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Identification
NameEpinephrine
Accession NumberDB00668  (APRD00450, EXPT00496)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

The active sympathomimetic hormone from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. [PubChem]

Structure
Thumb
Synonyms
(-)-(R)-Epinephrine
(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol
(-)-Adrenaline
(−)-adrenaline
(R)-(-)-Adnephrine
(R)-(-)-Adrenaline
(R)-(-)-Epinephrine
(R)-(-)-Epirenamine
(R)-(−)-adrenaline
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
Adrenalin
Adrenaline
Epinefrin
Epinefrina
Epinephrin
Epinephrine
Epinephrinum
L-Adrenaline
levoepinephrine
Primatene
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Adrenaclickinjection.3 mg/.3mLsubcutaneousAmedra Pharmaceuticals LLC2009-11-25Not applicableUs
Adrenaclickinjection.15 mg/.15mLsubcutaneousAmedra Pharmaceuticals LLC2009-11-25Not applicableUs
Adrenaclick 0.15mg Auto-injectorsolution0.15 mgintramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada
Adrenaclick 0.30mg Auto-injectorsolution0.30 mgintramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada
Adrenalininjection1 mg/mLintramuscular; subcutaneousPar Pharmaceutical, Inc.2014-03-01Not applicableUs
Adrenalininjection1 mg/mLintramuscular; intraocular; subcutaneousPar Pharmaceutical, Inc.2013-07-01Not applicableUs
Adrenalininjection1 mg/mLintramuscularREMEDYREPACK INC.2015-03-25Not applicableUs
Adrenalin Chloride Sol 1:1000solution1 mgnasalErfa Canada 2012 Inc1951-12-31Not applicableCanada
Adrenalin Chloride Sol 1:1000 Ampsolution1 mgintramuscular; intravenous; subcutaneousErfa Canada 2012 Inc1951-12-31Not applicableCanada
Allerjectsolution0.3 mgintramuscularSanofi Aventis Canada Inc2012-12-11Not applicableCanada
Allerjectsolution0.15 mgintramuscularSanofi Aventis Canada Inc2012-12-11Not applicableCanada
Anapensolution0.3 mgintramuscularLincoln Medical Limited2009-11-23Not applicableCanada
Anapen Juniorsolution0.15 mgintramuscularLincoln Medical Limited2009-11-23Not applicableCanada
Auvi-Qinjection.15 mg/1intramuscular; subcutaneousSanofi Aventis U.S. Llc2012-11-15Not applicableUs
Auvi-Qinjection.3 mg/1intramuscular; subcutaneousSanofi Aventis U.S. Llc2012-11-15Not applicableUs
Bronkaid Mistometer Aem 0.5%metered-dose aerosol0.5 %inhalationSanofi Canada, Inc.1973-12-311999-07-15Canada
Dysne Inhalspray3.5 %inhalationRougier Pharma Division Of Ratiopharm Inc1979-12-311999-09-27Canada
Epi E-Z Pen - Liquid - 0.3mg/0.3mlliquid0.3 mgintramuscularDey Pharma L.P.1997-07-152010-05-20Canada
Epinephrineinjection, solution, concentrate1 mg/mLintravenousBPI Labs, LLC2014-08-08Not applicableUs
Epinephrineinjection.3 mg/.3mLsubcutaneousLineage Therapeutics Inc.2010-04-01Not applicableUs
Epinephrineinjection, solution1 mg/mLintramuscular; subcutaneousGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
Epinephrineinjection, solution.1 mg/mLintravenousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Epinephrineinjection.3 mg/1subcutaneousPhysicians Total Care, Inc.2011-04-18Not applicableUs
Epinephrineinjection, solution.1 mg/mLintracardiac; intravenousPhysicians Total Care, Inc.2006-12-11Not applicableUs
Epinephrineinjection, solution.1 mg/mLintracardiac; intravenousMc Kesson Packaging Services Business Unit Of Mc Kesson Corporation2010-05-03Not applicableUs
Epinephrineinjection.3 mg/1subcutaneousRebel Distributors Corp2010-03-31Not applicableUs
Epinephrineinjection.3 mg/.3mLsubcutaneousPreferred Pharmaceuticals Inc.2016-04-14Not applicableUs
Epinephrineinjection, solution, concentrate1 mg/mLintravenousBelcher Pharmaceuticals, LLC2014-08-08Not applicableUs
Epinephrineinjection.15 mg/.15mLsubcutaneousLineage Therapeutics Inc.2010-04-01Not applicableUs
Epinephrineinjection.3 mg/.3mLsubcutaneousSina Health Inc2010-04-01Not applicableUs
Epinephrine 1:1000 Inj 1mg/ml USPliquid1 mgintramuscularInternational Medication Systems Ltd.1987-12-311997-08-15Canada
Epinephrine Inj 0.1mg/ml USPsolution0.1 mgintracardiac; intravenousHospira Healthcare Corporation1987-12-31Not applicableCanada
Epinephrine Inj 0.1mg/ml USPliquid.1 mgintracardiac; intravenousAstra Pharma Inc.1986-12-311998-11-02Canada
Epinephrine Inj 1mg/ml USPsolution1 mgintracardiac; intramuscular; intratracheal; intravenous; subcutaneousHospira Healthcare Corporation1988-12-31Not applicableCanada
Epinephrine Injectionsolution1 mgintracardiac; intramuscular; intratracheal; intravenous; subcutaneousAlveda Pharmaceuticals Inc2015-07-20Not applicableCanada
Epinephrine Injection USPsolution1 mgintramuscular; intravenous; subcutaneousMylan Pharmaceuticals Ulc1994-12-31Not applicableCanada
Epinephrine Injection USP 1 mg/mlsolution1 mgintramuscular; intravenous; subcutaneousAlveda Pharmaceuticals Inc2010-10-01Not applicableCanada
Epipeninjection.3 mg/.3mLintramuscularREMEDYREPACK INC.2013-06-11Not applicableUs
Epipeninjection.3 mg/.3mLintramuscularDispensing Solutions, Inc.1987-12-22Not applicableUs
Epipeninjection.3 mg/.3mLintramuscularTYA Pharmaceuticals1987-12-22Not applicableUs
Epipensolution1 mgintramuscularMylan Specialty Lp1980-12-31Not applicableCanada
Epipeninjection.3 mg/.3mLintramuscularPhysicians Total Care, Inc.2003-06-17Not applicableUs
Epipeninjection.3 mg/.3mLintramuscularMylan Specialty L.P.1987-12-22Not applicableUs
Epipen Jrsolution0.5 mgintramuscularMylan Specialty Lp1984-12-31Not applicableCanada
Epipen Jrinjection.15 mg/.3mLintramuscularDispensing Solutions, Inc.1987-12-22Not applicableUs
Epipen Jrinjection.15 mg/.3mLintramuscularTYA Pharmaceuticals1987-12-22Not applicableUs
Epipen Jrinjection.15 mg/.3mLintramuscularPhysicians Total Care, Inc.2003-06-17Not applicableUs
Epipen Jrinjection.15 mg/.3mLintramuscularMylan Specialty L.P.1987-12-22Not applicableUs
Episnap Epinephrine Convenience Kitinjection1 mg/1000mLintramuscular; subcutaneousFocus Health Group2015-09-01Not applicableUs
Gingi Pak Cord No 1cord.5 mgdentalGingi Pak Labs, Division Of Belport Co., Inc.1981-12-312004-08-16Canada
Taro-epinephrine Auto-injectorsolution0.5 mgintramuscularTaro Pharmaceuticals IncNot applicableNot applicableCanada
Taro-epinephrine Auto-injectorsolution1 mgintramuscularTaro Pharmaceuticals IncNot applicableNot applicableCanada
Twinject 0.15mg Auto-injectorsolution0.15 mgintramuscular; subcutaneousAmedra Pharmaceuticals LLC2005-08-232016-01-21Canada
Twinject 0.3mg Auto-injectorsolution0.3 mgintramuscular; subcutaneousAmedra Pharmaceuticals LLC2005-08-232016-01-21Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Prime Asthma ReliefkitDRNATURALHEALING2014-08-21Not applicableUs
Prime Asthma Reliefcapsule.22 mg/1respiratory (inhalation)DRNATURALHEALING2014-08-21Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ephinephrineinjection, solution.1 mg/mLintravenousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Epinephrineinjection, solution1 mg/mLintracardiac; intramuscular; intravenous; subcutaneousMc Kesson Packaging Services Business Unit Of Mc Kesson Corporation2010-05-03Not applicableUs
Epinephrineinjection, solution.1 mg/mLendotracheal; intracardiac; intravenousHospira, Inc.1985-05-01Not applicableUs
Epinephrineinjection1 mg/mLparenteralInternational Medication Systems, Limited2000-07-01Not applicableUs
Epinephrineinjection, solution1 mg/mLintramuscular; intravenous; subcutaneousValesco Pharmaceuticals LLC.1994-03-01Not applicableUs
Epinephrineinjection, solution.1 mg/mLendotracheal; intracardiac; intravenousCardinal Health1985-05-01Not applicableUs
Epinephrineinjection1 mg/mLparenteralAmphastar Pharmaceuticals, Inc.2000-07-01Not applicableUs
Epinephrineinjection, solution.1 mg/mLendotracheal; intracardiac; intravenousCardinal Health1985-04-05Not applicableUs
Epinephrineinjection.1 mg/mLparenteralAmphastar Pharmaceuticals, Inc.2010-08-25Not applicableUs
Epinephrineinjection1 mg/mLendotracheal; intracardiac; intramuscular; intravenous; subcutaneousCardinal Health2013-05-08Not applicableUs
Epinephrineinjection, solution1 mg/mLintramuscular; intravenous; subcutaneousAmerican Regent, Inc.1994-03-01Not applicableUs
Epinephrineinjection, solution1 mg/mLintracardiac; intramuscular; intravenous; subcutaneousGENERAL INJECTABLES AND VACCINES, INC.2010-07-01Not applicableUs
Epinephrineinjection, solution1 mg/mLintracardiac; intramuscular; intravenous; subcutaneousAmerican Regent, Inc.1990-09-30Not applicableUs
Epinephrineinjection, solution1 mg/mLintramuscular; subcutaneousSina Health Inc2005-09-08Not applicableUs
Epinephrineinjection.1 mg/mLintracardiac; intravenousInternational Medication Systems, Limited1976-12-01Not applicableUs
Epinephrineinjection, solution.1 mg/mLendotracheal; intracardiac; intravenousHospira, Inc.1985-04-05Not applicableUs
Epinephrineinjection, solution1 mg/mLintramuscular; subcutaneousHospira, Inc.2005-09-01Not applicableUs
Epinephrineinjection, solution1 mg/mLsubcutaneousREMEDYREPACK INC.2015-09-17Not applicableUs
International Brands
NameCompany
Epi EZ Pen JRNot Available
Medihaler-EpiNot Available
TwinjectNot Available
Brand mixtures
NameLabellerIngredients
2% Lidocaine and Epinephrine 1:100,000 Injection USPAlveda Pharmaceuticals Inc
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Dentsply Canada Limited
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Dentsply Canada Limited
4% Citanest Forte Dental With Epinephrine 1:200,000Dentsply Canada Limited
Ana-kitMiles Canada Inc. Pharmaceutical Division
Ana-kit (2mg/tab Orl, 1mg/ml Liq Sc Im)Hollister Stier Laboratories Llc
Anakit Insect Sting Treatment KitHollister Stier, Unit Pharm, Division Of Miles Canada Inc.
ArticadentDentsply Pharmaceutical
ArticaineNDC, Inc.
Articaine Hydrochloride and EpinephrineHenry Schein
Bupivacaine HCl 0.5% and Epinephrine 1:200,000 InjectionNovocol Pharmaceutical Of Canada Inc
Bupivacaine Hydrochloride and EpinephrineGeneral Injectables & Vaccines, Inc
Citanest ForteDentsply Pharmaceutical Inc.
Dentsply 2% Lidocaine With Epinephrine 1:100,000Dentsply Canada Limited
Dentsply 2% Lidocaine With Epinephrine 1:50,000Dentsply Canada Limited
Dentsply 4% Prilocaine and Epinephrine Injection 1:200,000Dentsply Canada Limited
E-pilo 1 Ophthalmic SolutionCiba Vision Canada Inc
E-pilo 2 Ophthalmic SolutionCiba Vision Canada Inc
E-pilo 4 Ophthalmic SolutionCiba Vision Canada Inc
E-pilo 6 Ophthalmic SolutionCiba Vision Canada Inc
E-pilo-1 Oph SolnIolab Pharmaceuticals
E-pilo-2 Oph SolnIolab Pharmaceuticals
E-pilo-4 Oph SolnIolab Pharmaceuticals
E-pilo-6 Oph SolnIolab Pharmaceuticals
KarticainePierrel S.P.A.
Karticaine FortePierrel S.P.A.
LidocaineHenry Schein Inc.
Lidocaine 2% and Epinephrine 1:100 000Kodak Canada Inc.
Lidocaine 2% and Epinephrine 1:100,000Carestream Health Canada Company
Lidocaine 2% and Epinephrine 1:100,000 InjectionAlveda Pharmaceuticals Inc
Lidocaine 2% and Epinephrine 1:50 000Kodak Canada Inc.
Lidocaine 2% and Epinephrine 1:50,000Carestream Health Canada Company
Lidocaine and Epinephrine Inj.usp 2% 1:100000Mylan Pharmaceuticals Ulc
Lidocaine HClPearson Dental
Lidocaine Hydrochloride 0.5% and Epinephrine 1:200000 Injection USPHospira Healthcare Corporation
Lidocaine Hydrochloride 1.5% and Epinephrine 1:200000 Injection USPHospira Healthcare Corporation
Lidocaine Hydrochloride 1.5% and Epinephrine 1:200000 Injection USP Test DoseHospira Healthcare Corporation
Lidocaine Hydrochloride 1% and Epinephrine 1:100 000 Injection USPHospira Healthcare Corporation
Lidocaine Hydrochloride 2% and Epinephrine 1:100 000 Injection USPHospira Healthcare Corporation
Lidocaine Hydrochloride 2% and Epinephrine 1:200000 Injection USPHospira Healthcare Corporation
Lidocaine Hydrochloride and EpinephrineHospira, Inc.
Lidocaine Hydrochloride and Epinephrine BitartrateIq Dental
Lignospan ForteNovocol Pharmaceutical of Canada, Inc.
Lignospan Speciale InjSeptodont
Lignospan StandardNovocol Pharmaceutical of Canada, Inc.
MarcaineCarestream Health Inc.
Marcaine 0.5% and Epinephrine 1:200,000 LiqKodak Canada Inc.
Marcaine E 0.25% Liq PrtSanofi Canada, Inc.
Marcaine E 2.5 mg/mlHospira Healthcare Corporation
Marcaine E 5.0 mg/mlHospira Healthcare Corporation
Marcaine E Liq Prt 0.50%Sanofi Canada, Inc.
Marcaine With EpinephrineHospira, Inc.
Numquick AnalgesicUnit Dose, Ltd.
Numquick Topical AnalgesicUnit Dose, Ltd.
Octocaine 100Septodont
Octocaine 100 Needleject InjNovocol Pharmaceutical Of Canada Inc
Octocaine 50Septodont
Octocaine HCl 2% Epinephrine 1:100000Novocol Pharmaceutical Of Canada Inc
Octocaine HCl 2% Epinephrine 1:50000Novocol Pharmaceutical Of Canada Inc
OrablocPierrel S.P.A.
Orabloc 1:100,000Pierrel S.P.A.
Orabloc 1:200,000Pierrel S.P.A.
Posicaine NNovocol Pharmaceutical Of Canada Inc
Posicaine SpNovocol Pharmaceutical Of Canada Inc
Prilocaine HCl 4% Epineph 1:200000injNovocol Pharmaceutical Of Canada Inc
Prilocaine Hydrochloride With EpinephrineSeptodont Inc.
Scandonest 2% Special InjSeptodont
SensorcaineFresenius Kabi USA, LLC
Sensorcaine 0.25% With EpinephrineAstrazeneca Canada Inc
Sensorcaine 0.5% With EpinephrineAstrazeneca Canada Inc
Sensorcaine ForteDentsply Canada Limited
Sensorcaine MpfCardinal Health
Septanest NSeptodont
Septanest SpSeptodont
Septocaine and EpinephrineSeptodont Inc.
Spinal Anaesthesia TrayBaxter Corporation
Spinal Anesthesia TrayBaxter Corporation
Ultracaine D-S Forte InjectionHansamed Limited
Ultracaine D-S InjectionHansamed Limited
Ultracaine DS Forte InjHoechst Canada Inc.
Ultracaine DS InjHoechst Canada Inc.
VivacaineSeptodont, Inc.
Vivacaine (bupivacaine HCl 0.5% & Epinephrine 1:200,000 Inj, USP)Septodont Inc
XylocaineGeneral Injectables & Vaccines, Inc
Xylocaine 0.5% W Epinephrine 1:100000Astrazeneca Canada Inc
Xylocaine 0.5% W Epinephrine 1:200000Astrazeneca Canada Inc
Xylocaine 1.5% W Epinephrine 1:200000Astrazeneca Canada Inc
Xylocaine 1.5% W Epinephrine 1:200000 Test DoseAstrazeneca Canada Inc
Xylocaine 1% W Epinephrine 1:100000Astrazeneca Canada Inc
Xylocaine 1% W Epinephrine 1:200000Astrazeneca Canada Inc
Xylocaine 2% W Epinephrine 1:100000Astrazeneca Canada Inc
Xylocaine 2% W Epinephrine 1:200000Astrazeneca Canada Inc
Xylocaine Dental Lidocaine HCl 2% and Epinephrine 1:100,000Dentsply Canada Limited
Xylocaine Dental Lidocaine Hydrochloride 2% and Epinephrine 1:50,000Dentsply Canada Limited
Xylocaine MpfCardinal Health
Xylocaine Mpf 1.5% With EpinephrineAstrazeneca L.P.
ZorcaineCareStream Health, Inc.
Salts
Name/CASStructureProperties
Epinephrine acetate
ThumbNot applicableDBSALT001650
Epinephrine bitartrate
Thumb
  • InChI Key: YLXIPWWIOISBDD-NDAAPVSOSA-N
  • Monoisotopic Mass: 333.105981211
  • Average Mass: 333.2913
DBSALT000788
Epinephrine chloride
Thumb
  • InChI Key: QMTJCDRNQYQRHF-WWPIYYJJSA-N
  • Monoisotopic Mass: 255.042898765
  • Average Mass: 256.126
DBSALT000384
Epinephrine hydrochloride
ThumbNot applicableDBSALT001484
Categories
UNIIYKH834O4BH
CAS number51-43-4
WeightAverage: 183.2044
Monoisotopic: 183.089543287
Chemical FormulaC9H13NO3
InChI KeyInChIKey=UCTWMZQNUQWSLP-VIFPVBQESA-N
InChI
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
IUPAC Name
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
SMILES
CNC[[email protected]](O)C1=CC(O)=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed to treat anaphylaxis and sepsis. Also one of the body's main adrenergic neurotransmitters.
PharmacodynamicsEpinephrine is indicated for intravenous injection in treatment of acute hypersensitivity, treatment of acute asthmatic attacks to relieve bronchospasm, and treatment and prophylaxis of cardiac arrest and attacks of transitory atrioventricular heart block with syncopal seizures (Stokes-Adams Syndrome). The actions of epinephrine resemble the effects of stimulation of adrenergic nerves. To a variable degree it acts on both alpha and beta receptor sites of sympathetic effector cells. Its most prominent actions are on the beta receptors of the heart, vascular and other smooth muscle. When given by rapid intravenous injection, it produces a rapid rise in blood pressure, mainly systolic, by (1) direct stimulation of cardiac muscle which increases the strength of ventricular contraction, (2) increasing the heart rate and (3) constriction of the arterioles in the skin, mucosa and splanchnic areas of the circulation. When given by slow intravenous injection, epinephrine usually produces only a moderate rise in systolic and a fall in diastolic pressure. Although some increase in pulse pressure occurs, there is usually no great elevation in mean blood pressure. Accordingly, the compensatory reflex mechanisms that come into play with a pronounced increase in blood pressure do not antagonize the direct cardiac actions of epinephrine as much as with catecholamines that have a predominant action on alpha receptors.
Mechanism of actionEpinephrine works via the stimulation of alpha and beta-1 adrenergic receptors, and a moderate activity at beta-2 adrenergic receptors.
Related Articles
AbsorptionUsually this vasodilator effect of the drug on the circulation predominates so that the modest rise in systolic pressure which follows slow injection or absorption is mainly the result of direct cardiac stimulation and increase in cardiac output.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Epinephrine is rapidly inactivated in the body and is degraded by enzymes in the liver and other tissues. The larger portion of injected doses is excreted in the urine as inactivated compounds and the remainder either partly unchanged or conjugated. The drug becomes fixed in the tissues and is inactivated chiefly by enzymatic transformation to metanephrine or normetanephrine either of which is subsequently conjugated and excreted in the urine in the form of sulfates and glucuronides. Either sequence results in the formation of 3-methoxy-4-hydroxy-mandelic acid which also is detectable in the urine. Main metabolic enzymes include MAO and COMT

SubstrateEnzymesProduct
Epinephrine
Not Available
Epinephrine sulfateDetails
Epinephrine
Not Available
Epinephrine glucuronideDetails
Route of eliminationRenal
Half life2 minutes
ClearanceNot Available
ToxicitySkin, LD50 = 62 mg/kg (rat)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Aromatic L-Aminoacid Decarboxylase DeficiencyDiseaseSMP00170
Catecholamine BiosynthesisMetabolicSMP00012
Tyrosine MetabolismMetabolicSMP00006
Tyrosinemia, transient, of the newbornDiseaseSMP00494
Tyrosinemia Type IDiseaseSMP00218
Disulfiram Action PathwayDrug actionSMP00429
Tyrosine hydroxylase deficiencyDiseaseSMP00497
Epinephrine Action PathwayDrug actionSMP00661
AlkaptonuriaDiseaseSMP00169
HawkinsinuriaDiseaseSMP00190
Dopamine beta-hydroxylase deficiencyDiseaseSMP00498
Monoamine oxidase-a deficiency (MAO-A)DiseaseSMP00533
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9934
Blood Brain Barrier-0.966
Caco-2 permeable-0.8958
P-glycoprotein substrateSubstrate0.5953
P-glycoprotein inhibitor INon-inhibitor0.9036
P-glycoprotein inhibitor IINon-inhibitor0.8465
Renal organic cation transporterNon-inhibitor0.8903
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6928
CYP450 1A2 substrateNon-inhibitor0.7862
CYP450 2C9 inhibitorNon-inhibitor0.9563
CYP450 2D6 inhibitorNon-inhibitor0.9638
CYP450 2C19 inhibitorNon-inhibitor0.9451
CYP450 3A4 inhibitorNon-inhibitor0.9121
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9516
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9322
BiodegradationReady biodegradable0.6459
Rat acute toxicity2.3715 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7514
hERG inhibition (predictor II)Non-inhibitor0.7961
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sterling health div sterling winthrop inc
  • Armstrong pharmaceuticals inc
  • Wyeth consumer healthcare
  • Shionogi pharma inc
  • Meridian medical technologies inc
  • Forest laboratories inc
  • 3m pharmaceuticals inc
  • Astrazeneca lp
  • Pharmaton ltd
  • Dentsply pharmaceutical
Packagers
Dosage forms
FormRouteStrength
Injectionsubcutaneous.15 mg/.15mL
Injectionsubcutaneous.3 mg/.3mL
Solutionintramuscular0.30 mg
Injectionintramuscular1 mg/mL
Injectionintramuscular; intraocular; subcutaneous1 mg/mL
Injectionintramuscular; subcutaneous1 mg/mL
Solutionnasal1 mg
Liquid; tabletintramuscular; oral; subcutaneous
Liquid; tabletoral; parenteral (unspecified)
Solutionintramuscular0.3 mg
Solutionintramuscular0.15 mg
Injectionintramuscular; subcutaneous.15 mg/1
Injectionintramuscular; subcutaneous.3 mg/1
Metered-dose aerosolinhalation0.5 %
Injectionepidural; infiltration; intracaudal
Injection, solutionepidural; infiltration; intracaudal
Injection, solutionepidural; intracaudal
Injection, solutiondental
Sprayinhalation3.5 %
Dropsophthalmic
Injection, solutionintravenous.1 mg/mL
Liquidintramuscular0.3 mg
Injectionendotracheal; intracardiac; intramuscular; intravenous; subcutaneous1 mg/mL
Injectionintracardiac; intravenous.1 mg/mL
Injectionparenteral.1 mg/mL
Injectionparenteral1 mg/mL
Injectionsubcutaneous.3 mg/1
Injection, solutionendotracheal; intracardiac; intravenous.1 mg/mL
Injection, solutionintracardiac; intramuscular; intravenous; subcutaneous1 mg/mL
Injection, solutionintracardiac; intravenous.1 mg/mL
Injection, solutionintramuscular; intravenous; subcutaneous1 mg/mL
Injection, solutionintramuscular; subcutaneous1 mg/mL
Injection, solutionsubcutaneous1 mg/mL
Injection, solution, concentrateintravenous1 mg/mL
Liquidintramuscular1 mg
Liquidintracardiac; intravenous.1 mg
Solutionintracardiac; intravenous0.1 mg
Solutionintracardiac; intramuscular; intratracheal; intravenous; subcutaneous1 mg
Solutionintramuscular; intravenous; subcutaneous1 mg
Injectionintramuscular.3 mg/.3mL
Solutionintramuscular1 mg
Injectionintramuscular.15 mg/.3mL
Solutionintramuscular0.5 mg
Injectionintramuscular; subcutaneous1 mg/1000mL
Corddental.5 mg
Injectioninfiltration
Injection, solutiondental; infiltration
Injection, solutionepidural
Liquidblock/infiltration; epidural
Injection, solutionepidural; infiltration
Injection, solutioninfiltration
Solutiontopical
Geltopical
Liquiddental; subcutaneous
Injection, solutionsubcutaneous
Liquidsubcutaneous
Injectionsubmucosal
Capsulerespiratory (inhalation).22 mg/1
Kit
Injection, solutionperineural
Solutionblock/infiltration; epidural
Injection, solutionepidural; intracaudal; perineural
Injection, solutionepidural; retrobulbar
Liquidblock/infiltration
Kitblock/infiltration; topical
Liquidparenteral (unspecified); topical
Solutionintramuscular; subcutaneous0.15 mg
Solutionintramuscular; subcutaneous0.3 mg
Solutionblock/infiltration
Injection, solutionepidural; infiltration; intracaudal; perineural
Injection, solutioninfiltration; perineural
Liquidepidural
Prices
Unit descriptionCostUnit
Twinject 2 0.3 mg/dose Device One Box Contains 2 Syringes200.43USD box
Epinephrine hcl powder189.0USD g
EpiPen 2-Pak (1 Package = 2 Syringes) Package155.13USD package
EpiPen Jr 2-Pak (1 Package = 2 Syringes) Package155.13USD package
Twinject 0.15 mg/dose Device Syringe104.14USD syringe
Epipen 0.3 mg/syr Syringe93.04USD syringe
Epipen Jr 0.15 mg/syr Syringe93.04USD syringe
Twinject 0.15 mg auto-injector86.63USD each
Twinject Auto Injector 0.15 mg/syr Syringe84.85USD syringe
Twinject Auto Injector 0.3 mg/syr Syringe84.85USD syringe
EpiPen (single Syringe) Syringe77.56USD syringe
EpiPen Jr (single Syringe) Syringe77.56USD syringe
Epipen jr 0.15 mg auto-inject74.58USD each
Epinephrine 0.3 mg auto-inject67.05USD each
Nephron FA 100 tablet Box49.99USD box
Epipen 0.3 mg auto-injector41.78USD each
Epinephrine powder4.68USD g
Epinephrine bitartrate crys4.2USD g
Adrenalin 1 mg/ml ampul2.93USD ml
Epinephrine 1 mg/ml ampul2.9USD ml
Adrenalin cl 1 mg/ml vial1.42USD ml
Epinephrine 0.1 mg/ml syringe1.32USD ml
Primatene mist inhaler1.0USD ml
Adrenalin 1:1000 nasal soln0.83USD ml
Bronchial mist inhaler0.8USD ml
Primatene mist inh refill0.68USD ml
Adrenalin 1 mg/ml0.62USD ml
Adrenalin 1 mg/ml Solution0.61USD ml
Nephron fa tablet0.44USD each
Epinephrine 1 mg/ml vial0.18USD ml
Bronkaid dual action caplet0.14USD caplet
Epinephrine-d5w 2 mg/250 ml0.07USD ml
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5665071 No1993-05-272013-05-27Us
US6629968 No2000-06-302020-06-30Us
US6635045 No2001-06-292021-06-29Us
US7297136 No2005-01-182025-01-18Us
US7449012 No2005-09-112025-09-11Us
US7621891 No2005-02-042025-02-04Us
US7731686 No2006-06-012026-06-01Us
US7731690 No2005-01-152025-01-15Us
US7749194 No2008-10-302028-10-30Us
US7794432 No2005-09-112025-09-11Us
US7918823 No2004-11-232024-11-23Us
US7947017 No2008-03-122028-03-12Us
US8016788 No2005-03-212025-03-21Us
US8021344 No2009-11-022029-11-02Us
US8048035 No2005-09-112025-09-11Us
US8206360 No2007-02-272027-02-27Us
US8226610 No2009-04-102029-04-10Us
US8231573 No2008-11-252028-11-25Us
US8313466 No2004-11-232024-11-23Us
US8361029 No2004-11-232024-11-23Us
US8425462 No2004-11-232024-11-23Us
US8608698 No2004-11-232024-11-23Us
US8870827 No2005-09-112025-09-11Us
US8920377 No2004-11-232024-11-23Us
US8926594 No2006-03-312026-03-31Us
US9056170 No2004-11-232024-11-23Us
US9119876 No2015-03-132035-03-13Us
US9149579 No2005-07-192025-07-19Us
US9238108 No2007-01-222027-01-22Us
US9259539 No2006-02-012026-02-01Us
US9278182 No2006-02-012026-02-01Us
US9283197 No2014-08-152034-08-15Us
US9295657 No2015-03-132035-03-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point211.5 °CPhysProp
water solubility180 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.37HANSCH,C & LEO,AJ (1985)
Caco2 permeability-6.02ADME Research, USCD
pKa8.59 (at 25 °C)HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
logP-0.82ALOGPS
logP-0.43ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.23 m3·mol-1ChemAxon
Polarizability19.04 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-0900000000-5ca773e378035e522e65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-7718bec49c1a109083e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4900000000-ec5581e838e2a4a66139View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-4572448ba3dadff2d2a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-9da12d9c8551de2507beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-12dd42d00be1feb2ea6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-57c9bc614d9bbbfeed6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00dj-0900000000-375b0df9797eb0a3db5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0fdk-1900000000-04c230e802b08770ccd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-b707acd2982b875d2b8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-0900000000-f3590054822872902032View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-1900000000-7d7916641e9f2b8c2a1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0adi-8900000000-5bbc248c0ddc66e4fe40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9300000000-af8ce8ce2cdd535404e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0159-0900000000-f2fafb87963f9f1c6960View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0uxr-2900000000-b54ca44315664cba912aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udi-4900000000-881b25fed45874c66e13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0ugi-9500000000-1fadd0dd0beb4816b39dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004j-9000000000-61011b8f179c08d62b62View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Pamela Albaugh, “Pharmaceutical epinephrine-pilocarpine compounds and process of preparation thereof.” U.S. Patent US5198545, issued October, 1988.

US5198545
General References
  1. Yamashima T: Jokichi Takamine (1854-1922), the samurai chemist, and his work on adrenalin. J Med Biogr. 2003 May;11(2):95-102. [PubMed:12717538 ]
  2. Bennett MR: One hundred years of adrenaline: the discovery of autoreceptors. Clin Auton Res. 1999 Jun;9(3):145-59. [PubMed:10454061 ]
External Links
ATC CodesA01AD01B02BC09C01CA24R01AA14R03AA01R03AK01S01EA01S01EA51
AHFS Codes
  • 12:12.12
  • 52:24.00
  • 52:32.00
  • 92:02.00*
PDB Entries
FDA labelDownload (369 KB)
MSDSDownload (73.4 KB)
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Epinephrine.
AcetaminophenThe risk or severity of adverse effects can be increased when Epinephrine is combined with Acetaminophen.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Epinephrine.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Epinephrine is combined with Acetylsalicylic acid.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Epinephrine.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Epinephrine.
AminophyllineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Aminophylline.
AmitriptylineAmitriptyline may increase the activities of Epinephrine.
AmphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Epinephrine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Epinephrine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Epinephrine.
Benzylpenicilloyl PolylysineEpinephrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
ButalbitalThe risk or severity of adverse effects can be increased when Epinephrine is combined with Butalbital.
CabergolineCabergoline may increase the hypertensive activities of Epinephrine.
CaffeineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Caffeine.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Epinephrine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Epinephrine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Epinephrine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Epinephrine.
CocaineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Cocaine.
DesfluraneDesflurane may increase the arrhythmogenic activities of Epinephrine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Epinephrine is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Epinephrine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Epinephrine.
DoxapramThe risk or severity of adverse effects can be increased when Epinephrine is combined with Doxapram.
DoxofyllineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Epinephrine.
DyphyllineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Ephedrine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Epinephrine.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Epinephrine is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Epinephrine.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Epinephrine.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Epinephrine.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Epinephrine.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Epinephrine.
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Epinephrine.
IndacaterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Indacaterol.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Epinephrine.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Epinephrine.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Epinephrine.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Epinephrine.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Epinephrine.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Epinephrine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Epinephrine.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Epinephrine is combined with Ipratropium bromide.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Epinephrine.
IsofluraneIsoflurane may increase the arrhythmogenic activities of Epinephrine.
IsomethepteneThe risk or severity of adverse effects can be increased when Epinephrine is combined with Isometheptene.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Epinephrine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Epinephrine.
LevonordefrinThe risk or severity of adverse effects can be increased when Epinephrine is combined with Levonordefrin.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Epinephrine.
LinezolidLinezolid may increase the hypertensive activities of Epinephrine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Lisdexamfetamine.
LurasidoneEpinephrine may increase the hypotensive activities of Lurasidone.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Epinephrine.
MepivacaineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Mepivacaine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Epinephrine.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Epinephrine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Epinephrine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Epinephrine.
MethylphenidateThe risk or severity of adverse effects can be increased when Epinephrine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Midodrine.
MoclobemideMoclobemide may increase the hypertensive activities of Epinephrine.
ModafinilThe risk or severity of adverse effects can be increased when Epinephrine is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Epinephrine.
NadololNadolol may increase the activities of Epinephrine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Epinephrine.
NorepinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Olodaterol.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Epinephrine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Epinephrine.
PhendimetrazineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Phendimetrazine.
PhenelzinePhenelzine may increase the hypertensive activities of Epinephrine.
PheniramineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Pheniramine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Epinephrine.
PhentermineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Phenylephrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Epinephrine.
PirbuterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Pirbuterol.
PrazosinPrazosin may decrease the vasoconstricting activities of Epinephrine.
ProcarbazineProcarbazine may increase the hypertensive activities of Epinephrine.
PromethazinePromethazine may decrease the vasoconstricting activities of Epinephrine.
PropylhexedrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Racepinephrine.
RasagilineRasagiline may increase the hypertensive activities of Epinephrine.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Epinephrine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Epinephrine.
SalbutamolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Epinephrine.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Epinephrine.
SelegilineSelegiline may increase the hypertensive activities of Epinephrine.
SevofluraneSevoflurane may increase the arrhythmogenic activities of Epinephrine.
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Epinephrine.
Technetium Tc-99m tilmanoceptEpinephrine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Epinephrine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Epinephrine.
TheophyllineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Theophylline.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Epinephrine.
TolcaponeThe metabolism of Epinephrine can be decreased when combined with Tolcapone.
TranylcypromineTranylcypromine may increase the hypertensive activities of Epinephrine.
TriprolidineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Triprolidine.
VenlafaxineVenlafaxine may increase the tachycardic activities of Epinephrine.
VilanterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Vilanterol.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Epinephrine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Sanbe A, Tanaka Y, Fujiwara Y, Tsumura H, Yamauchi J, Cotecchia S, Koike K, Tsujimoto G, Tanoue A: Alpha1-adrenoceptors are required for normal male sexual function. Br J Pharmacol. 2007 Oct;152(3):332-40. Epub 2007 Jul 2. [PubMed:17603545 ]
  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. [PubMed:17658513 ]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040 ]
  4. Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [PubMed:20857090 ]
Kind
Protein
Organism
Human
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Cotecchia S: The alpha1-adrenergic receptors: diversity of signaling networks and regulation. J Recept Signal Transduct Res. 2010 Dec;30(6):410-9. doi: 10.3109/10799893.2010.518152. Epub 2010 Oct 18. [PubMed:20954794 ]
  2. Shieh JP, Chu CC, Wang JJ, Lin MT: Epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via alpha1-adrenoceptors in rats. Acta Pharmacol Sin. 2009 Sep;30(9):1227-36. doi: 10.1038/aps.2009.129. [PubMed:19730427 ]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040 ]
  4. Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [PubMed:20857090 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774 ]
  3. Leineweber K, Bogedain P, Wolf C, Wagner S, Weber M, Jakob HG, Heusch G, Philipp T, Brodde OE: In patients chronically treated with metoprolol, the demand of inotropic catecholamine support after coronary artery bypass grafting is determined by the Arg389Gly-beta 1-adrenoceptor polymorphism. Naunyn Schmiedebergs Arch Pharmacol. 2007 Jul;375(5):303-9. Epub 2007 Jun 1. [PubMed:17541557 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774 ]
  3. Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [PubMed:17417877 ]
  4. Lucin KM, Sanders VM, Jones TB, Malarkey WB, Popovich PG: Impaired antibody synthesis after spinal cord injury is level dependent and is due to sympathetic nervous system dysregulation. Exp Neurol. 2007 Sep;207(1):75-84. Epub 2007 Jun 2. [PubMed:17597612 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Thioesterase binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
References
  1. Nyronen T, Pihlavisto M, Peltonen JM, Hoffren AM, Varis M, Salminen T, Wurster S, Marjamaki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS: Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. Mol Pharmacol. 2001 May;59(5):1343-54. [PubMed:11306720 ]
  2. MacLennan SJ, Reynen PH, Martin RS, Eglen RM, Martin GR: Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using extracellular acidification rate changes. Br J Pharmacol. 2000 Apr;129(7):1333-8. [PubMed:10742288 ]
  3. Hieble JP, Hehr A, Li YO, Ruffolo RR Jr: Molecular basis for the stereoselective interactions of catecholamines with alpha-adrenoceptors. Proc West Pharmacol Soc. 1998;41:225-8. [PubMed:9836297 ]
  4. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  5. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [PubMed:18680204 ]
  6. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Epinephrine binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular Weight:
49565.8 Da
References
  1. Gobbi M, Frittoli E, Mennini T: The modulation of [3H]noradrenaline and [3H]serotonin release from rat brain synaptosomes is not mediated by the alpha 2B-adrenoceptor subtype. Naunyn Schmiedebergs Arch Pharmacol. 1990 Oct;342(4):382-6. [PubMed:1979424 ]
  2. Vizi ES, Katona I, Freund TF: Evidence for presynaptic cannabinoid CB(1) receptor-mediated inhibition of noradrenaline release in the guinea pig lung. Eur J Pharmacol. 2001 Nov 16;431(2):237-44. [PubMed:11728431 ]
  3. Rudling JE, Richardson J, Evans PD: A comparison of agonist-specific coupling of cloned human alpha(2)-adrenoceptor subtypes. Br J Pharmacol. 2000 Nov;131(5):933-41. [PubMed:11053214 ]
  4. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236 ]
  5. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
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
Molecular Weight:
60462.205 Da
References
  1. Cotecchia S: The alpha1-adrenergic receptors: diversity of signaling networks and regulation. J Recept Signal Transduct Res. 2010 Dec;30(6):410-9. doi: 10.3109/10799893.2010.518152. Epub 2010 Oct 18. [PubMed:20954794 ]
  2. Shieh JP, Chu CC, Wang JJ, Lin MT: Epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via alpha1-adrenoceptors in rats. Acta Pharmacol Sin. 2009 Sep;30(9):1227-36. doi: 10.1038/aps.2009.129. [PubMed:19730427 ]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040 ]
  4. Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [PubMed:20857090 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
General Function:
Phenylalanine 4-monooxygenase activity
Specific Function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular Weight:
51861.565 Da
References
  1. Erlandsen H, Flatmark T, Stevens RC, Hough E: Crystallographic analysis of the human phenylalanine hydroxylase catalytic domain with bound catechol inhibitors at 2.0 A resolution. Biochemistry. 1998 Nov 10;37(45):15638-46. [PubMed:9843368 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name:
ADRA2C
Uniprot ID:
P18825
Molecular Weight:
49521.585 Da
References
  1. Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768 ]
  2. Shen, Howard (2007). Illustrated Pharmacology Memory Cards : PharMnemonics. Minireview LLC. [ISBN:1-59541-101-1 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular Weight:
43518.615 Da
References
  1. Shen, Howard (2007). Illustrated Pharmacology Memory Cards : PharMnemonics. Minireview LLC. [ISBN:1-59541-101-1 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Tumor necrosis factor receptor binding
Specific Function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs ...
Gene Name:
TNF
Uniprot ID:
P01375
Molecular Weight:
25644.15 Da
References
  1. van der Poll T, Coyle SM, Barbosa K, Braxton CC, Lowry SF: Epinephrine inhibits tumor necrosis factor-alpha and potentiates interleukin 10 production during human endotoxemia. J Clin Invest. 1996 Feb 1;97(3):713-9. [PubMed:8609227 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 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 N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  2. Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  2. Breidert T, Spitzenberger F, Grundemann D, Schomig E: Catecholamine transport by the organic cation transporter type 1 (OCT1). Br J Pharmacol. 1998 Sep;125(1):218-24. [PubMed:9776363 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
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Drug created on June 13, 2005 07:24 / Updated on July 26, 2016 02:27