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

Similar Structures

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

Ingredient	UNII	CAS	InChI Key
Ethambutol hydrochloride	QE4VW5FO07	1070-11-7	AUAHHJJRFHRVPV-BZDVOYDHSA-N

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ethambutol Hydrochloride	Tablet	400 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Etibi Tab 100mg	Tablet	100 mg	Oral	Valeant Canada Lp Valeant Canada S.E.C.	1972-12-31	Not applicable
Etibi Tab 400mg	Tablet	400 mg	Oral	Valeant Canada Lp Valeant Canada S.E.C.	1972-12-31	Not applicable
Myambutol	Tablet, film coated	400 mg/1	Oral	A-S Medication Solutions	2007-08-10	Not applicable
Myambutol	Tablet, film coated	400 mg/1	Oral	STI Pharma	2007-08-10	Not applicable
Myambutol	Tablet	400 mg/1	Oral	Cardinal Health	2011-06-27	2018-05-25
Myambutol	Tablet, film coated	400 mg/1	Oral	A-S Medication Solutions	2007-08-10	Not applicable
Myambutol	Tablet, film coated	400 mg/1	Oral	A S Medication Solutions	2007-08-10	Not applicable
Myambutol	Tablet	400 mg/1	Oral	Physicians Total Care, Inc.	2007-08-10	Not applicable
Myambutol	Tablet, film coated	100 mg/1	Oral	STI Pharma	2007-08-10	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ethambutol	Tablet, film coated	400 mg/1	Oral	Physicians Total Care, Inc.	2010-12-20	Not applicable
Ethambutol Hydrochloride	Tablet	400 mg/1	Oral	Remedy Repack	2010-06-30	2011-06-30
Ethambutol Hydrochloride	Tablet, film coated	100 mg/1	Oral	STI Pharma	2006-12-15	Not applicable
Ethambutol Hydrochloride	Tablet	400 mg/1	Oral	Amerincan Health Packaging	2009-11-02	Not applicable
Ethambutol Hydrochloride	Tablet, film coated	100 mg/1	Oral	VersaPharm Inc. - an Akorn Company	2015-03-18	Not applicable
Ethambutol Hydrochloride	Tablet	400 mg/1	Oral	Lupin Pharmaceuticals	2009-07-04	Not applicable
Ethambutol Hydrochloride	Tablet	100 mg/1	Oral	Remedy Repack	2013-03-09	2014-03-10
Ethambutol Hydrochloride	Tablet, film coated	400 mg/1	Oral	STI Pharma	2006-12-15	Not applicable
Ethambutol Hydrochloride	Tablet, film coated	400 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2001-11-27	Not applicable
Ethambutol Hydrochloride	Tablet, film coated	400 mg/1	Oral	REMEDYREPACK INC.	2017-04-25	Not applicable

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.

Target	Actions	Organism
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

Drug	Interaction
(R)-warfarin	The risk or severity of bleeding can be increased when Ethambutol is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of bleeding can be increased when Ethambutol is combined with (S)-Warfarin.
4-hydroxycoumarin	The risk or severity of bleeding can be increased when Ethambutol is combined with 4-hydroxycoumarin.
Abacavir	Ethambutol may decrease the excretion rate of Abacavir which could result in a higher serum level.
Acarbose	Acarbose may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Acenocoumarol	The risk or severity of bleeding can be increased when Ethambutol is combined with Acenocoumarol.
Acetaminophen	Acetaminophen may decrease the excretion rate of Ethambutol which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Ethambutol which could result in a lower serum level and potentially a reduction in efficacy.

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 Drug: D07925
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

J04AK02 — Ethambutol

J04AM03 — Ethambutol and isoniazid

J04AM06 — Rifampicin, pyrazinamide, ethambutol and isoniazid

J04AM07 — Rifampicin, 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

Phase	Status	Purpose	Conditions	Count
1	Completed	Diagnostic	Lung Function / Sarcoidosis, Pulmonary	1
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
1	Completed	Treatment	Tuberculosis Infection	1
1, 2	Recruiting	Treatment	Tuberculous Meningitis	1
2	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare	4
2	Completed	Treatment	Infection, Mycobacterium Avium-Intracellulare	1
2	Completed	Treatment	Pulmonary Tuberculosis (TB)	1
2	Completed	Treatment	Tuberculosis Infection	2
2	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
2	Recruiting	Treatment	Sarcoidosis; Antimycobacterial Therapy	1
2	Terminated	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
2	Unknown Status	Treatment	Pulmonary Tuberculosis Without Resistance to Rifampicin	1
2	Unknown Status	Treatment	Tuberculosis Infection	1
2, 3	Not Yet Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
2, 3	Recruiting	Treatment	Drug-resistant Tuberculosis / Extensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis Infection / Tuberculosis, Multidrug Resistant	1
2, 3	Recruiting	Treatment	Mycobacterium avium complex infection / Nontuberculous Mycobacterium Infection	1
2, 3	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
3	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare	3
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Pulmonary Tuberculosis (TB)	1
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
3	Completed	Treatment	Pulmonary Tuberculosis (TB)	1
3	Completed	Treatment	Tuberculosis Infection	1
3	Recruiting	Treatment	Lung Infection / Mycobacterium avium complex infection	1
3	Recruiting	Treatment	Multi-Drug Resistant Tuberculosis	1
3	Recruiting	Treatment	Tuberculosis Infection	1
3	Unknown Status	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
4	Active Not Recruiting	Prevention	Infection, Human Immunodeficiency Virus I	1
4	Completed	Not Available	BMI >30 kg/m2 / Tuberculosis Infection	1
4	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare	1
4	Completed	Treatment	Pulmonary Diseases	1
4	Recruiting	Treatment	AIDS With Tuberculosis	1
4	Recruiting	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
4	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
4	Recruiting	Treatment	Tuberculosis, Spinal	1
4	Unknown Status	Treatment	Reinfection Pulmonary Tuberculosis	1
Not Available	Completed	Supportive Care	Body Weight Changes / Motor Activities / Pulmonary Tuberculosis (TB)	1
Not Available	Completed	Treatment	Cystic Fibrosis (CF)	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Mycobacterium Avium-intracellular Infection	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	2
Not Available	Completed	Treatment	Tuberculosis Infection	1
Not Available	Recruiting	Not Available	Tuberculosis Infection	1
Not Available	Recruiting	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / Pulmonary Tuberculosis (TB)	1
Not Available	Unknown Status	Not Available	Pulmonary 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

Form	Route	Strength
Tablet, film coated	Oral	400 mg/1
Tablet	Oral	100 mg/1
Tablet	Oral	400 mg/1
Tablet, film coated	Oral	100 mg/1
Tablet	Oral	100 mg
Tablet	Oral	400 mg

Prices

Unit description	Cost	Unit
Ethambutol hcl powder	5.05USD	g
Ethambutol hcl 400 mg tablet	1.83USD	tablet
Myambutol 400 mg tablet	1.83USD	tablet
Myambutol 100 mg tablet	0.79USD	tablet
Ethambutol hcl 100 mg tablet	0.59USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	171.5-174.5	Wilkinson, R.G. and Shepherd, R.G.; U.S. Patent 3,297,707; January 10,1967; assigned to American Cyanamid Company.
logP	-0.3	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.58 mg/mL	ALOGPS
logP	-0.12	ALOGPS
logP	-0.059	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	64.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	57.89 m³·mol^-1	ChemAxon
Polarizability	24.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9157
Blood Brain Barrier	-	0.7803
Caco-2 permeable	+	0.5
P-glycoprotein substrate	Substrate	0.7142
P-glycoprotein inhibitor I	Non-inhibitor	0.9412
P-glycoprotein inhibitor II	Non-inhibitor	0.9374
Renal organic cation transporter	Non-inhibitor	0.8558
CYP450 2C9 substrate	Non-substrate	0.8575
CYP450 2D6 substrate	Non-substrate	0.6485
CYP450 3A4 substrate	Non-substrate	0.8023
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9251
CYP450 3A4 inhibitor	Non-inhibitor	0.972
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9763
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.6982
Biodegradation	Not ready biodegradable	0.8997
Rat acute toxicity	2.2797 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8706
hERG inhibition (predictor II)	Non-inhibitor	0.8672

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0900000000-1c5922845499f5b38b9c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4i-0090000000-d6867efe25d3bd98a3d6
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0900000000-c5e5bdae927a908239cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0900000000-c5e5bdae927a908239cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0900000000-3fd99ca7b30bbde49d3a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4i-0090000000-f3bae435be629eb01dfb
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0aor-0890000000-ccfd6d7643c035e85154
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0900000000-1c5922845499f5b38b9c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0900000000-c5e5bdae927a908239cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-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

Details1. Probable arabinosyltransferase C

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

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]
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]
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]
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]
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]
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]

Details2. Probable arabinosyltransferase B

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

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]
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]
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]
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]
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]
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]

Details3. Probable arabinosyltransferase A

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

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]
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]
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]
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]
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]
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 April 18, 2019 06:15

Ethambutol

Identification

Structure for Ethambutol (DB00330)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References