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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 of ETHAMBUTOL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MYAMBUTOL

Cmax

ValueDoseCo-administeredAnalytePopulation
4.5 μg/mL
25 mg/kg single, oral
ETHAMBUTOL serum
Homo sapiens
3.3 μg/mL
25 mg/kg single, oral
ETHAMBUTOL serum
Homo sapiens
3.8 μg/mL
25 mg/kg single, oral
ETHAMBUTOL serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
28 μg × h/mL
25 mg/kg single, oral
ETHAMBUTOL serum
Homo sapiens
27.5 μg × h/mL
25 mg/kg single, oral
ETHAMBUTOL serum
Homo sapiens
29.6 μg × h/mL
25 mg/kg single, oral
ETHAMBUTOL serum
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
8G167061QZ
Record Status Validated (UNII)
Record Version