Ethambutol
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Stereo, skeletal formula of ethambutol
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| Clinical data | |
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| Trade names | Myambutol, Etibi,[2] Servambutol, others |
| AHFS/Drugs.com | Monograph |
| Pregnancy category |
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| Routes of administration |
by mouth |
| ATC code | J04AK02 (WHO) |
| Pharmacokinetic data | |
| Protein binding | 20–30% |
| Metabolism | liver |
| Biological half-life | 3–4 hours |
| Identifiers | |
| Synonyms | (2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol[3] |
| CAS Number | 74-55-5  |
| PubChem (CID) | 14052 |
| DrugBank | DB00330 |
| ChemSpider | 13433 |
| UNII | 8G167061QZ |
| KEGG | D07925 |
| ChEBI | CHEBI:4877 |
| ChEMBL | CHEMBL44884 |
| ECHA InfoCard | 100.000.737 |
| Chemical and physical data | |
| 3D model (Jmol) | Interactive image |
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Ethambutol (EMB, E) is a medication primarily used to treat tuberculosis.[1] It is usually given in combination with other tuberculosis medications, such as isoniazid, rifampicin and pyrazinamide.[4] It may also be used to treat Mycobacterium avium complex, and Mycobacterium kansasii. It is taken by mouth.[1]
Common side effect include problems with vision, joint pain, nausea, headaches, and feeling tired. Other side effects include liver problems and allergic reactions.[1] It is not recommended in people with optic neuritis, significant kidney problems, or under the age of five.[4] Use during pregnancy or breastfeeding has not been found to cause harm.[4][5] In the United States the FDA has raised concerns about eye issues in the baby if used during pregnancy. Ethambutol is believed to work by interfering with the bacteria's metabolism.[1]
Ethambutol was discovered in 1961.[6] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] Ethambutol is available as a generic medication.[2] The wholesale cost in the developing world is about 2.58 to 4.73 USD per month.[8] In the United States it costs 100 to 200 USD per month.[2]
Contents
Medical uses[edit]
Ethambutol is used along with other medications to treat a number of infections including: tuberculosis, Mycobacterium avium complex, and Mycobacterium kansasii.[1]
Adverse effects[edit]
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- Optic neuritis[9] (hence contraindicated in children below six years of age)
- Red-green color blindness[10]
- Peripheral neuropathy
- Arthralgia
- Hepatotoxicity
- Hyperuricaemia
- Vertical nystagmus
- Milk skin reaction
Mechanism of action[edit]
Ethambutol is bacteriostatic against actively growing TB bacilli. It works by obstructing the formation of cell wall. Mycolic acids attach to the 5'-hydroxyl groups of D-arabinose residues of arabinogalactan and form mycolyl-arabinogalactan-peptidoglycan complex in the cell wall. It disrupts arabinogalactan synthesis by inhibiting the enzyme arabinosyl transferase. Disruption of the arabinogalactan synthesis inhibits the formation of this complex and leads to increased permeability of the cell wall.
Pharmacokinetics[edit]
It is well absorbed from the gastrointestinal tract and well distributed in body tissues and fluids. 50% is excreted unchanged in urine.
References[edit]
- ^ a b c d e f "Ethambutol Hydrochloride". The American Society of Health-System Pharmacists. Retrieved 10 December 2016.
- ^ a b c Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 48. ISBN 9781284057560.
- ^ "ethambutol (CHEBI:4877)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 August 2010. Main. Retrieved 26 April 2012.
- ^ a b c WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 136, 138, 588, 603. ISBN 9789241547659. Retrieved 8 December 2016.
- ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Retrieved 22 April 2014.
- ^ Landau, Ralph; Achilladelis, Basil; Scriabine, Alexander (1999). Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. p. 171. ISBN 9780941901215.
- ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016.
- ^ "Ethambutol". International Drug Price Indicator Guide. Retrieved 8 December 2016.
- ^ Lim SA (April 2006). "Ethambutol-associated optic neuropathy" (PDF). Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500.
- ^ Tripathi, K D (August 2015). Essentials of MEDICAL PHARMACOLOGY (Seventh ed.). India: JAYPEE BROTHERS MEDICAL PUBLISHERS. p. 769. ISBN 978-93-5025-937-5.
