ZEBULARINE

Product Name: ZEBULARINE
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
Formula Weight: 228.2
MOL File: 3690-10-6.mol

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ZEBULARINE Property

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|

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Safety

WGK Germany: 3
RTECS: UW7539720
HS Code: 2934999090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H320Causes eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 691400
Product name: Zebularine
Packaging: 10mg
Price: $222
Updated: 2025/07/31

Sigma-Aldrich

Product number: 691400
Product name: Zebularine
Packaging: 25mg
Price: $488
Updated: 2025/07/31

TCI Chemical

Product number: Z0022
Product name: Zebularine
Purity: >98.0%(HPLC)(T)
Packaging: 200mg
Price: $183
Updated: 2025/07/31

TCI Chemical

Product number: Z0022
Product name: Zebularine
Purity: >98.0%(HPLC)(T)
Packaging: 1g
Price: $542
Updated: 2025/07/31

Cayman Chemical

Product number: 10975
Product name: Zebularine
Purity: ≥98%
Packaging: 1mg
Price: $26
Updated: 2024/03/01

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ZEBULARINE Chemical Properties,Usage,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

52523-24-7

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

Preparation Products

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ZEBULARINE Suppliers

Canada 1 China 122 India 3 Japan 1 Switzerland 1 The Netherlands 1 United Kingdom 4 United States 21 Global 154

Panaishen (Henan) Pharmaceutical Science and Technology Co. , Ltd.

Tel: 0371-65325800 13700860222
Email: haifeng.zhang@pannacean.com
Country: China
ProdList: 705
Advantage: 58

Zhengzhou Granlen Sciences, ltd.

Tel: 0371-85513397 +86-18610099868
Email: info@granlen.com
Country: China
ProdList: 1890
Advantage: 58

Fuyang Ziyi Biological Pharmaceutical Co., Ltd.

Tel: 19308655899; 19308655899
Fax: -
Email: 2677609105@qq.com
Country: China
ProdList: 500
Advantage: 58

J & K SCIENTIFIC LTD.

Tel: 18210857532; 18210857532
Fax: 86-10-82849933
Email: jkinfo@jkchemical.com
Country: China
ProdList: 96815
Advantage: 76

3B Pharmachem (Wuhan) International Co.,Ltd.

Tel: 821-50328103-801 18930552037
Fax: 86-21-50328109
Email: 3bsc@sina.com
Country: China
ProdList: 15838
Advantage: 69

TCI (Shanghai) Development Co., Ltd.

Tel: 021-67121386
Fax: 021-67121385
Email: Sales-CN@TCIchemicals.com
Country: China
ProdList: 24529
Advantage: 81

Beijing HwrkChemical Technology Co., Ltd

Tel: 18515581800 18501085097
Fax: 010-89508210
Email: sales.bj@hwrkchemical.com
Country: China
ProdList: 9400
Advantage: 55

Chemsky（shanghai）International Co.,Ltd.

Tel: 021-50135380
Email: shchemsky@sina.com
Country: China
ProdList: 32321
Advantage: 50

Jinan Trio PharmaTech Co., Ltd.

Tel: 0531-88811783
Fax: +86 (531) 55696010 QQ 1762738062
Email: sales@trio-pharmatech.com
Country: China
ProdList: 1856
Advantage: 62

Hangzhou Sage Chemical Co., Ltd.

Tel: +86057186818502 13588463833
Fax: Pls mail us for more information!
Email: info@sagechem.com
Country: China
ProdList: 10266
Advantage: 58

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View Lastest Price from ZEBULARINE manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: ZEBULARINE 3690-10-6
Price: US $1.00/Kg
Min. Order: 1Kg
Purity: 98%
Supply Ability: 20T
Release date: 2024-07-19

3690-10-6, ZEBULARINERelated 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-

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