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E4630

Sigma-Aldrich

Ethambutol dihydrochloride

antimycobacterial

Synonym(s):

Ethambutol, Ethambutol HCL, 2,2′-(1,2-Ethanediyldiimino)bis-1-butanol dihydrochloride, Emb

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About This Item

Empirical Formula (Hill Notation):
C10H24N2O2 · 2HCl
CAS Number:
1070-11-7
Molecular Weight:
277.23
EC Number:
213-970-7
MDL number:
MFCD21364080
UNSPSC Code:
51281511
PubChem Substance ID:
24894566
NACRES:
NA.85

form

powder

optical activity

[α]25/D 6.0 to 6.7°, c = 10 in water

color

white

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

mycobacteria

Mode of action

cell wall synthesis | interferes

SMILES string

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

InChI

1S/C10H24N2O2.2ClH/c1-3-9(7-13)11-5-6-12-10(4-2)8-14;;/h9-14H,3-8H2,1-2H3;2*1H/t9-,10-;;/m0../s1

InChI key

AUAHHJJRFHRVPV-BZDVOYDHSA-N

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Application

Ethambutol is an antimycobacterial used to treat tuberculosis in combination with other antibiotics to reduce the development of drug resistance. It has been used to study multidrug-resistant tuberculosis (MDR-TB) in highest-incidence-rate areas in China.

Biochem/physiol Actions

Ethambutol is bacteriostatic against actively growing TB bacilli. Mycolic acids attach to the 5′-hydroxyl groups of D-arabinose residues of arabinogalactan and form mycolyl-arabinogalactan-peptidoglycan complex in the cell wall. Ethambutol disrupts arabinogalactan synthesis by inhibiting arabinosyltransferases, specifically those in Mycobacterium, interfering with the biosynthesis of arabinogalactans found in the cell wall of mycobacteria and leading to increased cell wall permeability.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Hassan Safi et al.
Nature genetics, 45(10), 1190-1197 (2013-09-03)
To study the evolution of drug resistance, we genetically and biochemically characterized Mycobacterium tuberculosis strains selected in vitro for ethambutol resistance. Mutations in decaprenylphosphoryl-β-D-arabinose (DPA) biosynthetic and utilization pathway genes Rv3806c, Rv3792, embB and embC accumulated to produce a wide
Hao Zeng et al.
International journal of clinical and experimental medicine, 8(6), 8398-8414 (2015-08-27)
To introduce a modified method, namely coaxial electrohydrodynamic atomization for the fabrication of distinct core/shell structured microspheres of four first-line ant-tuberculosis drugs with different characteristics in hydrophilic properties in one single step. In group B, we prepared microspheres in which
Joshua R Francis et al.
The Medical journal of Australia, 200(6), 328-332 (2014-04-08)
OBJECTIVE To describe the epidemiology, clinical features, health care resource use, treatment and outcomes of multidrug-resistant tuberculosis (MDR-TB) cases diagnosed in Western Australia, compared with matched controls with drug-susceptible TB. Retrospective case-control study of all MDR-TB cases notified in WA
A case of skin and lung tuberculosis: diagnostic difficulties.
P Colasanti et al.
Giornale italiano di dermatologia e venereologia : organo ufficiale, Societa italiana di dermatologia e sifilografia, 148(5), 538-540 (2013-09-06)
N Guo et al.
Letters in applied microbiology, 58(4), 344-349 (2013-12-18)
Previous studies have shown that isoimperatorin (IO), a furanocoumarin isolated from several medicinal plants, has antimycobacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294). This study demonstrated that IO has antimycobacterial activity against 2 drug-sensitive and 6 drug-resistant isolates, with
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