File:Ethambutol.svg · Wikimedia Commons · See Wikimedia Commons
ethambutol
Sign in to saveAlso 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.
OverviewAI-generated
Ethambutol is a chemical compound with the formula C₁₀H₂₄N₂O₂. Its IUPAC name is (2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol. The substance has a mass of 204.183778 and a weight of 204.31. It possesses a charge of 0, an xlogp of -0.1, and a tpsa of 64.5. The molecule contains four hydrogen bond donors and four hydrogen bond acceptors.
The compound is associated with 8407 entries in PubMed literature. It is referenced by 142 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- 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 sectionsContents
- Chirality and biological activity
- Medical uses
- Adverse effects
- Mechanism of action
- Pharmacokinetics
- References
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.
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.