Sulfaguanidine

Sulfaguanidine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A07AB03 (WHO) ;
Identifiers
	IUPAC name 4-Amino-N-[amino(imino)methyl]benzenesulfonamide;
CAS Number	57-67-0;
PubChem CID	5324;
ChemSpider	5133;
UNII	15XQ8043FN;
KEGG	D02437 ;
CompTox Dashboard (EPA)	DTXSID1023609 ;
ECHA InfoCard	100.000.314
Chemical and physical data
Formula	C7H10N4O2S
Molar mass	214.24 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	190 to 193 °C (374 to 379 °F)
	SMILES c1cc(N)ccc1S(=O)(=O)N=C(N)N;
	InChI InChI=1S/C7H10N4O2S/c8-5-1-3-6(4-2-5)14(12,13)11-7(9)10/h1-4H,8H2,(H4,9,10,11); Key:BRBKOPJOKNSWSG-UHFFFAOYSA-N;
	(verify)

Sulfaguanidine is a sulfonamide.

Sulfaguanidine is a guanidine derivative of sulfanilamide used in veterinary medicine. Sulfaguanidine is poorly absorbed from the gut which makes it suitable for the treatment of bacillary dysentery and other enteric infections.^[1]

Sulphaguanidine (II) was independently prepared by Marshall, Bratton, White, and Litchfield and Roblin, Williams, Winnek, and English in 1940, and introduced for the treatment of bacillary dysentery on the basis of its poor absorption from the gut. Its orally administered route of administration is now well established.^[2]

References

^ Smyth CJ, Finkelstein MB, Gould SE, Koppa TM, Leeder FS (April 1943). "Acute Bacillary Dysentery (Flexner): Treatment with Sulfaguanidine and Succinylsulfathiazole". Journal of the American Medical Association. 121 (17): 1325–30. doi:10.1001/jama.1943.02840170009003.
^ Rose FL, Spinks A (June 1947). "The absorption of some sulphaguanidine derivatives in mice". British Journal of Pharmacology and Chemotherapy. 2 (2): 65–78. doi:10.1111/j.1476-5381.1947.tb00322.x. PMC 1509772. PMID 19108113.

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[1] Smyth CJ, Finkelstein MB, Gould SE, Koppa TM, Leeder FS (April 1943). "Acute Bacillary Dysentery (Flexner): Treatment with Sulfaguanidine and Succinylsulfathiazole". Journal of the American Medical Association. 121 (17): 1325–30. doi:10.1001/jama.1943.02840170009003.

[2] Rose FL, Spinks A (June 1947). "The absorption of some sulphaguanidine derivatives in mice". British Journal of Pharmacology and Chemotherapy. 2 (2): 65–78. doi:10.1111/j.1476-5381.1947.tb00322.x. PMC 1509772. PMID 19108113.

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[2]

v t e Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
Rehydration	Oral rehydration therapy
Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline
Intestinal adsorbents	Charcoal Bismuth (including bismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: Diphenoxylate (+atropine) Difenoxin does not cross BBB: Eluxadoline Loperamide^# (+simethicone)
Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone^# Hydrocortisone Prednisone Betamethasone^# Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid Aminosalicylates Sulfasalazine Mesalazine Olsalazine Balsalazide
Antidiarrheal micro-organisms	Escherichia coli Saccharomyces boulardii
Other antidiarrheals	Albumin tannate Bismuth subsalicylate Ceratonia Crofelemer Octreotide Racecadotril Kaopectate
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III