Ethambutol




























































































Ethambutol
Ethambutol.svg

Ethambutol substance photo.jpg
Chemical structure of ethambutol (top) and photo of ethambutol crystals (bottom)

Clinical data
Trade names Myambutol, Etibi,[2] Servambutol, others
Synonyms (2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol[3]

AHFS/Drugs.com
 Monograph
Pregnancy
category


  • US: C (Risk not ruled out) [1]
Routes of
administration		 by mouth
ATC code

  • J04AK02 (WHO)

Pharmacokinetic data
Protein binding 20–30%
Metabolism liver
Elimination half-life
 3–4 hours
Identifiers
CAS Number

  • 74-55-5  ☑Y

PubChem CID
  • 14052
DrugBank
  • DB00330
ChemSpider
  • 13433
UNII
  • 8G167061QZ
KEGG
  • D07925
ChEBI
  • CHEBI:4877
ChEMBL
  • ChEMBL44884
ECHA InfoCard
100.000.737 Edit this at Wikidata
Chemical and physical data
3D model (JSmol)
  • Interactive image

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.[1] It is taken by mouth.[1]


Common side effects include problems with vision, joint pain, nausea, headaches, and feeling tired.[1] 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.[1] 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 US$2.58–4.73 per month.[8] In the United States it costs US$100–200 per month.[2]




Contents






  • 1 Medical uses


  • 2 Adverse effects


  • 3 Mechanism of action


  • 4 Pharmacokinetics


  • 5 References


  • 6 External links





Medical uses


Ethambutol is used along with other medications to treat a number of infections including: tuberculosis, Mycobacterium avium complex, and Mycobacterium kansasii.[1]



Adverse effects




  • Optic neuritis[9] (hence contraindicated in children below six years of age)


  • Red-green color blindness[10]

  • Peripheral neuropathy

  • Arthralgia

  • Hyperuricaemia

  • Vertical nystagmus

  • Milk skin reaction



Mechanism of action


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


It is well absorbed from the gastrointestinal tract and well distributed in body tissues and fluids. 50% is excreted unchanged in urine.



References





  1. ^ abcdefghi "Ethambutol Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 5 June 2016. Retrieved 10 December 2016..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  2. ^ abc Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 48. ISBN 9781284057560.


  3. ^ "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.


  4. ^ abc WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 136, 138, 588, 603. ISBN 9789241547659. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.


  5. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.


  6. ^ Landau, Ralph; Achilladelis, Basil; Scriabine, Alexander (1999). Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. p. 171. ISBN 9780941901215. Archived from the original on 2016-12-20.


  7. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.


  8. ^ "Ethambutol". International Drug Price Indicator Guide. Retrieved 8 December 2016.


  9. ^ Lim SA (April 2006). "Ethambutol-associated optic neuropathy" (PDF). Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500. Archived (PDF) from the original on 2009-08-16.


  10. ^ Tripathi, K D (August 2015). Essentials of MEDICAL PHARMACOLOGY (Seventh ed.). India: JAYPEE BROTHERS MEDICAL PUBLISHERS. p. 769. ISBN 978-93-5025-937-5.




External links


  • Medline Plus drug information









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