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Merck
CN

E4630

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
NACRES:
NA.85
PubChem Substance ID:
24894566
UNSPSC Code:
51281511
EC Number:
213-970-7
MDL number:
MFCD21364080

Key Documents

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Product Name

Ethambutol dihydrochloride, antimycobacterial

InChI key

AUAHHJJRFHRVPV-BZDVOYDHSA-N

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

SMILES string

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

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

Quality Level

200

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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.
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.
Ethambutol specifically inhibits arabinosyltransferases in Mycobacterium, interfering with the biosynthesis of arabinogalactans found in the cell wall of mycobacteria.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

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

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000380671
0000380671
WXBF1745V
0000213192
0000149807

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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
Mohammed Shafik El-Ridy et al.
Drug delivery, 22(1), 21-36 (2013-12-24)
Tuberculosis (TB) is a worldwide health concern. In 2011, about 8.7 million new cases developed TB and 1.4 million people died from it. Enhancement of ethambutol hydrochloride activity and safety in treatment of TB through niosomal encapsulation. Niosomes were prepared
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)
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