(2R)-2-[(2-{[(2R)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol dihydrochloride

• ChemBase ID: 53545
• Molecular Formular: C10H26Cl2N2O2
• Molecular Mass: 277.23164
• Monoisotopic Mass: 276.13713344
• SMILES: N([C@@H](CO)CC)CCN[C@@H](CO)CC.Cl.Cl
• Canonical SMILES: CC[C@@H](NCCN[C@@H](CO)CC)CO.Cl.Cl
• InChI: 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-;;/m1../s1
• InChIKey: AUAHHJJRFHRVPV-HSTMFJOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2-{[(2R)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol dihydrochloride
• IUPAC Traditional name: (2R)-2-[(2-{[(2R)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol dihydrochloride
• Synonyms: 2,2'-[1,2-Ethanediyldi(imino)]di(1-butanol) dihydrochloride; 2,2′-(1,2-Ethanediyldiimino)bis-1-butanol dihydrochloride; Emb; Ethambutol dihydrochloride

Database IDs

• CAS Number: 1070-11-7
• EC Number: 213-970-7
• MDL Number: MFCD01656163; MFCD00216025
• PubChem SID: 162058308; 24894566
• PubChem CID: 6419929

CALCULATED PROPERTIES

• Acid pKa: 14.819909
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -4.4261327
• LogD (pH = 7.4): -2.2525384
• Log P: -0.059291072
• Molar Refractivity: 57.888 cm^3
• Polarizability: 23.439148 Å^3
• Polar Surface Area: 64.52 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• RTECS: EL3854000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-22-36/37/39-45
• TSCA Listed: false
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Empirical Formula (Hill Notation): C10H24N2O2 · 2HCl

DETAILS

Sigma Aldrich - E4630

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.1
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.2,3