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Identification
NamePhenylephrine
Accession NumberDB00388  (APRD00365)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
(-)-m-Hydroxy-α-(methylaminomethyl)benzyl alcoholNot AvailableNot Available
FenilefrinaSpanishINN
l-(3-Hydroxyphenyl)-N-methylethanolamineNot AvailableNot Available
PhenylephrinumLatinINN
R(-)-PhenylephrineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Phenylephrine hydrochloride
Thumb Not applicable DBSALT000858
Brand names
NameCompany
AK-DilateNot Available
AK-NefrinNot Available
AlconefrinNot Available
DionephrineNot Available
MesatoneNot Available
Minims PhenylephrineNot Available
MydfrinAlcon Laboratories, Inc.
Neo-SynephrineBayer
NeofrinNot Available
OcugestrinNot Available
PhenopticNot Available
PrefrinNot Available
RhinallNot Available
SpersaphrineNot Available
VisadronNot Available
Brand mixtures
Brand NameIngredients
AK Vernacon Oph SolnPheniramine Maleate + Phenylephrine Hydrochloride
Biohisdex DM DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Biohisdine DM DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Chemhisdex DM DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Chemhisdine DM DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Citron Chaud Cumberland PwsAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Citron Chaud DM Cumberland PwsDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
CodalinCodeine Phosphate + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Cold & AllergyBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Cold & Allergy Relief - LiqBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Cough, Cold & Allergy ReliefBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
DayQuilAcetaminophen + Dextromethorphan + Phenylephrine
Decongestant Antihistaminic SyrupBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant LiqBrompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-C SyrBrompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-DC SyrBrompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
DimetappBrompheniramine Maleate + Phenylephrine Hydrochloride
Dimetapp Cold & SinusAcetaminophen + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp DM ElixirBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp DM TabBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp ElixirBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp ExtentabsBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Extra StrengthBrompheniramine Maleate + Phenylephrine Hydrochloride
Dimetapp Oral Infant Cold DropsBrompheniramine Maleate + Phenylephrine Hydrochloride
Dimetapp Oral Infant DropsBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp TabBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp-C SyrBrompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Hemorrhoidal OintmentMineral Oil + Petrolatum + Phenylephrine Hydrochloride + Shark Liver Oil
Hot Lemon for Colds PowderAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Hot Lemon Relief DM AdultDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride
Hot Lemon Relief for Cold Symptoms Ext StrAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Hot Lemon Relief for Cold Symptoms PwsAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Hot Lemon Relief PwsAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Lemon Relief for AdultsAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride
Lemon TimeAcetaminophen + Phenylephrine Hydrochloride + Pyrilamine Maleate + Vitamin C
Neo Citran A PowderPheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Neo Citran Extra StrengthAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride
Neo Citran NutrasweetAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride
Neo Citran PowderAcetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Neo Synephrine Nasal SprayPhenylephrine Hydrochloride + Thenyldiamine Hcl.
Neo-Synephrine Nasal SprayPhenylephrine Hydrochloride + Thenyldiamine Hcl.
Nezger TabAcetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride
Novahistex CCodeine Phosphate + Phenylephrine Hydrochloride
Novahistex Dh ExpectorantGuaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride
Occu-Cal DropsBoric Acid + Phenylephrine Hydrochloride + Sodium Borate
Occu-Cal LotionBoric Acid + Phenylephrine Hydrochloride + Sodium Borate
Pharmetapp ElixirBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Phenergan VC Expectorant SyrPhenylephrine Hydrochloride + Potassium Guaiacol Sulphonate + Promethazine Hydrochloride
Phenergan VC Expectorant W Codeine LiqCodeine Phosphate + Phenylephrine Hydrochloride + Potassium Guaiacol Sulphonate + Promethazine Hydrochloride
Soframycin Nasal SprayFramycetin Sulfate + Gramicidin + Phenylephrine Hydrochloride
Tantapp ElixirBrompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Vasosulf Oph SolnPhenylephrine Hydrochloride + Sulfacetamide Sodium
Categories
CAS number59-42-7
WeightAverage: 167.205
Monoisotopic: 167.094628665
Chemical FormulaC9H13NO2
InChI KeyInChIKey=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
IUPAC Name
3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
SMILES
CNC[C@H](O)C1=CC(O)=CC=C1
Mass Specshow(8.12 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentPhenols and Derivatives
Alternative parentsSecondary Alcohols; 1,2-Aminoalcohols; Polyamines; Dialkylamines; Enols
Substituents1,2-aminoalcohol; secondary alcohol; enol; secondary amine; polyamine; secondary aliphatic amine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the phenols and derivatives. These are compounds containing a phenol moiety, which is a benzene bearing an hydroxyl group.
Pharmacology
IndicationPhenylephrine 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.
PharmacodynamicsPhenylephrine 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 actionIn 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.
AbsorptionCompletely 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 distributionNot Available
Protein binding95% 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 eliminationNot Available
Half life2.1 to 3.4 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9943
Blood Brain Barrier - 0.9115
Caco-2 permeable - 0.7294
P-glycoprotein substrate Substrate 0.5308
P-glycoprotein inhibitor I Non-inhibitor 0.9527
P-glycoprotein inhibitor II Non-inhibitor 0.9109
Renal organic cation transporter Non-inhibitor 0.856
CYP450 2C9 substrate Non-substrate 0.7882
CYP450 2D6 substrate Non-substrate 0.7756
CYP450 3A4 substrate Non-substrate 0.6946
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9646
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9088
CYP450 3A4 substrate Non-inhibitor 0.858
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9594
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.8841
Biodegradation Ready biodegradable 0.7647
Rat acute toxicity 2.6480 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.5164
hERG inhibition (predictor II) Non-inhibitor 0.8717
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical0.25%
Injection, solutionIntramuscular10 mg/ml
Injection, solutionIntravenous10 mg/ml
LiquidOphthalmic
OintmentTopical0.25%
StripOral2.5 mg
SuppositoryRectal0.25%
TabletOral10 mg
Prices
Unit descriptionCostUnit
Mydfrin 2.5% Solution 5ml Bottle37.1USDbottle
Neo-synephrine 10 mg/ml amp5.68USDml
Mydfrin 2.5% eye drops5.28USDml
Phenylephrine 10 mg/ml vial3.0USDml
Phenylephrine 2.5% eye drop2.09USDml
Neofrin 10% eye drops1.93USDml
Ak-dilate 10% eye drops1.34USDml
Phenylephrine hcl crystals1.34USDg
Phenylephrine 10% eye drops1.25USDml
Phenylephrine-ns 0.8 mg/10 ml1.2USDml
Phenylephrine-ns 0.4 mg/10 ml1.17USDml
Mydfrin 2.5 % Solution1.09USDml
Neofrin 2.5% eye drops0.6USDml
Ak-dilate 2.5% eye drops0.45USDml
Neo-synephrine 0.25% drops0.36USDml
Hemorrhoidal suppository0.28USDsuppository
Neo-synephrine 12 hour spray0.28USDml
Neo-synephrine 1% drops0.26USDml
Sudafed pe 10 mg tablet0.25USDtablet
Neo-synephrine 0.5% drops0.23USDml
Little noses decon nose drp0.22USDml
Wal-phed pe 10 mg tablet0.22USDtablet
Tur-bi-kal nose drops0.21USDml
Industrial 0.12% eye drops0.17USDml
Ephrine 1% nose drops0.15USDml
Phenylephrine 10 mg tablet0.08USDtablet
Rhinall 0.25% nose drops0.07USDml
Non-pseudo sinus decongest tablet0.05USDtablet
Pv nasal decongestant 5 mg tablet0.03USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point140-145 °CNot Available
water solubilityFreely soluble in waterNot Available
logP-0.31HANSCH,C ET AL. (1995)
pKa8.97SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility2.20e+01 g/lALOGPS
logP-0.69ALOGPS
logP-0.07ChemAxon
logS-0.88ALOGPS
pKa (strongest acidic)9.07ChemAxon
pKa (strongest basic)9.69ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count3ChemAxon
polar surface area52.49ChemAxon
rotatable bond count3ChemAxon
refractivity47.25ChemAxon
polarizability18.2ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Franz Dietrich Klinger, Lienhard Wolter, Wolfgang Dietrich, “Method for preparing of L-phenylephrine hydrochloride.” U.S. Patent US6187956, issued February, 1976.

US6187956
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07441
PubChem Compound6041
PubChem Substance46506961
ChemSpider5818
ChEBI8093
ChEMBLCHEMBL1215
Therapeutic Targets DatabaseDAP000224
PharmGKBPA450935
IUPHAR485
Guide to Pharmacology485
Drug Product Database2238400
RxListhttp://www.rxlist.com/cgi/generic3/phenyleph.htm
Drugs.comhttp://www.drugs.com/cdi/phenylephrine-solution.html
PDRhealthhttp://www.pdrhealth.com/drugs/otc/otc-mono.aspx?contentFileName=DNX0283.xml&contentName=PHENYLEPHRINE+HYDROCHLORIDE&contentId=4034
WikipediaPhenylephrine
ATC CodesC01CA06R01AA04R01AB01R01BA03S01FB01S01GA05C05AX03
AHFS Codes
  • 52:24.00
  • 84:92.00
  • 52:32.00
  • 12:12.04
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(74.7 KB)
Interactions
Drug Interactions
Drug
AlseroxylonIncreased arterial pressure
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of phenylephrine.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of phenylephrine.
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of phenylephrine.
DeserpidineIncreased arterial pressure
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of phenylephrine.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of phenylephrine.
ErgonovinePossible marked increase of arterial pressure
GuanethidinePhenylephrine may decrease the effect of guanethidine.
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of phenylephrine.
IobenguaneSympathomimetic that increase chances of producing a false negative imaging result
IsocarboxazidIncreased arterial pressure
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MethylergometrinePossible marked increase of arterial pressure
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of phenylephrine.
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of phenylephrine.
OxytocinPossible marked increase of arterial pressure
PargylineIncreased arterial pressure
PhenelzineIncreased arterial pressure
ProtriptylineThe tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of phenylephrine.
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Phenylephrine. Concomitant therapy should be avoided.
TrimipramineTrimipramine may increase the vasopressor effect of the alpha1-agonist, Phenylephrine. Avoid combination if possible. Monitor sympathetic response to therapy if used concomitantly.
Food Interactions
  • Take without regard to meals.

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Alpha-1D adrenergic receptor P25100 Details

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.

1. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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 September 16, 2013 17:10