Pheniramine

Pheniramine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: A; ;
Routes of; administration	Oral; injection (intramuscular or slow intravenous); topical (ophthalmic/nasal solution)
ATC code	D04AA16 (WHO) R06AB05 (WHO);
Pharmacokinetic data
Metabolism	Hepatic hydroxylation, demethylation and glucuronidation
Elimination half-life	16 - 19 hrs (oral), 8 - 7 hrs (i.v.)
Excretion	Renal
Identifiers
	IUPAC name N,N-Dimethyl-3-phenyl-3-pyridin-2-yl-propan-1-amine;
CAS Number	86-21-5 ;
PubChem CID	4761;
IUPHAR/BPS	7267;
DrugBank	DB01620 ;
ChemSpider	4597 ;
UNII	134FM9ZZ6M;
KEGG	D08355 ;
ChEMBL	ChEMBL1193 ;
CompTox Dashboard (EPA)	DTXSID0023454 ;
ECHA InfoCard	100.001.506
Chemical and physical data
Formula	C16H20N2
Molar mass	240.350 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n1ccccc1C(c2ccccc2)CCN(C)C;
	InChI InChI=1S/C16H20N2/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16/h3-10,12,15H,11,13H2,1-2H3 ; Key:IJHNSHDBIRRJRN-UHFFFAOYSA-N ;
	(verify)

Pheniramine (trade name Avil among others) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an over-the-counter sleeping pill in a similar manner to other sedating antihistamines such as diphenhydramine. Pheniramine is also commonly found in eyedrops used for the treatment of allergic conjunctivitis.

It was patented in 1948.^[2] Pheniramine is generally sold in combination with other medications, rather than as a stand-alone drug, although some formulations are available containing pheniramine by itself.

Side effects

Pheniramine may cause drowsiness or Tachycardia, and over-dosage may lead to sleep disorders.^{[citation needed]}

Overdose may lead to seizures, especially in combination with alcohol.^{[citation needed]}

People combining with cortisol in the long term should avoid pheniramine as it may decrease levels of adrenaline (epinephrine) which may lead to loss of consciousness.^{[citation needed]}

Pheniramine is a deliriant (hallucinogen) in toxic doses. Recreational use of Coricidin for the dissociative (hallucinogenic) effect of its dextromethorphan is hazardous because it also contains chlorpheniramine.^{[citation needed]}

Chemical relatives

Halogenation of pheniramine increases its potency 20-fold. Halogenated derivatives of pheniramine include chlorphenamine, brompheniramine, dexchlorpheniramine, dexbrompheniramine, and zimelidine. Two other halogenated derivatives, fluorpheniramine and iodopheniramine, are currently in use for research on combination therapies for malaria and some cancers. ^{[citation needed]}

Other analogs include diphenhydramine, and doxylamine.

Stereoisomerism

Pheniramine contains a stereocenter and can exists as either of two enantiomers. The pharmaceutical drug is a racemate, an equal mixture of the (R)- and (S)-forms.^[3]

Enantiomers of pheniramine
(R)-Pheniramine CAS number: 56141-72-1	(S)-Pheniramine CAS number: 23201-92-5

References

^ Witte PU, Irmisch R, Hajdú P (January 1985). "Pharmacokinetics of pheniramine (Avil) and metabolites in healthy subjects after oral and intravenous administration". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 23 (1): 59–62. PMID 3988394.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.
^ von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U (2014). Hagers Handbuch der Pharmazeutischen Praxis. Vol. Band 9: Stoffe P-Z (5th ed.). Berlin: Springer Verlag. p. 121. ISBN 978-3-642-63389-8.

External links

Media related to Pheniramine at Wikimedia Commons
MedlinePlus Encyclopedia: Pheniramine overdose
Leaflet on Avil by The Royal Australian College of General Practitioners

[1] Witte PU, Irmisch R, Hajdú P (January 1985). "Pharmacokinetics of pheniramine (Avil) and metabolites in healthy subjects after oral and intravenous administration". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 23 (1): 59–62. PMID 3988394.

[Fis2006-2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.

[Hager-3] von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U (2014). Hagers Handbuch der Pharmazeutischen Praxis. Vol. Band 9: Stoffe P-Z (5th ed.). Berlin: Springer Verlag. p. 121. ISBN 978-3-642-63389-8.

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