Drug/Small Molecule:

phenylephrine

Overview

Generic Names:	Fenilefrina [INN-Spanish]; L-Phenylephedrine; L-Phenylephrine; M-Methylaminoethanolphenol; M-Oxedrine; Metaoxedrin; Metaoxedrine; Metaoxedrinum; Metasynephrine; Phenylephrinum [INN-Latin]
IUPAC Name:	3-[(1R)-1-hydroxy-2-methylaminoethyl]phenol
Trade Names:	AK-Dilate; AK-Nefrin; Adrianol; Alcon Efrin; Alconefrin Nasal Drops 12; Alconefrin Nasal Drops 25; Alconefrin Nasal Drops 50; Alconefrin Nasal Spray 25; Biomydrin; Dilatair; Dimetane; Dionephrine; Doktors; Duration; I-Phrine; Isophrim; Isophrin; Isopto Frin; M-Sympathol; M-Sympatol; M-Synephrine; Mesaton; Mesatone; Mesatonum; Metasympatol; Metsatonum; Mezaton; Minims Phenylephrine; Mydfrin; Neo-Synephrine; Neo-Synephrine Nasal Drops; Neo-Synephrine Nasal Jelly; Neo-Synephrine Nasal Spray; Neofrin; Neophryn; Neosynephrine; Nostril; Nostril Spray Pump; Nostril Spray Pump Mild; Ocu-Phrin Sterile Eye Drops; Ocugestrin; Phenoptic; Prefrin; Prefrin Liquifilm; Pyracort D; Relief Eye Drops for Red Eyes; Rhinall; Spersaphrine; Vicks Sinex; Visadron
Brand Mixtures:	AK Vernacon Oph Soln (Pheniramine Maleate + Phenylephrine Hydrochloride); Biohisdex DM Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride); Biohisdine DM Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride); Chemhisdex DM Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride); Chemhisdine DM Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride); Citron Chaud Cumberland Pws (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Citron Chaud DM Cumberland Pws (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Codalin (Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride); Cold & Allergy (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Cold & Allergy Relief - Liq (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Cough, Cold & Allergy Relief (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); DayQuil (Acetaminophen + Dextromethorphan + Phenylephrine); Decongestant Antihistaminic Syrup (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetane Expectorant Liq (Brompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetane Expectorant-C Syr (Brompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetane Expectorant-DC Syr (Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp (Brompheniramine Maleate + Phenylephrine Hydrochloride); Dimetapp Cold & Sinus (Acetaminophen + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp DM Elixir (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp DM Tab (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp Elixir (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp Extentabs (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp Extra Strength (Brompheniramine Maleate + Phenylephrine Hydrochloride); Dimetapp Oral Infant Cold Drops (Brompheniramine Maleate + Phenylephrine Hydrochloride); Dimetapp Oral Infant Drops (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp Tab (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetapp-C Syr (Brompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Hemorrhoidal Ointment (Mineral Oil + Petrolatum + Phenylephrine Hydrochloride + Shark Liver Oil); Hot Lemon Relief DM Adult (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride); Hot Lemon Relief Pws (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Hot Lemon Relief for Cold Symptoms Ext Str (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Hot Lemon Relief for Cold Symptoms Pws (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Hot Lemon for Colds Powder (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Lemon Relief for Adults (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride); Lemon Time (Acetaminophen + Phenylephrine Hydrochloride + Pyrilamine Maleate + Vitamin C); Neo Citran Extra Strength (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride); Neo Citran Nutrasweet (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride); Neo Citran Powder (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Neo Citran a Powder (Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C); Neo Synephrine Nasal Spray (Phenylephrine Hydrochloride + Thenyldiamine Hcl.); Neo-Synephrine Nasal Spray (Phenylephrine Hydrochloride + Thenyldiamine Hcl.); Nezger Tab (Acetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride); Novahistex C (Codeine Phosphate + Phenylephrine Hydrochloride); Novahistex Dh Expectorant (Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride); Occu-Cal Drops (Boric Acid + Phenylephrine Hydrochloride + Sodium Borate); Occu-Cal Lotion (Boric Acid + Phenylephrine Hydrochloride + Sodium Borate); Pharmetapp Elixir (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Phenergan VC Expectorant Syr (Phenylephrine Hydrochloride + Potassium Guaiacol Sulphonate + Promethazine Hydrochloride); Phenergan VC Expectorant W Codeine Liq (Codeine Phosphate + Phenylephrine Hydrochloride + Potassium Guaiacol Sulphonate + Promethazine Hydrochloride); Soframycin Nasal Spray (Framycetin Sulfate + Gramicidin + Phenylephrine Hydrochloride); Tantapp Elixir (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Vasosulf Oph Soln (Phenylephrine Hydrochloride + Sulfacetamide Sodium)
PharmGKB Accession Id:	PA450935

Description

An alpha-adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent. [PubChem]

Indication

For the treatment of ophthalmic disorders (hyperaemia of conjunctiva, posterior synechiae, acute atopic), nasal congestion, hemorrhoids, hypotension, shock, hypotension during spinal anesthesia, paroxysmal supraventricular tachycardia. It is also used as an aid in the diagnosis of heart murmurs and for prolongation of spinal anesthesia

ATC Therapeutic Categories

• C01CA:Adrenergic and dopaminergic agents
• C05AX:Other agents for treatment of hemorrhoids and anal fissures for topical use
• R01AA:Sympathomimetics, plain
• R01AB:Sympathomimetics, combinations excl. corticosteroids
• R01BA:Sympathomimetics
• S01FB:Sympathomimetics excl. antiglaucoma preparations
• S01GA:Sympathomimetics used as decongestants

Pharmacology and Interactions

Mechanism Of Action

Phenylephrine produces its ophthalmic and systemic actions by acting on alpha 1 adrenergic receptors in the pupillary dilator muscle and the vascular smooth musle, resulting in contraction of the dilator muscle and contraction of the smooth muscle in the arterioles of the conjunctiva and peripheral vasoconstriction. Phenylephrine decreases nasal congestion by acting on alpha 1 adrenergic receptors in the arterioles of the nasal mucosa to produce constriction.

Pharmacology

Phenylephrine is a powerful vasoconstrictor. It is used as a mydriatic, nasal decongestant, and cardiotonic agent. Phenylephrine is a postsynaptic alpha-receptor stimulant with little effect on the beta receptors of the heart. Parenteral administration of Phenylephrine causes a rise in systolic and diastolic pressures, cardiac output is slightly decreased and peripheral resistance is considerably increased, most vascular beds are constricted; renal, splanchnic, cutaneous, and limb blood flows are reduced but coronary blood flow is increased. Pulmonary vessels are constricted, and pulmonary arterial pressure is raised. This alpha receptor sympathetic agonist is also used locally because its vasoconstrictor and mydriatic action.

Food Interactions

Take without regard to meals.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Oral phenylephrine is extensively metabolised by monoamine oxidase, an enzyme which is present in the stomach and liver.

Protein Binding

95% binding-plasma proteins

Absorption

Reduced bioavailability (compared to pseudoephedrine) following oral administration due to significant first-pass metabolism.

Half Life

2.1 to 3.4 hours

Chemical Properties

Chemical Formula:

C₉H₁₃NO₂

SMILES Code:

CNC[C@@H](c1cccc(c1)O)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

167.205 / 167.0946

Curated Information

The following genes are in curated knowledge about this drug.

	Gene	Relationship	Evidence
	ACE	PD    FA	Publications
	NOS3	CO PD       GN	Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

• MAOA

Drug Targets

• ADRA1B
• ADRA1A

PharmGKB Curated Pathways

• Sympathetic Nerve Pathway (Neuroeffector Junction)

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Curated Information

The following diseases are in curated knowledge about this drug.

	Disease	Relationship	Evidence
	Angina Pectoris	PD       GN	Publications
	Cardiovascular Diseases	CO PD    FA GN	Publications
	Coronary Artery Disease	CO PD       GN	Publications
	Coronary Disease	CO PD       GN	Publications
	Heart Failure	CO PD       GN	Publications
	Hypertension	PD       GN	Publications
	Hypotension	PD    FA	Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Curated Phenotype Datasets

These datasets are sorted alphabetically by title.

1. Blood pressure measurements

   • 
   • 
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   • 
   • PD

   Submitted by Daniel T. O'Connor, MD involving ADRB2, acetylcholine, isoproterenol, NG-monomethyl-l-arginine, phenylephrine, and Cardiovascular Diseases

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.