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5719-85-7

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5719-85-7 Usage

Description

4-hydroxy Tolbutamide is a cytochrome P450 2C8 (CYP2C8) and CYP2C9 metabolite of tolbutamide, a first-generation potassium channel blocker. Tolbutamide 4-hydroxylation is an often used probe reaction in the pharmaceutical industry for the characterization of CYP2C8 and CYP2C9 involvement in the metabolism of clinical drugs.

Chemical Properties

White Solid

Uses

4-Hydroxytolbutamide has been used as a standard to assay the fungal biotransformation of tolbutamide to 4′-hydroxytolbutamide.

Definition

ChEBI: A urea that consists of 1-butylurea having a 4-hydroxymethylbenzenesulfonyl group attached at the 3-position.

Check Digit Verification of cas no

The CAS Registry Mumber 5719-85-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,1 and 9 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 5719-85:
(6*5)+(5*7)+(4*1)+(3*9)+(2*8)+(1*5)=117
117 % 10 = 7
So 5719-85-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H10FN3O3S/c17-11-3-5-12(6-4-11)18-16-19-15(21)14(24-16)9-10-1-7-13(8-2-10)20(22)23/h1-9H,(H,18,19,21)

5719-85-7 Well-known Company Product Price

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  • Sigma

  • (UC160)  4-Hydroxytolbutamide  ≥98% (HPLC)

  • 5719-85-7

  • UC160-5MG

  • 7,458.75CNY

  • Detail
  • Sigma

  • (UC160)  4-Hydroxytolbutamide  ≥98% (HPLC)

  • 5719-85-7

  • UC160-10MG

  • 13,689.00CNY

  • Detail
  • Cerilliant

  • (H-054)  4-Hydroxytolbutamidesolution  1.0 mg/mL in acetonitrile, ampule of 1 mL, certified reference material

  • 5719-85-7

  • H-054-1ML

  • 1,096.29CNY

  • Detail

5719-85-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-hydroxytolbutamide

1.2 Other means of identification

Product number -
Other names 1-butyl-3-[4-(hydroxymethyl)phenyl]sulfonylurea

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5719-85-7 SDS

5719-85-7Relevant articles and documents

In vitro modulatory effects of flavonoids on human cytochrome P450 2C8 (CYP2C8)

Pang, Chia Yong,Mak, Joon Wah,Ismail, Rusli,Ong, Chin Eng

, p. 495 - 502 (2012)

The inhibitory effects of five flavonoidswith distinct chemical classes (flavones [luteolin], flavonols [quercetin and quercitrin], and flavanones [hesperetin and hespiridin]) on cDNA-expressed CYP2C8 were investigated. CYP2C8 was co-expressed with NADPH-

An improved synthesis of N-(butylaminocarbonyl)-4-hydroxymethyl-benzenesulfonamide, one of the metabolites of tolbutamide, and synthesis of its formyl derivative

Makaya,Irie,Shibasaki

, p. 2518 - 2519 (1983)

An improved synthesis of N-(butylaminocarbonyl)-4-hydroxymethyl-benzenesulfonamide, one of the metabolites of tolbutamide, and its transformation to the formyl derivative are described.

Electrochemically driven drug metabolism via cytochrome P450 2C9 isozyme microsomes with cytochrome P450 reductase and indium tin oxide nanoparticle composites

Xu, Xuan,Wei, Wei,Huang, Minghe,Yao, Li,Liu, Songqin

, p. 7802 - 7804 (2012)

We describe herein an electrochemically driven drug metabolism strategy based on nanocomposites that integrate cyt P450 2C9 (CYP2C9) isozyme microsomes with cyt P450 reductase (CPR), indium tin oxide (ITO) nanoparticles and chitosan (CS). This novel bioel

Benchmarking of laboratory evolved unspecific peroxygenases for the synthesis of human drug metabolites

Gomez de Santos, Patricia,Cervantes, Fadia V.,Tieves, Florian,Plou, Francisco J.,Hollmann, Frank,Alcalde, Miguel

, p. 1827 - 1831 (2019/02/24)

By mimicking the role of human liver P450 monooxygenases, fungal unspecific peroxygenases (UPOs) can perform a range of highly selective oxyfunctionalization reactions on pharmacological compounds, including O-dealkylations and hydroxylations, thereby simulating drug metabolism. Here we have benchmarked human drug metabolite (HDM) synthesis by several evolved UPO mutants, focusing on dextromethorphan, naproxen and tolbutamide. The HDM from dextromethorphan was prepared at the semi-preparative scale as a proof of production. The structural analysis of mutations involved in the synthesis of HDMs highlights the heme access channel as the main feature on which to focus when designing evolved UPOs. These variants are becoming emergent tools for the cost-effective synthesis of HDMs from next-generation drugs.

Acetylshikonin is a novel non-selective cytochrome P450 inhibitor

Shon, Jong Cheol,Phuc, Nguyen Minh,Kim, Won Cheol,Heo, Jae Kyung,Wu, Zhexue,Lee, Hyunyoung,Liu, Kwang-Hyeon

, p. 553 - 556 (2017/12/15)

Acetylshikonin is a biologically active compound with anti-cancer and anti-inflammatory activity, which is isolated from the roots of Lithospermum erythrorhizoma. An inhibitory effect of acetylshikonin against CYP2J2 activity was discovered recently. Based on this result, this study was expanded to evaluate the inhibitory effects of acetylshikonin against nine different cytochrome P450 (P450) isoforms in human liver microsomes (HLMs) using substrate cocktails incubation assay. Acetylshikonin showed a strong inhibitory effect against all P450s tested with IC50 values of 1.4–4.0 μ m. Pre-incubation of acetylshikonin with HLMs and NADPH did not alter the inhibition potency, indicating that acetylshikonin is not a mechanism-based inhibitor. SKF-525A, a widely used non-specific P450 inhibitor, had no inhibitory activity against CYP1A2, 2A6, 2E1 and 2J2, while it showed an inhibitory effect against CYP2B6, CYP2C19 and 2D6 with IC50 values of 2.5, 3.6 and 0.5 μ m, respectively. Our findings indicate that acetylshikonin may be a novel general P450 inhibitor, which could replace SKF-525A.

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