancer. 2008 Jun;112(11):2341-51. doi: 10.1002/cncr.23463. Review. PubMed PMID: 18398832.

10: Plimack ER, Kantarjian HM, Issa JP. Decitabine and its role in the treatment of hematopoietic malignancies. Leuk Lymphoma. 2007 Aug;48(8):1472-81. Review. PubMed PMID: 17701577.

Decitabine

500.0mg / USD 150.0


Additional Information

Dacogen (decitabine) for Injection contains decitabine (5-aza-2'deoxycitidine), an analogue of the natural nucleoside 2'-deoxycytidine. Decitabine is a fine, white to almost white powder with the molecular formula of C8H12N4O4 and a molecular weight of 228.21. Its chemical name is 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin2(1H)-one. Decitabine is slightly soluble in ethanol/water (50/50), methanol/water (50/50) and methanol; sparingly soluble in water and soluble in dimethylsulfoxide (DMSO). Dacogen (decitabine) for Injection is a white to almost white sterile lyophilized powder supplied in a clear colorless glass vial. Each 20 mL, single dose, glass vial contains 50 mg decitabine, 68 mg monobasic potassium phosphate (potassium dihydrogen phosphate) and 11.6 mg sodium hydroxide.
 
Decitabine is indicated for the treatment of myelodysplastic syndromes (MDS) including previously treated and untreated, de novo and secondary MDS of all French-American-British subtypes (refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia) and Intermediate-1, Intermediate-2, and High-Risk International Prognostic Scoring System groups.
 
Mechanism of Action
Decitabine is believed to exert its antineoplastic effects after phosphorylation and direct incorporation into DNA and inhibition of DNA methyltransferase, causing hypomethylation of DNA and cellular differentiation or apoptosis. Decitabine inhibits DNA methylation in vitro , which is achieved at concentrations that do not cause major suppression of DNA synthesis. Decitabine-induced hypomethylation in neoplastic cells may restore normal function to genes that are critical for the control of cellular differentiation and proliferation. In rapidly dividing cells, the cytotoxicity of decitabine may also be attributed to the formation of covalent adducts between DNA methyltransferase and decitabine incorporated into DNA. Non-proliferating cells are relatively insensitive to decitabine.