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Ethambutol Hydrochloride

Synopsis, Chemistry

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TABLET;ORAL - 100MG, TABLET;ORAL - 400MG

TABLET;ORAL - 100MG
TABLET;ORAL - 400MG

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Also known as: Ethambutol dihydrochloride, Ethambutol hcl, 1070-11-7, Myambutol, Dadibutol, Dexambutol

Molecular Formula

C₁₀H₂₆Cl₂N₂O₂

Molecular Weight

277.23 g/mol

InChI Key

AUAHHJJRFHRVPV-BZDVOYDHSA-N

FDA UNII

QE4VW5FO07

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

Ethambutol Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;dihydrochloride

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)NCCNC(CC)CO.Cl.Cl

2.1.5 Isomeric SMILES

CC[C@@H](CO)NCCN[C@@H](CC)CO.Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

QE4VW5FO07

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dexambutol

2. Emb Fatol

3. Emb Hefa

4. Emb-fatol

5. Emb-hefa

6. Etambutol Llorente

7. Ethambutol

8. Etibi

9. Hydrochloride, Ethambutol

10. Llorente, Etambutol

11. Miambutol

12. Myambutol

2.3.2 Depositor-Supplied Synonyms

1. Ethambutol Dihydrochloride

2. Ethambutol Hcl

3. 1070-11-7

4. Myambutol

5. Dadibutol

6. Dexambutol

7. Etibi

8. Ethambutol (dihydrochloride)

9. Servambutol

10. Etapiam

11. Mycobutol

12. Tambutol

13. Ebutol

14. Cl 40881

15. Tibutol

16. (2s,2's)-2,2'-(ethane-1,2-diylbis(azanediyl))bis(butan-1-ol) Dihydrochloride

17. Jng307dj5x

18. Qe4vw5fo07

19. Ethambutol Dihydrochloride, Dl-

20. (+)-2,2'-(ethylenediimino)-di-1-butanol Dihydrochloride

21. Nsc-757022

22. Cl-40881

23. 22196-75-4

24. Dsstox_cid_25345

25. Dsstox_rid_80813

26. Dsstox_gsid_45345

27. Ethambutol 2hcl

28. Emb Dihydrochloride

29. Chebi:4878

30. (2s)-2-[2-[[(1s)-1-(hydroxymethyl)propyl]amino]ethylamino]butan-1-ol Dihydrochloride

31. (2s)-2-[2-[[(2s)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;dihydrochloride

32. Ccris 6606

33. Ncgc00178864-03

34. Einecs 213-970-7

35. Unii-jng307dj5x

36. Unii-qe4vw5fo07

37. (+-)-ethambutol Dihydrochloride

38. Myambutol (tn)

39. Ethambutol Hydrochloride [usan:usp:jan]

40. Ethambutoli Hydrochloridum

41. Emb

42. Ncgc00016560-01

43. Cas-1070-11-7

44. (2s)-2-[(2-{[(2s)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol Dihydrochloride

45. Schembl650049

46. Spectrum1500288

47. Chembl3140361

48. Dtxsid4045345

49. Hy-b0535a

50. (+-)-2,2'-(ethylenediimino)-di-1-butanol Dihydrochloride

51. Hms1920m18

52. Kuc109574c

53. (s-(r*,r*))-2,2'-(ethylenediimino)dibutan-1-ol Dihydrochloride

54. Ksc-27-052b

55. Tox21_110494

56. 1-butanol, 2,2'-(ethylenediimino)di-, Dihydrochloride, (+)-

57. Ccg-40232

58. Mfcd21364080

59. S4004

60. Ethambutol Hydrochloride (jp17/usp)

61. Ethambutol Hydrochloride [jan]

62. 1-butanol, (1,2-ethanediyldiimino)bis-, Dihydrochloride, (r*,r*)-(+-)-

63. Akos024258527

64. Tox21_110494_1

65. Cl40881

66. Ethambutol Dihydrochloride [mi]

67. Ethambutol Hydrochloride [usan]

68. Nsc 757022

69. 1-butanol, 2,2'-(1,2-ethanediyldiimino)bis-, Dihydrochloride, (r-(r*,r*))-

70. 1-butanol, 2,2'-(1,2-ethanediyldiimino)bis-, Dihydrochloride, (s-(r*,r*))-

71. Ethambutol Hydrochloride [mart.]

72. Ethambutol Hydrochloride [vandf]

73. Ethambutol Hydrochloride [usp-rs]

74. Ethambutol Hydrochloride [who-ip]

75. Ethambutol Dihydrochloride [who-dd]

76. Ethambutol Dihydrochloride, Antimycobacterial

77. E1011

78. Sw219109-1

79. Ethambutol Hydrochloride [ep Impurity]

80. Ethambutol Hydrochloride [orange Book]

81. D00878

82. Ethambutol Hydrochloride [ep Monograph]

83. Ethambutol Hydrochloride [usp Monograph]

84. Ethambutoli Hydrochloridum [who-ip Latin]

85. A895715

86. Q27106530

87. Z1558572530

88. 2,2'-(1,2-ethanediyldiimino)bis-1-butanol Dihydrochloride

89. 2,2'-[ethane-1,2-diyldi(imino)]dibutan-1-ol Dihydrochloride

90. (s,s)-2,2'-(1,2-ethanediyldiimino)bis-1-butanol Dihydrochloride

91. (s,s)-n,n'-bis(1-hydroxy-2-butyl)ethylenediamine Dihydrochloride

92. 1-butanol, 2,2'-(1,2-ethanediyldiimino)bis-, Dihydrochloride, (r*,r*)-

93. 1-butanol, 2,2'-(ethylenediimino)di-, Dihydrochloride, (+-)-

94. Ethambutol Hydrochloride, European Pharmacopoeia (ep) Reference Standard

95. 1-butanol, 2,2'(1,2-ethanediyldiimino)bis-, Dihydrochloride, (-(r*,r*))

96. 1-butanol, 2,2'-(1,2-ethanediyldiimino)bis-, Dihydrochloride, (2r,2'r)-rel-

97. 1-butanol, 2,2'-(1,2-ethanediyldiimino)bis-, Hydrochloride (1:2), (2s,2's)-

98. Ethambutol For System Suitability, European Pharmacopoeia (ep) Reference Standard

99. Ethambutol Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

100. Ethambutol Hydrochloride, United States Pharmacopeia (usp) Reference Standard

101. 29326-86-1

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₆Cl₂N₂O₂
Molecular Weight	277.23 g/mol
Hydrogen Bond Donor Count	6
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	64.5 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
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
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]