Ethambutol

Ethambutol
Chemical structure of ethambutol (top) and photo of ethambutol crystals (bottom)
Clinical data
Trade namesMyambutol, Etibi,[1] Servambutol, others
Other names(2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol[2]
AHFS/Drugs.comMonograph
License data
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding20–30%
Metabolismliver
Elimination half-life3–4 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.737 Edit this at Wikidata
Chemical and physical data
FormulaC10H24N2O2
Molar mass204.314 g·mol−1
3D model (JSmol)
  • CC[C@@H](CO)NCCN[C@@H](CC)CO
  • InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1 checkY
  • Key:AEUTYOVWOVBAKS-UWVGGRQHSA-N

Ethambutol (EMB, E) is a medication primarily used to treat tuberculosis.[4] It is usually given in combination with other tuberculosis medications, such as isoniazid, rifampicin and pyrazinamide.[5] It may also be used to treat Mycobacterium avium complex, and Mycobacterium kansasii.[4] It is taken by mouth.[4]

Common side effects include problems with vision, joint pain, nausea, headaches, and feeling tired.[4] Other side effects include liver problems and allergic reactions.[4] It is not recommended in people with optic neuritis, significant kidney problems, or under the age of five.[5] Use during pregnancy or breastfeeding has not been found to cause harm.[5][6] In the United States the FDA has raised concerns about eye issues in the baby if used during pregnancy.[4] Ethambutol is believed to work by interfering with the bacteria's metabolism.[4]

Ethambutol was discovered in 1961.[7] It is on the World Health Organization's List of Essential Medicines[8] and is available as a generic medication.[1]

  1. ^ a b Hamilton R (2015). Tarascon Pocket Pharmacopoeia (Deluxe Lab-Coat ed.). Jones & Bartlett Learning. p. 48. ISBN 9781284057560.
  2. ^ "ethambutol (CHEBI:4877)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 August 2010. Main. Archived from the original on 19 July 2014. Retrieved 26 April 2012 – via ebi.ac.uk.
  3. ^ "ETHAMBUTOL LUPIN, ETHAMBUTOL LAPL, ETHAMBUTOL GH (Lupin Australia Pty Limited)". Therapeutic Goods Administration (TGA). 28 September 2022. Retrieved 20 April 2023.
  4. ^ a b c d e f g "Ethambutol Hydrochloride". drugs.com. The American Society of Health-System Pharmacists. Archived from the original on 5 June 2016. Retrieved 10 December 2016.
  5. ^ a b c Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 136, 138, 588, 603. hdl:10665/44053. ISBN 9789241547659.
  6. ^ "Prescribing medicines in pregnancy database". TGA.gov.au. Therapeutic Goods Administration, Department of Health, Australia. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  7. ^ Landau R, Achilladelis B, Scriabine A (1999). Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. p. 171. ISBN 9780941901215. Archived from the original on 2016-12-20.
  8. ^ Organization WH (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.