SULFAPHENAZOLE | 526-08-9

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
UNSPSC Code	12352204
NACRES	NA.77

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 (K_i = 0.3 μM) that demonstrates at least 100-fold selectivity over other CYP450 isoforms (K_is = 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 synthesis

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( 190)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	33024	60
Hubei xin bonus chemical co. LTD	86-13657291602	linda@hubeijusheng.com	CHINA	22963	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49732	58
career henan chemical co	+86-0371-86658258 +8613203830695	factory@coreychem.com	China	29807	58
Zhengzhou Alfa Chemical Co.,Ltd	+8618530059196	sale04@alfachem.cn	China	12197	58
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	marketing@targetmol.com	United States	32268	58
Dideu Industries Group Limited	+86-29-89586680 +86-15129568250	1026@dideu.com	China	22866	58
AFINE CHEMICALS LIMITED	+86-0571-85134551	sales@afinechem.com	China	15417	58
Finetech Industry Limited	+86-27-8746-5837 +8619945049750	info@finetechnology-ind.com	China	9642	58
InvivoChem	+1-708-310-1919 +1-13798911105	sales@invivochem.cn	United States	6391	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
Zhengzhou Alfa Chemical Co.,Ltd	58
TargetMol Chemicals Inc.	58
Dideu Industries Group Limited	58
AFINE CHEMICALS LIMITED	58
Finetech Industry Limited	58
InvivoChem	58

View Lastest Price from SULFAPHENAZOLE manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2025-04-28	Sulfaphenazole 526-08-9	US $50.00 / mg		98.83%	10g	TargetMol Chemicals Inc.
2021-07-16	SULFAPHENAZOLE USP/EP/BP 526-08-9	US $1.10 / g	1g	99.9%	100 Tons Min	Dideu Industries Group Limited
2020-01-13	SULFAPHENAZOLE 526-08-9	US $5.50 / KG	1KG	98%min	1kg-100kg	Career Henan Chemical Co

Sulfaphenazole
526-08-9
US $50.00 / mg
98.83%
TargetMol Chemicals Inc.

SULFAPHENAZOLE USP/EP/BP
526-08-9
US $1.10 / g
99.9%
Dideu Industries Group Limited

SULFAPHENAZOLE
526-08-9
US $5.50 / KG
98%min
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 SP Sulfabid Sulfafenazolo Sulfanilamide, N¹-(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