Pheniramine

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Pheniramine
Pheniramine.svg
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
Pharmacokinetic data
Metabolism Hepatic hydroxylation, demethylation and glucuronidation
Elimination half-life 16 - 19 hrs (oral), 8 - 7 hrs (i.v.) [1]
Excretion Renal
Identifiers
  • N,N-Dimethyl-3-phenyl-3-pyridin-2-yl-propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.506 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H20N2
Molar mass 240.350 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 Yes check.svgY
  • Key:IJHNSHDBIRRJRN-UHFFFAOYSA-N Yes check.svgY
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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.

Contents

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)-Pheniramin Structural Formula V1.svg
(R)-Pheniramine
CAS number: 56141-72-1
(S)-Pheniramin Structural Formula V1.svg
(S)-Pheniramine
CAS number: 23201-92-5

See also

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References

  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.