ETHAMBUTOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H24N2O2
Molecular Weight	204.3098
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@H](CO)NCCN[C@@H](CC)CO

InChI

InChIKey=AEUTYOVWOVBAKS-UWVGGRQHSA-N

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

HIDE SMILES / InChI

Molecular Formula	C10H24N2O2
Molecular Weight	204.3098
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/016320s066lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00330

ETHAMBUTOL HYDROCHLORIDE 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. 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. ETHAMBUTOL HCl is indicated for the treatment of pulmonary tuberculosis. It should not be used as the sole antituberculous drug, but should be used in conjunction with at least one other antituberculous drug.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Probable arabinosyltransferase C 3 Target ID: Probable arabinosyltransferase C Sources: http://www.drugbank.ca/drugs/DB00330	Inhibitor 8504
Probable arabinosyltransferase B 3 Target ID: Probable arabinosyltransferase B Sources: http://www.drugbank.ca/drugs/DB00330	Inhibitor 8504
Arabinosyltransferase A 4 Target ID: CHEMBL1877 Sources: http://www.drugbank.ca/drugs/DB00330	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pulmonary tuberculosis 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/016320s066lbl.pdf	Primary		Approved 8583	MYAMBUTOL Approved Use pulmonary tuberculosis Launch Date 1967

C_max

Value	Dose	Co-administered	Analyte	Population
4.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10049268/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMBUTOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10049268/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered: aluminum-magnesium antacid	aluminum-magnesium antacid	ETHAMBUTOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10049268/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMBUTOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT

AUC

Value	Dose	Co-administered	Analyte	Population
28 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10049268/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMBUTOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
27.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10049268/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered: aluminum-magnesium antacid	aluminum-magnesium antacid	ETHAMBUTOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
29.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10049268/	25 mg/kg single, oral dose: 25 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ETHAMBUTOL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT

Doses

Dose	Population	Adverse events
25 mg/kg 1 times / day multiple, oral Recommended Dose: 25 mg/kg, 1 times / day Route: oral Route: multiple Dose: 25 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25861347	unhealthy, 79 years Health Status: unhealthy Age Group: 79 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/25861347	Disc. AE: Agranulocytosis... AEs leading to discontinuation/dose reduction: Agranulocytosis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25861347

AEs

AE	Significance	Dose	Population
Agranulocytosis	1 patient Disc. AE	25 mg/kg 1 times / day multiple, oral Recommended Dose: 25 mg/kg, 1 times / day Route: oral Route: multiple Dose: 25 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25861347	unhealthy, 79 years Health Status: unhealthy Age Group: 79 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/25861347

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 OCT1 620 OCT2 779 OCT3 159 OATP1B1 1079 OATP2B1 157 OATP1B3 961 MRP3 246 MRP2 499 MRP4 290 BSEP 550 CYP3A 227 UGT1A1 246 UGT1A4 98 UGT1A6 136 UGT1A9 148 UGT2B7 197 UGT2B15 84	P-gp 2052 OCT1 393 OCT2 434 OCTN1 55 OCTN2 59 OAT3 391 OCT3 92 MATE1 182 MATE2 98

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
OATP1B3 970	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862515/pdf/zac3096.pdf#page=1 Page: 1.0	moderate [IC50 53.9 uM]	likely Comment: Drug-drug interaction index prediction Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862515/pdf/zac3096.pdf#page=1 Page: 1.0
OATP1B1 1095	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862515/pdf/zac3096.pdf#page=1 Page: 1.0	moderate [IC50 57.6 uM]	likely Comment: Drug-drug interaction index prediction Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862515/pdf/zac3096.pdf#page=1 Page: 1.0
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	moderate [IC50 8.4 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	moderate [IC50 9.4 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	no
CYP3A 317	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	no
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no
UGT1A4 100	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	no
UGT1A6 171	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	no
UGT2B15 84	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	no
OATP2B1 162	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862515/pdf/zac3096.pdf#page=1 Page: 1.0	no	unlikely Comment: Drug-drug interaction index prediction Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862515/pdf/zac3096.pdf#page=1 Page: 1.0
OCT2 782	inhibitor 4027 Sources: https://aac.asm.org/content/aac/57/10/5053.full.pdf#page=1 Page: 1.0	strong [IC50 253.8 uM]	likely Comment: Drug-drug interaction index prediction Sources: https://aac.asm.org/content/aac/57/10/5053.full.pdf#page=1 Page: 1.0
OCT1 656	inhibitor 4027 Sources: https://aac.asm.org/content/aac/57/10/5053.full.pdf#page=1 Page: 1.0	strong [IC50 92.6 uM]	likely Comment: Drug-drug interaction index prediction Sources: https://aac.asm.org/content/aac/57/10/5053.full.pdf#page=1 Page: 1.0
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	strong [Ki 1.4 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	strong [Ki 2.9 uM]
OCT3 161	inhibitor 4027 Sources: https://aac.asm.org/content/aac/57/10/5053.full.pdf#page=1 Page: 1.0	weak [IC50 4100 uM]	likely Comment: Drug-drug interaction index prediction Sources: https://aac.asm.org/content/aac/57/10/5053.full.pdf#page=1 Page: 1.0
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	weak
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	weak
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24910189/ Page: 1.0	weak
UGT1A1 303	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	weak
UGT1A9 155	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	weak
UGT2B7 210	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/45/9/1035.full.pdf?with-ds=yes#page=4 Page: 4.0	weak
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 88.2 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
OCTN1 55	substrate 4014 Sources: https://aac.asm.org/content/aac/62/9/e00512-18.full.pdf#page_1 Page: 1.0	major
OCTN2 59	substrate 4014 Sources: https://aac.asm.org/content/aac/62/9/e00512-18.full.pdf#page_1 Page: 1.0	major
OAT3 391	substrate 4014 Sources: https://aac.asm.org/content/aac/62/9/e00512-18.full.pdf#page_4 Page: 4.0	no
MATE2 98	substrate 4014 Sources: https://aac.asm.org/content/aac/60/12/7105.full.pdf#page=1 Page: 1.0	yes
OCT2 434	substrate 4014 Sources: https://aac.asm.org/content/aac/62/9/e00512-18.full.pdf#page_1 Page: 1.0	yes
OCT3 92	substrate 4014 Sources: https://aac.asm.org/content/aac/60/12/7105.full.pdf#page=1 Page: 1.0	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17258938/ Page: 1.0	yes
MATE1 182	substrate 4014 Sources: https://aac.asm.org/content/aac/60/12/7105.full.pdf#page=1 Page: 1.0	yes	likely Comment: DDI index of >0.1 Sources: https://aac.asm.org/content/aac/60/12/7105.full.pdf#page=1 Page: 1.0
OCT1 393	substrate 4014 Sources: https://aac.asm.org/content/aac/62/9/e00512-18.full.pdf#page_1 Page: 1.0	yes	likely Comment: Drug-drug interaction index prediction Sources: https://aac.asm.org/content/aac/62/9/e00512-18.full.pdf#page_1 Page: 1.0

Sourcing

Vendor/Aggregator	ID	URL
ChemicalBook	CB3324345	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3324345
eMolecules	31225919	https://www.emolecules.com/cgi-bin/more?vid=31225919
MolPort	MolPort-006-110-202	https://www.molport.com/shop/molecule-link/MolPort-006-110-202
ZINC	ZINC000019364219	http://zinc15.docking.org/substances/ZINC000019364219
ChEBI	CHEBI:4877	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4877

PubMed

Title	Date	PubMed
Decreased retinal nerve fibre layer thickness detected by optical coherence tomography in patients with ethambutol-induced optic neuropathy.	2007-07	17215265
Rapid phenotypic assay of antimycobacterial susceptibility pattern by direct mycobacteria growth indicator tube and phage amplified biological assay compared to BACTEC 460 TB.	2007-03	17035089
Abnormal multifocal electroretinogram (mfERG) in ethambutol toxicity.	2006-12-22	17182409
[Case of SIADH caused by ethionamide in a patient with pulmonary tuberculosis].	2006-12	17240918
Activity of 7-methyljuglone in combination with antituberculous drugs against Mycobacterium tuberculosis.	2006-11	16987644
[Ocular toxicity by the use of ethambutol].	2006-10-07	17022723
Antituberculous therapy-induced fulminant hepatic failure: successful treatment with liver transplantation and nonstandard antituberculous therapy.	2006-09	16933231
Enhanced susceptibility of multidrug resistant strains of Mycobacterium tuberculosis to granulysin peptides correlates with a reduced fitness phenotype.	2006-07	16793311
Ethambutol-associated optic neuropathy.	2006-04	16710500
Ocular toxicity of ethambutol.	2006-02	16495590
Menstrual disorders in nongenital tuberculosis.	2006	17093348
[Vision impairment in the course of lung tuberculosis treatment].	2006	16848215
[Meningoencephalitis tuberculosis--primary isolation of resistant M. tuberculosis].	2006	16528937
Fluoroquinolones: an important class of antibiotics against tuberculosis.	2006	16475933
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.	2005-11	16251329
Is liver transplantation advisable for isoniazid fulminant hepatitis in active extrapulmonary tuberculosis?	2005-11	16212643
[Mycobacterium bovis tuberculosis in a female patient with AIDS].	2005-09-24	16178466
Diversity in domain architectures of Ser/Thr kinases and their homologues in prokaryotes.	2005-09-19	16171520
Multifocal ERG in ethambutol associated visual loss.	2005-08	16024847
Rapidly developing optic neuritis secondary to ethambutol: possible mechanism of injury.	2005-07	16108516
Multifocal electroretinogram demonstrated macular toxicity associated with ethambutol related optic neuropathy.	2005-06	15923521
Antimycobacterial agents differ with respect to their bacteriostatic versus bactericidal activities in relation to time of exposure, mycobacterial growth phase, and their use in combination.	2005-06	15917538
Phenotypic and molecular characterization of Mycobacterium tuberculosis isolates resistant to both isoniazid and ethambutol.	2005-06	15917515
In vitro activity of linezolid, clarithromycin and moxifloxacin against clinical isolates of Mycobacterium kansasii.	2005-06	15824090
Optical coherence tomography can measure axonal loss in patients with ethambutol-induced optic neuropathy.	2005-05	15565293
The role of ultrasound and echo-color Doppler in the diagnosis and follow-up of tuberculosis of the transplanted kidney.	2005-03	15906799
Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles.	2004-10-15	15388173
[Septic shock following intracavitary Bacillus Calmette-Guerin therapy for postcystectomy ureteral cancer].	2004-09	15518130
The activity of grepafloxacin in two murine models of Mycobacterium avium infection.	2004-06	15290460
Ethambutol-induced acute renal failure.	2004-05	15102986
Ethambutol-induced optic neuropathy in a patient with pituitary macroadenoma: case report.	2004-04-03	15058748
Ethambutol-induced optic neuritis in patients with end stage renal disease on hemodialysis: two case reports and literature review.	2004-03	15287205
Pancytopenia due to extensive hemophagocytosis following anti-tubercular treatment.	2004-02	14755385
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.	2004-01	14645324
[Unusual therapeutic approach in treatment of pulmonary tuberculosis in six year old girl].	2004	15484863
Evaluation of visual functions in patients on ethambutol therapy for tuberculosis: a prospective study.	2003-12	15909750
Familial clustering of rifampin-induced acute renal failure.	2003-12	14677899
Ocular ethambutol toxicity.	2003-11	14601701
Ethambutol and optic neuropathy.	2003-07	12948256
Mefloquine, moxifloxacin, and ethambutol are a triple-drug alternative to macrolide-containing regimens for treatment of Mycobacterium avium disease.	2003-06-15	12792877
Leber's hereditary optic neuropathy precipitated by ethambutol.	2003-05-04	16767386
Ten years of extrapulmonary tuberculosis in a Danish university clinic.	2003	12839152
Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs?	1992-12	1303690
The Garrod Lecture. Understanding the chemotherapy of tuberculosis--current problems.	1992-05	1624388
CI-960 (PD127391 or AM-1091), sparfloxacin, WIN 57273, and isepamicin activity against clinical isolates of Mycobacterium avium-intracellularae complex, M. chelonae, and M. fortuitum.	1992-02	1315233
Bacteriostatic and bactericidal activity of antituberculosis drugs against Mycobacterium tuberculosis, Mycobacterium avium-Mycobacterium intracellulare complex and Mycobacterium kansasii in different growth phases.	1992	1406364
Chlorpromazine: a drug potentially useful for treating mycobacterial infections.	1992	1288966
Antimycobacterial spectrum of sparfloxacin and its activities alone and in association with other drugs against Mycobacterium avium complex growing extracellularly and intracellularly in murine and human macrophages.	1991-12	1667250
In vivo activities of newer rifamycin analogs against Mycobacterium avium infection.	1991-10	1662021
Mode of action of ethambutol on Mycobacterium tuberculosis, strain H37R V.	1963-06	13927289

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Tuberculosis - Active Initial treatment: 15 mg/kg orally once a day for 6 to 8 weeks with concurrent isoniazid therapy. Retreatment: 25 mg/kg orally once a day for 60 days concurrently with at least one other anti-TB drug. After 60 days, decrease dose to 15 mg/kg orally once a day. As an alternative to single daily dose, a dose of 40 mg/kg orally twice a week or 30 mg/kg orally 3 times a week can be administered. This generally follows 2 weeks of daily therapy.

Route of Administration: Oral

In Vitro Use Guide

The antimycobacterial activity of ethambutol was assessed against Mycobacterium tuberculosis (H37Rv) strain using micro plate Alamar Blue assay (MABA). Compound showed inhibitory activity with MIC value 3.125 ug/mL

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:21 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:21 GMT 2025`
Record UNII	8G167061QZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHAMBUTOL [HSDB]

Preferred Name

English

ETHAMBUTOL

Official Name

English

Ethambutol [WHO-DD]

Common Name

English

(2S,2S)-2,2-(ETHANE-1,2-DIYLDIIMINO)DIBUTAN-1-OL

Systematic Name

English

ETHAMBUTOL [VANDF]

Common Name

English

ethambutol [INN]

Common Name

English

ETHAMBUTOL [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J04AM07