Ethambutol

Identification

Summary

Ethambutol is an antituberculosis agent used in the prophylaxis and treatment of tuberculosis (TB).

Brand Names

Etibi, Myambutol

Generic Name

Ethambutol

DrugBank Accession Number

DB00330

Background

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

Similar Structures

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

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Pharmacology

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

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Associated Conditions

Indication Type	Indication	Approval Level
Used in combination to treat	Mycobacterium avium complex	••• •••••
Adjunct therapy in prevention of	Mycobacterium avium complex	••• •••••
Used in combination to treat	Pulmonary tuberculosis	••••••••••••
Used in combination to treat	Mycobacteria infection	••• •••••

Contraindications & Blackbox Warnings

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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

Target	Actions	Organism
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 C_max of 2-5 µg/mL, with a T_max of 2-4 hours.^12,14 In a separate study, the AUC_0-8 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

Ethambutol
- Ethambutol Aldehyde
  - 2,2'-(Ethylenediimino)di-butryic acid

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

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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.

Pathways

Not Available

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
Integrate drug-drug interactions in your software
Abacavir	Ethambutol may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Ethambutol.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Ethambutol.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Ethambutol.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Ethambutol.

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

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Product Ingredients

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

Product Images

International/Other Brands

Etibi (Valeant Canada Limited) / Tibutol (Refasa)

Brand Name 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	Tablet	100 mg	Oral	Bausch Health, Canada Inc.	1972-12-31	Not applicable
Etibi	Tablet	400 mg	Oral	Bausch Health, Canada Inc.	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, LLC	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, film coated	400 mg/1	Oral	REMEDYREPACK INC.	2017-04-25	Not applicable
Ethambutol Hydrochloride	Tablet	400 mg/1	Oral	Clinical Solutions Wholsesale	2009-07-04	2017-06-22
Ethambutol Hydrochloride	Tablet	100 mg/1	Oral	Lupin Pharmaceuticals, Inc.	2009-07-10	Not applicable
Ethambutol Hydrochloride	Tablet, film coated	400 mg/1	Oral	Department Of State Health Services, Pharmacy Branch	2006-12-15	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
FORECOX-TRAC TABLETAS RECUBIERTAS	Ethambutol hydrochloride (275 mg) + Isoniazid (75 mg) + Pyrazinamide (400 mg) + Rifampicin (150 mg)	Tablet, coated	Oral	MACLEODS PHARMACEUTICAL LTD. INDIA	2010-10-11	2018-02-22
ISOTHAM	Ethambutol (400 MG) + Isoniazid (150 MG)	Tablet, film coated		บริษัท ยูเมด้า จำกัด	2016-07-10	2020-08-23
ฟอร์ค๊อส - แทรค	Ethambutol hydrochloride (275 MG) + Isoniazid (75 MG) + Pyrazinamide (400 MG) + Rifampicin (150 MG)	Tablet, coated	Oral	บริษัท แอตแลนต้า เมดดิคแคร์ จำกัด จำกัด	2019-10-10	Not applicable
ริมสตาร์ 4 - FDC	Ethambutol hydrochloride (275 MG) + Isoniazid (400 MG) + Pyrazinamide (75 MG) + Rifampicin (150 MG)	Tablet, film coated	Oral	องค์การเภสัชกรรม	2008-05-19	Not applicable
ไรป์ - 900	Ethambutol hydrochloride (275 mg) + Isoniazid (75 mg) + Pyrazinamide (400 mg) + Rifampicin (150 mg)	Tablet, coated	Oral	บริษัท ยูเมด้า จำกัด	2010-01-18	2020-08-23

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
Lee N, Nguyen H: Ethambutol . [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
FDA Approved Drug Products: Myambutol (Ethambutol) Oral Tablet [Link]
Public Health Agency of Canada: Canadian Tuberculosis Standards 7th Edition [Link]
Health Canada Approved Drug Products: Etibi (Ethambutol) Oral Tablets [Link]

External Links

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

PDB Entries

5nr3 / 7bvc / 7bve / 7bvf

FDA label

Download (25.3 KB)

MSDS

Download (73.7 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Obesity / Tuberculosis (TB)	1
4	Completed	Prevention	Human Immunodeficiency Virus Type 1 (HIV-1) Infection	1
4	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Mycobacterium avium complex infection	1
4	Completed	Treatment	Lung Disorder	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	Oral
Tablet	Oral
Tablet	Oral	500 mg
Tablet, film coated	Oral	100 mg
Tablet
Injection, solution	Intramuscular; Intravenous; Subcutaneous	200 mg
Injection, solution	Intramuscular; Intravenous; Subcutaneous	500 MG/3ML
Tablet, film coated	Oral
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	250 MG
Injection, solution	Intravenous	500 mg
Tablet, film coated
Injection, solution
Syrup
Tablet	Oral	100 mg / tab
Tablet	Oral	400 mg / tab
Tablet, film coated	Oral
Tablet	Oral	400 mg
Tablet, film coated	Oral	400 mg
Tablet, coated	Oral
Tablet, film coated	Oral	500 mg
Tablet, coated	Oral	400 mg
Tablet, coated	Oral	500 mg
Tablet, coated	Oral	200 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.
water solubility	1000 mg/mL	Becker et al, 2008
logP	0.4	Becker et al, 2008

Predicted Properties

Property	Value	Source
logP	-0.059	Chemaxon
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	splash10-0ul0-5900000000-89e4dd363b62972788dd
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0aor-2690000000-75bb76c46caf6a9e59a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-1390000000-901bc5a8b47c08604257
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-3900000000-fdf44ddb52a5c898e86e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0fki-9620000000-ef2ec8e7797697a07bc8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052f-9000000000-d46cd406fa8e890f157e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9000000000-bf0ec52905b78358ad21
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0aor-2690000000-75bb76c46caf6a9e59a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-1390000000-901bc5a8b47c08604257
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-3900000000-fdf44ddb52a5c898e86e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0fki-9620000000-ef2ec8e7797697a07bc8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052f-9000000000-d46cd406fa8e890f157e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9000000000-bf0ec52905b78358ad21
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	158.777106	predicted	DarkChem Lite v0.1.0
[M-H]-	158.927206	predicted	DarkChem Lite v0.1.0
[M-H]-	147.15623	predicted	DeepCCS 1.0 (2019)
[M-H]-	158.777106	predicted	DarkChem Lite v0.1.0
[M-H]-	158.927206	predicted	DarkChem Lite v0.1.0
[M-H]-	158.777106	predicted	DarkChem Lite v0.1.0
[M-H]-	158.927206	predicted	DarkChem Lite v0.1.0
[M-H]-	147.15623	predicted	DeepCCS 1.0 (2019)
[M-H]-	147.15623	predicted	DeepCCS 1.0 (2019)
[M+H]+	158.527906	predicted	DarkChem Lite v0.1.0
[M+H]+	158.658306	predicted	DarkChem Lite v0.1.0
[M+H]+	149.5518	predicted	DeepCCS 1.0 (2019)
[M+H]+	158.527906	predicted	DarkChem Lite v0.1.0
[M+H]+	158.658306	predicted	DarkChem Lite v0.1.0
[M+H]+	158.527906	predicted	DarkChem Lite v0.1.0
[M+H]+	158.658306	predicted	DarkChem Lite v0.1.0
[M+H]+	149.5518	predicted	DeepCCS 1.0 (2019)
[M+H]+	149.5518	predicted	DeepCCS 1.0 (2019)
[M+Na]+	158.279906	predicted	DarkChem Lite v0.1.0
[M+Na]+	158.182406	predicted	DarkChem Lite v0.1.0
[M+Na]+	155.68022	predicted	DeepCCS 1.0 (2019)
[M+Na]+	158.279906	predicted	DarkChem Lite v0.1.0
[M+Na]+	158.182406	predicted	DarkChem Lite v0.1.0
[M+Na]+	158.279906	predicted	DarkChem Lite v0.1.0
[M+Na]+	158.182406	predicted	DarkChem Lite v0.1.0
[M+Na]+	155.68022	predicted	DeepCCS 1.0 (2019)
[M+Na]+	155.68022	predicted	DeepCCS 1.0 (2019)

Targets

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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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

Enzymes

Details1. Cytochrome P450 1A2

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

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. [Article]

Details2. Cytochrome P450 2E1

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

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. [Article]

Details3. Cytochrome P450 2C19

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

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. [Article]

Details4. Cytochrome P450 2D6

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

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. [Article]

Details5. Cytochrome P450 2A6

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

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. [Article]

Details6. Cytochrome P450 2C9

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

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. [Article]

Details7. Cytochrome P450 3A4

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

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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Ethambutol

Identification

Structure for Ethambutol (DB00330)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

Enzymes

References

References

References

References

References

References

References