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Pheniramine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Pheniramine
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
Routes of
administration
Oral;injection (intramuscular or slowintravenous); topical (ophthalmic/nasal solution)
ATC code
Pharmacokinetic data
MetabolismHepatichydroxylation,demethylation andglucuronidation
Eliminationhalf-life16 - 19 hrs (oral), 8 - 17 hrs (i.v.)[1]
ExcretionRenal
Identifiers
  • N,N-Dimethyl-3-phenyl-3-pyridin-2-yl-propan-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.506Edit this at Wikidata
Chemical and physical data
FormulaC16H20N2
Molar mass240.350 g·mol−1
3D model (JSmol)
  • n1ccccc1C(c2ccccc2)CCN(C)C
  • 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 checkY
  • Key:IJHNSHDBIRRJRN-UHFFFAOYSA-N checkY
  (verify)

Pheniramine (trade nameAvil among others) is anantihistamine withanticholinergic properties used to treatallergic conditions such ashay fever orurticaria. It has relatively strongsedative effects, and may sometimes be used off-label as an over-the-counter sleeping pill in a similar manner to other sedating antihistamines such asdiphenhydramine. Pheniramine is also commonly found ineyedrops used for the treatment ofallergic 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

[edit]

Pheniramine may cause drowsiness orTachycardia, and over-dosage may lead to sleep disorders.[citation needed]

Overdose may lead toseizures, especially in combination withalcohol.[citation needed]

People combining withcortisol 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 adeliriant (hallucinogen) in toxic doses. Recreational use of Coricidin for thedissociative (hallucinogenic) effect of its dextromethorphan is hazardous because it also containschlorpheniramine.[citation needed]

Chemical relatives

[edit]

Halogenation of pheniramine increases its potency 20-fold. Halogenated derivatives of pheniramine includechlorphenamine,brompheniramine,dexchlorpheniramine,dexbrompheniramine, andzimelidine. Two other halogenated derivatives,fluorpheniramine andiodopheniramine, are currently in use for research on combination therapies for malaria and some cancers.[citation needed]

Other analogs includediphenhydramine, anddoxylamine.

Stereoisomerism

[edit]

Pheniramine contains a stereocenter and can exists as either of twoenantiomers. The pharmaceutical drug is aracemate, 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

See also

[edit]

References

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