Phenylephrine

Identification

Summary

Phenylephrine is an alpha-1 adrenergic agonist used in the management of hypotension, generally in the surgical setting associated with the use of anesthetics.

Brand Names
4-way, Advil Congestion Relief, Advil Sinus Congestion and Pain, Ala-hist PE, Allerest PE, Benadryl-D Allergy and Sinus, Biorphen, Contac Cold and Flu Non Drowsy Maximum Strength, Cyclomydril, Dayquil Sinex, Deconex, Despec Reformulated Jun 2008, Dimetane, Dimetapp, Dimetapp Children's Cold and Allergy Reformulated Jan 2011, Dimetapp Nighttime Cold & Congestion, Entex Lq, Gilphex, Histex Ac, Little Noses Decongestant, M-end PE, Mapap Sinus Congestion and Pain, Mucinex Stuffy Nose & Cold, Mydfrin, Nasopen PE, Neo-synephrine, Omidria, Poly Hist Forte Reformulated Nov 2013, Preparation H Cooling Gel, Preparation H Cream, Preparation H Reformulated Jun 2013, Refenesen PE, Rescon-GG, Rymed-D, Soframycin, Sudafed PE, Sudafed PE Children's Cold & Cough, Sudafed PE Children's Nasal Decongestant, Sudafed PE Head Congestion Plus Pain, Sudafed PE Sinus Headache, Sudo-tab, Sudogest PE, Triaminic Day Time Cold & Cough, Triaminic Night Time Cold & Cough, Vazculep, Wal-profen Congestion Relief and Pain
Generic Name
Phenylephrine
DrugBank Accession Number
DB00388
Background

Phenylephrine is an alpha-1 adrenergic receptor agonist used to treat hypotension,6,8 dilate the pupil,7 and induce local vasoconstriction.1 The action of phenylephrine, or neo-synephrine, was first described in literature in the 1930s.2

Phenylephrine was granted FDA approval in 1939.7

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 167.205
Monoisotopic: 167.094628665
Chemical Formula
C9H13NO2
Synonyms
  • (−)-m-hydroxy-α-(methylaminomethyl)benzyl alcohol
  • Fenilefrina
  • l-(3-Hydroxyphenyl)-N-methylethanolamine
  • Phenylephrine
  • Phenylephrinum
  • R(-)-Phenylephrine
External IDs
  • J8.601K

Pharmacology

Indication

Phenylephrine injections are indicated to treat hypotension caused by shock or anesthesia,6,8 an ophthalmic formulation is indicated to dilate pupils7 and induce vasoconstriction, an intranasal formulation is used to treat congestion, and a topical formulation is used to treat hemorrhoids.1 Off-label uses include situations that require local blood flow restriction such as the treatment of priapism.1

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Phenylephrine is an alpha-1 adrenergic agonist that raises blood pressure,6,8 dilates the pupils,7 and causes local vasoconstriction.1 Ophthalmic formulations of phenylephrine act for 3-8 hours7 while intravenous solutions have an effective half life of 5 minutes and an elimination half life of 2.5 hours.3,6 Patients taking ophthalmic formulations of phenylephrine should be counselled about the risk of arrhythmia, hypertension, and rebound miosis.7 Patients taking an intravenous formulation should be counselled regarding the risk of bradycardia, allergic reactions, extravasation causing necrosis or tissue sloughing, and the concomitant use of oxytocic drugs.6,8

Mechanism of action

Phenylephrine is an alpha-1 adrenergic agonist that mediates vasoconstriction1 and mydriasis7 depending on the route and location of administration. Systemic exposure to phenylephrine also leads to agonism of alpha-1 adrenergic receptors, raising systolic and diastolic pressure as well as peripheral vascular resistance.6,8 Increased blood pressure stimulates the vagus nerve, causing reflex bradycardia.6,8

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Humans
AAlpha-1B adrenergic receptor
agonist
Humans
AAlpha-1D adrenergic receptor
agonist
Humans
Absorption

Phenylephrine is 38% orally bioavailable.3 Clinically significant systemic absorption of ophthalmic formulations is possible, especially at higher strengths and when the cornea is damaged.6

Volume of distribution

The volume of distribution of phenylephrine is 340L.6,8

Protein binding

Data regarding the protein binding of phenylephrine in serum is not readily available.6,7,8

Metabolism

Phenylephrine is mainly metabolized by monoamine oxidase A, monoamine oxidase B, and SULT1A3.4,5,6,8 The major metabolite is the inactive meta-hydroxymandelic acid, followed by sulfate conjugates.5,6,8 Phenylephrine can also be metabolized to phenylephrine glucuronide.5

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Route of elimination

86% of a dose of phenylephrine is recovered in the urine3 with 16% as the unmetabolized drug, 57% as the inactive meta-hydroxymendelic acid, and 8% as inactive sulfate conjugates.6,8

Half-life

Intravenous phenylephrine has an effective half life of 5 minutes and an elimination half life of 2.5 hours.3,6,8

Clearance

Phenylephrine has an average clearance of 2100mL/min.6,8

Adverse Effects
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Toxicity

Patients experiencing and overdose may present with headache, hypertension, reflex bradycardia, tingling limbs, cardiac arrhythmias, and a feeling of fullness in the head.6,7,8 Overdose may be treated by supportive care and discontinuing phenylephrine, chronotropic medications, and vasodilators.1 Subcutaneous phentolamine may be used to treat tissue extravasation.1,7

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of hypertension can be decreased when 1,2-Benzodiazepine is combined with Phenylephrine.
AbaloparatideThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Phenylephrine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Phenylephrine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Phenylephrine is combined with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Phenylephrine.
AclidiniumThe risk or severity of Tachycardia can be increased when Phenylephrine is combined with Aclidinium.
AcyclovirThe metabolism of Acyclovir can be increased when combined with Phenylephrine.
AdenosineThe risk or severity of Tachycardia can be increased when Phenylephrine is combined with Adenosine.
AgomelatineThe metabolism of Agomelatine can be increased when combined with Phenylephrine.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Phenylephrine bitartrate27O3Q5ML5717162-39-9NHKOTKKHHYKARN-NDAAPVSOSA-N
Phenylephrine hydrochloride04JA59TNSJ61-76-7OCYSGIYOVXAGKQ-FVGYRXGTSA-N
Phenylephrine tannateDU5ATO7HYP1416-03-1HXLHQWSMCJUVMM-RVLWPPNGSA-N
Active Moieties
NameKindUNIICASInChI Key
Chloride ionionicQ32ZN4869816887-00-6VEXZGXHMUGYJMC-UHFFFAOYSA-M
Product Images
International/Other Brands
AK-Dilate / AK-Nefrin / Alconefrin / Mesatone / Minims Phenylephrine / Neofrin / Ocugestrin / Phenoptic / Phenylephrine Minims / Prefrin / Rhinall / Spersaphrine / Visadron
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BiorphenInjection, solution10 mg/1mLIntravenousEton Pharmaceuticals, Inc.2021-03-112021-04-01US flag
BiorphenInjection, solution0.1 mg/1mLIntravenousEton Pharmaceuticals, Inc.2019-11-15Not applicableUS flag
Fresh ClearSolution / drops1.2 mg/1mLOphthalmicAllergan, Inc.2011-11-01Not applicableUS flag
Minims Phenylephrine HydrochlorideSolution / drops10 % w/vOphthalmicBausch Health, Canada Inc.1995-12-31Not applicableCanada flag
Minims Phenylephrine HydrochlorideSolution / drops2.5 % w/vOphthalmicBausch Health, Canada Inc.1995-12-31Not applicableCanada flag
MydfrinSolution25 mg/1mLOphthalmicAlcon, Inc.1979-02-152014-04-30US flag
MydfrinSolution2.5 % w/vOphthalmicAlcon, Inc.1979-12-31Not applicableCanada flag
MydfrinSolution25 mg/1mLOphthalmicAlcon, Inc.1990-09-302014-04-30US flag
Neo-SynephrineSolution10 mg / mLIntramuscular; Intravenous; SubcutaneousPfizer Canada Ulc2002-11-01Not applicableCanada flag
Neo-SynephrineInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-08-012014-08-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Phenylephrine HydrochlorideInjection10 mg/1mLIntravenousGland Pharma Limited2020-10-21Not applicableUS flag
Phenylephrine hydrochlorideInjection10 mg/1mLIntravenousAmneal Pharmaceuticals LLC2018-07-24Not applicableUS flag
Phenylephrine hydrochlorideInjection10 mg/1mLIntravenousMedical Purchasing Solutions, Llc2020-08-12Not applicableUS flag
Phenylephrine HydrochlorideInjection10 mg/1mLIntravenousSandoz Inc2020-01-15Not applicableUS flag
Phenylephrine HydrochlorideInjection, solution10 mg/1mLIntravenousSagent Pharmaceuticals2020-10-15Not applicableUS flag
Phenylephrine hydrochlorideInjection10 mg/1mLIntravenousCardinal Health2018-07-07Not applicableUS flag
Phenylephrine HydrochlorideInjection10 mg/1mLIntravenousMeitheal Pharmaceuticals Inc.2018-04-27Not applicableUS flag
Phenylephrine hydrochlorideInjection10 mg/1mLIntravenousApollo Pharmaceuticals Inc.2020-08-12Not applicableUS flag
Phenylephrine hydrochlorideInjection10 mg/1mLIntravenousCipla USA Inc.2018-06-01Not applicableUS flag
Phenylephrine HydrochlorideInjection10 mg/1mLIntravenousCaplin Steriles Limited2020-06-30Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
4 Way Fast ActingSpray10 mg/1mLNasalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2010-01-01Not applicableUS flag
7 Select Nasal Decongestant PETablet, film coated10 mg/1Oral7-Eleven2016-10-072020-11-30US flag
Anti Hemorrhoidal H SuppositorySuppository0.25 % w/wRectalCellchem Pharmaceuticals Inc.Not applicableNot applicableCanada flag
Assured Maximum Strength Nasal DecongestantTablet10 mg/1OralSpirit Pharmaceuticals LLC2019-02-26Not applicableUS flag
Assured Maximum Strength Nasal DecongestantTablet10 mg/1OralSpirit Pharmaceuticals LLC2019-02-26Not applicableUS flag
Basic Care Sinus PETablet, film coated10 mg/1OralL. Perrigo Company2019-12-02Not applicableUS flag
Basic Care Sinus PETablet, film coated10 mg/1OralAmazon.com Services LLC2021-06-10Not applicableUS flag
Benylin Cold StripsStrip10 mgOralMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada flag
Benylin D for InfantsSolution1.25 mg / 0.8 mLOralPfizer Canada Inc., Consumer Healthcare Division2007-09-142007-11-05Canada flag
Berkley and Jensen Nasal Decongestant PE Non-Drowsy Maximum StrengthTablet10 mg/1OralBJWC2009-06-052017-11-17US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4248 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4356 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Calcium carbonate (420 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4390 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Ibuprofen (200 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4392 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Ibuprofen (200 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
7 Select Cold and Allergy ChildrensPhenylephrine hydrochloride (2.5 mg/5mL) + Brompheniramine maleate (1 mg/5mL)LiquidOral7 Eleven2014-08-052016-02-19US flag
7 Select Day Time ReliefPhenylephrine hydrochloride (5 mg/15mL) + Acetaminophen (325 mg/15mL) + Dextromethorphan hydrobromide monohydrate (10 mg/15mL)SolutionOral7-Eleven2014-08-052020-10-31US flag
7 Select Day Time ReliefPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1)Capsule, liquid filledOral7-Eleven2014-04-222020-01-31US flag
7 Select Hemorrhoidal Original StrengthPhenylephrine hydrochloride (2.5 mg/1g) + Mineral oil (140 mg/1g) + Petrolatum (749 mg/1g)OintmentTopical7-ELEVEN, INC.2016-12-07Not applicableUS flag
7 Select Night Time Severe Cold Cough and FluPhenylephrine hydrochloride (10 mg/1) + Acetaminophen (650 mg/1) + Diphenhydramine hydrochloride (25 mg/1)Powder, for solutionOral7-Eleven2016-01-252021-01-01US flag
7 Select Night Time severe cold, cough and fluPhenylephrine hydrochloride (10 mg/1) + Acetaminophen (650 mg/1) + Diphenhydramine hydrochloride (25 mg/1)Powder, for solutionOral7 Eleven2015-11-122017-08-01US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4248 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4356 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Calcium carbonate (420 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4390 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Ibuprofen (200 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4392 First Aid KitPhenylephrine hydrochloride (5 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Ibuprofen (200 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
A-Tan 12X SuspensionPhenylephrine tannate (5 mg/5mL) + Guaifenesin (100 mg/5mL) + Mepyramine tannate (30 mg/5mL)SuspensionOralAmneal Pharmaceuticals2006-01-062008-12-05US flag
AiracofPhenylephrine hydrochloride (7.5 mg/5mL) + Codeine phosphate hemihydrate (7.5 mg/5mL) + Diphenhydramine hydrochloride (12.5 mg/5mL)LiquidOralCenturion Labs2010-01-082016-05-02US flag
Allergy DN PEPhenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31US flag
Allergy DN PEPhenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31US flag
AlleRx Dose PackPhenylephrine hydrochloride (10 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)KitOralCornerstone Therapeutics Inc.2008-02-012012-10-31US flag
AlleRx Dose Pack PEPhenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralCornerstone Therapeutics Inc.2006-09-012012-10-31US flag

Categories

ATC Codes
S01FB01 — PhenylephrineR01AB01 — PhenylephrineC01CA06 — PhenylephrineR01AA04 — PhenylephrineS01FB51 — Phenylephrine and ketorolacR01BA53 — Phenylephrine, combinationsS01GA05 — PhenylephrineS01GA55 — Phenylephrine, combinationsR01BA03 — Phenylephrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-4-unsubstituted benzenoids
Direct Parent
1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines, secondary amino compound (CHEBI:8093)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
1WS297W6MV
CAS number
59-42-7
InChI Key
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

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 References
  1. Richards E, Maani CV: Phenylephrine . [Article]
  2. Prescott F: CLINICAL EVALUATION OF THE PRESSOR ACTIVITY OF METHEDRINE, NEO-SYNEPHRINE, PAREDRINE, AND PHOLEDRINE. Br Heart J. 1944 Oct;6(4):214-20. doi: 10.1136/hrt.6.4.214. [Article]
  3. Kanfer I, Dowse R, Vuma V: Pharmacokinetics of oral decongestants. Pharmacotherapy. 1993 Nov-Dec;13(6 Pt 2):116S-128S; discussion 143S-146S. [Article]
  4. Bairam AF, Rasool MI, Alherz FA, Abunnaja MS, El Daibani AA, Gohal SA, Alatwi ES, Kurogi K, Liu MC: Impact of SULT1A3/SULT1A4 genetic polymorphisms on the sulfation of phenylephrine and salbutamol by human SULT1A3 allozymes. Pharmacogenet Genomics. 2019 Jul;29(5):99-105. doi: 10.1097/FPC.0000000000000371. [Article]
  5. Gelotte CK, Zimmerman BA: Pharmacokinetics, safety, and cardiovascular tolerability of phenylephrine HCl 10, 20, and 30 mg after a single oral administration in healthy volunteers. Clin Drug Investig. 2015 Sep;35(9):547-58. doi: 10.1007/s40261-015-0311-9. [Article]
  6. FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection [Link]
  7. FDA Approved Drug Products: Phenylephrine Ophthalmic Solution [Link]
  8. FDA Approved Drug Products: Phenylephrine Intravenous Injection (Ready to Use) [Link]
Human Metabolome Database
HMDB0002182
KEGG Drug
D08365
KEGG Compound
C07441
PubChem Compound
6041
PubChem Substance
46506961
ChemSpider
5818
BindingDB
50067212
RxNav
8163
ChEBI
8093
ChEMBL
CHEMBL1215
ZINC
ZINC000000113355
Therapeutic Targets Database
DAP000224
PharmGKB
PA450935
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenylephrine
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCorneal Transplant / Grafting, Corneal / Keratoplasty, Lamellar / Transplantation, Cornea / Transplantation, Corneal1
4CompletedNot AvailableCommon Cold / Flu caused by Influenza1
4CompletedBasic ScienceEndotoxaemia1
4CompletedDiagnosticDiabetes Mellitus1
4CompletedDiagnosticPreterm, Infant1
4CompletedDiagnosticRetinopathy of Prematurity1
4CompletedOtherEndovascular Carotid Surgery / Preoperative Hypotension1
4CompletedPreventionAdverse Side Effects / Anesthesia, Spinal and Epidural / Complications; Cesarean Section / Hypotension1
4CompletedPreventionComplications; Cesarean Section / Spinal Anaesthesia3
4CompletedPreventionEffects of; Anesthesia, in Labor and Delivery1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Accutome Inc.
  • Advanced Pharmaceutical Services Inc.
  • Advent Pharmaceuticals Inc.
  • Aero Pharmaceuticals Inc.
  • AG Marin Pharmaceuticals
  • Akorn Inc.
  • Alba Pharmacal
  • Alcon Laboratories
  • Allegis Pharmaceuticals
  • Allergy Laboratories Inc.
  • Altaire Pharmaceuticals
  • Ambi Pharmaceuticals Inc.
  • Amend
  • American Regent
  • Amneal Pharmaceuticals
  • Anip Acquisition Co.
  • A-S Medication Solutions LLC
  • Athlon Pharmaceuticals Inc.
  • Auriga Pharmaceuticals LLC
  • Baroli
  • Bausch & Lomb Inc.
  • Baxter International Inc.
  • Bayer Healthcare
  • Bio Pharm Inc.
  • Blansett Pharmacal Co. Inc.
  • Boca Pharmacal
  • Breckenridge Pharmaceuticals
  • Brookstone Pharmaceuticals
  • Bryant Ranch Prepack
  • BTA Pharmaceuticals
  • Burel Pharmaceuticals Inc.
  • Capellon Pharmaceuticals LLC
  • Cardinal Health
  • Centurion Labs
  • Chain Drug
  • Chemins Co. Inc.
  • Claris Lifesciences Inc.
  • Conta Care Ophthalmics and Diagnostics
  • Contract Pharm
  • Cornerstone Pharmacy
  • Cypress Pharmaceutical Inc.
  • Deca Pharmaceuticals LLC
  • Deltex Pharmaceuticals Inc.
  • Deston Therapeutics
  • Dexo LLC
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DSC Laboratories
  • Ebewe Pharma
  • Econolab Inc.
  • Edwards Pharmaceuticals
  • Emerson Labs
  • Endo Pharmaceuticals Inc.
  • Everett Laboratories Inc.
  • Eye Care and Cure Corp.
  • Eye Supply Usa Inc.
  • Falcon Pharmaceuticals Ltd.
  • Gayheart Pharmaceutical Inc.
  • Gentex Pharma LLC
  • Gil Pharmaceutical Corp.
  • Gm Pharmaceuticals Inc.
  • Great Southern Laboratories
  • Hawthorn Pharmaceuticals
  • Hi Tech Pharmacal Co. Inc.
  • Hospira Inc.
  • HUB Pharmaceuticals
  • International Ethical Labs Inc.
  • Invision Pharmaceuticals
  • Iopharm Laboratories Inc.
  • Irisys Inc.
  • Jaymac Pharmaceuticals LLC
  • Kowa Pharmaceuticals America Inc.
  • Kylemore Pharmaceuticals
  • Lark Pharmaceuticals Inc.
  • Larken Laboratories Inc.
  • Laser Pharmaceuticals
  • Luitpold Pharmaceuticals Inc.
  • Lunsco Inc.
  • Macoven Pharmaceuticals LLC
  • Major Pharmaceuticals
  • Marnel Pharmaceuticals Inc.
  • MCR American Pharmaceuticals Inc.
  • Med Tek Pharmaceuticals Inc.
  • Meda AB
  • Medique Products
  • Midland Healthcare LLC
  • Midland Pharmaceutical LLC
  • Midlothian Labs
  • Monte Sano Pharmaceuticals Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nadin Co.
  • Neilgen Pharma Inc.
  • Nephron Pharmaceuticals Corp.
  • Nexgen Pharma Inc.
  • Nolco Pharmaceuticals Inc.
  • Norega Laboratories Inc.
  • Novis PR Inc.
  • Nucare Pharmaceuticals Inc.
  • Numark Laboratories Inc.
  • Ocusoft
  • Optopics
  • Palm Pharmaceuticals LLC
  • Palmetto Pharmaceuticals Inc.
  • Pamlab LLC
  • Pfizer Inc.
  • Pharmaceutical Association
  • Pharmaceutical Generic Developers Inc.
  • Pharmedium
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Portal Inc.
  • Prasco Labs
  • Preferred Pharmaceuticals Inc.
  • Prescript Pharmaceuticals
  • Provident Pharmaceuticals LLC
  • Qualitest
  • Quality Home Products
  • Quality Research Pharmaceutical Inc.
  • Rebel Distributors Corp.
  • Respa Pharmaceuticals Inc.
  • Rico Pharmacal
  • River's Edge Pharmaceuticals
  • Rugby Laboratories
  • Rx Formulations Corp.
  • Sanofi-Aventis Inc.
  • Scherer Labs
  • Schwarz Pharma Inc.
  • Scientific Laboratories Inc.
  • Seatrace Pharmaceuticals Inc.
  • Seyer Pharmatec Inc.
  • Silarx Pharmaceuticals
  • Sonar Products Inc.
  • Sorter Labs
  • Southwood Pharmaceuticals
  • Sovereign Pharmaceuticals Ltd.
  • Stesso Pharmaceuticals LLC
  • Summa Rx Laboratories Inc.
  • Teral Laboratories
  • Teva Pharmaceutical Industries Ltd.
  • TG United Inc.
  • Tiber Pharmaceuticals LLC
  • Tri Med Laboratories Inc.
  • Trigen Laboratories Inc.
  • United Research Laboratories Inc.
  • US Pharmaceutical Corp.
  • Varsity Laboratories
  • Vertical Pharmaceuticals Inc.
  • Vetco Pharma
  • Vindex Pharmaceuticals Inc.
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
  • Walgreen Co.
  • Wilson Ophthalmic Corp.
  • Wockhardt Ltd.
  • WraSer Pharmaceuticals
  • Zyber Pharmaceuticals
Dosage Forms
FormRouteStrength
KitOphthalmic; Oral; Respiratory (inhalation); Topical
SolutionOral
Capsule, coatedOral500 mg
Capsule, liquid filledNot applicable
Tablet, effervescentOral
Granule, effervescentOral
Capsule, gelatin coatedOral
KitOral
Tablet, coatedOral
SolutionIntramuscular; Intravenous; Subcutaneous10 mg
StripOral10 mg
SolutionOral1.25 mg / 0.8 mL
Capsule
CapsuleNasal
Suspension / dropsOral
Injection, solutionIntravenous0.1 mg/1mL
SolutionParenteral
Injection, solutionParenteral
LiquidTopical
ElixirOral
SolutionOral2.5 mg/5mL
LiquidAuricular (otic)
Suspension
Capsule, coated pelletsOral
SolutionNasal1.25 mg/1mL
GelRectal
CreamTopical
Kit; powder, for solutionOral
TabletOral5 1/1
Tablet, chewableOral
LiquidOral2.5 mg/5mL
SuspensionConjunctival; Ophthalmic
Aerosol, meteredRespiratory (inhalation)
SprayNasal21.73 mg/15mL
SprayNasal10 mg/1mL
Tablet
Injection, solution
SolutionConjunctival; Ophthalmic100 mg
SolutionIntravenous10 mg
SolutionOphthalmic25 mg
Solution / dropsNasal; Topical
ClothTopical
Powder, for suspensionOral
Kit; tabletOral
SolutionOphthalmic
Solution / dropsOphthalmic1.2 mg/1mL
SolutionConjunctival; Ophthalmic1.2 mg
Solution / dropsNasal
CreamRectal; Topical
GelTopical
OintmentTopical0.25 %
SprayTopical
Kit; powderOral
SprayNasal
Tablet, orally disintegratingOral
LiquidNasal1 g/100mL
Tablet, multilayerOral
LiquidNasal0.125 %
LiquidNasal1.25 mg/1mL
LiquidNasal0.00125 mg/1mL
Solution / dropsOral
Tablet, film coatedOral5 mg/1
OintmentRectal; Topical
Solution / dropsOphthalmic10 % w/v
Solution / dropsOphthalmic2.5 % w/v
CapsuleOral
Capsule, liquid filledOral
SolutionOphthalmic2.5 % w/v
Injection, solutionIntraocular
InsertOphthalmic
Tablet, coatedOral10 mg/1
Solution / dropsTopical0.25 g/100mL
SprayTopical0.25 g/100mL
Solution / dropsNasal1 %
SolutionIntramuscular; Intravenous; Subcutaneous10 mg / mL
Solution / dropsNasal
SprayNasal0.25 g/100mL
SprayNasal0.5 g/100mL
LiquidIntramuscular; Intravenous; Subcutaneous1 %
StripOral
Solution / drops; suspension / drops
Capsule, coatedOral
GranuleOral
Solution / dropsNasal1 g/100mL
SolutionNasal
LiquidOral5 mg / 5 mL
Capsule, coatedOral500 mg
Tablet, film coated
LotionOphthalmic
SolutionOphthalmic2.5 %
SolutionConjunctival; Ophthalmic
Injection, solution, concentrateIntraocular
Solution, concentrateOphthalmic
Solution, concentrateIntraocular; Irrigation
SolutionConjunctival; Ophthalmic25 mg
PowderOral10 mg
Granule, for solutionOral
Capsule, liquid filledOral30 mg
GranuleOral500 mg
Injection, solutionIntraocular; Ophthalmic
TabletOral10 mg/1
Injection, solution50 mcg/ml
LiquidOral
Injection, solutionIntravenous0.08 mg/1mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous100 ug/1mL
Injection, solutionIntravenous160 ug/1mL
Injection, solutionIntravenous300 ug/1mL
Injection, solutionIntravenous40 ug/1mL
Injection, solutionIntravenous50 ug/1mL
InjectionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous10 mg/1 mL
InjectionIntravenous100 mg/10mL
InjectionIntravenous50 mg/5mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
Injection, solutionIntravenous10 mg/1mL
PowderNot applicable1 g/1g
SolutionOphthalmic25 mg/1mL
Solution / dropsOphthalmic100 mg/1mL
Solution / dropsOphthalmic2.5 mg/1mL
Solution / dropsOphthalmic25 mg/1mL
SuppositoryRectal
SolutionIntravenous50 mcg / mL
LiquidIntramuscular; Intravenous; Subcutaneous10 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous10 mg / 1 mL
TabletOral
LiquidOphthalmic.12 %
KitRectal; Topical
GelRectal; Topical
SuspensionOral
SyrupOral
SuppositoryRectal0.25 % w/w
Solution / dropsOphthalmic
Tablet, multilayer, extended releaseOral
SolutionNasal; Respiratory (inhalation)2 mg
CreamRectal
TabletOral750 mg/1
OintmentTopical
SprayNasal1 g/100mL
TabletOral10 mg
TabletOral5 mg
TabletOral5 mg/1
Tablet, film coatedOral10 mg/1
SuspensionOphthalmic
LiquidOral2.5 mg/15mL
PowderOral
OintmentRectal
LiquidNasal1 mg/100mL
StripOral2.5 mg
Tablet, extended releaseOral
Tablet, film coatedOral
SuspensionOral1000 mg/1
Powder, for solutionOral
SuspensionIntraocular; Ophthalmic
SolutionParenteral10 mg
InjectionIntravenous10 mg/1mL
SprayNasal
Solution / drops; suspension / dropsNasal
SprayNasal0.0005 g/1mL
SprayNasal0.004975 g/1mL
Solution / dropsOphthalmic
LiquidOphthalmic
LiquidOphthalmic100 mg/1ml
SyrupNasal
Tablet, sugar coatedOral
LozengeOral
Syrup
LiquidOphthalmic0.9 mg/1ml
Elixir
Tablet, film coatedNasal
Prices
Unit descriptionCostUnit
Mydfrin 2.5% Solution 5ml Bottle37.1USD bottle
Neo-synephrine 10 mg/ml amp5.68USD ml
Mydfrin 2.5% eye drops5.28USD ml
Phenylephrine 10 mg/ml vial3.0USD ml
Phenylephrine 2.5% eye drop2.09USD ml
Neofrin 10% eye drops1.93USD ml
Ak-dilate 10% eye drops1.34USD ml
Phenylephrine hcl crystals1.34USD g
Phenylephrine 10% eye drops1.25USD ml
Phenylephrine-ns 0.8 mg/10 ml1.2USD ml
Phenylephrine-ns 0.4 mg/10 ml1.17USD ml
Mydfrin 2.5 % Solution1.09USD ml
Neofrin 2.5% eye drops0.6USD ml
Ak-dilate 2.5% eye drops0.45USD ml
Neo-synephrine 0.25% drops0.36USD ml
Hemorrhoidal suppository0.28USD suppository
Neo-synephrine 12 hour spray0.28USD ml
Neo-synephrine 1% drops0.26USD ml
Sudafed pe 10 mg tablet0.25USD tablet
Neo-synephrine 0.5% drops0.23USD ml
Little noses decon nose drp0.22USD ml
Wal-phed pe 10 mg tablet0.22USD tablet
Tur-bi-kal nose drops0.21USD ml
Industrial 0.12% eye drops0.17USD ml
Ephrine 1% nose drops0.15USD ml
Phenylephrine 10 mg tablet0.08USD tablet
Rhinall 0.25% nose drops0.07USD ml
Non-pseudo sinus decongest tablet0.05USD tablet
Pv nasal decongestant 5 mg tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8173707Yes2012-05-082024-01-30US flag
US9278101Yes2016-03-082024-01-30US flag
US8586633Yes2013-11-192024-01-30US flag
US9066856Yes2015-06-302034-04-23US flag
US8859623No2014-10-142033-11-14US flag
US9399040Yes2016-07-262024-01-30US flag
US9486406Yes2016-11-082034-04-23US flag
US9855246No2018-01-022033-10-23US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)140-145 °CNot Available
water solubilityFreely soluble in waterNot Available
logP-0.31HANSCH,C ET AL. (1995)
pKa8.97SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility22.0 mg/mLALOGPS
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 Area52.49 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m3·mol-1ChemAxon
Polarizability18.2 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier-0.9115
Caco-2 permeable-0.7294
P-glycoprotein substrateSubstrate0.5308
P-glycoprotein inhibitor INon-inhibitor0.9527
P-glycoprotein inhibitor IINon-inhibitor0.9109
Renal organic cation transporterNon-inhibitor0.856
CYP450 2C9 substrateNon-substrate0.7882
CYP450 2D6 substrateNon-substrate0.7756
CYP450 3A4 substrateNon-substrate0.6946
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9646
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9088
CYP450 3A4 inhibitorNon-inhibitor0.858
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9594
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8841
BiodegradationReady biodegradable0.7647
Rat acute toxicity2.6480 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5164
hERG inhibition (predictor II)Non-inhibitor0.8717
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.12 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-014i-0900000000-b11a2a880d1683fa6cae
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-01b9-6900000000-bbdd210a846be116dbcd
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0900000000-b11a2a880d1683fa6cae
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01b9-6900000000-bbdd210a846be116dbcd
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-0udi-0900000000-d95a741ffcfe3f7bb7e9
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-0006-9800000000-7695881b36499169fb71
MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)LC-MS/MSsplash10-054o-9200000000-888fce606d860cd39be2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-edfcbc18ccdb6872b791
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00di-0900000000-15132688bbc7ac0be42f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-2900000000-34ccc7192518d4c14210
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00di-3900000000-e619f4210f81c11f61be
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00dl-6900000000-3178337a019ac9bf313d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0gb9-0900000000-e738818606836c1d6d1a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0udi-0900000000-36b72327f64f1355a502
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-052o-4900000000-935a9659fe39602b138d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-052f-9800000000-7d83555b537d6fec673b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-054o-9400000000-5ef2f6d1da57087e6ac7
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-014i-0900000000-4a910a2109ba191b96e7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-edfcbc18ccdb6872b791
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-15132688bbc7ac0be42f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-2900000000-34ccc7192518d4c14210
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-3900000000-e8a5a4f1aae0796866a7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00dl-6900000000-3178337a019ac9bf313d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0900000000-c0d824f22be752d523b4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0900000000-4fb67ae2344d097c3abb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0900000000-113e95fddc78edd9df82
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0zg3-2900000000-a52b0d450061f2762c71
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052o-4900000000-1919f188c550710ea860
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052f-6900000000-93a02b958e60eadd5bfb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0gb9-0900000000-e738818606836c1d6d1a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-36b72327f64f1355a502
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052o-4900000000-5c34ff7c978e4b607f00
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052f-9800000000-036a3eb2e3b11f203fd4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-054o-9400000000-284961abd6764baa0d1d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-4a910a2109ba191b96e7
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. 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. [Article]
  2. Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [Article]
  3. Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]
  4. FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection [Link]
  5. FDA Approved Drug Products: Phenylephrine Ophthalmic Solution [Link]
  6. FDA Approved Drug Products: Phenylephrine Intravenous Injection (Ready to Use) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]
  3. FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection [Link]
  4. FDA Approved Drug Products: Phenylephrine Ophthalmic Solution [Link]
  5. FDA Approved Drug Products: Phenylephrine Intravenous Injection (Ready to Use) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]
  2. FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection [Link]
  3. FDA Approved Drug Products: Phenylephrine Ophthalmic Solution [Link]
  4. FDA Approved Drug Products: Phenylephrine Intravenous Injection (Ready to Use) [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Serotonin binding
Specific Function
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection [Link]
  4. FDA Approved Drug Products: Phenylephrine Intravenous Injection (Ready to Use) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Primary amine oxidase activity
Specific Function
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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Gelotte CK, Zimmerman BA: Pharmacokinetics, safety, and cardiovascular tolerability of phenylephrine HCl 10, 20, and 30 mg after a single oral administration in healthy volunteers. Clin Drug Investig. 2015 Sep;35(9):547-58. doi: 10.1007/s40261-015-0311-9. [Article]
  2. FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection [Link]
  3. FDA Approved Drug Products: Phenylephrine Intravenous Injection (Ready to Use) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Specific Function
Amine sulfotransferase activity
Gene Name
SULT1A3
Uniprot ID
P0DMM9
Uniprot Name
Sulfotransferase 1A3
Molecular Weight
34195.96 Da
References
  1. Bairam AF, Rasool MI, Alherz FA, Abunnaja MS, El Daibani AA, Gohal SA, Alatwi ES, Kurogi K, Liu MC: Impact of SULT1A3/SULT1A4 genetic polymorphisms on the sulfation of phenylephrine and salbutamol by human SULT1A3 allozymes. Pharmacogenet Genomics. 2019 Jul;29(5):99-105. doi: 10.1097/FPC.0000000000000371. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Konstandi M, Kostakis D, Harkitis P, Johnson EO, Marselos M, Adamidis K, Lang MA: Benzo(alpha)pyrene-induced up-regulation of CYP1A2 gene expression: role of adrenoceptor-linked signaling pathways. Life Sci. 2006 Jun 20;79(4):331-41. Epub 2006 Feb 28. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27