Tolazamide

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Tolazamide
Tolazamide.svg
Tolazamide ball-and-stick.png
Names
Trade namesTolinase, others
  • N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
Clinical data
Drug classSulfonylurea[1]
Main usesType 2 diabetes[1]
Side effectsNausea, loss of appetite, diarrhea, low blood sugar[1]
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Routes of
use
By mouth
Onset of actionWithin 20 min[1]
Duration of action10 hrs[1]
External links
AHFS/Drugs.comMonograph
MedlinePlusa682482
Legal
License data
Legal status
Pharmacokinetics
Bioavailability?
Metabolismmetabolized in the liver to active metabolites
Elimination half-life7 hours
ExcretionKidney (85%) and fecal (7%)
Chemical and physical data
FormulaC14H21N3O3S
Molar mass311.40 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) checkY
  • Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N checkY
  (verify)

Tolazamide, sold under the brand name Tolinase among others, is a medication used to treat type 2 diabetes.[1] It is taken by mouth.[1] Effects begin within 20 minutes and last for about 10 hours.[1]

Common side effects include nausea, loss of appetite, diarrhea, and abdominal pain.[1] Other side effects may include rash and low blood sugar.[1] Side effects are more common in people with liver or kidney problems.[1] It is a sulfonylurea.[1]

Tolazamide was approved for medical use in the United States in 1966.[1] It is available as a generic medication.[2] In the United States 90 tablets of 250 mg costs about 54 USD.[3]

Medical uses

Dosage

It is often started at 100 to 250 mg per day with a maximum dose of 1,000 mg per day.[1]

Synthesis

para-Toluenesulfonamide is converted to its carbamate with ethyl chloroformate in the presence of a base. Heating that intermediate with 1-amino-azepane leads to the displacement of the ethoxy group and the formation of tolazemide:[4]

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

References

  1. 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 "Tolazamide Monograph for Professionals". Drugs.com. Retrieved 5 October 2021.
  2. Skyler, Jay (4 April 2012). Atlas of Diabetes. Springer Science & Business Media. p. 186. ISBN 978-1-4614-1027-0.
  3. "Tolazamide Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 5 October 2021.
  4. 4.0 4.1 Wright JB, Willette RE (July 1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry. 91: 815–22. doi:10.1021/jm01239a016. PMID 14056414.

External links

Identifiers:
  • "Tolazamide". Medline Plus. U.S. National Library of Medicine.