Identification

Name
Ethambutol
Accession Number
DB00330
Description

Ethambutol is a bacteriostatic agent indicated alongside medications such as isoniazid, rifampin, and pyrazinamide in the treatment of pulmonary tuberculosis.13 Ethambutol was first described in the literature in 1961.11 It was developed out of a need for therapies active against isoniazid resistant strains of Mycobacterium tuberculosis.11

Ethambutol was granted FDA approval on 6 November 1967.12

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 204.3098
Monoisotopic: 204.183778022
Chemical Formula
C10H24N2O2
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

Pharmacology

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Indication

Ethambutol is indicated in combination with other anti-tuberculosis drugs in the treatment of pulmonary tuberculosis.12 Ethambutol is commonly used in combination with isoniazid, rifampin, and pyrazinamide.13

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Ethambutol is indicated in combination with other anti-tuberculosis drugs in the treatment of pulmonary tuberculosis.12 It has a long duration of action as it is administered daily, and a moderate therapeutic window.12 Patients should be counselled regarding the risk of optic neuritis and hepatic toxicity.12

Mechanism of action

Ethambutol diffuses into Mycobacterium cells.12 Once inside the cell, ethambutol inhibits the arabinosyltransferases (embA, embB, and embC), preventing formation of the cell wall components arabinogalactan and lipoarabinomannan, and preventing cell division.6,7,10,5 Decreased concentrations of arabinogalactan in the cell wall reduces the number of binding sites for mycolic acid, leading to the accumulation of mycolic acid, trehalose monomycolate, and trehalose dimycolate.9,7 Lipoarabinomannan is a component of a cell surface molecule involved in the interaction with host cells.7 Reduced levels of lipoarabinomannan may interfere with mycobacterial interaction with host cells.7

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

Oral ethambutol is approximately 75-80% orally bioavailable.12,14 A 25 mg/kg oral dose of ethambutol reaches a Cmax of 2-5 µg/mL, with a Tmax of 2-4 hours.12,14 In a separate study, the AUC0-8 varied from 6.3 ± 5.5 h*mg/L to 10.8 ± 7.6 h*mg/L depending on CYP1A2 genetic polymorphisms.3

Volume of distribution

Patients coinfected with tuberculosis and HIV have an estimated ethambutol volume of distribution of 76.2 L.3

Protein binding

Ethambutol is 20-30% bound to protein in plasma.14 Data regarding which proteins ethambutol binds to are not readily available.

Metabolism

Ethambutol is mainly oxidized by an aldehyde dehydrogenase to an aldehyde metabolite, followed by conversion to the dicarboxylic acid 2,2'-(ethylinediimino)di-butyric acid.2,4,12

Hover over products below to view reaction partners

Route of elimination

Ethambutol is 50% eliminated in the urine as the unmetabolized parent compound and 8-15% as inactive metabolites.12,14 20-22% of a dose is eliminated unchanged in the feces.12,14

Half-life

Ethambutol has a half life of 3.3 hours in patients with normal renal function.14 In patients with renal failure, the half life could be 7 hours or longer.14

Clearance

Patients coinfected with tuberculosis and HIV have an estimated ethambutol oral clearance of 77.4 L/h.3

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

Patients experiencing a chronic overdose of ethambutol may present with disturbances in colour vision and reduced visual acuity as symptoms of optic neuropathy.8 In these cases, ethambutol should be stopped.8 Data regarding acute overdose of ethambutol are not readily available. Patients experiencing an acute overdose of ethambutol may be experience an increased risk and severity of adverse effects such as pruritus, joint pain, gastrointestinal upset, abdominal pain, malaise, headache, dizziness, mental confusion, disorientation, and possible hallucinations.12,14 Patients should be treated with symptomatic and supportive measures.

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirEthambutol may decrease the excretion rate of Abacavir 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.
AcetazolamideAcetazolamide may increase the excretion rate of Ethambutol which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ethambutol which could result in a higher serum level.
AclidiniumEthambutol may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineEthambutol may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
  • Take separate from antacids. Do not take aluminum hydroxide containing antacids for at least 4 hours after ethambutol administration.
  • Take with food. Food reduces irritation.

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Ethambutol hydrochlorideJNG307DJ5X1070-11-7AUAHHJJRFHRVPV-BZDVOYDHSA-N
Product Images
International/Other Brands
Etibi (Valeant Canada Limited) / Tibutol (Refasa)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ethambutol HydrochlorideTablet400 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUS flag
EtibiTabletOralBausch Health, Canada Inc.1972-12-31Not applicableCanada flag
EtibiTabletOralBausch Health, Canada Inc.1972-12-31Not applicableCanada flag
MyambutolTablet, film coated400 mg/1OralSTI Pharma, LLC2007-08-10Not applicableUS flag
MyambutolTablet, film coated400 mg/1OralA-S Medication Solutions2007-08-10Not applicableUS flag
MyambutolTablet, film coated400 mg/1OralA S Medication Solutions2007-08-10Not applicableUS flag
MyambutolTablet, film coated400 mg/1OralA-S Medication Solutions2007-08-102018-10-31US flag
MyambutolTablet, film coated400 mg/1OralREMEDYREPACK INC.2020-04-14Not applicableUS flag
MyambutolTablet400 mg/1OralPhysicians Total Care, Inc.2007-08-10Not applicableUS flag
MyambutolTablet, film coated400 mg/1OralCardinal Health2011-06-272017-11-30US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EthambutolTablet, film coated400 mg/1OralPhysicians Total Care, Inc.2010-12-20Not applicableUS flag
Ethambutol HydrochlorideTablet, film coated400 mg/1OralA-S Medication Solutions2006-12-152019-01-31US flag
Ethambutol HydrochlorideTablet, film coated400 mg/1OralVersaPharm Incorporated2015-03-18Not applicableUS flag
Ethambutol HydrochlorideTablet100 mg/1OralRemedy Repack2013-03-092014-03-10US flag
Ethambutol HydrochlorideTablet400 mg/1OralClinical Solutions Wholsesale2009-07-042017-06-22US flag
Ethambutol HydrochlorideTablet, film coated400 mg/1OralREMEDYREPACK INC.2017-04-25Not applicableUS flag
Ethambutol HydrochlorideTablet, film coated400 mg/1OralDepartment Of State Health Services, Pharmacy Branch2006-12-15Not applicableUS flag
Ethambutol HydrochlorideTablet100 mg/1OralLupin Pharmaceuticals, Inc.2009-07-10Not applicableUS flag
Ethambutol HydrochlorideTablet100 mg/1OralA-S Medication Solutions2009-07-10Not applicableUS flag
Ethambutol HydrochlorideTablet, film coated100 mg/1OralSTI Pharma LLC2006-12-15Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FORECOX-TRAC TABLETAS RECUBIERTASEthambutol hydrochloride (275 mg) + Isoniazid (75 mg) + Pyrazinamide (400 mg) + Rifampicin (150 mg)Tablet, coatedOral2010-10-112018-02-22Colombia flag

Categories

ATC Codes
J04AK02 — EthambutolJ04AM03 — Ethambutol and isoniazidJ04AM06 — Rifampicin, pyrazinamide, ethambutol and isoniazidJ04AM07 — Rifampicin, ethambutol and isoniazid
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Alcohol / Aliphatic acyclic compound / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Secondary aliphatic amine / Secondary amine
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
ethanolamines, ethylenediamine derivative (CHEBI:4877)

Chemical Identifiers

UNII
8G167061QZ
CAS number
74-55-5
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

References

Synthesis Reference

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

US4450274
General References
  1. Becker C, Dressman JB, Amidon GL, Junginger HE, Kopp S, Midha KK, Shah VP, Stavchansky S, Barends DM: Biowaiver monographs for immediate release solid oral dosage forms: ethambutol dihydrochloride. J Pharm Sci. 2008 Apr;97(4):1350-60. doi: 10.1002/jps.21061. [PubMed:17879380]
  2. PEETS EA, SWEENEY WM, PLACE VA, BUYSKE DA: THE ABSORPTION, EXCRETION, AND METABOLIC FATE OF ETHAMBUTOL IN MAN. Am Rev Respir Dis. 1965 Jan;91:51-8. doi: 10.1164/arrd.1965.91.1.51. [PubMed:14260000]
  3. Sundell J, Bienvenu E, Birgersson S, Abelo A, Ashton M: Population Pharmacokinetics and Pharmacogenetics of Ethambutol in Adult Patients Coinfected with Tuberculosis and HIV. Antimicrob Agents Chemother. 2020 Jan 27;64(2). pii: AAC.01583-19. doi: 10.1128/AAC.01583-19. Print 2020 Jan 27. [PubMed:31712201]
  4. Hall RG 2nd, Swancutt MA, Meek C, Leff RD, Gumbo T: Ethambutol pharmacokinetic variability is linked to body mass in overweight, obese, and extremely obese people. Antimicrob Agents Chemother. 2012 Mar;56(3):1502-7. doi: 10.1128/AAC.05623-11. Epub 2011 Dec 12. [PubMed:22155817]
  5. Lee N, Nguyen H: Ethambutol . [PubMed:32644476]
  6. Zhang L, Zhao Y, Gao Y, Wu L, Gao R, Zhang Q, Wang Y, Wu C, Wu F, Gurcha SS, Veerapen N, Batt SM, Zhao W, Qin L, Yang X, Wang M, Zhu Y, Zhang B, Bi L, Zhang X, Yang H, Guddat LW, Xu W, Wang Q, Li J, Besra GS, Rao Z: Structures of cell wall arabinosyltransferases with the anti-tuberculosis drug ethambutol. Science. 2020 Jun 12;368(6496):1211-1219. doi: 10.1126/science.aba9102. Epub 2020 Apr 23. [PubMed:32327601]
  7. 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]
  8. Hasenbosch RE, Alffenaar JW, Koopmans SA, Kosterink JG, van der Werf TS, van Altena R: Ethambutol-induced optical neuropathy: risk of overdosing in obese subjects. Int J Tuberc Lung Dis. 2008 Aug;12(8):967-71. [PubMed:18647459]
  9. Takayama K, Armstrong EL, Kunugi KA, Kilburn JO: Inhibition by ethambutol of mycolic acid transfer into the cell wall of Mycobacterium smegmatis. Antimicrob Agents Chemother. 1979 Aug;16(2):240-2. doi: 10.1128/aac.16.2.240. [PubMed:485133]
  10. Amin AG, Goude R, Shi L, Zhang J, Chatterjee D, Parish T: EmbA is an essential arabinosyltransferase in Mycobacterium tuberculosis. Microbiology (Reading). 2008 Jan;154(Pt 1):240-248. doi: 10.1099/mic.0.2007/012153-0. [PubMed:18174142]
  11. THOMAS JP, BAUGHN CO, WILKINSON RG, SHEPHERD RG: A new synthetic compound with antituberculous activity in mice: ethambutol (dextro-2,2'-(ethylenediimino)-di-l-butanol). Am Rev Respir Dis. 1961 Jun;83:891-3. doi: 10.1164/arrd.1961.83.6.891. [PubMed:13776497]
  12. FDA Approved Drug Products: Myambutol (Ethambutol) Oral Tablet [Link]
  13. Public Health Agency of Canada: Canadian Tuberculosis Standards 7th Edition [Link]
  14. Health Canada Approved Drug Products: Etibi (Ethambutol) Oral Tablets [Link]
Human Metabolome Database
HMDB0014474
KEGG Drug
D07925
KEGG Compound
C06984
PubChem Compound
14052
PubChem Substance
46504788
ChemSpider
13433
BindingDB
50448407
RxNav
4110
ChEBI
4877
ChEMBL
CHEMBL44884
ZINC
ZINC000019364219
Therapeutic Targets Database
DAP000055
PharmGKB
PA164784021
PDBe Ligand
95E
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ethambutol
AHFS Codes
  • 08:16.04 — Antituberculosis Agents
PDB Entries
5nr3 / 7bvc / 7bve / 7bvf
FDA label
Download (25.3 KB)
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableBMI >30 kg/m2 / Tuberculosis (TB)1
4CompletedPreventionHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
4CompletedTreatmentPulmonary Diseases1
4Unknown StatusTreatmentAIDS With Tuberculosis1
4Unknown StatusTreatmentPulmonary Tuberculosis (TB)1
4Unknown StatusTreatmentReinfection Pulmonary Tuberculosis1
4Unknown StatusTreatmentTuberculosis, Spinal1
3Active Not RecruitingTreatmentMulti-Drug Resistant Tuberculosis1

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
TabletOral
TabletOral500 mg
Tablet
Injection, solutionIntramuscular; Intravenous; Subcutaneous
Tablet, film coatedOral400 mg/1
TabletOral100 mg/1
TabletOral400 mg/1
Tablet, film coatedOral100 mg/1
Injection, solutionIntravenous
TabletOral
Tablet, film coated
Injection, solution
Syrup
Tablet, film coatedOral
TabletOral400 mg
Tablet, film coatedOral400 mg
Tablet, coatedOral
Tablet, film coatedOral500 mg
Tablet, coatedOral
Tablet, film coatedOral
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.
water solubility1000 mg/mLBecker et al, 2008
logP0.4Becker et al, 2008
Predicted Properties
PropertyValueSource
logP-0.059ChemAxon
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

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Khoo KH, Jarboe E, Barker A, Torrelles J, Kuo CW, Chatterjee D: Altered expression profile of the surface glycopeptidolipids in drug-resistant clinical isolates of Mycobacterium avium complex. J Biol Chem. 1999 Apr 2;274(14):9778-85. doi: 10.1074/jbc.274.14.9778. [PubMed:10092667]
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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Khoo KH, Jarboe E, Barker A, Torrelles J, Kuo CW, Chatterjee D: Altered expression profile of the surface glycopeptidolipids in drug-resistant clinical isolates of Mycobacterium avium complex. J Biol Chem. 1999 Apr 2;274(14):9778-85. doi: 10.1074/jbc.274.14.9778. [PubMed:10092667]
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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Khoo KH, Jarboe E, Barker A, Torrelles J, Kuo CW, Chatterjee D: Altered expression profile of the surface glycopeptidolipids in drug-resistant clinical isolates of Mycobacterium avium complex. J Biol Chem. 1999 Apr 2;274(14):9778-85. doi: 10.1074/jbc.274.14.9778. [PubMed:10092667]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Lee SY, Jang H, Lee JY, Kwon KI, Oh SJ, Kim SK: Inhibition of cytochrome P450 by ethambutol in human liver microsomes. Toxicol Lett. 2014 Aug 17;229(1):33-40. doi: 10.1016/j.toxlet.2014.06.006. Epub 2014 Jun 5. [PubMed:24910189]

Drug created on June 13, 2005 13:24 / Updated on April 07, 2021 04:45