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Sulfaphenazole

Sulfaphenazole structure

CAS No:
526-08-9
Formula:
C15H14N4O2S
Chemical Name:
Sulfaphenazole
Synonyms:
Benzenesulfonamide,4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-;Sulfanilamide,N1-(1-phenylpyrazol-5-yl)-;4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide;3-(p-Aminobenzenesulfonamido)-2-phenylpyrazole;Depocid;Merian;Orisul;N1-(1-Phenylpyrazol-5-yl)sulfanilamide;1-Phenyl-5-sulfanilamidopyrazole;Sulfabid;5-Sulfanilamido-1-phenylpyrazole;Sulfaphenazol;Sulfaphenazole;Sulfaphenylpyrazole;Eftolon;2-Phenyl-3-sulfanilamidopyrazole;Depotsulfonamide;Sulfaphenazon;Sulphaphenazole;Inamil;Isarol;Paidazolo;Raziosulfa;Microtan pirazolo;Firmazolo;Plisulfan;Orisulf;Isarol V;165121-67-5
Categories:
Organic Chemistry > Amides

Description

Sulfaphenazole is a specific inhibitor of CYP2C9 which blocks atherogenic and pro-inflammatory effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Acts as an antibacterial and antimicrobial.

Solid

Sulfaphenazole is 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. It has a role as an antibacterial drug, an EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor, an EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor and a P450 inhibitor. It is a substituted aniline, a sulfonamide, a member of pyrazoles, a primary amino compound and a sulfonamide antibiotic.|Sulfaphenazole is a sulfonamide antibacterial.|Sulfaphenazole is a long-acting sulfonamide antibiotic used in the treatment of leprosy.|A sulfonilamide anti-infective agent.

Sulfaphenazole Basic Attributes

Molecular Weight：

314.36

Exact Mass：

314.36

EC Number：

208-384-3

UNII：

0J8L4V3F81

NSC Number：

757859

DSSTox ID：

DTXSID2044131

NCI Thesaurus Code：

C66569

ATC Code：

J - Antiinfectives for systemic use|S - Sensory organs

HScode：

2935009090

Characteristics

PSA：

98.4

XLogP3：

1.5

Appearance：

white to light yellow

Density：

1.397 g/cm³

Melting Point：

181 °C

Boiling Point：

541.9°C at 760 mmHg

Flash Point：

281.5±31.8 °C

Refractive Index：

1.684

Water Solubility：

0.6 [ug/mL]

Storage Conditions：

2-8°C

Toxicity：

Oral-mouse LD50: 4507 mg/kg; subcutaneous-rat LD50: 900 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Collision Cross Section：

170 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

24/25

RTECS Number：

DA9520000

Storage features：

Warehouse ventilated, low temperature and dry

Toxicity

Toxicity class：

moderately toxic

Drug Information

Drug Indication：

For the treatment bacterial infections.

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

Metabolism/Metabolites：

Hepatic.

Mechanism of Action：

Sulfaphenazole is a sulfonamide antibacterial. In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis. As such, the microorganism will be "starved" of folate and die.

MeSH Entry Terms：

Phenylsulfapyrazole

Sulfaphenazole Use and Manufacturing

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.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:314.4
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:314.08374688
Monoisotopic Mass:314.08374688
Topological Polar Surface Area:98.4
Heavy Atom Count:22
Complexity:451
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Hydrazine, phenyl-

Ethyl cyanoacetate

Sodium hydroxide

Ethyl acetate

Ethanol

Hydrochloric acid

Thionyl chloride

Chlorosulfonic acid

PETROLEUM ETHER

Recommended Suppliers of Sulfaphenazole

Compound Net Biotechnology Inc. Contact Supplier

CN
2 YRS

Business licensed Certified factory

Manufactory Supplier of 4-(Pentafluorothio)aniline,Pentafluoro,Pentafluorothio,Pentafluorosulfur,[4-(bromomethyl)phenyl]-pentafluoro-lambda6-sulfane,[4-(pentafluoro-sulfanyl)phenyl]acetic acid

526-08-9 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide

CAS No.: 526-08-9

Grade: Industrial Grade

Content: 95%

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