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Chemistry

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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

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

Ethambutol Dihydrochloride

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 Weight 277.23 g/mol
Molecular Formula C10H26Cl2N2O2
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Exact Mass276.1371335 g/mol
Monoisotopic Mass276.1371335 g/mol
Topological Polar Surface Area64.5 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
Active IngredientEthambutol hydrochloride
Dosage FormTablet
RouteOral
Strength100mg; 400mg
Market StatusPrescription
CompanyLupin; Barr

2 of 2  
Drug NameEthambutol hydrochloride
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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DOSAGE - TABLET;ORAL - 100MG

USFDA APPLICATION NUMBER - 16320

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DOSAGE - TABLET;ORAL - 400MG

USFDA APPLICATION NUMBER - 16320

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