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Sulfathiazole

Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug.[1] Formerly, it was a common oral and topical antimicrobial, until less toxic alternatives were discovered.[2]

Sulfathiazole
Imino (top) and amino (bottom) tautomers
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 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
KEGG
  • D01047 Y
ChEBI
  • CHEBI:9337 Y
ChEMBL
  • ChEMBL437 Y
CompTox Dashboard (EPA)
  • DTXSID8026068
ECHA InfoCard100.000.701
Chemical and physical data
FormulaC9H9N3O2S2
Molar mass255.31 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point202 to 202.5 °C (395.6 to 396.5 °F)
  • O=S(=O)(Nc1nccs1)c2ccc(N)cc2
  • 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 exists in various forms (polymorphs). The imine tautomer is dominant in solid samples.[3]

Cultural references edit

  • In the 1955 short story, Captive Audience by Philip K. Dick, Flannery recommends the use of sulfathiazole in lieu of the unavailable Penicillin for a ten-year-old boy's suppurating arm wound he received from "toxic crystalline poisoning".
  • 1960 Otto Preminger's 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."
  • 1963: Sulfathiazole is mentioned in Kurt Vonnegut's novel Cat's Cradle and New Dictionary, and several of his short stories.
  • 1964: Thomas Heggen's novel Mister Roberts mentions the use of sulfathiazole to treat gonorrhea.
  • 1978: John Irving's novel The World According to Garp in chapter 1 where Garp's mother witnesses it being dispensed to World War II soldiers.
  • 1988: The movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies.
  • 2003: F. Spencer Chapman D.S.O. in his WWII memoir, The Jungle is Neutral, refers to his personal use of sulphathiazole (M.&B.) in the jungles of Malaya during May 1942. He credits the use of the drug with preventing fever and pneumonia becoming fatal in arduous conditions during the guerilla actions undertaken by the Malayan Communist Party against the Japanese occupying forces.[4]

References edit

  1. ^ Mertschenk B, Beck F, Bauer W (2002). "Thiourea and Thiourea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a26_803. ISBN 3527306730.
  2. ^ Rouf A, Tanyeli C (June 2015). "Bioactive thiazole and benzothiazole derivatives". European Journal of Medicinal Chemistry. 97: 911–27. doi:10.1016/j.ejmech.2014.10.058. PMID 25455640.
  3. ^ Kruger GT, Gafner G (February 1971). "The crystal structure of sulphathiazole II". Acta Crystallographica Section B. 27 (2): 326–33. Bibcode:1971AcCrB..27..326K. doi:10.1107/S0567740871002176.
  4. ^ Chapman FS (1949). The Jungle is Neutral. WW norton. p. 108.


sulfathiazole, organosulfur, compound, used, short, acting, sulfa, drug, formerly, common, oral, topical, antimicrobial, until, less, toxic, alternatives, were, discovered, imino, amino, bottom, tautomersclinical, dataahfs, drugs, cominternational, drug, names. Sulfathiazole is an organosulfur compound used as a short acting sulfa drug 1 Formerly it was a common oral and topical antimicrobial until less toxic alternatives were discovered 2 SulfathiazoleImino top and amino bottom tautomersClinical dataAHFS Drugs comInternational Drug NamesATC codeD06BA02 WHO J01EB07 WHO QJ01EQ07 WHO IdentifiersIUPAC name 4 amino N 1 3 thiazol 2 yl benzenesulfonamideCAS Number72 14 0 YPubChem CID5340DrugBankDB06147 YChemSpider5148 YUNIIY7FKS2XWQHKEGGD01047 YChEBICHEBI 9337 YChEMBLChEMBL437 YCompTox Dashboard EPA DTXSID8026068ECHA InfoCard100 000 701Chemical and physical dataFormulaC 9H 9N 3O 2S 2Molar mass255 31 g mol 13D model JSmol Interactive imageMelting point202 to 202 5 C 395 6 to 396 5 F SMILES O S O Nc1nccs1 c2ccc N cc2InChI 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 YKey JNMRHUJNCSQMMB UHFFFAOYSA N Y verify Sulfathiazole exists in various forms polymorphs The imine tautomer is dominant in solid samples 3 Cultural references editIn the 1955 short story Captive Audience by Philip K Dick Flannery recommends the use of sulfathiazole in lieu of the unavailable Penicillin for a ten year old boy s suppurating arm wound he received from toxic crystalline poisoning 1960 Otto Preminger s 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 1963 Sulfathiazole is mentioned in Kurt Vonnegut s novel Cat s Cradle and New Dictionary and several of his short stories 1964 Thomas Heggen s novel Mister Roberts mentions the use of sulfathiazole to treat gonorrhea 1978 John Irving s novel The World According to Garp in chapter 1 where Garp s mother witnesses it being dispensed to World War II soldiers 1988 The movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies 2003 F Spencer Chapman D S O in his WWII memoir The Jungle is Neutral refers to his personal use of sulphathiazole M amp B in the jungles of Malaya during May 1942 He credits the use of the drug with preventing fever and pneumonia becoming fatal in arduous conditions during the guerilla actions undertaken by the Malayan Communist Party against the Japanese occupying forces 4 References edit Mertschenk B Beck F Bauer W 2002 Thiourea and Thiourea Derivatives Ullmann s Encyclopedia of Industrial Chemistry Wiley VCH doi 10 1002 14356007 a26 803 ISBN 3527306730 Rouf A Tanyeli C June 2015 Bioactive thiazole and benzothiazole derivatives European Journal of Medicinal Chemistry 97 911 27 doi 10 1016 j ejmech 2014 10 058 PMID 25455640 Kruger GT Gafner G February 1971 The crystal structure of sulphathiazole II Acta Crystallographica Section B 27 2 326 33 Bibcode 1971AcCrB 27 326K doi 10 1107 S0567740871002176 Chapman FS 1949 The Jungle is Neutral WW norton p 108 nbsp This systemic antibiotic related article is a stub You can help Wikipedia by expanding it vte nbsp This dermatologic drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Sulfathiazole amp oldid 1196152483, wikipedia, wiki, book, books, library,

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