Ethambutol

Last updated
Ethambutol
Ethambutol.svg
Ethambutol substance photo.jpg
Chemical structure of ethambutol (top) and photo of ethambutol crystals (bottom)
Clinical data
Trade names Myambutol, Etibi, [1] Servambutol, others
Other names(2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol [2]
AHFS/Drugs.com Monograph
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 binding 20–30%
Metabolism liver
Elimination half-life 3–4 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.737 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H24N2O2
Molar mass 204.314 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 Yes check.svgY
  • 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]

Contents

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]

Chirality and biological activity

(S,S)-(+)-Ethambutol is powerful and selective antitubercular drug. It is a typical example of an old drug that was introduced for clinical use in its unichiral form. Ethambutol contains two constitutionally symmetrical chiral centers in its structure and exists in three stereoisomeric forms, the enantiomeric pair (+)-(S,S)- and (−)-(R,R)-ethambutol, along with the achiral stereoisomer called meso-form. The (+)-(S,S)-enantiomer harbors the antitubercular activity. This enantiomer is 500 and 12 fold more potent than (−)-(R,R)-ethambutol and the meso-form respectively. On the other hand, all the three isomers are equipotent in terms of the major side-effect of the drug, optic neuritis. [9] Toxicity is associated to both dose and duration of treatment. Hence the use of (S,S)-enantiomer greatly improved the risk/benefit balance. [10] [11]

Medical uses

Ethambutol is used along with other medications to treat a number of infections including: tuberculosis, Mycobacterium avium complex, and Mycobacterium kansasii . [4]

Adverse effects

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.[ citation needed ]

Pharmacokinetics

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

See also

Related Research Articles

<i>Mycobacterium</i> Genus of bacteria

Mycobacterium is a genus of over 190 species in the phylum Actinomycetota, assigned its own family, Mycobacteriaceae. This genus includes pathogens known to cause serious diseases in mammals, including tuberculosis and leprosy in humans. The Greek prefix myco- means 'fungus', alluding to this genus' mold-like colony surfaces. Since this genus has cell walls with a waxy lipid-rich outer layer that contains high concentrations of mycolic acid, acid-fast staining is used to emphasize their resistance to acids, compared to other cell types.

<span class="mw-page-title-main">Isoniazid</span> Antibiotic for treatment of tuberculosis

Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. For latent tuberculosis, it is often used alone. It may also be used for atypical types of mycobacteria, such as M. avium, M. kansasii, and M. xenopi. It is usually taken by mouth, but may be used by injection into muscle.

<span class="mw-page-title-main">Rifampicin</span> Antibiotic medication

Rifampicin, also known as rifampin, is an ansamycin antibiotic used to treat several types of bacterial infections, including tuberculosis (TB), Mycobacterium avium complex, leprosy, and Legionnaires' disease. It is almost always used together with other antibiotics with two notable exceptions: when given as a "preferred treatment that is strongly recommended" for latent TB infection; and when used as post-exposure prophylaxis to prevent Haemophilus influenzae type b and meningococcal disease in people who have been exposed to those bacteria. Before treating a person for a long period of time, measurements of liver enzymes and blood counts are recommended. Rifampicin may be given either by mouth or intravenously.

<span class="mw-page-title-main">Succimer</span> Medication used to treat lead, mercury, and arsenic poisoning

Succimer, sold under the brand name Chemet among others, is a medication used to treat lead, mercury, and arsenic poisoning. When radiolabeled with technetium-99m, it is used in many types of diagnostic testing. A full course of Succimer lasts for 19 days of oral administration. A second course should be given when more than two weeks pass after the first course.

<span class="mw-page-title-main">Pyrazinamide</span> Medication

Pyrazinamide is a medication used to treat tuberculosis. For active tuberculosis, it is often used with rifampicin, isoniazid, and either streptomycin or ethambutol. It is not generally recommended for the treatment of latent tuberculosis. It is taken by mouth.

<span class="mw-page-title-main">4-Aminosalicylic acid</span> Anti-tuberculosis and anti-inflammatory drug

4-Aminosalicylic acid, also known as para-aminosalicylic acid (PAS) and sold under the brand name Paser among others, is an antibiotic primarily used to treat tuberculosis. Specifically it is used to treat active drug resistant tuberculosis together with other antituberculosis medications. It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease. It is typically taken by mouth.

<span class="mw-page-title-main">Amikacin</span> Antibiotic medication

Amikacin is an antibiotic medication used for a number of bacterial infections. This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used by injection into a vein using an IV or into a muscle.

<span class="mw-page-title-main">Clofazimine</span> Medication

Clofazimine, sold under the brand name Lamprene, is a medication used together with rifampicin and dapsone to treat leprosy. It is specifically used for multibacillary (MB) leprosy and erythema nodosum leprosum. Evidence is insufficient to support its use in other conditions though a retrospective study found it 95% effective in the treatment of Mycobacterium avium complex (MAC) when administered with a macrolide and ethambutol, as well as the drugs amikacin and clarithromycin. However, in the United States, clofazimine is considered an orphan drug, is unavailable in pharmacies, and its use in the treatment of MAC is overseen by the Food and Drug Administration. It is taken orally.

<span class="mw-page-title-main">Rifabutin</span> Chemical compound

Rifabutin (Rfb) is an antibiotic used to treat tuberculosis and prevent and treat Mycobacterium avium complex. It is typically only used in those who cannot tolerate rifampin such as people with HIV/AIDS on antiretrovirals. For active tuberculosis it is used with other antimycobacterial medications. For latent tuberculosis it may be used by itself when the exposure was with drug-resistant TB.

<span class="mw-page-title-main">Capreomycin</span> Pharmaceutical drug

Capreomycin is an antibiotic which is given in combination with other antibiotics for the treatment of tuberculosis. Specifically it is a second line treatment used for active drug resistant tuberculosis. It is given by injection into a vein or muscle.

<span class="mw-page-title-main">Rifampicin/isoniazid/pyrazinamide</span> Combination drug

Rifampicin/isoniazid/pyrazinamide, also known as rifampin/isoniazid/pyrazinamide, and sold under the trade name Rifater, is a medication used to treat tuberculosis. It is a fixed dose combination of rifampicin, isoniazid, and pyrazinamide. It is used either by itself or along with other antituberculosis medication. It is taken by mouth.

<span class="mw-page-title-main">Ethionamide</span> Chemical compound

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<span class="mw-page-title-main">Bedaquiline</span> Medication used to treat tuberculosis

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<span class="mw-page-title-main">Pretomanid</span> Chemical compound

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<span class="mw-page-title-main">Abacavir/lamivudine</span> Combination drug for HIV

Abacavir/lamivudine, sold under the brand name Kivexa among others, is a fixed-dose combination antiretroviral medication used to treat HIV/AIDS. It contains abacavir and lamivudine. It is generally recommended for use with other antiretrovirals. It is commonly used as part of the preferred treatment in children. It is taken by mouth as a tablet.

Delamanid, sold under the brand name Deltyba, is a medication used to treat tuberculosis. Specifically it is used, along with other antituberculosis medications, for active multidrug-resistant tuberculosis. It is taken by mouth.

Ethambutol/isoniazid is a fixed-dose combination medication used to treat tuberculosis. It is a fixed dose combination of ethambutol and isoniazid. It is used along with other antituberculosis medication. It is taken by mouth.

Ethambutol/isoniazid/rifampicin, also known as ethambutol/isoniazid/rifampin, is a fixed-dose combination medication used to treat tuberculosis. It contains ethambutol, isoniazid, and rifampicin. It is used either along or with other anti-tuberculosis medication. It is taken by mouth. Side effects are those of the underlying medications. Use may not be suitable in children.

Ethambutol/isoniazid/pyrazinamide/rifampicin, also known as ethambutol/isoniazid/pyrazinamide/rifampin, is a medication used for tuberculosis. It is a fixed dose combination of ethambutol, isoniazid, pyrazinamide, and rifampicin. It is used either alone or with other antituberculosis medication. It is taken by mouth.

Chemical compounds that come as mirror-image pairs are referred to by chemists as chiral or handed molecules. Each twin is called an enantiomer. Drugs that exhibit handedness are referred to as chiral drugs. Chiral drugs that are equimolar (1:1) mixture of enantiomers are called racemic drugs and these are obviously devoid of optical rotation. The most commonly encountered stereogenic unit, that confers chirality to drug molecules are stereogenic center. Stereogenic center can be due to the presence of tetrahedral tetra coordinate atoms (C,N,P) and pyramidal tricoordinate atoms (N,S). The word chiral describes the three-dimensional architecture of the molecule and does not reveal the stereochemical composition. Hence "chiral drug" does not say whether the drug is racemic, single enantiomer or some other combination of stereoisomers. To resolve this issue Joseph Gal introduced a new term called unichiral. Unichiral indicates that the stereochemical composition of a chiral drug is homogenous consisting of a single enantiomer.

References

  1. 1 2 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. 1 2 3 4 5 6 7 8 "Ethambutol Hydrochloride". drugs.com. The American Society of Health-System Pharmacists. Archived from the original on 5 June 2016. Retrieved 10 December 2016.
  5. 1 2 3 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.
  9. ↑ Sheldon RA (1993). Chirotechnology : industrial synthesis of optically active compounds. New York: Marcel Dekker. ISBN   0-8247-9143-6. OCLC   27897833.
  10. ↑ Stereochemical aspects of drug action and disposition. S. K. Branch, Michel Eichelbaum, Bernard Testa, Andrew Somogyi. Berlin: Springer. 2003. ISBN   978-3-540-41593-0. OCLC   52515592.{{cite book}}: CS1 maint: others (link)
  11. ↑ Kannappan V. "Ethambutol – Chiralpedia" . Retrieved 2022-08-29.
  12. ↑ Lim SA (April 2006). "Ethambutol-associated optic neuropathy" (PDF). Annals of the Academy of Medicine, Singapore. 35 (4): 274–8. doi:10.47102/annals-acadmedsg.V35N4p274. PMID   16710500. S2CID   12478013. Archived (PDF) from the original on 2009-08-16.
  13. 1 2 Lewis SM, Dirksen SR, Heitkemper MM, Bucher L, Harding M (5 December 2013). Medical-surgical nursing : assessment and management of clinical problems (9th ed.). St. Louis, Missouri. ISBN   978-0-323-10089-2. OCLC   228373703.{{cite book}}: CS1 maint: location missing publisher (link)
  14. ↑ Tripathi KD (August 2015). Essentials of Medical Pharmacology (Seventh ed.). India: Jaypee Brothers Medical Publishers. p. 769. ISBN   978-93-5025-937-5.
  15. ↑ "Ethambutol: MedlinePlus Drug Information". medlineplus.gov. Retrieved 2023-05-17.
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