Pheniramine

Structural formula
Structural formula without stereochemistry
General
Non-proprietary name	Pheniramine
other names	( RS ) - N , N -dimethyl-3-phenyl-3- (2-pyridyl) propylamine ( IUPAC ) (±) - N , N -dimethyl-3-phenyl-3- (2-pyridyl) propylamine Latin : Pheniraminum
Molecular formula	C 16 H 20 N 2 C 16 H 20 N 2 C 4 H 4 O 4 (maleate) C 16 H 20 N 2 C 7 H 7 NO 3 (aminosalicylate)
Brief description	White, crystalline powder (maleate)
External identifiers / databases
CAS number 86-21-5 132-20-7 (maleate) 3269-83-8 (aminosalicylate) PubChem 4761 DrugBank DB01620 Wikidata Q656259
Drug information
ATC code	D04 AA16 R06 AB05
Drug class	Antihistamine
Mechanism of action	Histamine - antagonist at H 1 receptors
properties
Molar mass	240.34 g mol −1 356.42 g mol −1 (maleate) 393.48 g mol −1 (aminosalicylate)
Physical state	firmly
Melting point	<25 ° C 106 to 109 ° C (maleate)
boiling point	181 ° C at 1.30E + 01 mm Hg
pK s value	9.48
solubility	Easily soluble in water
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances (Maleate) Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	48 mg kg −1 ( LD 50 ,  mouse ,  iv ) Maleate: 268 mg kg −1 ( LD 50 ,  mouse ,  oral ) 520 mg kg −1 ( LD 50 ,  rat ,  oral ) Aminosalicylate: 48 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pheniramine is an antiallergic drug from the class of H1 antihistamines of the 1st generation with anticholinergic properties. It is used to treat hay fever , hives , allergic rhinitis or motion sickness , in Switzerland and Austria only in combination with other active substances to treat the symptoms of flu and colds.

Due to its strong sedative effects, it is sometimes used off-label as a sleep aid. Pheniramine is an alkylamine and pyridine derivative.

Extraction

In 1951 a process was described starting from 4-chlorobenzyl cyanide and 2-chloropyridine in the presence of sodium amide . In the process patented in 1954, pyridine-2-aldehyde reacts with phenylmagnesium bromide , pheniramine is formed by reductive removal of the hydroxyl group and subsequent alkylation with dimethylaminoethyl chloride in the presence of sodium amide:

Chlorphenamine is a derivative of pheniramine; the effect of the halogen is increased by a factor of 10–20.

Stereoisomerism

Pheniramine contains a stereocenter and consists of two enantiomers. This is a racemate , i.e. a 1: 1 mixture of ( R ) - and ( S ) -form:

Enantiomers of pheniramine
CAS number: 56141-72-1	CAS number: 23201-92-5

pharmacology

The hydrochloride , the maleate salt and the 4-amino salicylate (C ₁₆ H ₂₀ N ₂ C ₇ H ₇ NO ₃ ) are used in medicine.

Pharmacokinetics

The breakdown takes place mainly in the liver through hydroxylation , demethylation and glucuronidation , the two metabolites are N- desmethylpheniramine and N -didesmethylpheniramine. The plasma half-life is up to 19 hours.

Indications

In Switzerland and Austria, pheniramine is only approved in combination with other active ingredients for the short-term and symptomatic treatment of flu and cold symptoms in adults.

Other indications for pheniramine ( maleate ) include allergic symptoms, Quincke's edema , asthma , conjunctivitis , dermatitis , eczema , hay fever , rhinitis , hives , vertigo , Menière's disease and motion sickness .

Side effects

Pheniramine can cause somnolence , bradycardia, or gastrointestinal discomfort. Overdosing can lead to insomnia and cramps, especially in combination with alcohol. Once ingested, do not drive a car.

Contraindications

Together with cortisol , the adrenaline level can drop to the point of loss of consciousness. Pheniramine should not be taken if the prostate has symptoms.

Interactions

MAOIs cause slower breakdown and overdose if taken repeatedly. Central depressant drugs, alcohol and parasympatholytics can increase undesirable effects.

Trade names

Pheniramine is often combined with acetylsalicylic acid , acetaminophen, and / or naphazoline .

Monopreparations

Avil (SRB, TR, AU), Fenamed (TR), Aviject (TR)

Combination preparations

NeoCitran (A, CH), Fervex (F), Stillergy (I), Tetramil (I). In Switzerland, pheniramine maleate with paracetamol and phenylephrine is available without a prescription as "NeoCitran powder for adults" .

Web links

• Pheniramine Overdose at MedlinePlus (English)

Individual evidence

1. ↑ ^{a b c} Entry on pheniramine. In: Römpp Online . Georg Thieme Verlag, accessed on July 23, 2019.
2. ↑ V Alagarsamy: Textbook of Medicinal Chemistry, Volume 2, page 27 . ISBN 978-81-312-3259-0 .
3. ↑ ^{a b c} Datasheet Pheniramine Maleate from Sigma-Aldrich , accessed on February 11, 2016 ( PDF ).
4. ↑ ^{a b c} Entry on pheniramine in the ChemIDplus database of the United States National Library of Medicine (NLM)
5. ↑ European Pharmacopoeia 9th edition, basic work 2017. Deutscher Apotheker Verlag, Stuttgart 2017, ISBN 978-3-7692-6641-2 . Pheniramine Maleate.
6. ↑ ^{a b} Entry on pheniramine in Pharmawiki , accessed on February 19, 2016.
7. ^ ^{A b c} Kleemann , Engel, Kutscher, Reichert: Pharmaceutical Substances, 4th edition, Thieme-Verlag Stuttgart 2000, ISBN 978-1-58890-031-9 . Page 1613.
8. ↑ Pheniramine Maleat at drugs.com (English), accessed on February 19, 2016.
9. ↑ ^{a b c d} package insert from Avil in Australia (English).
10. ↑ Patent application US2567245 : Aryl- (2-pyridyl) -amino alkanes and their production. Applied on May 10, 1948 , published on September 11, 1951 , Applicant: Schering Corp, Inventor: D. Papa, E. Schwenk, N. Sperber. ‌
11. ↑ Patent application US2676964 : 3-pyridyl propylamine antihistamine substances. Applied on June 7, 1950 , published April 27, 1954 , Applicant: Schering Corp. Inventors: D. Papa, E. Schwenk, N. Sperber. ‌
12. ↑ ^{a b} D. Sriram: Medicinal Chemistry, Pearson Education India 2010 ISBN 81-317-3144-8 page 285
13. ↑ F. v. Bruchhausen, G. Dannhardt, S. Ebel, AW Frahm, E. Hackenthal, U. Holzgrabe (Eds.): Hagers Handbook of Pharmaceutical Practice: Volume 9: Material PZ , Springer Verlag, Berlin, Edition 5, 2014, p. 121, ISBN 978-3-642-63389-8 .
14. ↑ PU Witte, R. Irmisch, P. Hajdú: Pharmacokinetics of pheniramine (Avil) and metabolites in healthy subjects after oral and intravenous administration. In: International journal of clinical pharmacology, therapy, and toxicology. Volume 23, Number 1, January 1985, pp. 59-62, PMID 3988394 .
15. ^ Search in the AGES medicinal specialties register - February 2016.
16. ↑ Pheniramine in the Swiss Pharmaceutical Compendium - February 2016.
17. ↑ pheniramine maleate at druginfosys .
18. ↑ Enclosed text from NeoCitran® ( Memento of the original dated February 11, 2016 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. . 
19. ↑ Drugs.com International: Pheniramine .

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !