Identification

Name
Ethambutol
Accession Number
DB00330  (APRD00957)
Type
Small Molecule
Groups
Approved
Description

An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)

Structure
Thumb
Synonyms
  • (+)-2,2'-(ethylenediimino)di-1-butanol
  • (+)-ethambutol
  • (+)-N,N'-bis(1-(hydroxymethyl)propyl)ethylenediamine
  • (+)-S,S-ethambutol
  • (2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diol
  • (S,S)-Ethambutol
  • EMB
  • Etambutol
  • Etambutolo
  • Ethambutol
  • Ethambutolum
  • S,S-Ethambutol
Product Ingredients
IngredientUNIICASInChI Key
Ethambutol HydrochlorideQE4VW5FO071070-11-7AUAHHJJRFHRVPV-BZDVOYDHSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ethambutol HydrochlorideTablet400 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Etibi Tab 100mgTablet100 mgOralValeant Canada Lp Valeant Canada S.E.C.1972-12-31Not applicableCanada
Etibi Tab 400mgTablet400 mgOralValeant Canada Lp Valeant Canada S.E.C.1972-12-31Not applicableCanada
MyambutolTablet, film coated400 mg/1OralA-S Medication Solutions2007-08-10Not applicableUs
MyambutolTablet400 mg/1OralPhysicians Total Care, Inc.2007-08-10Not applicableUs
MyambutolTablet400 mg/1OralCardinal Health2011-06-272018-05-25Us
MyambutolTablet, film coated100 mg/1OralSTI Pharma2007-08-10Not applicableUs
MyambutolTablet, film coated400 mg/1OralA S Medication Solutions2007-08-10Not applicableUs
MyambutolTablet, film coated400 mg/1OralSTI Pharma2007-08-10Not applicableUs
MyambutolTablet, film coated400 mg/1OralA-S Medication Solutions2007-08-10Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EthambutolTablet, film coated400 mg/1OralPhysicians Total Care, Inc.2010-12-20Not applicableUs
Ethambutol HydrochlorideTablet, film coated100 mg/1OralA-S Medication Solutions2006-12-152018-01-31Us
Ethambutol HydrochlorideTablet400 mg/1OralAmerincan Health Packaging2009-11-02Not applicableUs
Ethambutol HydrochlorideTablet, film coated400 mg/1OralDepartment Of State Health Services, Pharmacy Branch2006-12-15Not applicableUs
Ethambutol HydrochlorideTablet, film coated100 mg/1OralSTI Pharma2006-12-15Not applicableUs
Ethambutol HydrochlorideTablet, film coated400 mg/1OralRemedy Repack2017-05-09Not applicableUs
Ethambutol HydrochlorideTablet100 mg/1OralLupin Pharmaceuticals2009-07-04Not applicableUs
Ethambutol HydrochlorideTablet, film coated400 mg/1OralTeva Pharmaceuticals USA, Inc.2001-11-27Not applicableUs00555 0923 02 nlmimage10 8b35c5ee
Ethambutol HydrochlorideTablet, film coated400 mg/1OralRemedy Repack2016-07-132017-02-16Us
Ethambutol HydrochlorideTablet, film coated400 mg/1OralVersaPharm Inc. - an Akorn Company2015-03-18Not applicableUs
International/Other Brands
Etibi (Valeant Canada Limited) / Tibutol (Refasa)
Categories
UNII
8G167061QZ
CAS number
74-55-5
Weight
Average: 204.3098
Monoisotopic: 204.183778022
Chemical Formula
C10H24N2O2
InChI Key
AEUTYOVWOVBAKS-UWVGGRQHSA-N
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
IUPAC Name
(2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol
SMILES
CC[C@@H](CO)NCCN[C@@H](CC)CO

Pharmacology

Indication

For use, as an adjunct, in the treatment of pulmonary tuberculosis.

Associated Conditions
Pharmacodynamics

Ethambutol is an oral chemotherapeutic agent which is specifically effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Ethambutol inhibits RNA synthesis and decreases tubercle bacilli replication. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of strains of MAC are sensitive to ethambutol.

Mechanism of action

Ethambutol inhibits arabinosyl transferases which is involved in cell wall biosynthesis. By inhibiting this enzyme, the bacterial cell wall complex production is inhibited. This leads to an increase in cell wall permeability.

TargetActionsOrganism
AProbable arabinosyltransferase C
inhibitor
Mycobacterium tuberculosis
AProbable arabinosyltransferase B
inhibitor
Mycobacterium tuberculosis
AProbable arabinosyltransferase A
inhibitor
Mycobacterium tuberculosis
Absorption

About 75% to 80% of an orally administered dose of ethambutol is absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

20-30%

Metabolism

Hepatic. Up to 15% of administered drug is metabolized to inactive metabolites. The main path of metabolism appears to be an initial oxidation of the alcohol to an aldehydic intermediate, followed by conversion to a dicarboxylic acid.

Route of elimination

During the 24-hour period following oral administration of ethambutol hydrochloride approximately 50 percent of the initial dose is excreted unchanged in the urine, while an additional 8 to 15 percent appears in the form of metabolites. From 20 to 22 percent of the initial dose is excreted in the feces as unchanged drug.

Half life

In patients with normal renal function, 3 to 4 hours. In patients with impaired renal function, up to 8 hours.

Clearance
Not Available
Toxicity

The most commonly recognized toxic effect of ethambutol is optic neuropathy, which generally is considered uncommon and reversible in medical literature. Other side effects that have been observed are pruritus, joint pain, gastrointestinal upset, abdominal pain, malaise, headache, dizziness, mental confusion, disorientation, and possible hallucinations.

Affected organisms
  • Humans and other mammals
  • Mycobacterium tuberculosis
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Ethambutol is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Ethambutol is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Ethambutol is combined with 4-hydroxycoumarin.
AbacavirEthambutol may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Ethambutol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ethambutol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ethambutol which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Ethambutol is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Food Interactions
  • Take with food to reduce irritation.

References

Synthesis Reference

Sang-Woo Park, "Preparation of ethambutol-diisoniazide methane sulfonic acid salt." U.S. Patent US4450274, issued February, 1973.

US4450274
General References
Not Available
External Links
Human Metabolome Database
HMDB0014474
KEGG Compound
C06984
PubChem Compound
14052
PubChem Substance
46504788
ChemSpider
13433
BindingDB
50448407
ChEBI
4877
ChEMBL
CHEMBL44884
Therapeutic Targets Database
DAP000055
PharmGKB
PA164784021
HET
95E
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ethambutol
ATC Codes
J04AM06 — Rifampicin, pyrazinamide, ethambutol and isoniazidJ04AK02 — EthambutolJ04AM03 — Ethambutol and isoniazid
AHFS Codes
  • 08:16.04 — Antituberculosis Agents
PDB Entries
5nr3
FDA label
Download (25.3 KB)
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticLung Function / Sarcoidosis, Pulmonary1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
1CompletedTreatmentTuberculosis Infection1
1, 2RecruitingTreatmentTuberculous Meningitis1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare4
2CompletedTreatmentInfection, Mycobacterium Avium-Intracellulare1
2CompletedTreatmentPulmonary Tuberculosis (TB)1
2CompletedTreatmentTuberculosis Infection2
2RecruitingTreatmentDrug-resistant Tuberculosis / Extensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis Infection / Tuberculosis, Multidrug Resistant1
2RecruitingTreatmentPulmonary Tuberculosis (TB)1
2RecruitingTreatmentSarcoidosis; Antimycobacterial Therapy1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2Unknown StatusTreatmentPulmonary Tuberculosis Without Resistance to Rifampicin1
2Unknown StatusTreatmentTuberculosis Infection1
2, 3Not Yet RecruitingTreatmentMycobacterium avium complex infection / Nontuberculous Mycobacterium Infection1
2, 3Not Yet RecruitingTreatmentPulmonary Tuberculosis (TB)1
2, 3RecruitingTreatmentPulmonary Tuberculosis (TB)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pulmonary Tuberculosis (TB)1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentPulmonary Tuberculosis (TB)1
3CompletedTreatmentTuberculosis Infection1
3RecruitingTreatmentLung Infection / Mycobacterium avium complex infection1
3RecruitingTreatmentMulti-Drug Resistant Tuberculosis1
3RecruitingTreatmentTuberculosis Infection1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4CompletedNot AvailableBMI >30 kg/m2 / Tuberculosis Infection1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
4CompletedTreatmentPulmonary Diseases1
4RecruitingTreatmentAIDS With Tuberculosis1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentPulmonary Tuberculosis (TB)1
4RecruitingTreatmentTuberculosis, Spinal1
4Unknown StatusTreatmentReinfection Pulmonary Tuberculosis1
Not AvailableCompletedSupportive CareBody Weight Changes / Motor Activities / Pulmonary Tuberculosis (TB)1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mycobacterium Avium-intracellular Infection1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection2
Not AvailableCompletedTreatmentTuberculosis Infection1
Not AvailableRecruitingNot AvailableTuberculosis Infection1
Not AvailableRecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Pulmonary Tuberculosis (TB)1
Not AvailableUnknown StatusNot AvailablePulmonary Tuberculosis (TB)1

Pharmacoeconomics

Manufacturers
  • Barr laboratories inc
  • Lupin ltd
  • West ward pharmaceutical corp
  • Sti pharma llc
Packagers
  • Amerisource Health Services Corp.
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Belgomex Sprl
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Heritage Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lupin Pharmaceuticals Inc.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Patheon Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Stat Trade Inc.
  • Tya Pharmaceuticals
  • Versapharm Inc.
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, film coatedOral400 mg/1
TabletOral100 mg/1
TabletOral400 mg/1
Tablet, film coatedOral100 mg/1
TabletOral100 mg
TabletOral400 mg
Prices
Unit descriptionCostUnit
Ethambutol hcl powder5.05USD g
Ethambutol hcl 400 mg tablet1.83USD tablet
Myambutol 400 mg tablet1.83USD tablet
Myambutol 100 mg tablet0.79USD tablet
Ethambutol hcl 100 mg tablet0.59USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)171.5-174.5Wilkinson, R.G. and Shepherd, R.G.; U.S. Patent 3,297,707; January 10,1967; assigned to American Cyanamid Company.
logP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.58 mg/mLALOGPS
logP-0.12ALOGPS
logP-0.059ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)14.82ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area64.52 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity57.89 m3·mol-1ChemAxon
Polarizability24.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9157
Blood Brain Barrier-0.7803
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.7142
P-glycoprotein inhibitor INon-inhibitor0.9412
P-glycoprotein inhibitor IINon-inhibitor0.9374
Renal organic cation transporterNon-inhibitor0.8558
CYP450 2C9 substrateNon-substrate0.8575
CYP450 2D6 substrateNon-substrate0.6485
CYP450 3A4 substrateNon-substrate0.8023
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9251
CYP450 3A4 inhibitorNon-inhibitor0.972
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9763
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6982
BiodegradationNot ready biodegradable0.8997
Rat acute toxicity2.2797 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8706
hERG inhibition (predictor II)Non-inhibitor0.8672
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-1c5922845499f5b38b9c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-d6867efe25d3bd98a3d6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-c5e5bdae927a908239cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-c5e5bdae927a908239cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-3fd99ca7b30bbde49d3a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-f3bae435be629eb01dfb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0aor-0890000000-ccfd6d7643c035e85154
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-1c5922845499f5b38b9c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-c5e5bdae927a908239cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-f11341611c9cfa579095

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
1,2-aminoalcohols
Alternative Parents
Dialkylamines / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Secondary amine / Secondary aliphatic amine / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
ethanolamines, ethylenediamine derivative (CHEBI:4877)

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
Actions
Inhibitor
General Function
Arabinosyl transferase responsible for the polymerization of arabinose into the arabinan of arabinogalactan.
Specific Function
Arabinosyltransferase activity
Gene Name
embC
Uniprot ID
P9WNL5
Uniprot Name
Probable arabinosyltransferase C
Molecular Weight
117488.655 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Zhang J, Khoo KH, Wu SW, Chatterjee D: Characterization of a distinct arabinofuranosyltransferase in Mycobacterium smegmatis. J Am Chem Soc. 2007 Aug 8;129(31):9650-62. Epub 2007 Jul 14. [PubMed:17630736]
  4. Berg S, Starbuck J, Torrelles JB, Vissa VD, Crick DC, Chatterjee D, Brennan PJ: Roles of conserved proline and glycosyltransferase motifs of EmbC in biosynthesis of lipoarabinomannan. J Biol Chem. 2005 Feb 18;280(7):5651-63. Epub 2004 Nov 16. [PubMed:15546869]
  5. Sharma K, Gupta M, Pathak M, Gupta N, Koul A, Sarangi S, Baweja R, Singh Y: Transcriptional control of the mycobacterial embCAB operon by PknH through a regulatory protein, EmbR, in vivo. J Bacteriol. 2006 Apr;188(8):2936-44. [PubMed:16585755]
  6. Goude R, Amin AG, Chatterjee D, Parish T: The arabinosyltransferase EmbC is inhibited by ethambutol in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2009 Oct;53(10):4138-46. doi: 10.1128/AAC.00162-09. Epub 2009 Jul 13. [PubMed:19596878]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
Actions
Inhibitor
General Function
Arabinosyl transferase responsible for the polymerization of arabinose into the arabinan of arabinogalactan.
Specific Function
Arabinosyltransferase activity
Gene Name
embB
Uniprot ID
P9WNL7
Uniprot Name
Probable arabinosyltransferase B
Molecular Weight
118020.235 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Hazbon MH, Bobadilla del Valle M, Guerrero MI, Varma-Basil M, Filliol I, Cavatore M, Colangeli R, Safi H, Billman-Jacobe H, Lavender C, Fyfe J, Garcia-Garcia L, Davidow A, Brimacombe M, Leon CI, Porras T, Bose M, Chaves F, Eisenach KD, Sifuentes-Osornio J, Ponce de Leon A, Cave MD, Alland D: Role of embB codon 306 mutations in Mycobacterium tuberculosis revisited: a novel association with broad drug resistance and IS6110 clustering rather than ethambutol resistance. Antimicrob Agents Chemother. 2005 Sep;49(9):3794-802. [PubMed:16127055]
  4. Lee HY, Myoung HJ, Bang HE, Bai GH, Kim SJ, Kim JD, Cho SN: Mutations in the embB locus among Korean clinical isolates of Mycobacterium tuberculosis resistant to ethambutol. Yonsei Med J. 2002 Feb;43(1):59-64. [PubMed:11854934]
  5. Plinke C, Rusch-Gerdes S, Niemann S: Significance of mutations in embB codon 306 for prediction of ethambutol resistance in clinical Mycobacterium tuberculosis isolates. Antimicrob Agents Chemother. 2006 May;50(5):1900-2. [PubMed:16641474]
  6. Goude R, Amin AG, Chatterjee D, Parish T: The arabinosyltransferase EmbC is inhibited by ethambutol in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2009 Oct;53(10):4138-46. doi: 10.1128/AAC.00162-09. Epub 2009 Jul 13. [PubMed:19596878]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
Actions
Inhibitor
General Function
Arabinosyl transferase responsible for the polymerization of arabinose into the arabinan of arabinogalactan.
Specific Function
Arabinosyltransferase activity
Gene Name
embA
Uniprot ID
P9WNL9
Uniprot Name
Probable arabinosyltransferase A
Molecular Weight
115722.825 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Zhang J, Khoo KH, Wu SW, Chatterjee D: Characterization of a distinct arabinofuranosyltransferase in Mycobacterium smegmatis. J Am Chem Soc. 2007 Aug 8;129(31):9650-62. Epub 2007 Jul 14. [PubMed:17630736]
  4. Alderwick LJ, Seidel M, Sahm H, Besra GS, Eggeling L: Identification of a novel arabinofuranosyltransferase (AftA) involved in cell wall arabinan biosynthesis in Mycobacterium tuberculosis. J Biol Chem. 2006 Jun 9;281(23):15653-61. Epub 2006 Apr 4. [PubMed:16595677]
  5. Berg S, Starbuck J, Torrelles JB, Vissa VD, Crick DC, Chatterjee D, Brennan PJ: Roles of conserved proline and glycosyltransferase motifs of EmbC in biosynthesis of lipoarabinomannan. J Biol Chem. 2005 Feb 18;280(7):5651-63. Epub 2004 Nov 16. [PubMed:15546869]
  6. Goude R, Amin AG, Chatterjee D, Parish T: The arabinosyltransferase EmbC is inhibited by ethambutol in Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2009 Oct;53(10):4138-46. doi: 10.1128/AAC.00162-09. Epub 2009 Jul 13. [PubMed:19596878]

Drug created on June 13, 2005 07:24 / Updated on December 12, 2018 07:03