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(+)-(S,S)-ethambutol Dihydrochloride

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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

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 Formula	C₁₀H₂₆Cl₂N₂O₂
Molecular Weight	277.23 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	9
Exact Mass	276.1371335 g/mol
Monoisotopic Mass	276.1371335 g/mol
Topological Polar Surface Area	73.7 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	109
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Ethambutol hydrochloride
Drug Label	MYAMBUTOL 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 Ingredient	Ethambutol hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	100mg; 400mg
Market Status	Prescription
Company	Lupin; Barr

2 of 2
Drug Name	Ethambutol hydrochloride
Drug Label	MYAMBUTOL 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 Ingredient	Ethambutol hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	100mg; 400mg
Market Status	Prescription
Company	Lupin; 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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