E4630

Ethambutol dihydrochloride

antimycobacterial

• Synonym(s): Ethambutol, Ethambutol HCL, 2,2′-(1,2-Ethanediyldiimino)bis-1-butanol dihydrochloride, Emb
• 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

Properties

• Quality Level: 200
• 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

Description

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.

Safety Information

• Pictograms: 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