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SULFAPHENAZOLE

Product Name
SULFAPHENAZOLE
CAS No.
526-08-9
Chemical Name
SULFAPHENAZOLE
Synonyms
SP;TFF2;Sulfabid;Sulfaphenazol;Sulphaphenazole;Sulfaphenylpyrazole;SML1;Orisul;Inamil;Isarol
CBNumber
CB4160540
Molecular Formula
C15H14N4O2S
Formula Weight
314.36
MOL File
526-08-9.mol
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SULFAPHENAZOLE Property

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
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Safety

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S0758
Product name
Sulfaphenazole
Purity
≥98%
Packaging
1g
Price
$294.4
Updated
2024/03/01
Sigma-Aldrich
Product number
S0758
Product name
Sulfaphenazole
Purity
≥98%
Packaging
5x1g
Price
$1390
Updated
2024/03/01
Sigma-Aldrich
Product number
SRP4745
Product name
TFF-2 human
Purity
recombinant, expressed in E. coli, ≥98% (SDS-PAGE), ≥98% (HPLC)
Packaging
20μg
Price
$353
Updated
2023/01/07
Cayman Chemical
Product number
14844
Product name
Sulfaphenazole
Purity
≥98%
Packaging
1g
Price
$232
Updated
2024/03/01
Cayman Chemical
Product number
14844
Product name
Sulfaphenazole
Purity
≥98%
Packaging
5g
Price
$923
Updated
2024/03/01
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SULFAPHENAZOLE Chemical Properties,Usage,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 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 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.

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 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

Preparation Products

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View Lastest Price from SULFAPHENAZOLE manufacturers

Dideu Industries Group Limited
Product
SULFAPHENAZOLE 526-08-9
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-14
Career Henan Chemical Co
Product
SULFAPHENAZOLE 526-08-9
Price
US $5.50/KG
Min. Order
1KG
Purity
98%min
Supply Ability
1kg-100kg
Release date
2020-01-10

526-08-9, SULFAPHENAZOLERelated Search:

Sulfadimethoxine sodium salt Sulfameter SULFAMETHIZOLE Sulfamonomethoxine Sulfamethazine Ketoconazole Enoxacin Voriconazole Janibacter melonis Aspergillus flavipes Sulfabenz 5-AMINO-1-PHENYLPYRAZOLE SULFAPHENAZOLE sulfapyrazole 1-PHENYLPYRAZOLE Sulfaclorazole N1-Acetyl sulfaphenazole sulfaphenazole-N2-glucuronide

  • 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
  • N<sup>1</sup>-(1-Phenylpyrazol-5-yl)sulfanilamide
  • Orisul
  • Orisulf
  • Paidazolo
  • Plisulfan
  • Raziosulfa
  • SP
  • Sulfabid
  • Sulfafenazolo
  • Sulfanilamide, N<sup>1</sup>-(1-phenylpyrazol-5-yl)-
  • Sulfaphenazon
  • Sulfaphenylpipazol
  • Sulfaphenylpyrazole
  • Sulphaphenazole
  • 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
  • Sulfaphenazole - Depocid | Depotsulfonamide | Plisulfan | Raziosulfa
  • 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
  • TFF2
  • Trefoil factor 2
  • 4-amino-N-(2-phenyl-3-pyrazolyl)benzenesulfonamide
  • N1-(1-Phenylpyraz