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Azosemide has been found as an adulterant in ].<ref>{{cite web |title=Drug Checking Report 2011 |url=https://energycontrol.org/files/analisis/Annual_Drug_Checking_Report_Energy_Control_2011.pdf |website=Energy Control |access-date=20 January 2022}}</ref> Azosemide has been found as an adulterant in ].<ref>{{cite web |title=Drug Checking Report 2011 |url=https://energycontrol.org/files/analisis/Annual_Drug_Checking_Report_Energy_Control_2011.pdf |website=Energy Control |access-date=20 January 2022}}</ref>
==Synthesis== ==Synthesis==
Patents:<ref>DE1815922 idem A. Popelak et al., {{US patent|3665002}} (1972 to Boehringer, Mann.).</ref><ref>Ansgar Dr Rer Nat Lerch, 4 More », DE2353388 (1975 to Boehringer Mannheim Gmbh).</ref> Alternative route:<ref>www.lookchem.com/Chempedia/Chemical-Technology/Organic-Chemical-Technology/18708.html</ref> Korean:<ref>KR20110129622</ref> Sino:<ref>高朋, 习富刚, & 武乾刚, CN106749068 (2017 to KUNSHAN RIKITA PHARMACEUTICAL Co Ltd).</ref>]] Patents:<ref>DE1815922 idem A. Popelak et al., {{US patent|3665002}} (1972 to Boehringer, Mann.).</ref><ref>Ansgar Dr Rer Nat Lerch, 4 More », DE2353388 (1975 to Boehringer Mannheim Gmbh).</ref> Alternative route:<ref>www.lookchem.com/Chempedia/Chemical-Technology/Organic-Chemical-Technology/18708.html</ref> Korean:<ref>장명식, et al. KR20110129622 (2012 to LEADGENE CO LTD).</ref> Sino:<ref>高朋, 习富刚, & 武乾刚, CN106749068 (2017 to KUNSHAN RIKITA PHARMACEUTICAL Co Ltd).</ref>]]


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 ('''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'''). 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 ('''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''').

Revision as of 14:29, 14 December 2022

Chemical compound Pharmaceutical compound
Azosemide
Structural formula of azosemide
Space-filling model of the azosemide molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
IUPAC name
  • 2-chloro-5-(2H-tetrazol-5-yl)-4-benzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.044.121 Edit this at Wikidata
Chemical and physical data
FormulaC12H11ClN6O2S2
Molar mass370.83 g·mol
3D model (JSmol)
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

Thieme Patents: Alternative route: Korean: Sino:

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 CID:68423892 (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. 장명식, et al. KR20110129622 (2012 to LEADGENE CO LTD).
  9. 高朋, 习富刚, & 武乾刚, CN106749068 (2017 to KUNSHAN RIKITA PHARMACEUTICAL Co Ltd).
Diuretics (C03)
Sulfonamides
(and etacrynic acid)
CA inhibitors (at PT)
Loop (Na-K-Cl at AL)
Thiazides (Na-Cl at DCT,
Calcium-sparing)
Thiazide-likes (primarily DCT)
Potassium-sparing (at CD)
ESC blockers
Aldosterone antagonists
Osmotic diuretics (PT, DL)
Vasopressin receptor inhibitors
(DCT and CD)
Other
Combination products
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