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ZEBULARINE

ZEBULARINE Structure
ZEBULARINE structure
CAS No.
3690-10-6
Chemical Name:
ZEBULARINE
Synonyms
NSC 309132;4-Deoyuridine;4-Deoxyuridine;Zebularine Zebularine;Zebularine (NSC309132;NSC309132;4-DEOXYURIDINE;4-Deoyuridine,Zebularine;Zebularine, 10 mM in DMSO;2-Pyrimidone-1-β-D-riboside;Zebularine (NSC 309132) ，S7113
CBNumber:
CB4497499
Molecular Formula:
C9H12N2O5
Molecular Weight:
228.2
MDL Number:
MFCD04973699
MOL File:
3690-10-6.mol
MSDS File:
SDS
Last updated:2025-10-18 16:00:31
Product description Number Pack Size Price
Zebularine 691400 10mg $222
Zebularine 691400 25mg $488
Zebularine >98.0%(HPLC)(T) Z0022 200mg $183
Zebularine >98.0%(HPLC)(T) Z0022 1g $542
Zebularine ≥98% 10975 1mg $26
Request For Quotation

ZEBULARINE Properties

Melting point 160-162?C
Boiling point 499.0±55.0 °C(Predicted)
Density 1.73±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: 16 mg/mL, soluble
form solid
pka 13.48±0.70(Predicted)
color White
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
InChI InChI=1/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/s3
InChIKey RPQZTTQVRYEKCR-WCTZXXKLSA-N
SMILES N1(C=CC=NC1=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |&1:7,9,12,14,r|
FDA UNII 7A9Y5SX0GY
UNSPSC Code 12352203
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H320-H335
Precautionary statements  P264-P270-P301+P312-P330
WGK Germany  3
RTECS  UW7539720
HS Code  2934999090

ZEBULARINE price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 691400 Zebularine 3690-10-6 10mg $222 2025-07-31 Buy
Sigma-Aldrich 691400 Zebularine 3690-10-6 25mg $488 2025-07-31 Buy
TCI Chemical Z0022 Zebularine >98.0%(HPLC)(T) 3690-10-6 200mg $183 2025-07-31 Buy
TCI Chemical Z0022 Zebularine >98.0%(HPLC)(T) 3690-10-6 1g $542 2025-07-31 Buy
Cayman Chemical 10975 Zebularine ≥98% 3690-10-6 1mg $26 2024-03-01 Buy
Product number Packaging Price Buy
691400 10mg $222 Buy
691400 25mg $488 Buy
Z0022 200mg $183 Buy
Z0022 1g $542 Buy
10975 1mg $26 Buy

ZEBULARINE Chemical Properties,Uses,Production

Description

Zebularine (3690-10-6) is an orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC50 = 120 μM) and re-activates silenced genes in T24 bladder carcinoma cells. Zebularine inhibits cytidine deaminase (Ki ~ 2 μM and; induces differentiation of mesenchymal stem cells into cardiomyocytes.

Chemical Properties

White Solid

Uses

It is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.

Definition

ChEBI: Zebularine is a member of pyrimidine ribonucleosides.

Biological Activity

Orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC 50 = 120 μ M) and re-activates silenced genes in T24 bladder carcinoma cells. Also inhibits cytidine deaminase (K i ~ 2 μ M).

Biochem/physiol Actions

Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.

Synthesis

2(1H)-Pyrimidinone, 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-

52523-24-7

ZEBULARINE

3690-10-6

The general procedure for the synthesis of 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one from the compound (CAS: 52523-24-7) was as follows: compound 15 (9.5 g, 17.6 mmol) was dissolved in methanol (100 mL) and cooled to 0 °C. To this cooled solution a methanol solution of 7N ammonia (245 mL) was slowly added. The reaction mixture was stirred at 25°C for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was diluted with water and extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 10:1) to afford compound 16 (3.8 g, 94% yield) as a white solid. Its 1H NMR (400 MHz, methanol-d4) data were as follows: δ 8.79 (dd, J = 6.8, 2.8 Hz, 1H), 8.57 (dd, J = 4.0, 2.8 Hz, 1H), 6.58 (dd, J = 6.8, 4.4 Hz, 1H), 5.86 (s, 1H), 4.15-4.10 (m, 3H), 3.98 ( dd, J = 12.4, 2.0 Hz, 1H), 3.79 (dd, J = 12.8, 2.0 Hz, 1H).

storage

Desiccate at RT

References

[1] Patent: WO2015/72784, 2015, A1. Location in patent: Page/Page column 21; 22
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 1, p. 127 - 130
[3] Tetrahedron Letters, 1994, vol. 35, # 10, p. 1597 - 1600
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 6, p. 662 - 666

ZEBULARINE Preparation Products And Raw materials

Raw materials

2(1H)-Pyrimidinone, 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)- Ammonia Methanol

Preparation Products

ZEBULARINE Suppliers

Global( 152)Suppliers
Supplier Tel Email Country ProdList Advantage
Career Henan Chemica Co
+86-0371-86658258 +8613203830695 laboratory@coreychem.com China 30229 58
Shaanxi Dideu Medichem Co. Ltd 		+86-029-81138252 +86-173 9270 1263 1057@dideu.com China 4000 58
Shenzhen Nexconn Pharmatechs Ltd 		+86-755-89396905 +86-15013857715 admin@nexconn.com China 10405 58
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19552 58
TargetMol Chemicals Inc. 		+1-781-999-5354; +17819995354 marketing@targetmol.com United States 32434 58
Finetech Industry Limited 		+86-27-8746-5837 +8619945049750 info@finetechnology-ind.com China 9629 58
NewCan Biotech Limited 		+86-0571-86912261 +8613735419629 sales@newcanbio.com China 9985 58
InvivoChem 		+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6391 58
Wuhu Nuowei chemistry Co., Ltd. 		+86-0553-2911116-802 +86-18055326116 sales1@nuowei-chem.com China 1627 58
HANGZHOU LEAP CHEM CO., LTD. 		+86-571-87711850 market18@leapchem.com China 43339 58
Supplier Advantage
Career Henan Chemica Co
58
Shaanxi Dideu Medichem Co. Ltd 		58
Shenzhen Nexconn Pharmatechs Ltd 		58
BOC Sciences 		58
TargetMol Chemicals Inc. 		58
Finetech Industry Limited 		58
NewCan Biotech Limited 		58
InvivoChem 		58
Wuhu Nuowei chemistry Co., Ltd. 		58
HANGZHOU LEAP CHEM CO., LTD. 		58

View Lastest Price from ZEBULARINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Zebularine pictures 2025-10-18 Zebularine
3690-10-6
 US $38.00-127.00 / mg 99.84% 10g TargetMol Chemicals Inc.
ZEBULARINE pictures 2024-07-20 ZEBULARINE
3690-10-6
 US $1.00 / Kg 1Kg 98% 20T Shaanxi Dideu Medichem Co. Ltd
  • Zebularine pictures
  • Zebularine
    3690-10-6
  • US $38.00-127.00 / mg
  • 99.84%
  • TargetMol Chemicals Inc.
  • ZEBULARINE pictures
  • ZEBULARINE
    3690-10-6
  • US $1.00 / Kg
  • 98%
  • Shaanxi Dideu Medichem Co. Ltd

ZEBULARINE Spectrum

ZEBULARINE(3690-10-6)1HNMR

3690-10-6(ZEBULARINE)Related Search:

6-[(3-chloropropyl)amino]-1,3-dimethyluracil URAPIDIL 5-METHYL- Uridine 5''-Monophosphate N,N-Dibutyl-1-butanamine Pseudouridine 6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione
2-Demethoxy-4-methoxy urapidil Quillaic acid (8α,9β,14β,23S,24R)-11β,23-Dihydroxy-24,25-epoxy-5α-dammar-13(17)-ene-3,16-dione Alisol B acetate SAPONIN, PRACT. FROM QUILLAJA SAPONARIA MOLINA
Anisodine hydrobromide velutin Zearalenone 5-Methylcytidine Urapidil Impurity 20
2,4(1H,3H)-Pyrimidinedione, 5-[5-O-[(1,1-dimethylethyl)diphenylsilyl]-β-D-ribofuranosyl]- 2,4(1H,3H)-Pyrimidinedione, 1-α-L-arabinofuranosyl- 2,4(1H,3H)-Pyrimidinedione, 1-β-L-arabinofuranosyl-

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Zebularine - CAS 3690-10-6 - Calbiochem NSC309132;4-DEOXYURIDINE 1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one pyrimidin-2-one beta-ribofuranoside 1--D-Ribofuranosyl-2(1H)-pyrimidinone 4-Deoxyuridine NSC 309132 Pyrimidin-2-one -D-Ribofuranoside 1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 2-Pyrimidone-1-β-D-riboside 2(1H)-PyriMidinone, 1-b-D-ribofuranosyl- 4-Deoyuridine 1-b-D-ribofuranosyl-2-(1H)-pyriMidinone anticancer drug, DNA Methylation inhibitor 2(1H)-Pyrimidinone, 1-β-D-ribofuranosyl- 2-Pyrimidone-1-β-D-riboside 1-beta-D-Ribofuranosyl-2(1H)-pyrimidinone Pyrimidin-2-one beta-D-ribofuranoside Zebularine Zebularine Uridine Impurity 23 (Zebularine) 4-Deoyuridine, 1-beta-D-ribofuranosyl-2-(1H)-pyrimidinone Zebularine (NSC309132 2-HYDROXY-PYRIMIDINE-1-B-D-RIBOSIDE 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one 1-beta-D-Ribofuranosyl -l ,2-dihydropyrimidin-2-one NSC 309132,NSC-309132,DNMTs,Inhibitor,DNA MTases,Autophagy,Zebularine,DNA Methyltransferase,inhibit 4-Deoyuridine,Zebularine 2(1H)-Pyrimidinone, 1-beta-D-ribofuranosyl- Zebularine, DNA methyltransferase (DNMT) inhibitor Zebularine, 10 mM in DMSO Zebularine (NSC 309132) ，S7113 3690-10-6 Carbohydrates & Derivatives Inhibitors Intermediates & Fine Chemicals Pharmaceuticals