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ZEBULARINE

ZEBULARINE Structure
ZEBULARINE structure
CAS No.
3690-10-6
Chemical Name:
ZEBULARINE
Synonyms
1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one;1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one;NSC 309132;4-Deoyuridine;4-Deoxyuridine;Zebularine Zebularine;Zebularine (NSC309132;NSC309132;4-DEOXYURIDINE;4-Deoyuridine,Zebularine;Zebularine, 10 mM in DMSO
CBNumber:
CB4497499
Molecular Formula:
C9H12N2O5
Molecular Weight:
228.2
MDL Number:
MFCD04973699
MOL File:
3690-10-6.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-06-15 22:31:22
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ZEBULARINE Properties

Melting point 160-162C
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)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H320-H335
Precautionary statements  P264-P270-P301+P312-P330
PPE Eyeshields, Gloves, type N95 (US)
WGK Germany  3
RTECS  UW7539720
HS Code  2934999090
Storage Class 11 - Combustible Solids

ZEBULARINE price More Price(75)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 691400 Zebularine 3690-10-6 10mg $238 2026-04-30 Buy
Sigma-Aldrich 691400 Zebularine 3690-10-6 25mg $523 2026-04-30 Buy
TCI Chemical Z0022 Zebularine >98.0%(HPLC)(T) 3690-10-6 200mg $183 2026-04-30 Buy
TCI Chemical Z0022 Zebularine >98.0%(HPLC)(T) 3690-10-6 1g $542 2026-04-30 Buy
Cayman Chemical 10975 Zebularine ≥98% 3690-10-6 1mg $29 2026-04-30 Buy
Product number Packaging Price Buy
691400 10mg $238 Buy
691400 25mg $523 Buy
Z0022 200mg $183 Buy
Z0022 1g $542 Buy
10975 1mg $29 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( 154)Suppliers
Supplier Tel Email Country ProdList Advantage
Panaishen (Henan) Pharmaceutical Science and Technology Co. , Ltd. 0371-65325800 13700860222 haifeng.zhang@pannacean.com China 1455 58
Zhengzhou Granlen Sciences, ltd. 0371-85513397 +86-18610099868 info@granlen.com China 1890 58
Fuyang Ziyi Biological Pharmaceutical Co., Ltd. 19308655899; 19308655899 2677609105@qq.com China 500 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
3B Pharmachem (Wuhan) International Co.,Ltd. 18930552037 3bsc@sina.com China 15813 69
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Beijing HwrkChemical Technology Co., Ltd 89508211 18501085097 sales.bj@hwrkchemical.com China 9407 55
Chemsky（shanghai）International Co.,Ltd. 021-50135380 shchemsky@sina.com China 32273 50
Jinan Trio PharmaTech Co., Ltd. 0531-88811783 sales@trio-pharmatech.com China 1856 62
Hangzhou Sage Chemical Co., Ltd. +86057186818502 13588463833 info@sagechem.com China 10265 58
Supplier Advantage
Panaishen (Henan) Pharmaceutical Science and Technology Co. , Ltd. 58
Zhengzhou Granlen Sciences, ltd. 58
Fuyang Ziyi Biological Pharmaceutical Co., Ltd. 58
J & K SCIENTIFIC LTD. 76
3B Pharmachem (Wuhan) International Co.,Ltd. 69
TCI (Shanghai) Development Co., Ltd. 81
Beijing HwrkChemical Technology Co., Ltd 55
Chemsky（shanghai）International Co.,Ltd. 50
Jinan Trio PharmaTech Co., Ltd. 62
Hangzhou Sage Chemical Co., Ltd. 58

View Lastest Price from ZEBULARINE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Deoxyuridine; Zebularine; pictures 2026-06-30 4-Deoxyuridine; Zebularine;
3690-10-6
 1KG 98%+ 20Tons Shaanxi Dideu New Materials Co. Ltd
Zebularine pictures 2026-06-02 Zebularine
3690-10-6
 $38.00-127.00 99.84% 10g TargetMol Chemicals Inc.
ZEBULARINE pictures 2024-07-20 ZEBULARINE
3690-10-6
 $1.00 1Kg 98% 20T Shaanxi Dideu Medichem Co. Ltd
  • Zebularine pictures
  • Zebularine
    3690-10-6
  • $38.00-127.00
  • 99.84%
  • TargetMol Chemicals Inc.
  • ZEBULARINE pictures
  • ZEBULARINE
    3690-10-6
  • $1.00
  • 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
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Zebularine - CAS 3690-10-6 - Calbiochem NSC309132;4-DEOXYURIDINE 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 1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one 1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one 3690-10-6 Carbohydrates & Derivatives Inhibitors Intermediates & Fine Chemicals Pharmaceuticals