526-08-9
| Name | SULFAPHENAZOLE |
| CAS | 526-08-9 |
| EINECS(EC#) | 208-384-3 |
| Molecular Formula | C15H14N4O2S |
| MDL Number | MFCD00057226 |
| Molecular Weight | 314.36 |
| MOL File | 526-08-9.mol |
Synonyms
SP
SML1
TFF2
Inamil
Isarol
Merian
Orisul
roseum
maydis
minuta
melonis
humphik
Orisulf
Eftolan
Sulfiam
Depocid
Eftolon
sp. L-1
aesculi
sp. S13
Isarol V
Sulfabid
rostrata
faecalis
graminis
glutinis
herbarum
hirsutum
digitata
minitans
candidum
lignicola
byssoides
abyssalis
Paidazolo
Plisulfan
Firmazolo
coniospora
Raziosulfa
rubra B072
stemonitis
sp. YJ0218
carmocolor
chroococcum
macrocladum
minutissima
destructans
sp. Xmu 198
pS2 protein
TFF-2 human
Sulphenazole
deliquescens
halotolerans
mucilaginosa
Humicola sp.
Laceyella sp.
laevolacticus
missouriensis
Mitsuaria sp.
candidum A040
chenghaiensis
Sulfaphenazol
sp. YMF1.1504
sp. YIM 95754
Sulfafenazolo
Sulfaphenazon
sp. JSM071073
sp. YIM 49053
sp. YIM 93033
sp. YIM 93155
sp. YIM 93306
sp. YIM 93390
sp. YIM 690225
SULFAPHENAZOLE
SULFAPHENZAOLE
rubra GIM2.157
sphacrospermum
sp. JSM 078151
sp. JSM 081008
sp. JSM 084035
sp. JSM 102045
Gordonia sputi
Idiomarina Sp.
sp. DSM 100964
sp. DSM 100965
sp. DSM 101017
Janibacter sp.
Rhodobacter sp.
mucilaginosa B1
nanticum NH64H1
Gliocladium sp.
Gilmaniella sp.
Gemmobacter sp.
Sulphaphenazole
sp. SCSIO 00235
Trefoil factor 2
microtanpirazolo
Depotsulfonamide
enshiensis DW2-9
Geotrichum gigas
indicus NIO-1018
candidum GIM2.69
candidum AS2.616
citrea DSM 44097
Rhodotorula sp.
Microbulbifer sp.
mediolanus JPSC-2
candidum AS 2.361
candidum AS2.1035
glutinis AS 2.703
Gordonia amicalis
Microtan pirazolo
N1-(1-Phenylpyraz
Sulfaphenylpipazol
Janibacter limosus
Herbaspirillum sp.
coxensis DSM 44901
aurea CGMCC 4.7147
Catellatospora sp.
melonis An-10-2C-P
Marinococcus luteus
Staphylotrichum sp.
Acidovorax radicis
Mortierella vinacea
Sulfaphenylpyrazole
Sulfaphenazole ,99%
Nectria haematococca
Mortierella elongata
Rhodotorula glutinis
Jiangella gansuensis
kunshanensis sp/ nov/
Rhodobacter capsulata
Geotrichum fermentans
Macrophoma kuwatsukai
Rhodotorula glacialis
Dactylosporangium sp.
Herbaspirillum putei
Idiomarina loihiensis
LABOTEST-BB LT00772280
Trefoil Factor peptide
Mortierella isabellina
Mortierella ramanniana
Microbispora griseola
missouriensis Na-5-1-p
chokoriensis DSM 44900
Caulobacter vibrioides
Microbulbifer elongate
Janthinobacterium sp.
Agromyces aurantiacus
Lentzea flaviverrucosa
Geotrichum sp. AS 2.572
Mortierella polycephala
Spasmolytic polypeptide
Gliocladium catenulatum
Gordonia rubripertincta
Acidiphilium cryptumy1
sp. HSLHS2（=MCCC1A06712）
Rhodotorula mucilaginosa
Georgenia ruanii sp. nov
candidum B 043 =AS 2.361
Bipolaris australiensis
alkaliphilus SCSIO 10480
Rhodotorula creatinivora
SULFAPHENAZOLE USP/EP/BP
Laceyella tengchongensis
Jiangella alba DSM 45237
Rhodobacter azotoformans
Microbulbifer maritimus
Microbulbifer salipaludis
Jeotgalibacillus marinus
italicus ATCC =ATCC 27366
fuscoaurantiacum Y80-2063
Gliocladium deliguescens
faecalis subsp. Phenolicus
Rhodotorula rubra AS 2.166
Rhodotorula rubra AS 2.167
methionotrophica DSM 44098
Rhodotorula rubra AS 2.21
Rhodotorula rubra AS 2.670
Chryseobacterium taiwanense
Circinella mudcae AS 3.2695
Actinopolymorpha DSM 45243
Rhodotorula minuta AS 2.277
Idiomarina maris KACC 13974
Circinella aspera AS 3.3397
Catellatospora chokoriensis
Caulobacter hibisci sp. nov.
Geotrichum candidum AS 2.1175
Gliocladium roseum AS 3.3657
Geotrichum candidum AS 2.361
Geotrichum candidum AS 2.498
Geotrichum ludwigii AS 2.363
Gliocladium roseum AS 3.3655
Georgenia halophila DSM 21365
Rhodotorula sinensis AS 2.1391
Dendryphiopsis atra AS 3.3619
Geotrichum candidum AS 2.1183
Marinococcus luteus KCTC 13214
Mangrovibacter yixingense 
missouriensis ATCC =ATCC 14538
Rhodotorula glutinis AS 2.499
Kushneria sinocarnis DSM 23229
Circinella umbellata AS 3.3399
Herbaspirillum rubrisubalbicans
Geotrichum suaveolens AS 2.364
Alcaligenes aquatilis LMG 22996
Sulfaphenazole Solution, 100ppm
1-Phenyl-5-sulfanilamidopyrazole
5-Sulfanilamido-1-phenylpyrazole
Laceyella sediminis sp DSM 45263
Janthinobacterium agaricidamnosum
Actinopolymorpha rutila DSM 18448
Cylindrocarpon magnusiana AS 3.3677
Geotrichum penicillatum ATCC 42397
Georgenia satyanarayanai KCTC 19802
Gordonia neofelifaecis NRRL B-59395
Idiomarina xiamenensis MCCC 1A01370
N'-(1-Phenylpyrazol-5-yl)sulfanilamide
N1-(1-Phenylpyrazol-5-yl)sulfanilamide
n’-(1-phenylpyrazol-5-yl)sulfanilamide
Alcaligenes faecalis subsp. Phenolicus
Recombinant Human TFF2 Protein, His Tag
N1-(1-phenylpyrazol-5-yl)sulphanilamide
n(sup1)-(1-phenylpyrazol-5-yl)sulfanilamide
n(sup1)-(1-phenylpyrazol-5-yl)-sulfanilamid
Marinactinospora thermotolerans sp DSM 45154
3-(p-aminobenzenesulfonamido)-2-phenylpyrazole
N<sup>1</sup>-(1-Phenylpyrazol-5-yl)sulfanilamide
halophilus DSM 20408=CCM 2706=JCM 2479=NRCC 14033
3-(p-Aminobenzenesulfonamido)-2-pheny-2H-lpyrazole
4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
4-amino-N-(2-phenyl-3-pyrazolyl)benzenesulfonamide
4-azanyl-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
Sulfanilamide, N<sup>1</sup>-(1-phenylpyrazol-5-yl)-
4-AMINO-N-(1-PHENYL-1H-PYRAZOL-5-YL)BENZENESULFONAMIDE
4-amino-n-(1-phenyl-1h-pyrazol-5-yl)-benzenesulfonamid
Benzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-
Sulfaphenazole - Depocid | Depotsulfonamide | Plisulfan | Raziosulfa
Sulfaphenazole,4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide
Chemical 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 |
| 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 |
Safety Data
| Safety Statements | |
| WGK Germany | 2 |
| RTECS | DA9520000 |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Toxicity |
LD50 orally in mice: 5800 mg/kg (Seki)
|
Hazard Information
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.1 Sulfaphenazole is an inhibitor of CYP2C9 (Ki = 0.3 μM) that demonstrates at least 100-
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-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.
[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.
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