Benproperin

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Structural formula
Structural formulas of (±) -benproperin
1: 1 mixture of ( R ) -form (top)
and ( S ) -form (bottom)
General
Non-proprietary name Benproperin
other names
  • ( RS ) -1- (1- (2-Benzylphenoxy) -2-propyl) -piperidine ( IUPAC )
  • ( RS ) -1- [1- (2-Benzylphenoxy) -2-propyl] piperidine
Molecular formula C 21 H 27 NO
External identifiers / databases
CAS number
  • 2156-27-6
  • 19428-14-9 (phosphate salt)
PubChem 2326
ChemSpider 2236
Wikidata Q818139
Drug information
ATC code

R05 DB02

properties
Molar mass 309.445 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
Toxicological data
  • 192 mg kg −1 ( LD 50 , albino mouse ,  ip , dihydrogen phosphate)
  • 1365 mg kg −1 ( LD 50 , albino mouse ,  oral , dihydrogen phosphate)
  • 620 mg kg −1 ( LD 50 ,  rabbit ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benproperin is a medicinal substance that is used as an alternative to codeine , especially for dry coughs .

Benproperin belongs to the peripherally effective antitussives and chemically to the group of piperidine derivatives.

Clinical information

application areas

Benproperin is used to treat acute and chronic cough disorders, especially dry coughs.

Contraindications and restrictions on use

Apart from hypersensitivity to the drug, there are no known contraindications. There is insufficient experience with the use of benproperin during pregnancy, and animal experiments have not provided any indications of teratogenicity or foetotoxicity . Specific interactions with other drugs have not been investigated and are not known.

Side effects

Isolated cases of drowsiness, dry mouth and nausea have been reported.

pharmacology

Pharmacodynamics

The exact molecular mechanism of action of benproperine is not known. An inhibition of the cough stimulus in the afferent part of the reflex arc is assumed. In contrast to codeine, it speeds up the respiratory drive.

Pharmacokinetics

The plasma half-life of benproperine is approximately six hours.

chemistry

Stereochemistry

Benproperine is a chiral drug that is used as a racemic mixture of its two enantiomers ( R ) - (+) - benproperine and ( S ) - (-) - benproperine. Both enantiomers are about as effective in animal experiments as the racemate .

synthesis

Benproperine can be obtained by reacting 2-benzylphenol with propene oxide to form 2- phenylphenoxypropanol , which is then reacted with thionyl chloride or tosyl chloride and then converted into benproperine by substitution with piperidine.

Commercial preparations

Benproperin is available in the form of dragées in pharmacies in Germany under the brand name Tussafug .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ a b entry on benproperin. In: Römpp Online . Georg Thieme Verlag, accessed on August 22, 2011.
  3. ↑ a b c d e f g h Technical information Tussafug. Robugen GmbH. As of October 2007.
  4. ↑ Chen S, Min L, Li Y, Li W, Zhong D, Kong W: Anti-tussive activity of benproperine enantiomers on citric-acid-induced cough in conscious guinea-pigs . In: J. Pharm. Pharmacol. . 56, No. 2, February 2004, pp. 277-280. doi : 10.1211 / 0022357022719 . PMID 15005888 .
  5. ↑ Hermann Hager, Walter Reuss; Hager's Handbook of Pharmaceutical Practice; ISBN 978-3-540-60330-6 .