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    (+)-(S,S)-ethambutol dihydrochloride

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    2D Structure
    Also known as: Ethambutol hydrochloride, Ethambutol dihydrochloride, (+)-(s,s)-ethambutol dihydrochloride, (+)-2,2'-(ethylenediimino)di-1-butanol dihydrochloride, (+)-n,n'-bis(1-(hydroxymethyl)propyl)ethylenediamine dihydrochloride, (2s,2'e)-2,2'-(ethane-1,2-diyldiimino)dibutan-1-ol dihydrochloride
    Molecular Formula
    C10H26Cl2N2O2
    Molecular Weight
    277.23  g/mol
    InChI Key
    AUAHHJJRFHRVPV-BZDVOYDHSA-N
    An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S)-1-hydroxybutan-2-yl]-[2-[[(2S)-1-hydroxybutan-2-yl]azaniumyl]ethyl]azanium;dichloride
    2.1.2 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-;;/m0../s1
    2.1.3 InChI Key
    AUAHHJJRFHRVPV-BZDVOYDHSA-N
    2.1.4 Canonical SMILES
    CCC(CO)[NH2+]CC[NH2+]C(CC)CO.[Cl-].[Cl-]
    2.1.5 Isomeric SMILES
    CC[C@@H](CO)[NH2+]CC[NH2+][C@@H](CC)CO.[Cl-].[Cl-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Dexambutol

    2. Emb Fatol

    3. Emb Hefa

    4. Emb-fatol

    5. Emb-hefa

    6. Etambutol Llorente

    7. Ethambutol

    8. Ethambutol Hydrochloride

    9. Etibi

    10. Hydrochloride, Ethambutol

    11. Llorente, Etambutol

    12. Miambutol

    13. Myambutol

    2.2.2 Depositor-Supplied Synonyms

    1. Ethambutol Hydrochloride

    2. Ethambutol Dihydrochloride

    3. (+)-(s,s)-ethambutol Dihydrochloride

    4. (+)-2,2'-(ethylenediimino)di-1-butanol Dihydrochloride

    5. (+)-n,n'-bis(1-(hydroxymethyl)propyl)ethylenediamine Dihydrochloride

    6. (2s,2'e)-2,2'-(ethane-1,2-diyldiimino)dibutan-1-ol Dihydrochloride

    7. N,n'-bis[(2s)-1-hydroxybutan-2-yl]ethane-1,2-diaminium Dichloride

    8. Chebi:4878

    9. (+)-2,2'-(ethylenediimino)-di-1-butanol Dihydrochloride

    10. 1070-11-7

    11. 134566-79-3

    12. [(2s)-1-hydroxybutan-2-yl](2-{[(2s)-1-hydroxybutan-2-yl]azaniumyl}ethyl)azanium Dichloride

    2.3 Create Date
    2010-09-20
    3 Chemical and Physical Properties
    Molecular Weight 277.23 g/mol
    Molecular Formula C10H26Cl2N2O2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count9
    Exact Mass276.1371335 g/mol
    Monoisotopic Mass276.1371335 g/mol
    Topological Polar Surface Area73.7 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity109
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameEthambutol hydrochloride
    Drug LabelMYAMBUTOL ethambutol hydrochloride is an oral chemotherapeutic agent which is specifically effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. The structural formula is:MYAMBUTOL 100 and 400 mg tab...
    Active IngredientEthambutol hydrochloride
    Dosage FormTablet
    RouteOral
    Strength100mg; 400mg
    Market StatusPrescription
    CompanyLupin; Barr

    2 of 2  
    Drug NameEthambutol hydrochloride
    Drug LabelMYAMBUTOL ethambutol hydrochloride is an oral chemotherapeutic agent which is specifically effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. The structural formula is:MYAMBUTOL 100 and 400 mg tab...
    Active IngredientEthambutol hydrochloride
    Dosage FormTablet
    RouteOral
    Strength100mg; 400mg
    Market StatusPrescription
    CompanyLupin; Barr

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antitubercular Agents

    Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Antimycobacterial [EPC]