Grundinformationen
- CAS
526-08-9- Standard-SMILES
Nc1ccc(S(=O)(=O)Nc2ccnn2-c2ccccc2)cc1- InChIKey
QWCJHSGMANYXCW-UHFFFAOYSA-N- Summenformel
- C15H14N4O2S
- Durchschnittliche Molmasse
- 314,4 g/mol
- Monoisotopische Masse
- 314,08374688
Überblick
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, a P450 inhibitor, an EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor and an EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor. It is a member of pyrazoles, a sulfonamide, a substituted aniline, a primary amino compound and a sulfonamide antibiotic.
Namen und Bezeichner
- Bevorzugter Name
- Sulfaphenazole
- IUPAC
- 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
- Lokaler Name
- Sulfaphenazol
- Englischer Name
- SULFAPHENAZOLE
- Summenformel
- C15H14N4O2S
- Molmasse
- 314.36
Namen und Synonyme
sulfaphenazole526-08-9SulphaphenazoleSulfabid4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamideSulfafenazolSulfaphenazolSulfaphenazolumSulfafenazoloSulfaphenylpyrazol1-Phenyl-5-sulfanilamidopyrazole5-Sulfanilamido-1-phenylpyrazole
Weitere Namen anzeigen
SPTFF2Trefoil factor 2SulfaphenylpyrazoleSML1OrisulInamil
N'-(1-Phenylpyrazol-5-yl)sulfanilamide4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamidePhenylsulfapyrazoleOrisulf3-(p-Aminobenzenesulfonamido)-2-phenylpyrazoleBenzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-DTXSID20441314-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide
Datenbank-Bezeichner
- CAS
526-08-9- PubChem CID
- 5335
- DTXSID
DTXSID2044131- ChEMBL
CHEMBL1109- ChEBI
CHEBI:77780- UNII
- 0J8L4V3F81
- EC Number
- 208-384-3
- Nikkaji
- J2.062A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 98,4 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 451
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
1.52
1.35
Solubility0.6 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point101 °C
Physical DescriptionSolid
Collision Cross Section
157.93 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 179 · 179-183 °C
- Siedepunkt
- 541.9 · 541.9±56.0 °C(Predicted)
- Dichte
- 1.39 · 1.39
- Brechungsindex
- 1.644 · 1.6440 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 5.71 · pKa 5.71(H2O t = 25 I = 0.05) (Uncertain)
- Farbe
- white to light yellow
- InChI
- InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2
- InChIKey
- QWCJHSGMANYXCW-UHFFFAOYSA-N
- SMILES
- C1(S(NC2N(C3=CC=CC=C3)N=CC=2)(=O)=O)=CC=C(N)C=C1
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 2
- hs_code
- 29339900
- RTECS-Nr.
- DA9520000
- Toxizität
- LD50 orally in mice: 5800 mg/kg (Seki)
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QS - Sensory organs
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.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Cellular LocationsMembrane
Verwendung und Herstellung
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Anwendungen
BeschreibungCYP2C9 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter100 Anbieter
国药集团化学试剂有限公司86-21-63210123 · [email protected]
汇智和源生物技术(苏州)有限公司010-59755330 13701268334 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
上海钰博生物科技有限公司021-60514606 18321282235 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
上海腾准生物科技有限公司19821570922 · [email protected]
武汉布林科技有限公司3456065315 13260619011 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Syntechem Co.,Ltd[email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
欧利希（湖北）医药科技有限公司17316404525 17316404525 · [email protected]
上海臻科生物科技有限公司17317792356 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
上海艾梯西生物科技有限公司18721763493 · [email protected]
学研惠（武汉）科技有限公司15727060112 · [email protected]
VDM Biochemicals0330-2528181 · [email protected]
郑州研德生物科技有限公司0371-63682289 15538176268 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海心语生物科技有限公司13301728348 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
成都麦卡希化工有限公司028-85632863 18108198598 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
北京奥秘佳得医药科技有限公司+86-13522808617 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海鑫圭生物科技有限公司15121041756 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海楼岚生物科技有限公司021-52996696，15000506266 15000506266
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海博湖生物科技有限公司57763112 18930344717 · [email protected]
Ergänzende Hinweise
DefinitionChEBI: 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.
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…