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MedKoo Cat#: 100250 | Name: Decitabine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Decitabine
Decitabine
CAS#2353-33-5

Theoretical Analysis

MedKoo Cat#: 100250

Name: Decitabine

CAS#: 2353-33-5

Chemical Formula: C8H12N4O4

Exact Mass: 228.0859

Molecular Weight: 228.20

Elemental Analysis: C, 42.10; H, 5.30; N, 24.55; O, 28.04

Price and Availability

Size Price Availability Quantity
250mg USD 150.00 Ready to ship
500mg USD 250.00 Ready to ship
1g USD 450.00 Ready to ship
2g USD 800.00 2 weeks
5g USD 1,450.00 2 Weeks
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No Data
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
More Info
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.
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/
Solvent mg/mL mM
Solubility
DMSO 45.0 197.19
Water 18.0 78.87
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 228.20 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.
1: Dhillon S. Decitabine/Cedazuridine: First Approval. Drugs. 2020 Sep;80(13):1373-1378. doi: 10.1007/s40265-020-01389-7. Erratum in: Drugs. 2021 Jan;81(1):179. PMID: 32860582; PMCID: PMC7708383. 2: Garcia-Manero G, Griffiths EA, Steensma DP, Roboz GJ, Wells R, McCloskey J, Odenike O, DeZern AE, Yee K, Busque L, O'Connell C, Michaelis LC, Brandwein J, Kantarjian H, Oganesian A, Azab M, Savona MR. Oral cedazuridine/decitabine for MDS and CMML: a phase 2 pharmacokinetic/pharmacodynamic randomized crossover study. Blood. 2020 Aug 6;136(6):674-683. doi: 10.1182/blood.2019004143. PMID: 32285126; PMCID: PMC7414597. 3: Kim K, Maiti A, Loghavi S, Pourebrahim R, Kadia TM, Rausch CR, Furudate K, Daver NG, Alvarado Y, Ohanian M, Sasaki K, Short NJ, Takahashi K, Yilmaz M, Tang G, Ravandi F, Kantarjian HM, DiNardo CD, Konopleva MY. Outcomes of TP53-mutant acute myeloid leukemia with decitabine and venetoclax. Cancer. 2021 Oct 15;127(20):3772-3781. doi: 10.1002/cncr.33689. Epub 2021 Jul 13. PMID: 34255353; PMCID: PMC10462434. 4: Patel AA, Cahill K, Saygin C, Odenike O. Cedazuridine/decitabine: from preclinical to clinical development in myeloid malignancies. Blood Adv. 2021 Apr 27;5(8):2264-2271. doi: 10.1182/bloodadvances.2020002929. PMID: 33904891; PMCID: PMC8095139. 5: Pollyea DA, Pratz K, Letai A, Jonas BA, Wei AH, Pullarkat V, Konopleva M, Thirman MJ, Arellano M, Becker PS, Chyla B, Hong WJ, Jiang Q, Potluri J, DiNardo CD. Venetoclax with azacitidine or decitabine in patients with newly diagnosed acute myeloid leukemia: Long term follow-up from a phase 1b study. Am J Hematol. 2021 Feb 1;96(2):208-217. doi: 10.1002/ajh.26039. Epub 2020 Nov 10. PMID: 33119898. 6: DiNardo CD, Maiti A, Rausch CR, Pemmaraju N, Naqvi K, Daver NG, Kadia TM, Borthakur G, Ohanian M, Alvarado Y, Issa GC, Montalban-Bravo G, Short NJ, Yilmaz M, Bose P, Jabbour EJ, Takahashi K, Burger JA, Garcia-Manero G, Jain N, Kornblau SM, Thompson PA, Estrov Z, Masarova L, Sasaki K, Verstovsek S, Ferrajoli A, Weirda WG, Wang SA, Konoplev S, Chen Z, Pierce SA, Ning J, Qiao W, Ravandi F, Andreeff M, Welch JS, Kantarjian HM, Konopleva MY. 10-day decitabine with venetoclax for newly diagnosed intensive chemotherapy ineligible, and relapsed or refractory acute myeloid leukaemia: a single-centre, phase 2 trial. Lancet Haematol. 2020 Oct;7(10):e724-e736. doi: 10.1016/S2352-3026(20)30210-6. Epub 2020 Sep 5. PMID: 32896301; PMCID: PMC7549397. 7: Li X, Li Y, Dong L, Chang Y, Zhang X, Wang C, Chen M, Bo X, Chen H, Han W, Nie J. Decitabine priming increases anti-PD-1 antitumor efficacy by promoting CD8+ progenitor exhausted T cell expansion in tumor models. J Clin Invest. 2023 Apr 3;133(7):e165673. doi: 10.1172/JCI165673. PMID: 36853831; PMCID: PMC10065084. 8: Wei Y, Xiong X, Li X, Lu W, He X, Jin X, Sun R, Lyu H, Yuan T, Sun T, Zhao M. Low-dose decitabine plus venetoclax is safe and effective as post-transplant maintenance therapy for high-risk acute myeloid leukemia and myelodysplastic syndrome. Cancer Sci. 2021 Sep;112(9):3636-3644. doi: 10.1111/cas.15048. Epub 2021 Jul 21. PMID: 34185931; PMCID: PMC8409404. 9: Sekeres MA, Taylor J. Diagnosis and Treatment of Myelodysplastic Syndromes: A Review. JAMA. 2022 Sep 6;328(9):872-880. doi: 10.1001/jama.2022.14578. PMID: 36066514. 10: Ni X, Wang L, Wang H, Yu T, Xie J, Li G, Liu Y, Zhou H, Xu M, Hou M, Peng J, Hou Y. Low-dose decitabine modulates myeloid-derived suppressor cell fitness via LKB1 in immune thrombocytopenia. Blood. 2022 Dec 29;140(26):2818-2834. doi: 10.1182/blood.2022016029. PMID: 36037415. 11: Maiti A, Qiao W, Sasaki K, Ravandi F, Kadia TM, Jabbour EJ, Daver NG, Borthakur G, Garcia-Manero G, Pierce SA, Montalbano KS, Pemmaraju N, Naqvi K, Ohanian M, Short NJ, Alvarado Y, Takahashi K, Yilmaz M, Jain N, Kornblau SM, Andreeff M, Bose P, Ferrajoli A, Issa GC, Masarova L, Thompson PA, Rausch CR, Ning J, Kantarjian HM, DiNardo CD, Konopleva MY. Venetoclax with decitabine vs intensive chemotherapy in acute myeloid leukemia: A propensity score matched analysis stratified by risk of treatment-related mortality. Am J Hematol. 2021 Mar 1;96(3):282-291. doi: 10.1002/ajh.26061. Epub 2020 Dec 24. PMID: 33264443; PMCID: PMC8128145. 12: Cazzola M. Myelodysplastic Syndromes. N Engl J Med. 2020 Oct 1;383(14):1358-1374. doi: 10.1056/NEJMra1904794. PMID: 32997910. 13: DiNardo CD, Pratz KW, Letai A, Jonas BA, Wei AH, Thirman M, Arellano M, Frattini MG, Kantarjian H, Popovic R, Chyla B, Xu T, Dunbar M, Agarwal SK, Humerickhouse R, Mabry M, Potluri J, Konopleva M, Pollyea DA. Safety and preliminary efficacy of venetoclax with decitabine or azacitidine in elderly patients with previously untreated acute myeloid leukaemia: a non-randomised, open-label, phase 1b study. Lancet Oncol. 2018 Feb;19(2):216-228. doi: 10.1016/S1470-2045(18)30010-X. Epub 2018 Jan 12. PMID: 29339097. 14: Qu C, Zou R, Wang P, Zhu Q, Kang L, Ping N, Xia F, Liu H, Kong D, Yu L, Wu D, Jin Z. Decitabine-primed tandem CD19/CD22 CAR-T therapy in relapsed/refractory diffuse large B-cell lymphoma patients. Front Immunol. 2022 Aug 17;13:969660. doi: 10.3389/fimmu.2022.969660. PMID: 36059523; PMCID: PMC9429371. 15: Gao L, Zhang Y, Wang S, Kong P, Su Y, Hu J, Jiang M, Bai H, Lang T, Wang J, Liu L, Yang T, Huang X, Liu F, Lou S, Liu Y, Zhang C, Liu H, Gao L, Liu J, Zhu L, Wen Q, Chen T, Wang P, Rao J, Mao M, Wang C, Duan X, Luo L, Peng X, Cassady K, Zhong JF, Zhang X. Effect of rhG-CSF Combined With Decitabine Prophylaxis on Relapse of Patients With High-Risk MRD-Negative AML After HSCT: An Open-Label, Multicenter, Randomized Controlled Trial. J Clin Oncol. 2020 Dec 20;38(36):4249-4259. doi: 10.1200/JCO.19.03277. Epub 2020 Oct 27. PMID: 33108244; PMCID: PMC7768335. 16: Farhadfar N, Li Y, May WS, Adams CB. Venetoclax and decitabine for treatment of relapsed T-cell acute lymphoblastic leukemia: A case report and review of literature. Hematol Oncol Stem Cell Ther. 2021 Sep;14(3):246-251. doi: 10.1016/j.hemonc.2019.10.002. Epub 2020 Mar 19. PMID: 32199933. 17: Kang S, Wang L, Xu L, Wang R, Kang Q, Gao X, Yu L. Decitabine enhances targeting of AML cells by NY-ESO-1-specific TCR-T cells and promotes the maintenance of effector function and the memory phenotype. Oncogene. 2022 Oct;41(42):4696-4708. doi: 10.1038/s41388-022-02455-y. Epub 2022 Sep 12. PMID: 36097193; PMCID: PMC9568428. 18: Decitabine and Cedazuridine. Am J Health Syst Pharm. 2020 Oct 30;77(22):1809-1811. doi: 10.1093/ajhp/zxaa276. PMID: 32945859. 19: Goswami M, Gui G, Dillon LW, Lindblad KE, Thompson J, Valdez J, Kim DY, Ghannam JY, Oetjen KA, Destefano CB, Smith DM, Tekleab H, Li Y, Dagur P, Hughes T, Marté JL, Del Rivero J, Klubo-Gwiezdzinksa J, Gulley JL, Calvo KR, Lai C, Hourigan CS. Pembrolizumab and decitabine for refractory or relapsed acute myeloid leukemia. J Immunother Cancer. 2022 Jan;10(1):e003392. doi: 10.1136/jitc-2021-003392. PMID: 35017151; PMCID: PMC8753450. 20: Santini V, Lübbert M, Wierzbowska A, Ossenkoppele GJ. The Clinical Value of Decitabine Monotherapy in Patients with Acute Myeloid Leukemia. Adv Ther. 2022 Apr;39(4):1474-1488. doi: 10.1007/s12325-021-01948-8. Epub 2021 Nov 16. Erratum in: Adv Ther. 2022 Feb 15;: PMID: 34786648; PMCID: PMC8989816.