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    Ambroxol

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    ANALYTICAL

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    $ API Ref.Price (USD/KG) : 65Xls

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    2D Structure
    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

    2D Structure

    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 Weight 378.10 g/mol
    Molecular Formula C13H18Br2N2O
    XLogP32.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass377.97654 g/mol
    Monoisotopic Mass375.97859 g/mol
    Topological Polar Surface Area58.3 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity259
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.