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Benproperine: Difference between revisions

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{{short description|Chemical compound}}
{{Drugbox {{Drugbox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 413885787 | verifiedrevid = 447813319
| IUPAC_name = 1-piperidine | IUPAC_name = (''RS'')-1-piperidine
| image = (RS)-Benproperine Enantiomers Formulae V.1.svg
| image = benproperine.png

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Blascorid, Pectipront, Pirexyl, Tussafug
| Drugs.com = {{drugs.com|international|benproperine}} | Drugs.com = {{drugs.com|international|benproperine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 2156-27-6 | CAS_number = 2156-27-6
| CAS_supplemental = 19428-14-9 (] salt) | CAS_supplemental = 19428-14-9 (] salt)
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| ATC_suffix = DB02 | ATC_suffix = DB02
| PubChem = 2326 | PubChem = 2326
| ChEMBL = 2105910
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07512 | KEGG = D07512

<!--Chemical data--> <!--Chemical data-->
| C=21 | H=27 | N=1 | O=1 | C=21 | H=27
| N=1 | O=1
| molecular_weight = 309.445 g/mol
| smiles = O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C | smiles = O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C
| InChI = 1/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3
| InChIKey = JTUQXGZRVLWBCR-UHFFFAOYAA
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3 | StdInChI = 1S/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3
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| StdInChIKey = JTUQXGZRVLWBCR-UHFFFAOYSA-N | StdInChIKey = JTUQXGZRVLWBCR-UHFFFAOYSA-N
}} }}
'''Benproperine''' (]) is a ].<ref>{{cite journal | vauthors = Li Y, Zhong DF, Chen SW, Maeba I | title = Identification of some benproperine metabolites in humans and investigation of their antitussive effect | journal = Acta Pharmacologica Sinica | volume = 26 | issue = 12 | pages = 1519–26 | date = December 2005 | pmid = 16297353 | doi = 10.1111/j.1745-7254.2005.00212.x | doi-access = free }}</ref> It has been marketed in multiple countries in Central America and Europe, as the ] or ] salts in either tablet, ], or syrup form. Trade names include Blascorid in Italy and Sweden, Pectipront and Tussafug in Germany, and Pirexyl in Scandinavia. The recommended dosage for adults is 25 to 50 mg two to four times daily, and for children 25 mg once or twice daily. Adverse effects include dry mouth, dizziness, fatigue, and heartburn.<ref>{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |page=6 |date=1991 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref>
'''Benproperine''' (]) is a ].
==Synthesis==
Patents:<ref>DK96113 idem Rubenstein K, {{Cite patent|GB|914008}} (1962 to Pharmacia AS). </ref><ref>Kurt Rubinstein, {{US patent|3117059}} (1964 to Aktieselskabet Pharmacia).</ref> Revised:<ref>Byoung Mog Kwon, et al. {{Cite patent|WO|2012064150}} (to Korea Research Institute of Bioscience and Biotechnology KRIBB).</ref> China:<ref></ref>]]


The base catalyzed ether formation between 2-Benzylphenol ('''1''') and ] ('''2''') gives 1-benzyl-2-(2-chloropropoxy)benzene ('''3'''). Displacement of the remaining halogen with piperidine completes the synthesis of ''benproperine'' ('''4''').


== References ==
{{reflist}}


{{Cough and cold preparations}} {{Cough and cold preparations}}


] ]
] ]
] ]
]




{{respiratory-system-drug-stub}} {{respiratory-system-drug-stub}}

]

Latest revision as of 21:41, 2 February 2024

Chemical compound Pharmaceutical compound
Benproperine
Clinical data
Trade namesBlascorid, Pectipront, Pirexyl, Tussafug
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • (RS)-1-piperidine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H27NO
Molar mass309.453 g·mol
3D model (JSmol)
SMILES
  • O(c1ccccc1Cc2ccccc2)CC(N3CCCCC3)C
InChI
  • InChI=1S/C21H27NO/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3
  • Key:JTUQXGZRVLWBCR-UHFFFAOYSA-N
  (verify)

Benproperine (INN) is a cough suppressant. It has been marketed in multiple countries in Central America and Europe, as the phosphate or pamoate salts in either tablet, dragée, or syrup form. Trade names include Blascorid in Italy and Sweden, Pectipront and Tussafug in Germany, and Pirexyl in Scandinavia. The recommended dosage for adults is 25 to 50 mg two to four times daily, and for children 25 mg once or twice daily. Adverse effects include dry mouth, dizziness, fatigue, and heartburn.

Synthesis

Thieme Patents: Revised: China:

The base catalyzed ether formation between 2-Benzylphenol (1) and 1,2-dichloropropane (2) gives 1-benzyl-2-(2-chloropropoxy)benzene (3). Displacement of the remaining halogen with piperidine completes the synthesis of benproperine (4).

References

  1. Li Y, Zhong DF, Chen SW, Maeba I (December 2005). "Identification of some benproperine metabolites in humans and investigation of their antitussive effect". Acta Pharmacologica Sinica. 26 (12): 1519–26. doi:10.1111/j.1745-7254.2005.00212.x. PMID 16297353.
  2. Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 6. ISBN 0-8103-7177-4.
  3. DK96113 idem Rubenstein K, GB 914008  (1962 to Pharmacia AS).
  4. Kurt Rubinstein, U.S. patent 3,117,059 (1964 to Aktieselskabet Pharmacia).
  5. Byoung Mog Kwon, et al. WO 2012064150  (to Korea Research Institute of Bioscience and Biotechnology KRIBB).
  6. Chin. J. Org. Chem. 2011, Vol. 31, Issue (02): 212-215.
Cough and cold preparations (R05)
Expectorants
Mucolytics
Cough suppressants
Opium alkaloids,
opioids,
and derivatives
Other


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