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Chemistry

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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

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

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

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]

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