Tolazamide

Tolazamide
Names
Trade namesTolinase, others
IUPAC name
  • 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]
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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)
    SMILES
    • O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
    InChI
    • 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

    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

    Tolazemide synthesis:[4] U.S. Patent 3,063,903 GB 887886  DE 1196200 

    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 2 3 4 5 6 7 8 9 10 11 12 13 14 "Tolazamide Monograph for Professionals". Drugs.com. Archived from the original on 4 September 2019. 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. Archived from the original on 9 October 2021. Retrieved 5 October 2021.
    3. ↑ "Tolazamide Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 5 October 2021.
    4. 1 2 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.
    Identifiers:
    • "Tolazamide". Medline Plus. U.S. National Library of Medicine. Archived from the original on 2020-10-19. Retrieved 2020-06-19.
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