| Revision as of 18:14, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456800701 of page Sulfanilamide for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 15:36, 8 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,128 edits added Category:4-Aminophenyl compounds using HotCat |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
|
{{Use dmy dates|date=September 2024}} |
|
|
{{cs1 config |name-list-style=vanc |display-authors=6}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| verifiedrevid = 470473303 |
|
| Verifiedfields = changed |
|
|
|
| image = Sulfanilamide-skeletal.svg |
|
| Watchedfields = changed |
|
|
|
| image2 = sulfanilamida-3D.png |
|
| verifiedrevid = 418565956 |
|
|
|
|
|
| IUPAC_name = 4-aminobenzenesulfonamide |
|
|
|
<!-- Clinical data --> |
|
| image = Sulfanilamide-skeletal.png |
|
|
|
| pronounce = |
|
|
| tradename = |
|
|
| Drugs.com = salonemide {{drugs.com|CDI|sulfanilamide}} |
|
|
| MedlinePlus = |
|
|
| DailyMedID = <!-- DailyMed may use generic or brand name (generic name preferred) --> |
|
|
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
|
| pregnancy_AU_comment = |
|
|
| pregnancy_category = |
|
|
| routes_of_administration = |
|
|
| class = |
|
|
| ATC_prefix = J01 |
|
|
| ATC_suffix = EB06 |
|
|
| ATC_supplemental = {{ATC|D06|BA05}} {{ATCvet|J01|EQ06}} |
|
|
|
|
|
<!--Clinical data--> |
|
<!-- Legal status --> |
|
|
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
|
| tradename = |
|
|
|
| legal_AU_comment = |
|
| Drugs.com = {{drugs.com|CDI|sulfanilamide}} |
|
|
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
|
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
|
|
| legal_BR_comment = |
|
| pregnancy_US = <!-- A / B / C / D / X --> |
|
|
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
|
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
|
| legal_CA_comment = |
|
| legal_UK = <!-- GSL / P / POM / CD --> |
|
|
| legal_US = <!-- OTC / Rx-only --> |
|
| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
|
|
| legal_DE_comment = |
|
|
| legal_NZ = <!-- Class A, B, C --> |
|
|
| legal_NZ_comment = |
|
|
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> |
|
|
| legal_UK_comment = |
|
|
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
|
|
| legal_US_comment = |
|
|
| legal_EU = |
|
|
| legal_EU_comment = |
|
|
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
|
|
| legal_UN_comment = |
|
|
| legal_status = <!-- For countries not listed above --> |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number = 63-74-1 |
|
| CAS_number = 63-74-1 |
|
| ATC_prefix = J01 |
|
|
| ATC_suffix = EB06 |
|
|
| ATC_supplemental = {{ATC|D06|BA05}} {{ATCvet|J01|EQ06}} |
|
|
| PubChem = 5333 |
|
| PubChem = 5333 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| Line 32: |
Line 55: |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D08543 |
|
| KEGG = D08543 |
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI = 45373 |
|
| ChEBI = 45373 |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL = 21 |
|
| ChEMBL = 21 |
|
|
| NIAID_ChemDB = 019103 |
|
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
|
| IUPAC_name = 4-aminobenzenesulfonamide |
|
| C=6 | H=8 | N=2 | O=2 | S=1 |
|
|
|
| C=6 | H=8 | N=2 | O=2 | S=1 |
|
| molecular_weight = 172.20 g/mol |
|
|
| smiles = O=S(=O)(c1ccc(N)cc1)N |
|
| smiles = O=S(=O)(c1ccc(N)cc1)N |
|
| InChI = 1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) |
|
|
| InChIKey = FDDDEECHVMSUSB-UHFFFAOYAI |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) |
|
| StdInChI = 1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) |
| Line 50: |
Line 72: |
|
| melting_point = 165 |
|
| melting_point = 165 |
|
}} |
|
}} |
|
|
'''Sulfanilamide''' (also spelled '''sulphanilamide''') is a ] ] drug. Chemically, it is an ] consisting of an ] ] with a ] group.<ref>{{ Ullmann | vauthors = Actor P, Chow AW, Dutko FJ, McKinlay MA | title = Chemotherapeutics | doi = 10.1002/14356007.a06_173 }}</ref> Powdered sulfanilamide was used by the ] in ] to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars.<ref>{{cite web | vauthors = Steinert D | date = 2000 | title = The Use of Sulfanilamide in World War II | work = The History of WWII Medicine | url = http://www.mtaofnj.org/content/WWII%20Combat%20Medic%20-%20Dave%20Steinert/wwii.htm#The%20Use%20of%20Sulfanilamide%20in%20World%20War%20II | archive-url= https://web.archive.org/web/20160607143502/http://www.mtaofnj.org/content/WWII%20Combat%20Medic%20-%20Dave%20Steinert/wwii.htm#The%20Use%20of%20Sulfanilamide%20in%20World%20War%20II | archive-date=7 June 2016 }}</ref><ref>{{cite web |url=http://www.med-dept.com/sulfa.php |title= Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs | work = Library of Congress Web Archives |access-date=13 June 2014 |url-status=dead |archive-url=http://webarchive.loc.gov/all/20131204174732/http%3A//med%2Ddept.com/sulfa.php |archive-date=4 December 2013 }}</ref> Sulfanilamide is rarely if ever used ] due to ] and because more effective sulfonamides are available for this purpose. Modern ] have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of ] preparations, primarily for treatment of ]s such as ] caused by '']''.<ref>{{cite web |url= https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5333 |title=Sulfanilamide |work = PubChem | publisher = National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine }}</ref><ref name=":0">{{cite book | vauthors = Scholar E | chapter = Sulfanilamide|date=1 January 2007|chapter-url=https://www.sciencedirect.com/science/article/pii/B9780080552323626947| title = xPharm: The Comprehensive Pharmacology Reference|pages=1–5| veditors = Enna SJ, Bylund DB |place=New York|publisher=Elsevier|language=en|doi=10.1016/b978-008055232-3.62694-7|isbn=978-0-08-055232-3|access-date=2 October 2021}}</ref><ref>{{cite web|title=US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf|access-date=3 October 2021|website=United States Food & Drug Administration}}</ref><ref>{{cite web|title=Drugs@FDA: FDA-Approved Drugs|url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=006530|access-date=2 October 2021|website=www.accessdata.fda.gov}}</ref> |
|
|
|
|
|
The term "sulfanilamides" is also sometimes used to describe a family of molecules containing these ]s. Examples include: |
|
|
* ], a ] |
|
|
* ], an ] |
|
|
* ], an ] |
|
|
|
|
|
==Mechanism of action== |
|
|
As a sulfonamide antibiotic, sulfanilamide functions by ] (that is, by acting as a substrate analogue of) enzymatic reactions involving ] (PABA).<ref>{{cite journal | vauthors = Castelli LA, Nguyen NP, Macreadie IG | title = Sulfa drug screening in yeast: fifteen sulfa drugs compete with p-aminobenzoate in Saccharomyces cerevisiae | journal = FEMS Microbiology Letters | volume = 199 | issue = 2 | pages = 181–4 | date = May 2001 | pmid = 11377864 | doi = 10.1111/j.1574-6968.2001.tb10671.x | doi-access = free }}</ref><ref>{{cite book| vauthors = Kent M |title=Advanced Biology|publisher=Oxford University Press|date=2000|page=46|isbn=978-0-19-914195-1}}</ref> Specifically, it ] the enzyme ].<ref name=":0" /><ref>{{cite book | vauthors = Sharma S | chapter = Chapter 18 - Antifolates|date= January 1997 | title = Pharmacochemistry Library|volume=25|pages=439–454| veditors = Sharma S, Anand N |series=Approaches to Design and Synthesis of Antiparasitic Drugs|publisher=Elsevier|language=en|doi=10.1016/s0165-7208(97)80040-2 |isbn=9780444894762 }}</ref> PABA is needed in enzymatic reactions that produce ], which acts as a ] in the synthesis of ]s and ]s. ]s do not synthesize their own folic acid so are unaffected by PABA inhibitors, which selectively kill bacteria.<ref name=":1">{{cite book| vauthors = Brunton LL, Hilal-Dandan R, Knollmann BC |url=https://www.worldcat.org/oclc/993810322|title=Goodman & Gilman's the pharmacological basis of therapeutics|publisher=]|year=2018|isbn=978-1-259-58473-2|edition=13th|location=New York|oclc=993810322}}</ref> |
|
|
|
|
|
However, this effect can be reversed by adding the end products of one-carbon transfer reactions, such as ], ]s, ], and ]. PABA can also reverse the effects of sulfonamides.<ref name=":0" /><ref>{{cite journal| vauthors = Wormser GP, Chambers HF |date=1 February 2001|title=The Antimicrobial Drugs, Second Edition by Eric Scholar and William Pratt New York: Oxford University Press, 2000. 607 pp., illustrated. $98.50 (cloth); $69.50 (paper)|journal=Clinical Infectious Diseases|volume=32|issue=3|pages=521|doi=10.1086/318515|issn=1058-4838|doi-access=free}}</ref><ref name=":1" /> |
|
|
|
|
|
==History== |
|
|
Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961)<ref>{{cite journal| vauthors = Gelmo P |date=1908|title=Über Sulfamide der p-Amidobenzolsulfonsäure|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/prac.19080770129|journal=Journal für Praktische Chemie|language=en|volume=77|issue=1|pages=369–382|doi=10.1002/prac.19080770129|issn=1521-3897}}</ref><ref>{{cite web|title=Paul Gelmo|url=http://www.encyclopedia.com/doc/1G2-2830901608.html|website=Encyclopedia.com}}</ref> as part of his dissertation for a doctoral degree from the ] of ].<ref>{{cite journal | vauthors = Gelmo P | date = 14 May 1908 |url= http://gallica.bnf.fr/ark:/12148/bpt6k90849c/f378.image |title=Über Sulfamide der ''p''-Amidobenzolsulfonsäure |journal=Journal für Praktische Chemie |volume=77 |pages=369–382 |doi=10.1002/prac.19080770129 }}</ref> It was patented in 1909.<ref>On 18 May 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.</ref> |
|
|
|
|
|
], who directed the testing of the ] ] in 1935,<ref>{{cite journal |vauthors = Domagk G |title=Ein Beitrag zur Chemotherapie der bakteriellen Infektionen|journal=Deutsche Medizinische Wochenschrift|volume=61|issue=7|date=15 February 1935|page=250|doi=10.1055/s-0028-1129486|s2cid=70515565 }}</ref> and ] and ], who along with Federico Nitti and ] in the laboratory of ] at the ], determined sulfanilamide as the active form,<ref>{{cite journal| vauthors = Tréfouël J, Tréfouël T, Nitti F, Bovet D| title = Activité du ''p''-aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin|journal=C. R. Soc. Biol.|volume=120|date=23 November 1935|page=756}}</ref> are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.<ref>{{cite book|language=fr| vauthors = Bovet D |chapter=Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927–1932)|title=Une chimie qui guérit : Histoire de la découverte des sulfamides|series=Médecine et Société|publisher=Payot|location=Paris|date=1988|page=307}}</ref> |
|
|
|
|
|
In 1937, ], a medicine consisting of sulfanilamide dissolved in ], poisoned and killed more than one hundred people as a result of acute ], prompting new US regulations for drug testing. In 1938, the ] was passed. It was only the solvent and not the sulfanilamide that was the problem, as sulfanilamide was widely and safely used at the time in both tablet and powder form.<ref>{{cite web | vauthors = Ballentine C |title=Sulfanilamide Disaster |url=https://www.fda.gov/files/about%20fda/published/The-Sulfanilamide-Disaster.pdf |website=fda.gov |publisher=FDA |access-date=5 May 2022}}</ref> |
|
|
|
|
|
== Chemical and physical properties == |
|
|
] Sulfanilamide is a yellowish-white or white crystal or fine powder. It has a ] of 1.08 g/cm<sup>3</sup> and a ] of 164.5-166.5 °C. The ] of a 0.5% ] of Sulfanilamide is 5.8 to 6.1. It has a λ<sub>max</sub> of 255 and 312 nm.<ref name=":0" /> |
|
|
|
|
|
]: One gram of sulphanilamide dissolves in approximately 37 ml ] or in 5 ml ]. It is practically insoluble in ], ], or ].<ref name=":0" /> |
|
|
|
|
|
== Contraindications == |
|
|
Sulfanilamide is ] in those known to be ] to sulfonamides, in ], during ] near term, and in infants less than two months of age.<ref name=":0" /> |
|
|
|
|
|
== Adverse effects == |
|
|
|
|
|
Since sulfanilamide is used almost exclusively in topical vaginal preparations these days, adverse effects are typically limited to ] or local skin reactions. If ], systemic side effects commonly seen with sulfanilamides may occur.<ref name=":0" /> |
|
|
|
|
|
== Pharmacokinetics == |
|
|
A small amount of sulfanilamide is absorbed following topical application or when administered as a ]l cream or ] (through the vaginal mucosa). It is ] by ] like other ]s and excreted through the urine.<ref name=":0" /> |
|
|
|
|
|
== External links == |
|
|
* {{MeshName|Sulfanilamides}} |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{Antibiotics and chemotherapeutics for dermatological use}} |
|
|
{{Sulfonamides and trimethoprim}} |
|
|
{{Portal bar | Medicine}} |
|
|
{{Authority control}} |
|
|
|
|
|
] |
|
|
] |