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targets (3) enzymes (2)
for drugs
Identification
Name Phenylephrine
Accession Number DB00388 (APRD00365)
Type small molecule
Groups approved
Description

Phenylephrine is a sympathomimetic amine that acts predominantly on α-adrenergic receptors. It 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Fenilefrina [INN-Spanish]
  • L-Phenylephedrine
  • L-Phenylephrine
  • M-Methylaminoethanolphenol
  • M-Oxedrine
  • Metaoxedrin
  • Metaoxedrine
  • Metaoxedrinum
  • Metasynephrine
  • Phenylephrinum [INN-Latin]
Brand names
  • Adrianol
  • AK-Dilate
  • AK-Nefrin
  • 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 name 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 for Colds Powder (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C)
  • Hot Lemon Relief DM Adult (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride)
  • 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 Relief Pws (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 a Powder (Pheniramine Maleate + Phenylephrine Hydrochloride + 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 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)
Categories
  • Vasoconstrictor Agents
  • Sympathomimetics
  • Adrenergic alpha-Agonists
  • Mydriatics
  • Cardiotonic Agents
  • Nasal Decongestants
CAS number 59-42-7
Weight Average: 167.205
Monoisotopic: 167.094628665
Chemical Formula C9H13NO2
InChI Key InChIKey=SONNWYBIRXJNDC-VIFPVBQESA-N
InChI
InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
Plain Text
IUPAC Name
3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
SMILES
CNC[C@H](O)C1=CC(O)=CC=C1
Plain Text
Mass Spec show (8.1 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
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.
Pharmacodynamics 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.
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, Gq/11. Three α1-receptor subtypes, which share approximately 75% homology in their transmembrane domains, have been identified: α1A (chromosome 8), α1B (chromosome 5), and α1D (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 α1A-receptor maintains basal vascular tone while the α1B-receptor mediates the vasocontrictory effects of exogenous α1-agonists. Activation of the α1-receptor activates Gq-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.
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.
Volume of distribution Not Available
Protein binding 95% binding-plasma proteins
Metabolism

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/ .

Route of elimination Not Available
Half life 2.1 to 3.4 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Cream Topical 0.25%
Injection, solution Intramuscular 10 mg/ml
Injection, solution Intravenous 10 mg/ml
Liquid Ophthalmic
Ointment Topical 0.25%
Strip Oral 2.5 mg
Suppository Rectal 0.25%
Tablet Oral 10 mg
Prices
Unit description Cost Unit
Mydfrin 2.5% Solution 5ml Bottle 37.1 USD bottle
Neo-synephrine 10 mg/ml amp 5.68 USD ml
Mydfrin 2.5% eye drops 5.28 USD ml
Phenylephrine 10 mg/ml vial 3.0 USD ml
Phenylephrine 2.5% eye drop 2.09 USD ml
Neofrin 10% eye drops 1.93 USD ml
Ak-dilate 10% eye drops 1.34 USD ml
Phenylephrine hcl crystals 1.34 USD g
Phenylephrine 10% eye drops 1.25 USD ml
Phenylephrine-ns 0.8 mg/10 ml 1.2 USD ml
Phenylephrine-ns 0.4 mg/10 ml 1.17 USD ml
Mydfrin 2.5 % Solution 1.09 USD ml
Neofrin 2.5% eye drops 0.6 USD ml
Ak-dilate 2.5% eye drops 0.45 USD ml
Neo-synephrine 0.25% drops 0.36 USD ml
Hemorrhoidal suppository 0.28 USD suppository
Neo-synephrine 12 hour spray 0.28 USD ml
Neo-synephrine 1% drops 0.26 USD ml
Sudafed pe 10 mg tablet 0.25 USD tablet
Neo-synephrine 0.5% drops 0.23 USD ml
Little noses decon nose drp 0.22 USD ml
Wal-phed pe 10 mg tablet 0.22 USD tablet
Tur-bi-kal nose drops 0.21 USD ml
Industrial 0.12% eye drops 0.17 USD ml
Ephrine 1% nose drops 0.15 USD ml
Phenylephrine 10 mg tablet 0.08 USD tablet
Rhinall 0.25% nose drops 0.07 USD ml
Non-pseudo sinus decongest tablet 0.05 USD tablet
Pv nasal decongestant 5 mg tablet 0.03 USD tablet
Patents Not Available
Properties
State solid
Melting point 140-145 oC
Experimental Properties
Property Value Source
water solubility Freely soluble in water PhysProp
logP 0.5 PhysProp
Predicted Properties
Property Value Source
water solubility 2.20e+01 g/l ALOGPS
logP -0.69 ALOGPS
logP -0.10 ChemAxon Molconvert
logS -0.88 ALOGPS
pKa 14.24 ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 52.49 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 47.25 ChemAxon Molconvert
polarizability 18.20 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07441 Link_out
PubChem Compound 6041 Link_out
PubChem Substance 46506961 Link_out
ChemSpider 5818 Link_out
ChEBI 8093 Link_out
ChEMBL 8093 Link_out
Therapeutic Targets Database DAP000224 Link_out
PharmGKB PA450935 Link_out
Drug Product Database 2238400 Link_out
RxList http://www.rxlist.com/cgi/generic3/phenyleph.htm Link_out
Drugs.com http://www.drugs.com/cdi/phenylephrine-solution.html Link_out
PDRhealth http://www.pdrhealth.com/drugs/otc/otc-mono.aspx?contentFileName=DNX0283.xml&contentName=PHENYLEPHRINE+HYDROCHLORIDE&contentId=4034 Link_out
Wikipedia http://en.wikipedia.org/wiki/Phenylephrine Link_out
ATC Codes
  • C01CA06
  • R01AA04
  • R01AB01
  • R01BA03
  • S01FB01
  • S01GA05
  • C05AX03
AHFS Codes
  • 52:24.00
  • 84:92.00
  • 52:32.00
  • 12:12.04
PDB Entries Not Available
FDA label Not Available
MSDS show (74.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hein, L. (2004). α-Adrenergic system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin, Germany: Springer.
  2. Martinez-Salas SG, Campos-Peralta JM, Pares-Hipolito J, Gallardo-Ortiz IA, Ibarra M, Villalobos-Molina R: Alpha1A-adrenoceptors predominate in the control of blood pressure in mouse mesenteric vascular bed. Auton Autacoid Pharmacol. 2007 Jul;27(3):137-42. Pubmed
  3. Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha(1)-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. Pubmed

2. Alpha-1B adrenergic receptor

Pharmacological action: yes

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system

Organism class: human
UniProt ID: P35368 Link_out
Gene: ADRA1B Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Hein, L. (2004). α-Adrenergic system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin, Germany: Springer.

3. Alpha-1D adrenergic receptor

Pharmacological action: yes

This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium

Organism class: human
UniProt ID: P25100 Link_out
Gene: ADRA1D Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hein, L. (2004). α-Adrenergic system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin, Germany: Springer.
Enzymes

1. Amine oxidase [flavin-containing] A

Actions: substrate

Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine

UniProt ID: P21397 Link_out
Gene: MAOA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Raffel DM, Corbett JR, del Rosario RB, Gildersleeve DL, Chiao PC, Schwaiger M, Wieland DM: Clinical evaluation of carbon-11-phenylephrine: MAO-sensitive marker of cardiac sympathetic neurons. J Nucl Med. 1996 Dec;37(12):1923-31. Pubmed
  2. Raffel DM, Corbett JR, del Rosario RB, Mukhopadhyay SK, Gildersleeve DL, Rose P, Wieland DM: Sensitivity of [11C]phenylephrine kinetics to monoamine oxidase activity in normal human heart. J Nucl Med. 1999 Feb;40(2):232-8. Pubmed

2. Cytochrome P450 1A2

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:38

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.