Import Your Data

FAQ

More QuickView FAQs

QuickView

0
Meta-
Analysis

Bookmark Forward

QuickView for Phenylephrine (compound)

Summary
General Info

PubChem

PubChem Compound 11819418

PubChem Compound 11819418

Name:	Phenylephrine
PubChem Compound ID:	11819418
Description:	An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.
Molecular formula:	C₉H₁₃NO₂
Molecular weight:	168.218 g/mol

DrugBank

Identification

Name:	Phenylephrine
Name (isomeric):	DB00388
Drug Type:	small molecule
Description:	An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.
Synonyms:	Metasynephrine; Phenylephrinum [INN-Latin]; M-Oxedrine; M-Methylaminoethanolphenol; Metaoxedrin; L-Phenylephedrine; L-Phenylephrine; Metaoxedrine; Fenilefrina [INN-Spanish]; Metaoxedrinum
Brand:	Ocugestrin, Alconefrin Nasal Spray 25, AK-Nefrin, Mezaton, Neo-Synephrine Nasal Spray, Phenoptic, Adrianol, Neophryn, Metsatonum, Relief Eye Drops for Red Eyes, Minims Phenylephrine, Mesaton, Nostril Spray Pump, Isophrin, Isophrim, Alconefrin Nasal Drops 25, Dimetane, Neo-Synephrine, Neofrin, Ocu-Phrin Sterile Eye Drops, Mesatonum, I-Phrine, Dionephrine, Dilatair, Isopto Frin, M-Synephrine, Neo-Synephrine Nasal Jelly, Mydfrin, Spersaphrine, Metasympatol, Duration, Nostril Spray Pump Mild, Nostril, Visadron, Neo-Synephrine Nasal Drops, Doktors, Prefrin, Biomydrin, Mesatone, AK-Dilate, Alcon Efrin, M-Sympatol, Alconefrin Nasal Drops 50, Prefrin Liquifilm, Vicks Sinex, M-Sympathol, Rhinall, Pyracort D, Neosynephrine, Alconefrin Nasal Drops 12
Brand name mixture:	Biohisdine DM Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Citron Chaud DM Cumberland Pws(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Lemon Relief for Adults(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride), Vasosu... show more » Biohisdine DM Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Citron Chaud DM Cumberland Pws(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Lemon Relief for Adults(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride), Vasosulf Oph Soln(Phenylephrine Hydrochloride + Sulfacetamide Sodium), Hot Lemon for Colds Powder(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Neo Citran Nutrasweet(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride), Novahistex C(Codeine Phosphate + Phenylephrine Hydrochloride), Dimetapp Extra Strength(Brompheniramine Maleate + Phenylephrine Hydrochloride), Dimetapp(Brompheniramine Maleate + Phenylephrine Hydrochloride), Dimetapp DM Tab(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Dimetane Expectorant-DC Syr(Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Chemhisdine DM Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Phenergan VC Expectorant Syr(Phenylephrine Hydrochloride + Potassium Guaiacol Sulphonate + Promethazine Hydrochloride), Citron Chaud Cumberland Pws(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Cough, Cold & Allergy Relief(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Chemhisdex DM Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Phenergan VC Expectorant W Codeine Liq(Codeine Phosphate + Phenylephrine Hydrochloride + Potassium Guaiacol Sulphonate + Promethazine Hydrochloride), Hot Lemon Relief Pws(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Neo Citran a Powder(Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Hot Lemon Relief for Cold Symptoms Pws(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Occu-Cal Drops(Boric Acid + Phenylephrine Hydrochloride + Sodium Borate), Dimetapp Oral Infant Drops(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Hot Lemon Relief for Cold Symptoms Ext Str(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Dimetapp DM Elixir(Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Occu-Cal Lotion(Boric Acid + Phenylephrine Hydrochloride + Sodium Borate), Neo-Synephrine Nasal Spray(Phenylephrine Hydrochloride + Thenyldiamine Hcl.), Dimetapp Cold & Sinus(Acetaminophen + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Hemorrhoidal Ointment(Mineral Oil + Petrolatum + Phenylephrine Hydrochloride + Shark Liver Oil), Lemon Time(Acetaminophen + Phenylephrine Hydrochloride + Pyrilamine Maleate + Vitamin C), Tantapp Elixir(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), DayQuil(Acetaminophen + Dextromethorphan + Phenylephrine), Nezger Tab(Acetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride), Soframycin Nasal Spray(Framycetin Sulfate + Gramicidin + Phenylephrine Hydrochloride), Codalin(Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Dimetapp-C Syr(Brompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Cold & Allergy Relief - Liq(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Dimetapp Extentabs(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Dimetapp Oral Infant Cold Drops(Brompheniramine Maleate + Phenylephrine Hydrochloride), Neo Citran Extra Strength(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride), Neo Citran Powder(Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C), Novahistex Dh Expectorant(Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride), Decongestant Antihistaminic Syrup(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Dimetapp Elixir(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Dimetane Expectorant-C Syr(Brompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Hot Lemon Relief DM Adult(Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride), Dimetapp Tab(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Biohisdex DM Decongestant(Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride), Dimetane Expectorant Liq(Brompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Cold & Allergy(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride), Neo Synephrine Nasal Spray(Phenylephrine Hydrochloride + Thenyldiamine Hcl.), AK Vernacon Oph Soln(Pheniramine Maleate + Phenylephrine Hydrochloride), Pharmetapp Elixir(Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride) show less «
Category:	Mydriatics, Adrenergic alpha-Agonists, Cardiotonic Agents, Sympathomimetics, Vasoconstrictor Agents, Nasal Decongestants
CAS number:	59-42-7

Pharmacology

Indication:	Phenylephrine is mainly used to treat nasal congestion, but may also be useful in treating hypotension and shock, hypotension during spinal anaesthesia, prolongation of spinal anaesthesia, paroxysmal supraventricular tachycardia, symptomatic relief of external or internal hemorrhoids, and to increase blood pressure as an aid in the diagnosis of heart murmurs.
Pharmacology:	Phenylephrine is a powerful vasoconstrictor. It is used as a nasal decongestant and cardiotonic agent. Phenylephrine is a postsynaptic α₁-receptor agonist with little effect on β-receptors of the heart. Parenteral administration of phenylephrine causes a rise in systolic and diastolic pressures, a slight decrease in cardiac ou... show more » Phenylephrine is a powerful vasoconstrictor. It is used as a nasal decongestant and cardiotonic agent. Phenylephrine is a postsynaptic α₁-receptor agonist with little effect on β-receptors of the heart. Parenteral administration of phenylephrine causes a rise in systolic and diastolic pressures, a slight decrease in cardiac output, and a considerable increase in peripheral resistance; most vascular beds are constricted, and renal, splanchnic, cutaneous, and limb blood flows are reduced while coronary blood flow is increased. Phenelephrine also causes pulmonary vessel constriction and subsequent increase in pulmonary arterial pressure. Vasoconstriction in the mucosa of the respiratory tract leads to decreased edema and increased drainage of sinus cavities. show less «
Mechanism of Action:	In general, α₁-adrenergic receptors mediate contraction and hypertrophic growth of smooth muscle cells. α₁-receptors are 7-transmembrane domain receptors coupled to G proteins, G_q/11. Three α₁-receptor subtypes, which share approximately 75% homology in their transmembrane domains, have ... show more » In general, α₁-adrenergic receptors mediate contraction and hypertrophic growth of smooth muscle cells. α₁-receptors are 7-transmembrane domain receptors coupled to G proteins, G_q/11. Three α₁-receptor subtypes, which share approximately 75% homology in their transmembrane domains, have been identified: α_1A (chromosome 8), α_1B (chromosome 5), and α_1D (chromosome 20). Phenylephrine appears to act similarly on all three receptor subtypes. All three receptor subtypes appear to be involved in maintaining vascular tone. The α_1A-receptor maintains basal vascular tone while the α_1B-receptor mediates the vasocontrictory effects of exogenous α₁-agonists. Activation of the α₁-receptor activates G_q-proteins, which results in intracellular stimulation of phospholipases C, A₂, and D. This results in mobilization of Ca²⁺ from intracellular stores, activation of mitogen-activated kinase and PI₃ kinase pathways and subsequent vasoconstriction. Phenylephrine produces its local and systemic actions by acting on α₁-adrenergic receptors peripheral vascular smooth muscle. Stimulation of the α₁-adrenergic receptors results in contraction arteriolar smooth muscle in the periphery. Phenylephrine decreases nasal congestion by acting on α₁-adrenergic receptors in the arterioles of the nasal mucosa to produce constriction; this leads to decreased edema and increased drainage of the sinus cavities. show less «
Absorption:	Completely absorbed after oral administration. It has a reduced bioavailability (compared to pseudoephedrine) following oral administration due to significant first-pass metabolism in the intestinal wall. Compared to IV administration, bioavailability is approximately 38%. Peak serum concentrations are achieved approximately 0.75-2 hours following oral administration. Phenylephrine should be administered parenterally to achieve cardiovascular effects. Occasionally, systemic effects are observed following oral inhalation.
Protein binding:	95% binding-plasma proteins
Biotransformation:	Undergoes extensive first-pass metabolism in the intestinal wall and extensive metabolism in the liver. Sulfate conjugation, primarily in the intestinal wall, and oxidative metabolism by monoamine oxidase (MAO) represent the principle routes of metabolism. Glucuronidation occurs to a lesser extent. Phenylephrine and its metabolites are mainly excreted in urine/ .
Half Life:	2.1 to 3.4 hours
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Phenelzine	Increased arterial pressure
Alseroxylon	Increased arterial pressure
Ergonovine	Possible marked increase of arterial pressure
Reserpine	Increased arterial pressure
Clomipramine	The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of phenylephrine.

Targets

Alpha-1A adrenergic receptor

Alpha-1B adrenergic receptor

Alpha-1D adrenergic receptor

Enzymes

Amine oxidase [flavin-containing] A

Cytochrome P450 1A2