ethambutol

Also known as (+)-S,S-ethambutol, EMB, Etambutolo, (+)-2,2'-(ethylenediimino)di-1-butanol, (+)-N,N'-bis(1-(hydroxymethyl)propyl)ethylenediamine, S,S-Ethambutol, (+)-ethambutol, (S,S)-Ethambutol

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

Key facts

Drug.IUPAC_name: (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol | image = Ethambutol.svg | image_class = skin-invert-image | width = | alt = | image2 = Ethambutol substance photo.jpg | width2 = | alt2 = | caption = Chemical structure of ethambutol (top) and photo of ethambutol crystals (bottom) | pronounce = | tradename = Myambutol, Etibi, Servambutol, others | Drugs.com = | MedlinePlus = | DailyMedID = Ethambutol | pregnancy_AU = | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth | ATC_prefix = J04 | ATC_suffix = AK02 | ATC_supplemental = | legal_AU = S4 | legal_AU_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = | legal_UK_comment = | legal_US = | legal_US_comment = | legal_UN = | legal_UN_comment = | legal_status = Rx-only | bioavailability = | protein_bound = 20–30% | metabolism = liver | metabolites = | onset = | elimination_half-life = 3–4 hours | duration_of_action = | excretion = | CAS_number = 74-55-5 | CAS_supplemental = | PubChem = 14052 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = DB00330 | ChemSpiderID = 13433 | UNII = 8G167061QZ | KEGG = D07925 | ChEBI = 4877 | ChEMBL = 44884 | NIAID_ChemDB = | synonyms = (2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol | C = 10 | H = 24 | N = 2 | O = 2 | molecular_weight = | SMILES = CC[C@@H](CO)NCCN[C@@H](CC)CO | Jmol = | StdInChI = 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 | StdInChI_Ref = | StdInChIKey = AEUTYOVWOVBAKS-UWVGGRQHSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | specific_rotation =

via Wikipedia infobox

Chemical data

Formula: C10H24N2O2
Molecular weight: 204.31 g/mol
IUPAC name: (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol
SMILES: CC[C@@H](CO)NCCN[C@@H](CC)CO
InChIKey: AEUTYOVWOVBAKS-UWVGGRQHSA-N
XLogP: -0.1
Polar surface area: 64.5 Å²
H-bond donors: 4
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

8,407 papers

Ethambutol optic neuropathy.Current opinion in ophthalmology · 2017
Ethambutol.Tuberculosis (Edinburgh, Scotland) · 2008
Ethambutol neuroretinopathy.Seminars in ophthalmology · 2007
Ocular ethambutol toxicity.Mayo Clinic proceedings · 2003
Ethambutol and viomycin.The Medical clinics of North America · 1970

via PubMed

~3 min read

Encyclopedic overview

6 sections

Contents

Chirality and biological activity
Medical uses
Adverse effects
Mechanism of action
Pharmacokinetics
References

Common side effects include problems with vision, joint pain, nausea, headaches, and feeling tired. Other side effects include liver problems and allergic reactions. It is not recommended in people with optic neuritis, significant kidney problems, or under the age of five. Use during pregnancy or breastfeeding has not been found to cause harm. 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.

Excerpted from Wikipedia’s “ethambutol” article, available under the CC BY-SA 4.0 licence.

Gallery (3)

Available in 37 languages

Show 18 more

via Wikidata sitelinks · CC0