Protionamide

Protionamide
Names
Trade namesTrevintix
Other namesProthionamide
IUPAC name
  • 2-propylpyridine-4-carbothioamide
Clinical data
Main usesTuberculosis, leprosy[1]
Side effectsHeadache, metallic taste, dry mouth, nausea[1]
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Chemical and physical data
FormulaC9H12N2S
Molar mass180.27 g·mol−1
3D model (JSmol)
SMILES
  • CCCc1cc(ccn1)C(=S)N
InChI
  • InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12) ☒N
  • Key:VRDIULHPQTYCLN-UHFFFAOYSA-N ☒N

Protionamide, also spelling prothionamide, is an antibiotic used to treat tuberculosis and leprosy.[1] Specifically it is used in multi-drug resistant tuberculosis when other treatment, such as clofazimine, are not suitable.[1][2] It is used together with other antituberculosis medication.[1] It is taken by mouth for up to two years.[1]

Common side effects include headache, metallic taste, dry mouth, and nausea.[1] Other side effects may include liver problems.[1] Alcohol should be avoided when it is used.[1] Safety in pregnancy and breastfeeding is unclear.[1] It is chemically similar to ethionamide.[2]

Protionamide was discovered in 1956.[3] It is not available in the United Kingdom or United States.[4][2] It is on the World Health Organization's List of Essential Medicines as an alternative to ethionamide.[5] It was relatively expensive in 2009.[2]

References

  1. 1 2 3 4 5 6 7 8 9 10 "Protionamide 250 mg Tablets" (PDF). WHO. Archived (PDF) from the original on 16 September 2023. Retrieved 13 September 2023.
  2. 1 2 3 4 Bennett, John E.; Dolin, Raphael; Blaser, Martin J.; Mandell, Gerald L. (19 October 2009). Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases E-Book. Elsevier Health Sciences. p. 546. ISBN 978-1-4377-2060-0. Archived from the original on 16 September 2023. Retrieved 13 September 2023.
  3. ↑ Dougherty, Thomas J.; Pucci, Michael J. (21 December 2011). Antibiotic Discovery and Development. Springer Science & Business Media. p. 720. ISBN 978-1-4614-1399-8. Archived from the original on 16 September 2023. Retrieved 13 September 2023.
  4. ↑ "Prothionamide". TB DRUG MONOGRAPHS. Archived from the original on 30 November 2021. Retrieved 13 September 2023.
  5. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
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