Ambroxol: Difference between revisions

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Ambroxol
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	R05CB06 (WHO) ;
Identifiers
	IUPAC name trans-4-(2-Amino-3,5-dibrombenzylamino)-cyclohexanol;
CAS Number	18683-91-5 ;
PubChem CID	2132;
ChemSpider	10276826 ;
UNII	200168S0CL;
KEGG	D07442 ;
ChEMBL	ChEMBL153479 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C13H18Br2N2O
Molar mass	378.10
3D model (JSmol)	Interactive image;
	SMILES O[C@H]2CC[C@H](NCc1cc(Br)cc(Br)c1N)CC2;
	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/t10-,11- ; Key:JBDGDEWWOUBZPM-XYPYZODXSA-N ;
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VisualWikitext

Revision as of 15:28, 7 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [2]

Overview

Ambroxol is a secretolytic agent used in the treatment of respiratory diseases associated with viscid or excessive mucus. It is the active ingredient of Mucosolvan, Mucobrox, Mucol, Lasolvan, Mucoangin, Surbronc, Ambolar, and Lysopain. The substance is a mucoactive drug with several properties including secretolytic and secretomotoric actions that restore the physiological clearance mechanisms of the respiratory tract, which play an important role in the body’s natural defence mechanisms. It stimulates synthesis and release of surfactant by type II pneumocytes. Surfactant acts as an anti-glue factor by reducing the adhesion of mucus to the bronchial wall, in improving its transport and in providing protection against infection and irritating agents.^[1]^[2] Ambroxol is often administered as an active ingredient in cough syrup.

Ambroxol is indicated as "secretolytic therapy in bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport. It promotes mucus clearance, facilitates expectoration and eases productive cough, allowing patients to breathe freely and deeply".^[3]

There are many different formulations developed since the first marketing authorisation in 1978. Ambroxol is available as syrup, tablets, pastilles, dry powder sachets, inhalation solution, drops and ampules as well as effervescent tablets.

Ambroxol also provides pain relief in acute sore throat. Pain in sore throat is the hallmark of acute pharyngitis.^[4] Sore throat is usually caused by a viral infection. The infection is self limited and the patient recovers normally after a few days. What is most bothering for the patient is the continuous pain in the throat maximized when the patient is swallowing. The main goal of treatment is thus to reduce pain. The main property of Ambroxol for treating sore throat is the local anaesthetic effect, described first in the late 1970s,^[5]^[6] but explained and confirmed in more recent work.

Ambroxol is a potent inhibitor of the neuronal Na+ channels.^[7] This property led to the development of a lozenge containing 20 mg of ambroxol. Many state-of-the-art clinical studies^[4] have demonstrated the efficacy of Ambroxol in relieving pain in acute sore throat, with a rapid onset of action, with its effect lasting at least three hours. Ambroxol is also anti-inflammatory, reducing redness in a sore throat.

Ambroxol has recently been shown to increase activity of the lysosomal enzyme glucocerebrosidase. Because of this it may be a useful therapeutic agent for both Gaucher disease and Parkinson's disease.^[8]

Side effects

Field tests to date have not uncovered specific contraindications of Ambroxol. However, caution is suggested for patients with gastric ulceration, and usage during the first trimester of pregnancy is not recommended.^[9]

Synthesis

References

↑ Sanderson RJ et al. (1976), "Morphological and physical basis for lung surfactant action", Respir Phys, 27 (3): 379–92, doi:10.1016/0034-5687(76)90066-9, PMID 989610
↑ Kido H et al. (Nov 2004), "Secretory leukoprotease inhibitor and pulmonary surfactant serve as principal defenses against influenza A virus infection in the airway and chemical agents up-regulating their levels may have therapeutic potential.", Biol Chem, 385 (11): 1029–34, doi:10.1515/bc.2004.133, PMID 15576322
↑ Malerba M, Ragnoli B. (August 2008), "Ambroxol in the 21st century: pharmacological and clinical update", Expert Opin Drug Metab Toxicol., 4 (8): 1119–29, doi:10.1517/17425255.4.8.1119, PMID 18680446
↑ ^4.0 ^4.1 de Mey C. et al. (2008), "Efficacy and safety of ambroxol lozenges in the treatment of acute uncomplicated sore throat", Arzneimittelforschung, 58 (11): 557–68, doi:10.1055/s-0031-1296557, PMID 19137906
↑ Püschmann S, Engelhorn R. (1978), "Pharmakologische Untersuchungen des Bromhexin-Metaboliten Ambroxol (Pharmacological study on the bromhexine-metabolite ambroxol)", Arzneimittelforschung, 28 (5a): 889–98, PMID 581987
↑ Klier KF, Papendick U. (1977), "Die lokalanaesthetische Wirkung von NA-872-haltigen Augentropfen (The local anesthetic effect of NA872-containing eyedrops)", Med Monatsschr., 31 (12): 575–8, PMID 593223
↑ Weiser T. (2006), "Comparison of the effects of four Na+ channel analgesics on TTX-resistant Na+ currents in rat sensory neurons and recombinant Nav1.2 channels", Neurosci Lett., 395 (3): 179–84, doi:10.1016/j.neulet.2005.10.058, PMID 16293367
↑ Alisdair McNeill et al. (2014), "Ambroxol improves lysosomal biochemistry in glucocerebrosidase mutation-linked Parkinson disease cells", Oxford Journals, 137 (5): 1481–1495, PMID 24574503
↑ [1] Drugs.com, Ambroxol, accessed 21 January 2014
↑ http://drugsynthesis.blogspot.co.uk/2011/11/laboratory-synthesis-of-ambroxol_30.html

Template:Cough and cold preparations

[1] Sanderson RJ et al. (1976), "Morphological and physical basis for lung surfactant action", Respir Phys, 27 (3): 379–92, doi:10.1016/0034-5687(76)90066-9, PMID 989610

[2] Kido H et al. (Nov 2004), "Secretory leukoprotease inhibitor and pulmonary surfactant serve as principal defenses against influenza A virus infection in the airway and chemical agents up-regulating their levels may have therapeutic potential.", Biol Chem, 385 (11): 1029–34, doi:10.1515/bc.2004.133, PMID 15576322

[3] Malerba M, Ragnoli B. (August 2008), "Ambroxol in the 21st century: pharmacological and clinical update", Expert Opin Drug Metab Toxicol., 4 (8): 1119–29, doi:10.1517/17425255.4.8.1119, PMID 18680446

[pmid19137906-4] 4.0 ^4.1 de Mey C. et al. (2008), "Efficacy and safety of ambroxol lozenges in the treatment of acute uncomplicated sore throat", Arzneimittelforschung, 58 (11): 557–68, doi:10.1055/s-0031-1296557, PMID 19137906

[5] Püschmann S, Engelhorn R. (1978), "Pharmakologische Untersuchungen des Bromhexin-Metaboliten Ambroxol (Pharmacological study on the bromhexine-metabolite ambroxol)", Arzneimittelforschung, 28 (5a): 889–98, PMID 581987

[6] Klier KF, Papendick U. (1977), "Die lokalanaesthetische Wirkung von NA-872-haltigen Augentropfen (The local anesthetic effect of NA872-containing eyedrops)", Med Monatsschr., 31 (12): 575–8, PMID 593223

[7] Weiser T. (2006), "Comparison of the effects of four Na+ channel analgesics on TTX-resistant Na+ currents in rat sensory neurons and recombinant Nav1.2 channels", Neurosci Lett., 395 (3): 179–84, doi:10.1016/j.neulet.2005.10.058, PMID 16293367

[8] Alisdair McNeill et al. (2014), "Ambroxol improves lysosomal biochemistry in glucocerebrosidase mutation-linked Parkinson disease cells", Oxford Journals, 137 (5): 1481–1495, PMID 24574503

[9] [1] Drugs.com, Ambroxol, accessed 21 January 2014

[10] ttp://drugsynthesis.blogspot.co.uk/2011/11/laboratory-synthesis-of-ambroxol_30.html

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@@ Line 1: / Line 1: @@
-{{Drugbox|
+{{Drugbox
-|IUPAC_name = ''trans''-4-(2-Amino-3,5-dibrombenzylamino)-cyclohexanol
+| Verifiedfields = changed
-| image=Ambroxol.svg
+| verifiedrevid = 464186402
-| CAS_number= 18683-91-5
+| IUPAC_name = ''trans''-4-(2-Amino-3,5-dibrombenzylamino)-cyclohexanol
-| ATC_prefix=R05
+| image = Ambroxol structural formulae.png
-| ATC_suffix=CB02
+| image2 = Ambroxol ball-and-stick.png
-| ATC_supplemental=
+| Drugs.com = {{drugs.com|international|ambroxol}}
-| PubChem=2442
+| pregnancy_category =
-| DrugBank=
+| legal_status =
-| C=13 | H=18 | Br=2 | N=2 | O=1
+| bioavailability =
-| molecular_weight = 378.10
-| bioavailability=
 | metabolism =
-| elimination_half-life=
+| excretion =
-| excretion =
+| CAS_number_Ref = {{cascite|changed|??}}
-| pregnancy_category =
+| CAS_number = 18683-91-5
-| legal_status =
+| ATC_prefix = R05
-| routes_of_administration=
+| ATC_suffix = CB06
+| PubChem = 2132
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 10276826
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 200168S0CL
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D07442
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 153479
+| C=13 | H=18 | Br=2 | N=2 | O=1
+| molecular_weight = 378.10
+| smiles = O[C@H]2CC[C@H](NCc1cc(Br)cc(Br)c1N)CC2
+| InChI = 1/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/t10-,11-
+| InChIKey = JBDGDEWWOUBZPM-XYPYZODXBS
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 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/t10-,11-
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = JBDGDEWWOUBZPM-XYPYZODXSA-N
 }}
+__Notoc__
+{{SI}}
+{{CMG}}
+==Overview==
+'''Ambroxol''' is a secretolytic agent used in the treatment of [[respiratory|respiratory diseases]] associated with viscid or excessive [[mucus]]. It is the active ingredient of Mucosolvan, Mucobrox, Mucol, Lasolvan, Mucoangin, Surbronc, Ambolar, and Lysopain. The substance is a mucoactive [[drug]] with several properties including secretolytic and [[secretomotoric]] actions that restore the physiological clearance mechanisms of the [[respiratory tract]], which play an important role in the body’s natural defence mechanisms. It stimulates [[Biosynthesis|synthesis]] and release of [[surfactant]] by type II [[pneumocytes]]. Surfactant acts as an anti-glue factor by reducing the adhesion of mucus to the [[bronchial]] wall, in improving its transport and in providing protection against [[infection]] and irritating agents.<ref>{{citation|authors=Sanderson RJ et al.|title=Morphological and physical basis for lung surfactant action|journal=Respir Phys|year=1976|volume=27|issue=3|pages=379–92|pmid=989610|doi=10.1016/0034-5687(76)90066-9}}</ref><ref>{{citation|authors=Kido H et al.|title=Secretory leukoprotease inhibitor and pulmonary surfactant serve as principal defenses against influenza A virus infection in the airway and chemical agents up-regulating their levels may have therapeutic potential.|journal=Biol Chem|date=Nov 2004|volume=385|issue=11|pages=1029–34|pmid=15576322|doi=10.1515/bc.2004.133}}</ref> Ambroxol is often administered as an active ingredient in cough syrup.
+Ambroxol is indicated as "secretolytic therapy in bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport. It promotes mucus clearance, facilitates expectoration and eases [[productive cough]], allowing patients to breathe freely and deeply".<ref>{{citation|authors=Malerba M, Ragnoli B.|title=Ambroxol in the 21st century: pharmacological and clinical update|journal=Expert Opin Drug Metab Toxicol.|date=August 2008|volume=4|issue=8|pages=1119–29|doi=10.1517/17425255.4.8.1119|pmid=18680446}}</ref>
+[[File:Antbron 15mg by Towa Pharmaceutical.jpg|thumb|left|upright=0.5|Ambroxol [[hydrochloride]] tablets in Japan]]
+There are many different formulations developed since the first marketing authorisation in 1978. Ambroxol is available as [[cough syrup|syrup]], [[Tablet (pharmacy)|tablets]], [[pastilles]], dry powder [[sachet]]s, inhalation solution, drops and [[ampules]] as well as [[effervescent tablets]].
+Ambroxol also provides pain relief in [[acute sore throat]]. Pain in sore throat is the hallmark of acute [[pharyngitis]].<ref name="pmid19137906">{{citation|authors=de Mey C. et al.|title=Efficacy and safety of ambroxol lozenges in the treatment of acute uncomplicated sore throat|journal=Arzneimittelforschung|year=2008|volume=58|issue=11|pages=557–68|doi=10.1055/s-0031-1296557|pmid=19137906}}</ref> Sore throat is usually caused by a [[viral infection]]. The infection is self limited and the patient recovers normally after a few days. What is most bothering for the patient is the continuous pain in the throat maximized when the patient is swallowing. The main goal of treatment is thus to reduce pain. The main property of Ambroxol for treating sore throat is the local [[anaesthetic]] effect, described first in the late 1970s,<ref>{{citation|authors=Püschmann S, Engelhorn R.|title=Pharmakologische Untersuchungen des Bromhexin-Metaboliten Ambroxol (Pharmacological study on the bromhexine-metabolite ambroxol)|journal=Arzneimittelforschung|year=1978|volume=28|issue=5a|pages=889–98|pmid=581987}}</ref><ref>{{citation|authors=Klier KF, Papendick U.|title=Die lokalanaesthetische Wirkung von NA-872-haltigen Augentropfen (The local anesthetic effect of NA872-containing eyedrops)|journal=Med Monatsschr.|year=1977|volume=31|issue=12|pages=575–8|pmid=593223}}</ref> but explained and confirmed in more recent work.
+Ambroxol is a potent inhibitor of the [[neuron]]al [[Na+ channel]]s.<ref>{{citation|author=Weiser T.|title=Comparison of the effects of four Na+ channel analgesics on TTX-resistant Na+ currents in rat sensory neurons and recombinant Nav1.2 channels|journal=Neurosci Lett.|year=2006|volume=395|issue=3|pages=179–84|doi=10.1016/j.neulet.2005.10.058|pmid=16293367}}</ref> This property led to the development of a [[lozenge]] containing 20&nbsp;mg of ambroxol. Many state-of-the-art clinical studies<ref name="pmid19137906"/> have demonstrated the efficacy of Ambroxol in relieving pain in acute sore throat, with a rapid onset of action, with its effect lasting at least three hours. Ambroxol is also [[anti-inflammatory]], reducing redness in a sore throat.
+Ambroxol has recently been shown to increase activity of the lysosomal enzyme glucocerebrosidase.  Because of this it may be a useful therapeutic agent for both Gaucher disease and Parkinson's disease.<ref>{{citation|authors=Alisdair McNeill et al.|title=Ambroxol improves lysosomal biochemistry in glucocerebrosidase mutation-linked Parkinson disease cells|journal=Oxford Journals|year=2014|volume=137|issue=5|pages=1481-1495|pmid=24574503}}</ref>
-'''Ambroxol''' is a [[mucolytic]] agent used in the treatment of [[respiratory system|respiratory]] disorders associated with viscid or excessive [[mucus]]. It is the active ingredient of Mucosolvan or Mucoangin.
+==Side effects==
+Field tests to date have not uncovered specific contraindications of Ambroxol. However, caution is suggested for patients with gastric ulceration, and usage during the first trimester of pregnancy is not recommended.<ref>[http://www.drugs.com/ambroxol.html] Drugs.com, ''Ambroxol'', accessed 21 January 2014</ref>
-It is also a [[metabolite]] of the closely related [[bromhexine]].
+==Synthesis==
+[[File:Ambroxol synthesis.png|thumb|center|600px|Ambroxol synthesis.<ref>http://drugsynthesis.blogspot.co.uk/2011/11/laboratory-synthesis-of-ambroxol_30.html</ref>]]
-[[category:Mycotoxins]]
+==References==
+{{reflist|2}}
-[[de:Ambroxol]]
+{{Commons category}}
-[[es:Ambroxol]]
+{{Cough and cold preparations}}
-[[hu:Ambroxol]]
-[[pl:Ambroksol]]
-{{WH}}
+[[Category:Expectorants]]
-{{WS}}
+[[Category:Anilines]]
+[[Category:Organobromides]]
+[[Category:Amines]]
+[[Category:Alcohols]]