Pheniramine

Pheniramine
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a606008
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
Excretion	Renal
Identifiers
	show IUPAC name
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;
	show SMILES
	show InChI

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.^[1] 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, and , are currently in use for research on combination therapies for malaria and some cancers.^{[citation needed]}

Other analogs include triprolidine. Similar molecules include diphenhydramine, doxylamine, and fluoxetine

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.^[2]

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

References[]

^ 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. 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

[Fis2006-1] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.

[Hager-2] von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U (2014). Hagers Handbuch der Pharmazeutischen Praxis. Band 9: Stoffe P-Z (5th ed.). Berlin: Springer Verlag. p. 121. ISBN 978-3-642-63389-8.

[1]

[2]

show v t Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine (+naproxen) Diphenylpyraline Doxylamine Ebastine Orphenadrine Diphenylmethanolpiperidines: Fexofenadine Terfenadine Diphenylmethylpiperazines: Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Etodroxizine Hydroxyzine Meclizine Oxatomide Phenylpyridinylpropanamines: Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Pheniramine Others: Acrivastine Bamipine Dimetindene Phenyltoloxamine Pyrrobutamine Quifenadine Triprolidine
Ethylenediamines	Antazoline Chloropyramine Histapyrrodine Mepyramine (pyrilamine) Methapyrilene Phenbenzamine Thenalidine Tripelennamine (pyribenzamine)
Tricyclics	Dibenzocycloheptenes: Antidepressants (e.g., amitriptyline) Azatadine Cyproheptadine Deptropine Desloratadine Ketotifen Loratadine Rupatadine Phenothiazines: Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Others: Antidepressants (e.g., doxepin, mirtazapine, trimipramine) Epinastine Latrepirdine Mebhydrolin Olopatadine Perlapine Phenindamine Pimethixene
Others	Phenylpiperazines: Antidepressants (e.g., trazodone) Phenbenzamine
For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine