Sulfafurazole - Misplaced Pages

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Not to be confused with sulfadiazine.

Pharmaceutical compound

Sulfafurazole
Clinical data

AHFS/Drugs.com	International Drug Names
MedlinePlus	a601049
Pregnancy category	To be avoided within two months of term
Routes of administration	Oral
ATC code	J01EB05 (WHO) S01AB02 (WHO) QJ01EQ05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Excretion	Excreted unchanged in urine
Identifiers
IUPAC name 4-Amino-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide
CAS Number	127-69-5
PubChem CID	5344
DrugBank	DB00263
ChemSpider	5151
UNII	740T4C525W
KEGG	D00450
ChEMBL	ChEMBL453
CompTox Dashboard (EPA)	DTXSID6021292
ECHA InfoCard	100.004.418
Chemical and physical data
Formula	C₁₁H₁₃N₃O₃S
Molar mass	267.30 g·mol
3D model (JSmol)	Interactive image
Melting point	194 °C (381 °F)
SMILES CC1=C(ON=C1C)NS(=O)(=O)C2=CC=C(C=C2)N
InChI InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3 Key:NHUHCSRWZMLRLA-UHFFFAOYSA-N
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Sulfafurazole (INN, also known as sulfisoxazole) is a sulfonamide antibacterial with a dimethyl-isoxazole substituent. It possesses antibiotic activity against a wide range of Gram-negative and Gram-positive organisms. It is sometimes given in combination with erythromycin (see erythromycin/Sulfafurazole) or phenazopyridine. It is used locally in a 4% solution or ointment.

References

Holmes NE, Grauson ML (October 2017). "Sulfonamides". In Paterson DL, McCarthy JS, Mouton JW, Mills J, Grayson ML, Cosgrove SE, Crowe S, Hope W (eds.). Kucers' The Use of Antibiotics (7th ed.). CRC Press. pp. 1571–1624. ISBN 978-1-4987-4796-7.

External links

Sulfisoxazole at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
MedlinePlus DrugInfo medmaster-a601049
MedlinePlus DrugInfo medmaster-a601115
Diseases Database (DDB): 30455

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine (Sulfamethazine, Sulfadimerazine, Sulfadimezine) Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin Ofloxacin Enoxacin Fleroxacin Lomefloxacin Nadifloxacin/Levonadifloxacin/Alalevonadifloxacin Norfloxacin Pefloxacin Rufloxacin
3rd generation	Levofloxacin Balofloxacin Grepafloxacin Pazufloxacin Sparfloxacin Temafloxacin Tosufloxacin
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin Garenoxacin Prulifloxacin Sitafloxacin Trovafloxacin/Alatrofloxacin
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin Rifabutin Rifapentine Rifaximin Rifalazil
Lipiarmycins	Fidaxomicin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

v t e Ophthalmologicals: anti-infectives (S01A)
Antibiotics	amphenicols (Chloramphenicol Azidamfenicol) tetracyclines (Tetracycline Chlortetracycline Oxytetracycline) aminoglycosides (Dihydrostreptomycin Neomycin Framycetin Kanamycin Amikacin Tobramycin Gentamicin Netilmicin Micronomicin) macrolides (Erythromycin Natamycin) beta-lactams (Ampicillin Benzylpenicillin) polypeptides (Polymyxin B Tyrothricin) Rifamycin Fusidic acid
Sulfonamides	Sulfacetamide Sulfadicramide Sulfafenazol Sulfafurazole Sulfamethizole
Antivirals	Aciclovir Famciclovir Fomivirsen Ganciclovir Idoxuridine Interferon Trifluridine Vidarabine
Fluoroquinolones	Besifloxacin Ciprofloxacin Gatifloxacin Levofloxacin (+dexamethasone) Lomefloxacin Moxifloxacin Norfloxacin Ofloxacin Tosufloxacin
Other	Bibrocathol Chlorhexidine Dibrompropamidine Hexamidine Nitrofural Picloxydine Polihexanide Povidone-iodine Propamidine Resorcinol Sodium borate Sodium propionate

v t e Xenobiotic-sensing receptor modulators
CARTooltip Constitutive androstane receptor	Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Pregnanedione (5β-dihydroprogesterone) Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproic acid Antagonists: 3,17β-Estradiol 3α-Androstanol 3α-Androstenol 3β-Androstanol 17-Androstanol AITC Ethinylestradiol Meclizine Nigramide J Okadaic acid PK-11195 S-07662 T-0901317
PXRTooltip Pregnane X receptor	Agonists: 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Δ-Androstenedione Δ-Androstenediol Δ-Androstenedione AA-861 Allopregnanediol Allopregnanedione (5α-dihydroprogesterone) Allopregnanolone (brexanolone) Alpha-Lipoic acid Ambrisentan AMI-193 Amlodipine besylate Antimycotics Artemisinin Aurothioglucose Bile acids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproterone acetate Demecolcine Dexamethasone DHEA (prasterone) DHEA-S (prasterone sulfate) Dibunate sodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusate calcium Dodecylbenzenesulfonic acid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene Epothilone B Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillin potassium Hyperforin Hypericum perforatum (St John's wort) Indinavir sulfate Lasalocid sodium Levothyroxine Linolenic acid: α-Linolenic acid and γ-Linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanediol Pregnanedione (5β-dihydroprogesterone) Pregnanolone Pregnenolone Pregnenolone 16α-carbonitrile Proadifen Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR-12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosterone isocaproate Tetracycline Thiamylal sodium Thiothixene Thonzonium bromide Tianeptine Troglitazone Troleandomycin Tropanyl 3,5-dimethulbenzoate Zafirlukast Zeranol Antagonists: Ketoconazole Sesamin
See also Receptor/signaling modulators

Xenobiotic-sensing receptor modulators

CARTooltip Constitutive androstane receptor

PXRTooltip Pregnane X receptor

Antagonists: Ketoconazole
Sesamin

See also: Receptor/signaling modulators

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