Ethambutol

Ethambutol

Systematic (IUPAC) name
(2S,2′S)-2,2′-(ethane-1,2-diyldiimino)dibutan-1-ol
Clinical data
Trade names	Myambutol
AHFS/Drugs.com	monograph
MedlinePlus	a682550
Pregnancy cat.	B
Legal status	?
Routes	Oral
Pharmacokinetic data
Bioavailability	Well-absorbed from GI tract
Protein binding	20 to 30%
Metabolism	Liver
Half-life	3-4 hr (increased in impaired renal function)
Excretion	Renal
Identifiers
CAS number	74-55-5 Y
ATC code	J04AK02
PubChem	CID 14052
DrugBank	APRD00957
ChemSpider	13433 Y
UNII	8G167061QZ Y
KEGG	D07925 Y
ChEBI	CHEBI:4877 Y
ChEMBL	CHEMBL44884 Y
Chemical data
Formula	C10H24N2O2
Mol. mass	204.31 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:AEUTYOVWOVBAKS-UWVGGRQHSA-N Y
Y(what is this?)  (verify)

Ethambutol (commonly abbreviated EMB or simply E) is a bacteriostatic antimycobacterial drug prescribed to treat tuberculosis.^[1] It is usually given in combination with other tuberculosis drugs, such as isoniazid, rifampicin and pyrazinamide.

It is sold under the trade names Myambutol and Servambutol.

Adverse effects

• Optic neuritis.^[2] Hence contraindicated in children below 6 yrs of age.
• Red-green color blindness
• 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. ^ Yendapally R, Lee RE (March 2008). "Design, synthesis, and evaluation of novel ethambutol analogues". Bioorg. Med. Chem. Lett. 18 (5): 1607–11. doi:10.1016/j.bmcl.2008.01.065. PMC 2276401. PMID 18242089. http://linkinghub.elsevier.com/retrieve/pii/S0960-894X(08)00082-6. 
2. ^ Lim SA (April 2006). "Ethambutol-associated optic neuropathy". Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500. http://www.annals.edu.sg/pdf/35VolNo4200605/V35N4p274.pdf. 

External links

• Medline Plus drug information