Available from stock

Decitabine

SKU: A0563

Category: API's & Intermediates

Synonyms: 5-Aza-2'-deoxycytidine , DAC , 2'-Deoxy-5-azacytidine , 4-Amino-1-(2-deoxy-beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one , NSC 127716; 2353-33-5
CAS-Number: C₈H₁₂N₄O₄
Molecular Formula: 228.21
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99% (HPLC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: DMSO (30mg/ml), DMF (20mg/ml), water (1mg/ml)
Melting Point: 177-182 °C

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H302-H315-H319-H335-H341-H360
Precautionary statements: P201-P261-P281-P305 + P351 + P338-P308 + P313
GHS Symbol: GHS07+GHS08
Signal word: Danger
Transportation: Not dangerous goods

Description: Decitabine is an epigenetic modifier that inhibits DNA methyltransferase activity which results in DNA demethylation (hypomethylation) and gene activation by remodeling ""opening"" chromatin. This cytosine analog incorporates into DNA, inhibit DNA methyltransferases, and cause hypomethylation of cytosine residues in the absence of any significant mutagenic effects. Decitabine is a potent antileukaemic agent with activity in the treatment of haematological malignancies such as acute myeloid leukaemia (AML), chronic myeloid leukaemia (CML) and myelodysplastic syndrome (preleukaemia) and has been suggested to reverse chemotherapy resistance in several cancer types. It is used as a chemotherapeutic agent, suppresses growth of human tumor cell lines, shown to reverse embryonic stem cell differentiation and prevent atherosclerosis lesion formation and reduces the production of inflammatory cytokines by macrophages."
Smiles: O[C@H]1C[C@H](N2C(N=C(N)N=C2)=O)O[C@@H]1CO
InChi Key: XAUDJQYHKZQPEU-KVQBGUIXSA-N
References: (1) T. Ando, et al., Leukemia 14, 1915 (2000) , (2) D. Lavelle, et al., Leuk. Res. 27, 999 (2003) , (3) No Author, Drugs R.D. 4, 179 (2003) (Review) , (4) J. Lyons, et al., Curr. Opin. Investig. Drugs 4, 1442 (2003) (Review) , (5) C. Stresemann & F. Lyko, Int. J. Cancer 123, 8 (2008) (Review) , (6) M. Al-Salihi, et al., Epigenetics 6, 1021 (2011) , (7) V.V. Konkankit, et al., J. Transl. Med. 9, 192 (2011) , (8) D. Yang, et al., J. Immunol. 188, 4441 (2012) , (9) D.Y. Shin, et al., Int. J. Oncol. 41, 910 (2012) , (10) M. Soncini, et al., Biochim. Biophys. Acta 1832, 114 (2013) , (11) J. Nie, et al., Cancer Lett. 354, 12 (2014) (Review) , (12) X. Li, et al., Expert Rev. Clin. Immunol. 11, 363 (2015) (Review) , (13) S. Ramakrishnan, et al., Cell Death Dis. 8, 3217 (2017) , (14) R.S. Seelan, et al., Drug Metab. Rev. 50, 193 (2018) (Review)
InChi: 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

Decitabine is an epigenetic modifier that inhibits DNA methyltransferase activity which results in DNA demethylation (hypomethylation) and gene activation by remodeling “”opening”” chromatin. This cytosine analog incorporates into DNA, inhibit DNA methyltransferases, and cause hypomethylation of cytosine residues in the absence of any significant mutagenic effects. Decitabine is a potent antileukaemic agent with activity in the treatment of haematological malignancies such as acute myeloid leukaemia (AML), chronic myeloid leukaemia (CML) and myelodysplastic syndrome (preleukaemia) and has been suggested to reverse chemotherapy resistance in several cancer types. It is used as a chemotherapeutic agent, suppresses growth of human tumor cell lines, shown to reverse embryonic stem cell differentiation and prevent atherosclerosis lesion formation and reduces the production of inflammatory cytokines by macrophages.”

SKU: A0563 Category: API's & Intermediates

Additional information

Additional information

Synonyms	5-Aza-2'-deoxycytidine, DAC, 2'-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, NSC 127716
Purity	≥99% (HPLC)
Appearance	White to off-white powder
CAS-Number	2353-33-5
Molecular Formula	C8H12N4O4
Molecular Weight	228.21
Identity	1H-NMR
Solvents	DMSO (30mg/ml), DMF (20mg/ml), water (1mg/ml)
Melting Point	177-182 °C
Smiles	O[C@H]1C[C@H](N2C(N=C(N)N=C2)=O)O[C@@H]1CO
InChi Key	XAUDJQYHKZQPEU-KVQBGUIXSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H302-H315-H319-H335-H341-H360
Precautionary statements	P201-P261-P281-P305 + P351 + P338-P308 + P313
GHS Symbol	GHS07+GHS08
Signal word	Danger
Transportation	Not dangerous goods
References	(1) T. Ando, et al., Leukemia 14, 1915 (2000), (2) D. Lavelle, et al., Leuk. Res. 27, 999 (2003), (3) No Author, Drugs R.D. 4, 179 (2003) (Review), (4) J. Lyons, et al., Curr. Opin. Investig. Drugs 4, 1442 (2003) (Review), (5) C. Stresemann & F. Lyko, Int. J. Cancer 123, 8 (2008) (Review), (6) M. Al-Salihi, et al., Epigenetics 6, 1021 (2011), (7) V.V. Konkankit, et al., J. Transl. Med. 9, 192 (2011), (8) D. Yang, et al., J. Immunol. 188, 4441 (2012), (9) D.Y. Shin, et al., Int. J. Oncol. 41, 910 (2012), (10) M. Soncini, et al., Biochim. Biophys. Acta 1832, 114 (2013), (11) J. Nie, et al., Cancer Lett. 354, 12 (2014) (Review), (12) X. Li, et al., Expert Rev. Clin. Immunol. 11, 363 (2015) (Review), (13) S. Ramakrishnan, et al., Cell Death Dis. 8, 3217 (2017), (14) R.S. Seelan, et al., Drug Metab. Rev. 50, 193 (2018) (Review)
InChi	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
Quantity	5 mg, 10 mg, 50 mg, Bulk