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Azosemide

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	none
Identifiers
IUPAC name 2-chloro-5-(2H-tetrazol-5-yl)-4-benzenesulfonamide
CAS Number	27589-33-9
PubChem CID	2273
DrugBank	DB08961
ChemSpider	2186
UNII	MR40VT1L8Z
KEGG	D01323
ChEBI	CHEBI:31248
ChEMBL	ChEMBL1097235
CompTox Dashboard (EPA)	DTXSID7046910
ECHA InfoCard	100.044.121
Chemical and physical data
Formula	C12H11ClN6O2S2
Molar mass	370.83 g·mol
3D model (JSmol)	Interactive image
SMILES O=S(=O)(N)c2c(Cl)cc(c(c1nnn1)c2)NCc3sccc3
InChI InChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19) Key:HMEDEBAJARCKCT-UHFFFAOYSA-N
(what is this?)  (verify)

Azosemide is a high-ceiling loop diuretic agent that was brought to market in 1981 by Boehringer Mannheim. As of 2015 it was available as a generic in some Asian countries.

Azosemide has been found as an adulterant in ketamine.

Synthesis

Chlorosulfonation of 2-fluoro-4-chloro-benzonitrile (1) followed by ammonolysis of the product gives 4-chloro-2-fluoro-5-sulfamoylbenzonitrile (2). Selective displacement of the fluoride leaving group by 2-aminomethylthiophene (3) gives PC68423892 (4). Treatment with sodium azide and hydrochloric acid leads to 1,3 addition of the elements of hydrazoic acid to the nitrile and the formation of a tetrazole ring. This yields the high ceiling diuretic agent azosemide (5).

References

1. Sittig M (1988). Pharmaceutical Manufacturing Encyclopedia (PDF). Vol. 1. Noyes Publications. p. 122. ISBN 978-0-8155-1144-1. Archived from the original (PDF) on 2007-10-23.
2. Bormann D (January 1980). "Diuretics". In Hess HJ (ed.). Annual Reports in Medicinal Chemistry. Vol. 15. Academic Press. pp. 100–105 (101). ISBN 978-0-08-058359-4.
3. "International listings for azosemide". Drugs.com. Retrieved 23 July 2015.
4. "Drug Checking Report 2011" (PDF). Energy Control. Retrieved 20 January 2022.
5. DE1815922 idem A. Popelak et al., U.S. patent 3,665,002 (1972 to Boehringer, Mann.).
6. Ansgar Dr Rer Nat Lerch, 4 More », DE2353388 (1975 to Boehringer Mannheim Gmbh).
7. www.lookchem.com/Chempedia/Chemical-Technology/Organic-Chemical-Technology/18708.html
8. KR20110129622
9. 高朋, 习富刚, & 武乾刚, CN106749068 (2017 to KUNSHAN RIKITA PHARMACEUTICAL Co Ltd).

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