Sulfanilamide

Overview

Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. Sulfanilamide is rarely if ever used systemically due to toxicity and because more effective sulfonamides are available for this purpose. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of topical preparations, primarily for treatment of vaginal yeast infections such as vulvovaginitis caused by Candida albicans.[1–7] WP

The term "sulfanilamides" is also sometimes used to describe a family of molecules containing these functional groups. Examples include: WP

Furosemide, a loop diuretic WP

Sulfadiazine, an antibiotic WP

Sulfamethoxazole, an antibiotic WP

Risks and side effects

Contraindications

Sulfanilamide is contraindicated in those known to be hypersensitive to sulfonamides, in nursing mothers, during pregnancy near term, and in infants less than two months of age.[5] WP

Adverse effects

Since sulfanilamide is used almost exclusively in topical vaginal preparations these days, adverse effects are typically limited to hypersensitivity or local skin reactions. If absorbed, systemic side effects commonly seen with sulfanilamides may occur.[5] WP

Pharmacology

Mechanism of action

As a sulfonamide antibiotic, sulfanilamide functions by competitively inhibiting (that is, by acting as a substrate analogue of) enzymatic reactions involving para-aminobenzoic acid (PABA). Specifically, it competitively inhibits the enzyme dihydropteroate synthase. PABA is needed in enzymatic reactions that produce folic acid, which acts as a coenzyme in the synthesis of purines and pyrimidines. Mammals do not synthesize their own folic acid so are unaffected by PABA inhibitors, which selectively kill bacteria.[5][8–11] WP

However, this effect can be reversed by adding the end products of one-carbon transfer reactions, such as thymidine, purines, methionine, and serine. PABA can also reverse the effects of sulfonamides.[5][11][12] WP

Pharmacokinetics

A small amount of sulfanilamide is absorbed following topical application or when administered as a vaginal cream or suppository (through the vaginal mucosa). It is metabolized by acetylation like other sulfonamides and excreted through the urine.[5] WP

History

History

Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961) as part of his dissertation for a doctoral degree from the Technische Hochschule of Vienna. It was patented in 1909.[13][14][15] WP

Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935, and Jacques Tréfouël and Thérèse Tréfouël, who along with Federico Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, determined sulfanilamide as the active form, are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[16][17][18] WP

In 1937, Elixir sulfanilamide, a medicine consisting of sulfanilamide dissolved in diethylene glycol, poisoned and killed more than one hundred people as a result of acute kidney failure, prompting new US regulations for drug testing. In 1938, the Food, Drug and Cosmetic Act 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.[19] WP

Chemistry

Formula

C6H8N2O2S PC

CAS number

63-74-1 PC

Molar mass (g/mol)

172.21 PC

IUPAC name (computed by PubChem)

4-aminobenzenesulfonamide PC

SMILES

C1=CC(=CC=C1N)S(=O)(=O)N PC

InChIKey

FDDDEECHVMSUSB-UHFFFAOYSA-N PC

PubChem CID

5333

IUPAC name

4-aminobenzenesulfonamide WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Ullmann
2. Other Steinert D. The Use of Sulfanilamide in World War II. 2000
3. Other Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs
4. Journal / agency Sulfanilamide
5. Journal / agency Scholar E. xPharm: The Comprehensive Pharmacology Reference. 1 January 2007. doi:10.1016/b978-008055232-3.62694-7
6. Journal / agency US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%
7. Journal / agency Drugs@FDA: FDA-Approved Drugs
8. Journal / agency Castelli LA, Nguyen NP, Macreadie IG. Sulfa drug screening in yeast: fifteen sulfa drugs compete with p-aminobenzoate in Saccharomyces cerevisiae. FEMS Microbiology Letters. May 2001. doi:10.1111/j.1574-6968.2001.tb10671.x · PMID 11377864
9. Other Kent M. Advanced Biology. 2000
10. Journal / agency Sharma S. Pharmacochemistry Library. January 1997. doi:10.1016/s0165-7208(97)80040-2
11. Other Brunton LL, Hilal-Dandan R, Knollmann BC. Goodman & Gilman's the pharmacological basis of therapeutics. 2018
12. Journal / agency Wormser GP, Chambers HF. 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). Clinical Infectious Diseases. 1 February 2001. doi:10.1086/318515
13. Journal / agency Gelmo P. Über Sulfamide der p-Amidobenzolsulfonsäure. Journal für Praktische Chemie. 1908. doi:10.1002/prac.19080770129
14. Other Paul Gelmo
15. Other On 18 May 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation
16. Journal / agency Domagk G. Ein Beitrag zur Chemotherapie der bakteriellen Infektionen. Deutsche Medizinische Wochenschrift. 15 February 1935. doi:10.1055/s-0028-1129486
17. Journal / agency Tréfouël J, Tréfouël T, Nitti F, Bovet D. Activité du p-aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin. C. R. Soc. Biol. 23 November 1935
18. Other Bovet D. Une chimie qui guérit: Histoire de la découverte des sulfamides. 1988
19. Journal / agency Ballentine C. Sulfanilamide Disaster

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.