Sulfathiazole

Sulfathiazole
Clinical data
Imino (top) and amino (bottom) tautomers
AHFS/Drugs.com	International Drug Names
ATC code	D06BA02 (WHO) J01EB07 (WHO) QJ01EQ07 (WHO)
Identifiers
IUPAC name 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide
CAS Number	72-14-0^Y
PubChem (CID)	5340
DrugBank	DB06147^Y
ChemSpider	5148^Y
UNII	Y7FKS2XWQH^Y
KEGG	D01047^Y
ChEBI	CHEBI:9337^Y
ChEMBL	CHEMBL437^Y
ECHA InfoCard	100.000.701
Chemical and physical data
Formula	C₉H₉N₃O₂S₂
Molar mass	255.319 g/mol
3D model (Jmol)	Interactive image
Melting point	202 to 202.5 °C (395.6 to 396.5 °F)
SMILES O=S(=O)(Nc1nccs1)c2ccc(N)cc2
InChI InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)^Y Key:JNMRHUJNCSQMMB-UHFFFAOYSA-N^Y
(verify)

Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug. It is an organic compound. Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide, and in aquariums.

It exists in various forms (polymorphs). The imine tautomer is dominant, at least in the solid state. In this tautomer, the proton resides on the ring nitrogen.^[1]

Cultural references

Sulfathiazole is mentioned in chapter 104 of Kurt Vonnegut's novel Cat's Cradle and New Dictionary, and several of his short stories. Thomas Heggen's 1946 novel Mister Roberts mentions the use of sulfathiazole to treat gonorrhea, and Sonya Dorman's short story When I was Miss Dow in 1966. Also the 1988 movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies. In Otto Preminger's 1960 movie Exodus, American nurse Kitty Fremont tells Dr. Odenheimer that sulfathiazole is the treatment for impetigo. Dr. Odenheimer tells her that sulfathiazole is not available on the ship; soaking of the lesions and exposure to sunlight "is also a cure."

Sulfathiazole is mentioned in "The World According To Garp" in chapter 1 where Garps mother witnesses it being dispensed to World War II soldiers.

References

↑ G. J. Kruger and G. Gafner "The crystal structure of sulphathiazole II" Acta Crystallogr. (1971). B27, 326-333.doi:10.1107/S0567740871002176

Antibiotics and chemotherapeutics for dermatological use (D06)

Antibiotics

Tetracycline and derivatives	Demeclocycline Chlortetracycline Oxytetracycline Tetracycline

Others	Amphenicol: Chloramphenicol Aminoglycosides: Neomycin Gentamicin Amikacin Quinolone: Nadifloxacin Streptogramin: Virginiamycin Rifamycin: Rifaximin other: Fusidic acid Bacitracin Tyrothricin Mupirocin

Chemotherapeutics

Sulfonamides	Silver sulfadiazine Sulfathiazole Mafenide Sulfamethizole Sulfanilamide Sulfamerazine

Antivirals	Aciclovir Penciclovir Idoxuridine Edoxudine Imiquimod Resiquimod Podophyllotoxin Docosanol Tromantadine Inosine Lysozyme Ibacitabine Lysine

Other	Ingenol mebutate Metronidazole

Antibacterials: nucleic acid inhibitors (J01E, J01M)

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

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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