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Prestwick3_000366

Prestwick3_000366

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Also known as: 18683-91-5, 107814-37-9, Rac-cis-ambroxol, 36557-04-7, Ambroxol base, 4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol

Molecular Formula

C₁₃H₁₈Br₂N₂O

Molecular Weight

378.10 g/mol

InChI Key

JBDGDEWWOUBZPM-UHFFFAOYSA-N

FDA UNII

QH6ZT6J071

A metabolite of BROMHEXINE that stimulates mucociliary action and clears the air passages in the respiratory tract. It is usually administered as the hydrochloride.

1 2D Structure

Prestwick3_000366

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol

2.1.2 InChI

InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2

2.1.3 InChI Key

JBDGDEWWOUBZPM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CC(CCC1NCC2=C(C(=CC(=C2)Br)Br)N)O

2.2 Other Identifiers

2.2.1 UNII

QH6ZT6J071

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(((2-amino-3,5-dibromophenyl)methyl)amino)cyclohexanol

2. Abrohexal

3. Am, Bisolvon

4. Ambril

5. Ambro Puren

6. Ambro-puren

7. Ambrobeta

8. Ambrofur

9. Ambrohexal

10. Ambrols

11. Ambrolitic

12. Ambropp

13. Ambropuren

14. Ambroten

15. Ambroxin

16. Ambroxocompren

17. Bisolvon Am

18. Bromhexine Metabolite Viii

19. Bronchopront

20. Bronchowern

21. Broxol

22. Contac Husten Trunk

23. Contac Husten-trunk

24. Contac Hustentrunk

25. Dinobroxol

26. Duramucal

27. Ebromin

28. Expeflen

29. Expit

30. Farmabroxol

31. Flavamed

32. Frenopect

33. Gelopol

34. Hustenlser, Pect

35. Hustenlser, Therapin

36. Larylin Husten Lser

37. Larylin Husten-lser

38. Larylin Hustenlser

39. Lasolvan

40. Metabolite Viii, Bromhexine

41. Mibrox

42. Motosol

43. Muco Fips

44. Muco-fips

45. Mucofips

46. Mucosolvan

47. Mucotablin

48. Na 872

49. Na-872

50. Na872

51. Pdiamuc

52. Pect Hustenlser

53. Pulmonal S

54. Pulmonal, Ringelheimer

55. Ringelheimer Pulmonal

56. Sekretovit

57. Stas Hustenlser

58. Stas-hustenlser

59. Stashustenlser

60. Surbronc

61. Therapin Hustenlser

2.3.2 Depositor-Supplied Synonyms

1. 18683-91-5

2. 107814-37-9

3. Rac-cis-ambroxol

4. 36557-04-7

5. Ambroxol Base

6. 4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol

7. Ambroxolum

8. Bisolvon Metabolite Viii

9. 4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol

10. Bromhexine-metabolite Viii

11. Na-872

12. Tabcin

13. Trans-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexanol

14. Ambroxol, Cis-

15. Cis-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexanol

16. Ambroxol [inn]

17. Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-, Trans-

18. 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol

19. Trans-4-((2-amino-3,5-dibromobencil)amino)ciclohexanol

20. Trans-4-((2-amino-3,5-dibromobenzyl)amine)cyclohexanol

21. Trans-4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol

22. Qh6zt6j071

23. Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)- (e)-

24. N-(2-amino-3,4-dibromocyclohexyl)-trans-4-aminocyclohexanol

25. 4-hydroxydemethylbromhexine, Cis-

26. N-(trans-4-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine

27. N-(trans-p-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amine

28. Ambroxol (inn)

29. Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, Trans-

30. 200168s0cl

31. N-(2-amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol

32. N-(trans-4-hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina

33. Ambroxol [inn:ban]

34. Cis-4-(((2-amino-3,5-dibromophenyl)methyl)amino)cyclohexanol

35. Ambroxolum [inn-latin]

36. Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, Cis-

37. Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, Trans- (9ci)

38. Bromhexine Metabolite Viii

39. Ncgc00016781-04

40. Einecs 242-500-3

41. Cas-23828-92-4

42. Amboxol

43. Cis-ambroxol

44. Sr-05000001463

45. Unii-200168s0cl

46. Tabcin (tn)

47. Spectrum_001346

48. 4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol

49. Ambroxol [mi]

50. Rac-cis-ambroxol-[d5]

51. Prestwick0_000366

52. Prestwick1_000366

53. Prestwick2_000366

54. Prestwick3_000366

55. Spectrum2_001518

56. Spectrum3_000955

57. Spectrum4_001068

58. Spectrum5_001021

59. Trans-4-((2-amino-3,5-dibromobencil)amino)ciclohexanol [spanish]

60. N-(2-amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol [spanish]

61. Ambroxol [who-dd]

62. Ec 242-500-3

63. N-(trans-4-hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina [spanish]

64. Unii-qh6zt6j071

65. Oprea1_766685

66. Schembl18702

67. Bspbio_000491

68. Kbiogr_001396

69. Kbioss_001826

70. Mls001306470

71. Divk1c_000027

72. Schembl423712

73. Spbio_001595

74. Spbio_002412

75. Bpbio1_000541

76. Chembl153479

77. Schembl7855003

78. 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol

79. Chembl1477775

80. Dtxsid8022583

81. Schembl21765132

82. Bcbcmap01_000092

83. Chebi:92994

84. Gtpl10692

85. Kbio1_000027

86. Kbio2_001826

87. Kbio2_004394

88. Kbio2_006962

89. Kbio3_002050

90. Dtxsid60860228

91. Chebi:135590

92. Ninds_000027

93. Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-

94. Hms2089d06

95. Hms2231b19

96. Hms3373j22

97. Hms3886m18

98. Zinc587613

99. Albb-022461

100. Bcp04489

101. Hy-b1039

102. Bbl009896

103. Bdbm50395322

104. Mfcd00242702

105. Mfcd28143339

106. S5710

107. Stk711075

108. Akos005530704

109. Akos015889660

110. Akos027338704

111. Zinc100001905

112. Zinc100070274

113. Ac-8362

114. Ambroxol Hydrochloride Impurity D [ep]

115. Bcp9000283

116. Ccg-207907

117. Cs-4558

118. Db06742

119. Sb17463

120. Sb82866

121. Idi1_000027

122. Smp1_000014

123. Ncgc00016781-01

124. Ncgc00016781-02

125. Ncgc00016781-08

126. Ncgc00159399-02

127. Ncgc00371077-02

128. As-56023

129. Smr000718792

130. Vs-02240

131. 4-hydroxydemethylbromhexine, Trans-

132. Bcp0726000066

133. Sbi-0051766.p002

134. Ab00514663

135. Cs-0323348

136. Ft-0622261

137. Ft-0630430

138. Ft-0661549

139. D07442

140. 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol

141. Ab00053639_13

142. Ab01275465-01

143. 683a915

144. A813089

145. Q221637

146. Sr-05000001463-1

147. Ambroxol Hydrochloride Impurity D [ep Impurity]

148. Brd-k11223672-003-03-7

149. Brd-k11223672-003-04-5

150. Brd-k56558538-003-02-8

151. 4-[(2-amino-3,5-dibromophenyl)methylamino-]cyclohexanol

152. 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexanol

153. (1s,4s)-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexanol

154. 4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol, Trans-

155. (1r,4r)-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol

156. Trans-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexanol

157. Cyclohexanol, 4-[[(2-amino-3,5-dibromo-phenyl)methyl]amino]-, Trans

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₈Br₂N₂O
Molecular Weight	378.10 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	377.97654 g/mol
Monoisotopic Mass	375.97859 g/mol
Topological Polar Surface Area	58.3 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	259
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Ambroxol is indicated for secretolytic therapy in bronchoplmonary disease with abnormal mucus secretion and transport. It allows the mucus to be more easily cleared and ease a patient's breathing.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Expectorants

Agents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here. (See all compounds classified as Expectorants.)

5.2 ATC Code

R05CB06

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

R - Respiratory system

R05 - Cough and cold preparations

R05C - Expectorants, excl. combinations with cough suppressants

R05CB - Mucolytics

R05CB06 - Ambroxol

5.3 Absorption, Distribution and Excretion

Absorption

Rapid and almost complete.

5.4 Metabolism/Metabolites

Ambroxol has known human metabolites that include 2-Amino-3,5-dibromobenzaldehyde and 4-Aminocyclohexanol, cis-.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.5 Biological Half-Life

7-12 hours

5.6 Mechanism of Action

Ambroxol is a mucolytic agent. Excessive Nitric oxide (NO) is associated with inflammatory and some other disturbances of airways function. NO enhances the activation of soluble guanylate cyclase and cGMP accumulation. Ambroxol has been shown to inhibit the NO-dependent activation of soluble guanylate cyclase. It is also possible that the inhibition of NO-dependent activation of soluble guanylate cyclase can suppress the excessive mucus secretion, therefore it lowers the phlegm viscosity and improves the mucociliary transport of bronchial secretions.