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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/11/06 10:06:37」(JST)
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Sulfathiazole
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Systematic (IUPAC) name |
4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
? |
Identifiers |
CAS number |
72-14-0 |
ATC code |
D06BA02 J01EB07 QJ01EQ07 |
PubChem |
CID 5340 |
DrugBank |
DB06147 |
ChemSpider |
5148 Y |
UNII |
Y7FKS2XWQH Y |
KEGG |
D01047 Y |
ChEBI |
CHEBI:9337 Y |
ChEMBL |
CHEMBL437 Y |
Chemical data |
Formula |
C9H9N3O2S2 |
Mol. mass |
255.319 g/mol |
SMILES
- O=S(=O)(Nc1nccs1)c2ccc(N)cc2
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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
|
Y (what is this?) (verify)
|
Sulfathiazole is an organosulfur compound used as a short-acting sulfa drug. 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 imide tautomer is dominant, at least in the solid state. In this tautomer, the proton resides on the ring nitrogen, not the structure shown above.[1]
Cultural references[edit]
Sulfathiazole is mentioned in chapter 104 of Kurt Vonnegut's novel Cat's Cradle and New Dictonary, and several of his short stories. Thoma 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 1998 movie Dead Heat mentions the chemical as a drug used with reanimation of dead bodies.
References[edit]
- ^ G. J. Kruger and G. Gafner "The crystal structure of sulphathiazole II" Acta Cryst. (1971). B27, 326-333.doi:10.1107/S0567740871002176
Antibiotics and chemotherapeutics for dermatological use (D06)
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Antibiotics |
Tetracycline and derivatives
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- Demeclocycline
- Chlortetracycline
- Oxytetracycline
- Tetracycline
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Others
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- Amphenicol: Chloramphenicol
- Aminoglycosides: Neomycin
- Gentamicin
- Amikacin
- Streptogramin: Virginiamycin
- other: Fusidic acid
- Bacitracin
- Tyrothricin
- Mupirocin
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Chemotherapeutics |
Sulfonamides
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- Silver sulfadiazine
- Sulfathiazole
- Mafenide
- Sulfamethizole
- Sulfanilamide
- Sulfamerazine
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Antivirals
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- Aciclovir
- Penciclovir
- Idoxuridine
- Edoxudine
- Imiquimod/Resiquimod
- Podophyllotoxin
Docosanol
- Tromantadine
- Inosine
- Lysozyme
- Ibacitabine
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Other
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- Ingenol mebutate
- Metronidazole
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noco (i/b/d/q/u/r/p/m/k/v/f)/cong/tumr (n/e/d), sysi/epon
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proc, drug (D2/3/4/5/8/11)
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Antibacterials: nucleic acid inhibitors (J01E, J01M)
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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
- Sulfathiazole
- Sulfathiourea
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Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
|
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Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
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Other/ungrouped |
- sulfanilamide
- Sulfacetamide
- Sulfametrole
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Combinations |
- Trimethoprim/sulfamethoxazole#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine
- Nalidixic acid
- Oxolinic acid
- Pipemidic acid
- Piromidic acid
- Rosoxacin
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Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin
- Nadifloxacin
- Ofloxacin
- Norfloxacin
- Pefloxacin
- Rufloxacin
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3rd g. |
- Balofloxacin
- Grepafloxacin‡
- Levofloxacin
- Pazufloxacin
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin
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|
4th g. |
- Besifloxacin
- Clinafloxacin†
- Garenoxacin
- Gemifloxacin
- Moxifloxacin
- Gatifloxacin‡
- Sitafloxacin
- Trovafloxacin‡/Alatrofloxacin‡
- Prulifloxacin
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Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
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Related (DG) |
- Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
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Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
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RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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English Journal
- An appropriate and systematized procedure for validating qualitative methods: Its application in the detection of sulfonamide residues in raw milk.
- Gondim Cde S1, Coelho OA1, Alvarenga RL1, Junqueira RG1, Souza SV2.
- Analytica chimica acta.Anal Chim Acta.2014 Jun 9;830:11-22. doi: 10.1016/j.aca.2014.04.050. Epub 2014 Apr 28.
- The lack of well-established references for the validation of qualitative analyses and the increasing demand for reliable binary responses were the main motivating factors for this study. A detailed procedure for single-laboratory validation of qualitative methods is proposed. The experimental desig
- PMID 24856507
- Occurrence and distribution of antibiotics in the surface sediments of the Yangtze Estuary and nearby coastal areas.
- Shi H1, Yang Y2, Liu M1, Yan C3, Yue H1, Zhou J3.
- Marine pollution bulletin.Mar Pollut Bull.2014 May 9. pii: S0025-326X(14)00260-4. doi: 10.1016/j.marpolbul.2014.04.034. [Epub ahead of print]
- The occurrence and distribution of five groups of antibiotics were investigated in the surface sediments of the Yangtze Estuary over four seasons. Four tetracyclines (TCs), sulfaquinoxaline (SQ), enrofloxacin (EFC) and thiamphenicol (TAP) were detected in all the samples, while sulfamerazine (SM) an
- PMID 24820640
- Confirmation of 13 sulfonamides in honey by liquid chromatography-tandem mass spectrometry for monitoring plans: validation according to European Union Decision 2002/657/EC.
- Dubreil-Chéneau E1, Pirotais Y2, Verdon E2, Hurtaud-Pessel D2.
- Journal of chromatography. A.J Chromatogr A.2014 Apr 25;1339:128-36. doi: 10.1016/j.chroma.2014.03.003. Epub 2014 Mar 11.
- A rapid and reliable liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the simultaneous confirmation of 13 sulfonamides in honey was developed and fully validated in accordance with the European Commission Decision No 2002/657/EC. The validation scheme was built in accordance with
- PMID 24666935
Japanese Journal
- アドミセルクロマトグラフィーにおける薬剤成分の分離挙動
- Recrystallization of Pharmaceutical Compounds using the Supercritical Antisolvent Process
- Estimation of Transition Temperature of Pharmaceutical Polymorphs by Measuring Heat of Solution and Solubility.
Related Links
- Sulfathiazole definition, a sulfanilamide derivative, C 9 H 9 N 3 O 2 S 2 , formerly used in the treatment of pneumonia and staphylococcal infections, but now largely replaced because of its toxicity. See more. Thesaurus Translate ...
- Sulfathiazole is a medicine available in a number of countries worldwide. A list of US medications equivalent to Sulfathiazole is available on the Drugs.com website. ... Drugs.com provides accurate and independent information on ...
Related Pictures
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- ノルスルファゾール norsulfazole
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