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SULFAPHENAZOLE

SULFAPHENAZOLE Structure
SULFAPHENAZOLE structure
CAS No.
526-08-9
Chemical Name:
SULFAPHENAZOLE
Synonyms
SP;TFF2;Sulfabid;Sulfaphenazol;Sulphaphenazole;Sulfaphenylpyrazole;SML1;Orisul;Inamil;Isarol
CBNumber:
CB4160540
Molecular Formula:
C15H14N4O2S
Molecular Weight:
314.36
MDL Number:
MFCD00057226
MOL File:
526-08-9.mol
MSDS File:
SDS
Last updated:2023-05-18 11:31:06
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SULFAPHENAZOLE Properties

Melting point 179-183 °C
Boiling point 541.9±56.0 °C(Predicted)
Density 1.39
refractive index 1.6440 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka pKa 5.71(H2O t = 25 I = 0.05) (Uncertain)
color white to light yellow
EWG's Food Scores 1
FDA UNII 0J8L4V3F81
ATC code J01ED08

SAFETY

Risk and Safety Statements

Safety Statements  24/25
WGK Germany  2
RTECS  DA9520000
HS Code  29339900
Toxicity LD50 orally in mice: 5800 mg/kg (Seki)

SULFAPHENAZOLE price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich S0758 Sulfaphenazole ≥98% 526-08-9 1g $294.4 2024-03-01 Buy
Sigma-Aldrich S0758 Sulfaphenazole ≥98% 526-08-9 5x1g $1390 2024-03-01 Buy
Sigma-Aldrich SRP4745 TFF-2 human recombinant, expressed in E. coli, ≥98% (SDS-PAGE), ≥98% (HPLC) 526-08-9 20μg $353 2023-01-07 Buy
Cayman Chemical 14844 Sulfaphenazole ≥98% 526-08-9 1g $232 2024-03-01 Buy
Cayman Chemical 14844 Sulfaphenazole ≥98% 526-08-9 5g $923 2024-03-01 Buy
Product number Packaging Price Buy
S0758 1g $294.4 Buy
S0758 5x1g $1390 Buy
SRP4745 20μg $353 Buy
14844 1g $232 Buy
14844 5g $923 Buy

SULFAPHENAZOLE Chemical Properties,Uses,Production

Description

CYP2C9 is a major cytochrome P450 enzyme that is involved in the metabolic clearance of various therapeutic agents. Disruption of this enzyme’s activity can lead to adverse drug reactions. Sulfaphenazole is an inhibitor of CYP2C9 (Ki = 0.3 μM) that demonstrates at least 100-fold selectivity over other CYP450 isoforms (Kis = 63 and 29 μM for CYP2C8 and CYP2C18, respectively, and no activity at CYP1A1, CYP1A2, CYP3A4, CYP2C19). At 10 μM, sulfaphenazole has been shown to inhibit endothelium-derived hyperpolarizing factor synthase, a CYP450 isozyme in the porcine coronary artery homologous to CYP2C8/9 that generates reactive oxygen species in coronary endothelial cells and modulates vascular tone and homeostasis.

Chemical Properties

White to off-white powder

Uses

Sulfaphenazole has been used as a positive control to inhibit cytochrome P450 2C9 (cyp2c9) to quantify Rhodiola rosea inhibition. It has also been used as cytochrome P450 2C9 (cyp2c9) inhibitor in endothelial cells and microsomal preparations.

Uses

Sulfaphenazole is used as an inhibitor for mammalian CYP2C9, an enzyme of the cytochrome P450 family allowing for pharmacological application.Sulfaphenazole can help protect against ischemia-reperfusion, and resulting tissue damage by inhibition of CYP2C9.

Uses

Sulfaphenazole is used as an inhibitor for mammalian CYP2C9, an enzyme of the cytochrome P450 family allowing for pharmacological application. Sulfaphenazole can help protect against ischemia-reperfus ion, and resulting tissue damage by inhibition of CYP2C9.

Definition

ChEBI: A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.

Biochem/physiol Actions

Antibacterial. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Inhibits bradykinin-induced tPA release.

in vitro

in yeast expressed human cytochromes p450 of the 1a, 3a, and 2c subfamilies, sulfaphenazole acts as a strong and competitive inhibitor of cyp 2c9 with the ki value of 0.3 ± 0.1 μm. the ki values of sulfaphenazole for cyp 2c8 and 2c18 were 63 and 29 μm, respectively. sulfaphenazole failed to inhibit cyp 1a1, 1a2, 3a4, and 2c19 [1].

in vivo

in diabetic male mice (db/db strain), daily intraperitoneal injections of either the cyp 2c inhibitor sulfaphenazole (5.13 mg/kg) for 8 weeks, sulfaphenazole restored endothelium-mediated relaxation in db/db mice. sulfaphenazole reduced oxidative stress, increased no bioavailability and restored endothelial function in db/db mice [3].

Purification Methods

Crystallise it from EtOH or aqueous EtOH. [Schmidt & Druey Helv Chim Acta 41 309 1958, Beilstein 25 III/IV 2029.]

References

[1] mancy a, dijols s, poli s, et al. interaction of sulfaphenazole derivatives with human liver cytochromes p450 2c: molecular origin of the specific inhibitory effects of sulfaphenazole on cyp 2c9 and consequences for the substrate binding site topology of cyp 2c9[j]. biochemistry, 1996, 35(50): 16205-16212.
[2] rettie a e, jones j p. clinical and toxicological relevance of cyp2c9: drug-drug interactions and pharmacogenetics[j]. annu. rev. pharmacol. toxicol., 2005, 45: 477-494.
[3] elmi s, sallam n a, rahman m m, et al. sulfaphenazole treatment restores endothelium-dependent vasodilation in diabetic mice[j]. vascular pharmacology, 2008, 48(1): 1-8.

SULFAPHENAZOLE synthesis

93880-94-5
526-08-9
Synthesis of SULFAPHENAZOLE from [4-(2-Phenyl-2H-pyrazol-3-ylsulfamoyl)-phenyl]-carbamic acid ethyl ester

SULFAPHENAZOLE Preparation Products And Raw materials

Raw materials

Sodium dithionite Ethanol Triethyl orthoformate 5-AMINO-1-PHENYLPYRAZOLE Chlorosulfonic acid
Ethyl acetate Hydrochloric acid Sodium hydroxide Thionyl chloride 4-NITROBENZENESULFONIC ACID
Phenylhydrazine PETROLEUM ETHER PHENYLURETHANE Ethyl cyanoacetate

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Preparation Products

SULFAPHENAZOLE Suppliers

Global( 167)Suppliers
Supplier Tel Email Country ProdList Advantage
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32480 60
Hubei xin bonus chemical co. LTD 		86-13657291602 linda@hubeijusheng.com CHINA 22968 58
CONIER CHEM AND PHARMA LIMITED 		+8618523575427 sales@conier.com China 49390 58
career henan chemical co 		+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
Shaanxi Dideu Medichem Co. Ltd 		+86-029-81148696 +8615536356810 1047@dideu.com China 3408 58
Dideu Industries Group Limited 		+86-29-89586680 +86-15129568250 1026@dideu.com China 29220 58
AFINE CHEMICALS LIMITED 		0571-85134551 info@afinechem.com CHINA 15377 58
InvivoChem 		+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6393 58
TargetMol Chemicals Inc. 		+1-781-999-5354 support@targetmol.com United States 19973 58
ZHEJIANG JIUZHOU CHEM CO., LTD 		+86-0576225566889 +86-13454675544 admin@jiuzhou-chem.com；jamie@jiuzhou-chem.com；alice@jiuzhou-chem.com China 20000 58
Supplier Advantage
ATK CHEMICAL COMPANY LIMITED 		60
Hubei xin bonus chemical co. LTD 		58
CONIER CHEM AND PHARMA LIMITED 		58
career henan chemical co 		58
Shaanxi Dideu Medichem Co. Ltd 		58
Dideu Industries Group Limited 		58
AFINE CHEMICALS LIMITED 		58
InvivoChem 		58
TargetMol Chemicals Inc. 		58
ZHEJIANG JIUZHOU CHEM CO., LTD 		58

View Lastest Price from SULFAPHENAZOLE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
SULFAPHENAZOLE USP/EP/BP pictures 2021-07-16 SULFAPHENAZOLE USP/EP/BP
526-08-9
 US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
Sulfaphenazole pictures 2020-06-20 Sulfaphenazole
526-08-9
 US $884.00 / KG 1KG 98.0% 21T Shaanxi Dideu Medichem Co. Ltd
SULFAPHENAZOLE pictures 2020-01-13 SULFAPHENAZOLE
526-08-9
 US $5.50 / KG 1KG 98%min 1kg-100kg Career Henan Chemical Co

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LABOTEST-BB LT00772280 4-AMINO-N-(1-PHENYL-1H-PYRAZOL-5-YL)BENZENESULFONAMIDE n(sup1)-(1-phenylpyrazol-5-yl)sulfanilamide n’-(1-phenylpyrazol-5-yl)sulfanilamide N1-(1-Phenylpyrazol-5-yl)sulfanilamide Orisul Orisulf Paidazolo Plisulfan Raziosulfa Sulfafenazolo Sulfanilamide, N1-(1-phenylpyrazol-5-yl)- Sulfaphenazon Sulfaphenylpipazol Sulphenazole SULFAPHENAZOLE Eftolan Sulfiam 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide 4-azanyl-N-(2-phenylpyrazol-3-yl)benzenesulfonamide Sulfaphenazole ,99% Sulfaphenazole,4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide N1-(1-phenylpyrazol-5-yl)sulphanilamide SULFAPHENZAOLE N1-(1-Phenylpyrazol-5-yl)sulfanilamide Sulfaphenazole Solution, 100ppm pS2 protein 1-Phenyl-5-sulfanilamidopyrazole 3-(p-Aminobenzenesulfonamido)-2-pheny-2H-lpyrazole 3-(p-aminobenzenesulfonamido)-2-phenylpyrazole 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)-benzenesulfonamid 5-Sulfanilamido-1-phenylpyrazole Benzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)- Depocid Depotsulfonamide Eftolon Firmazolo Inamil Isarol Isarol V Merian Microtan pirazolo microtanpirazolo N'-(1-Phenylpyrazol-5-yl)sulfanilamide n(sup1)-(1-phenylpyrazol-5-yl)-sulfanilamid TFF-2 human Trefoil Factor peptide SML1 Spasmolytic polypeptide Trefoil factor 2 4-amino-N-(2-phenyl-3-pyrazolyl)benzenesulfonamide N1-(1-Phenylpyraz Sulfaphenazole - Depocid | Depotsulfonamide | Plisulfan | Raziosulfa aesculi coniospora sp. JSM071073 sp. L-1 sp. S13