Drug Details

General Information of the Drug (ID: DR5938)
Name
Ethambutol
Synonyms
ethambutol; 74-55-5; Ethambutolum; Aethambutolum; D-Ethambutol; (+)-S,S-Ethambutol; Ethambutol Hydrochloride; (+)-ethambutol; (S,S)-ethambutol; Myambutol; (2S,2'S)-2,2'-(Ethane-1,2-diylbis(azanediyl))bis(butan-1-ol); Etambutolo [DCIT]; Tibutol; Etambutol [INN-Spanish]; Ethambutolum [INN-Latin]; S,S-Ethambutol; Diambutol; CHEBI:4877; UNII-8G167061QZ; (+)-2,2'-(Ethylenediimino)di-1-butanol; Purderal; (+)-N,N'-Bis(1-(hydroxymethyl)propyl)ethylenediamine; EMB; 8G167061QZ; 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (2S,2'S)-; (2S,7S)-2,7-diethyl-3,6-diazaoctane-1,8-diol; (2S,2'S)-2,2'-(ethane-1,2-diyldiimino)dibutan-1-ol; Etambutolo; C10H24N2O2; Ebutol; D-2,2'-(Ethylenediimino)di-1-butanol; D-2,2'-(Ethylenediimino)bis(1-butanol); 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (S-(R*,R*))-; Ethambutol, racemic mixture; 1-Butanol, 2,2'-(ethylenediimino)di-, (+)-; d,N,N'-Bis(1-hydroxymethylpropyl)ethylenediamine; D-N,N'-Bis(1-hydroxymethylpropyl)ethylenediamine; Ethambutol [INN:BAN]; (R)-2,2'-(1,2-Ethanediyldiimino)bis-1-butanol; NCGC00178864-03; 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (R-(R*,R*))-; HSDB 3078; Servambutol (TN); 95E; Ethambutol (INN); EINECS 200-810-6; Spectrum_001058; Spectrum2_001014; Spectrum3_000426; Spectrum4_000545; Spectrum5_000702; 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, (R)-; Myambutol (dihydrochloride); SCHEMBL3399; BSPBio_002012; KBioGR_001209; KBioSS_001538; CHEMBL44884; DivK1c_000561; SPBio_001167; CL 40881 (dihydrochloride); DTXSID8023006; KBio1_000561; KBio2_001538; KBio2_004106; KBio2_006674; KBio3_001232; NINDS_000561; HY-B0535; 2860AH; BDBM50448407; ZINC19364219; DB00330; MCULE-9663372083; IDI1_000561; NCGC00178864-01; SBI-0051375.P003; C06984; D07925; E-3950; AB00053473_04; AB00053473_05; Q412318; (S,S)-2,2'-(1,2-Ethanediyldiimino)bis-1-butanol; BRD-K93231391-300-03-1; (+)-(S,S)-2,2'-(1,2-Ethylenediimino)-di-1-butanol; Ethambutol dihydrochloride, Antibiotic for Culture Media Use Only; (2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol; (2S)-2-[2-[[(1S)-1-(hydroxymethyl)propyl]amino]ethylamino]butan-1-ol
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Molecular Type
Small molecule
Disease Tuberculosis [ICD-11: 1B10] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 6.3-10.8 mgh/L
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 2-5 mg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2-4 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Bioavailability
The bioavailability of drug is 75-80%
Clearance
The apparent oral clearance of drug is 77.4 L/h
Elimination
Ethambutol is 50% eliminated in the urine as the unmetabolized parent compound, 8 - 15% as inactive metabolites, and 20-22% of a dose is eliminated unchanged in the feces
Half-life
The concentration or amount of drug in body reduced by one-half in 3.3 hours
Metabolism
The drug is metabolized via the an aldehyde dehydrogenase to an aldehyde metabolite
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 122.36009 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.18%
Vd
The volume of distribution (Vd) of drug is 76.2 L
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C10H24N2O2
PubChem CID
14052
Canonical SMILES
CCC(CO)NCCNC(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
InChIKey
AEUTYOVWOVBAKS-UWVGGRQHSA-N
CAS Number
CAS 74-55-5
ChEBI ID
CHEBI:4877
TTD Drug ID
D08QME
DrugBank ID
DB00330
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Allium sativum      Allium sativum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 Garlic extracts or compounds have a good potential as antitubercular(s) drug if given as a supplement to ATT.
          Oleanolic acid      Olea europaea     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Vero CVCL_0059 Healthy Chlorocebus sabaeus
                    Experimental
                    Result(s)		 Oleanolic acid and combination displayed either a synergistic interaction or did not show any interaction against two drug-sensitive strains.
Target and Pathway
Target(s) Mycobacterium Arabinosyltransferase C (MycB embC)  Molecule Info  [4]
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Antitubercular activity of garlic (allium sativum) extract on combination with conventional antitubercular drugs in tubercular lymphadenitis. Indian J Clin Biochem. 1999 Jan;14(1):12-8.
Reference 3 In vitro synergistic interactions of oleanolic acid in combination with isoniazid, rifampicin or ethambutol against Mycobacterium tuberculosis. J Med Microbiol. 2010 May;59(Pt 5):567-572.
Reference 4 The arabinosyltransferase EmbC is inhibited by ethambutol in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2009 Oct;53(10):4138-46.
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