Tolazamide

Last updated
Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Clinical data
Trade names Tolinase
AHFS/Drugs.com Monograph
MedlinePlus a682482
License data
Pregnancy
category
  • AU:C
Routes of
administration 		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability ?
Metabolism metabolized in the liver to active metabolites
Elimination half-life 7 hours
Excretion Renal (85%) and fecal (7%)
Identifiers
  • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.013.262 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H21N3O3S
Molar mass 311.40 g·mol−1
3D model (JSmol)
  • O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
  • InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18) Yes check.svgY
  • Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N Yes check.svgY
   (verify)

Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).

Contents

Synthesis

Tolazamide synthesis.png

The reaction between p-toluenesulfonamide (1) and ethyl chloroformate (2) in the presence of base gives tosylurethane [5577-13-9] (3). Heating that intermediate with azepane (4) leads to the displacement of the ethoxy group and the formation of tolazemide (5). [1] [2] [3] [4] [5]

Azepane proper would lead to [13078-23-4].

References

  1. ↑ Vardanyan, Ṛuben, Hruby, V. J. (2006). Synthesis of essential drugs. Elsevier. ISBN   9780444521668.
  2. ↑ Wright JB, Willette RE (July 1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91 (4): 815–22. doi:10.1021/jm01239a016. PMID   14056414.
  3. ↑ John B Wright, U.S. patent 3,063,903 (1962 to Upjohn Co).
  4. ↑ Wright John Brenton, GB 887886 (1962 to Upjohn).
  5. ↑ DE1196200 idem Korger Gerhard, Weber Helmut, Aumuller Walter, U.S. patent 3,248,384 (1966 to Hoechst Ag).
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