Identification

Name
Epinephrine
Accession Number
DB00668  (APRD00450, EXPT00496)
Type
Small Molecule
Groups
Approved, 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
  • Adrenaline
  • Epinefrin
  • Epinefrina
  • Epinephrin
  • Epinephrine
  • Epinephrinum
  • L-Adrenaline
  • levoepinephrine
External IDs
NSC-62786
Product Ingredients
IngredientUNIICASInChI Key
Epinephrine acetateM1NJX34RVJ97289-42-4CEBXQLPKMNOIHN-FVGYRXGTSA-N
Epinephrine bitartrate30Q7KI53AK51-42-3YLXIPWWIOISBDD-NDAAPVSOSA-N
Epinephrine chlorideNot AvailableNot AvailableQMTJCDRNQYQRHF-WWPIYYJJSA-N
Epinephrine hydrochlorideWBB047OO3855-31-2ATADHKWKHYVBTJ-FVGYRXGTSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdrenaclickInjection.15 mg/.15mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252017-02-10Us
AdrenaclickInjection.3 mg/.3mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252017-02-10Us
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 Pharmaceutical2013-07-01Not applicableUs
AdrenalinInjection1 mg/mLIntramuscular; SubcutaneousGeneral Injectables & Vaccines2017-09-26Not applicableUs
AdrenalinInjection1 mg/mLIntramuscular; Intraocular; SubcutaneousRemedy Repack2015-03-242017-04-14Us
AdrenalinInjection1 mg/mLIntramuscular; SubcutaneousPar Pharmaceutical2014-03-01Not 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
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Prime Asthma ReliefKitDrnaturalhealing Inc2014-08-21Not applicableUs
Prime Asthma ReliefCapsule.22 mg/1Respiratory (inhalation)Drnaturalhealing Inc2014-08-21Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EphinephrineInjection, solution.1 mg/mLIntravenousGeneral Injectables & Vaccines2010-08-012017-01-19Us
EpinephrineInjection, solution.1 mg/mLEndotracheal; Intracardiac; IntravenousHospira, Inc.1985-05-012017-10-18Us
EpinephrineInjection.1 mg/mLIntracardiac; IntravenousInternational Medication Systems, Limited1976-12-01Not applicableUs
EpinephrineInjection, solution1 mg/mLIntracardiac; Intramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-07-012017-01-19Us
EpinephrineInjection, solution.1 mg/mLEndotracheal; Intracardiac; IntravenousCardinal Health1985-05-01Not applicableUs
EpinephrineInjection.1 mg/mLParenteralAmphastar Pharmaceuticals, Inc.2010-08-252016-12-06Us
EpinephrineInjection, solution1 mg/mLIntramuscular; SubcutaneousSina Health Inc2005-09-08Not applicableUs
EpinephrineInjection, solution.1 mg/mLEndotracheal; Intracardiac; IntravenousHospira, Inc.1985-04-05Not applicableUs
EpinephrineInjection, solution1 mg/mLSubcutaneousRemedy Repack2015-09-172017-02-17Us
EpinephrineInjection, solution.1 mg/mLEndotracheal; Intracardiac; IntravenousRemedy Repack2017-05-12Not applicableUs
International/Other Brands
Adrenalin / Epi EZ Pen JR / Medihaler-Epi / Twinject
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2% Lidocaine and Epinephrine 1:100,000 Injection USPEpinephrine (0.01 mg) + Lidocaine hydrochloride (20 mg)LiquidInfiltrationAlveda Pharmaceuticals Inc2008-12-01Not applicableCanada
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Epinephrine (0.005 mg) + Articaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Epinephrine (0.005 mg) + Articaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Epinephrine (0.01 mg) + Articaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Epinephrine (0.01 mg) + Articaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada
4% Citanest Forte Dental With Epinephrine 1:200,000Epinephrine (5 mcg) + Prilocaine Hydrochloride (40 mg)LiquidInfiltrationDentsply Pharmaceutical2011-01-18Not applicableCanada
Adyphren Amp II KitEpinephrine + Isopropyl AlcoholKitIntramuscular; Subcutaneous; TopicalAsclemed Usa, Inc.2016-10-27Not applicableUs
Adyphren Amp KitEpinephrine + Isopropyl AlcoholKitIntramuscular; Subcutaneous; TopicalAsclemed Usa, Inc.2016-10-27Not applicableUs
Adyphren II KitEpinephrine + Isopropyl AlcoholKitIntramuscular; Intraocular; SubcutaneousAsclemed Usa, Inc.2016-10-04Not applicableUs
Adyphren KitEpinephrine + Isopropyl AlcoholKitIntramuscular; Intraocular; SubcutaneousAsclemed Usa, Inc.2016-10-04Not applicableUs
Categories
UNII
YKH834O4BH
CAS number
51-43-4
Weight
Average: 183.2044
Monoisotopic: 183.089543287
Chemical Formula
C9H13NO3
InChI Key
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

Pharmacology

Indication

Used to treat anaphylaxis and sepsis. Also one of the body's main adrenergic neurotransmitters.

Structured Indications
Pharmacodynamics

Epinephrine 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 action

Epinephrine works via the stimulation of alpha and beta-1 adrenergic receptors, and a moderate activity at beta-2 adrenergic receptors.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-1B adrenergic receptor
agonist
Human
ABeta-1 adrenergic receptor
agonist
Human
ABeta-2 adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
UAlpha-1D adrenergic receptor
antagonist
Human
NPhenylalanine-4-hydroxylase
antagonist
Human
UAlpha-2C adrenergic receptor
agonist
Human
UBeta-3 adrenergic receptor
agonist
Human
UTumor necrosis factor
antagonist
Human
USuperoxide dismutase [Cu-Zn]Not AvailableHuman
Absorption

Usually 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 distribution
Not Available
Protein binding
Not 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

Route of elimination

Renal

Half life

2 minutes

Clearance
Not Available
Toxicity

Skin, LD50 = 62 mg/kg (rat)

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Aromatic L-Aminoacid Decarboxylase DeficiencyDisease
Catecholamine BiosynthesisMetabolic
Tyrosine MetabolismMetabolic
Tyrosinemia, transient, of the newbornDisease
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
Tyrosine hydroxylase deficiencyDisease
Epinephrine Action PathwayDrug action
AlkaptonuriaDisease
HawkinsinuriaDisease
Dopamine beta-hydroxylase deficiencyDisease
Monoamine oxidase-a deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Epinephrine.Investigational
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Epinephrine.Approved, Investigational
AcebutololEpinephrine may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Epinephrine.Withdrawn
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Epinephrine.Experimental
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Epinephrine.Approved, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Epinephrine.Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Epinephrine.Approved
AlprenololEpinephrine may increase the atrioventricular blocking (AV block) activities of Alprenolol.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of Epinephrine.Illicit, Withdrawn
AmitriptylineAmitriptyline may decrease the antihypertensive activities of Epinephrine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Epinephrine.Approved, Illicit
ArotinololEpinephrine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
AtenololEpinephrine may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Epinephrine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Epinephrine is combined with Atorvastatin.Approved
AtosibanThe risk or severity of adverse effects can be increased when Epinephrine is combined with Atosiban.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Epinephrine.Investigational
BefunololEpinephrine may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Epinephrine.Investigational
BendroflumethiazideEpinephrine may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenzphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineEpinephrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Epinephrine can be decreased when used in combination with Betahistine.Approved
BetaxololEpinephrine may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
BevantololEpinephrine may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
BisoprololEpinephrine may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
BopindololEpinephrine may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Epinephrine.Approved, Investigational
BucindololEpinephrine may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Epinephrine.Withdrawn
BufuralolEpinephrine may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BumetanideEpinephrine may increase the hypokalemic activities of Bumetanide.Approved
BunazosinBunazosin may decrease the vasoconstricting activities of Epinephrine.Investigational
BupranololEpinephrine may increase the atrioventricular blocking (AV block) activities of Bupranolol.Approved
BupropionThe serum concentration of Epinephrine can be increased when it is combined with Bupropion.Approved
CabergolineCabergoline may increase the hypertensive activities of Epinephrine.Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Epinephrine.Approved
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Epinephrine.Experimental
CarteololEpinephrine may increase the atrioventricular blocking (AV block) activities of Carteolol.Approved
CarvedilolEpinephrine may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Epinephrine.Experimental
CeliprololEpinephrine may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Epinephrine.Withdrawn
ChlorothiazideEpinephrine may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorphentermineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Chlorphentermine.Illicit, Withdrawn
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Epinephrine.Approved
ChlorthalidoneEpinephrine may increase the hypokalemic activities of Chlorthalidone.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Epinephrine.Experimental
ClenbuterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may decrease the antihypertensive activities of Epinephrine.Approved, Vet Approved
CloranololEpinephrine may increase the atrioventricular blocking (AV block) activities of Cloranolol.Experimental
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive activities of Epinephrine.Approved
CyclopenthiazideEpinephrine may increase the hypokalemic activities of Cyclopenthiazide.Experimental
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Epinephrine.Investigational
DesfluraneDesflurane may increase the arrhythmogenic activities of Epinephrine.Approved
DesipramineDesipramine may decrease the antihypertensive activities of Epinephrine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Epinephrine.Approved
DibenzepinDibenzepin may decrease the antihypertensive activities of Epinephrine.Experimental
Diethyl etherDiethyl ether may increase the arrhythmogenic activities of Epinephrine.Experimental
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Epinephrine.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Epinephrine.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Epinephrine.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Epinephrine.Approved
DobutamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dopamine.Approved
DosulepinDosulepin may decrease the antihypertensive activities of Epinephrine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Epinephrine.Approved
DoxepinDoxepin may decrease the antihypertensive activities of Epinephrine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Epinephrine.Approved, Illicit
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Epinephrine.Approved
DuloxetineDuloxetine may increase the tachycardic activities of Epinephrine.Approved
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Epinephrine.Approved
EnfluraneEnflurane may increase the arrhythmogenic activities of Epinephrine.Approved, Vet Approved
EpanololEpinephrine may increase the atrioventricular blocking (AV block) activities of Epanolol.Experimental
EphedrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Ephedrine.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Epinephrine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Epinephrine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Epinephrine.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of Epinephrine.Investigational
EsmololEpinephrine may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
Etacrynic acidEpinephrine may increase the hypokalemic activities of Etacrynic acid.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Etilefrine.Withdrawn
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Epinephrine.Approved, Investigational
FenoterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Fenoterol.Approved
FenozoloneThe risk or severity of adverse effects can be increased when Epinephrine is combined with Fenozolone.Experimental
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Epinephrine.Approved
FurosemideEpinephrine may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Epinephrine.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Epinephrine.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Epinephrine.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Epinephrine.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Epinephrine.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Epinephrine.Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Epinephrine.Investigational
HalothaneHalothane may increase the arrhythmogenic activities of Epinephrine.Approved, Vet Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Epinephrine.Approved, Investigational
HydrochlorothiazideEpinephrine may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideEpinephrine may increase the hypokalemic activities of Hydroflumethiazide.Approved
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Hydroxyamphetamine.Approved
ImipramineImipramine may decrease the antihypertensive activities of Epinephrine.Approved
IndapamideEpinephrine may increase the hypokalemic activities of Indapamide.Approved
IndenololEpinephrine may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndoraminIndoramin may decrease the vasoconstricting activities of Epinephrine.Withdrawn
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Epinephrine.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Epinephrine.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Epinephrine.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Epinephrine.Approved
Insulin HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Epinephrine.Approved, Investigational
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Epinephrine.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Epinephrine.Approved
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Epinephrine.Approved
IprindoleIprindole may decrease the antihypertensive activities of Epinephrine.Experimental
IsofluraneIsoflurane may increase the arrhythmogenic activities of Epinephrine.Approved, Vet Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Isoxsuprine.Approved, Withdrawn
LabetalolEpinephrine may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
LandiololEpinephrine may increase the atrioventricular blocking (AV block) activities of Landiolol.Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Epinephrine.Approved
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Epinephrine.Approved
LinezolidLinezolid may increase the hypertensive activities of Epinephrine.Approved, Investigational
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Epinephrine.Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Epinephrine.Approved
LofepramineLofepramine may decrease the antihypertensive activities of Epinephrine.Experimental
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Epinephrine.Approved, Investigational
LurasidoneEpinephrine may increase the hypotensive activities of Lurasidone.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Epinephrine.Illicit, Withdrawn
MefenorexThe risk or severity of adverse effects can be increased when Epinephrine is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Mephentermine.Approved
MepindololEpinephrine may increase the atrioventricular blocking (AV block) activities of Mepindolol.Experimental
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Epinephrine.Approved, Investigational
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Epinephrine.Experimental
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Epinephrine.Approved
MethamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Methoxamine.Approved
MethoxyfluraneMethoxyflurane may increase the arrhythmogenic activities of Epinephrine.Approved, Vet Approved
MethyclothiazideEpinephrine may increase the hypokalemic activities of Methyclothiazide.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Epinephrine.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Epinephrine.Approved
MetolazoneEpinephrine may increase the hypokalemic activities of Metolazone.Approved
MetoprololEpinephrine may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Epinephrine.Experimental
MianserinThe therapeutic efficacy of Epinephrine can be decreased when used in combination with Mianserin.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Epinephrine.Approved
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Epinephrine.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Epinephrine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Epinephrine.Approved
MirtazapineMirtazapine may decrease the antihypertensive activities of Epinephrine.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Epinephrine.Approved, Investigational
NabiloneNabilone may increase the tachycardic activities of Epinephrine.Approved, Investigational
NadololEpinephrine may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Epinephrine.Approved, Investigational
NebivololNebivolol may decrease the bronchodilatory activities of Epinephrine.Approved, Investigational
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Epinephrine.Approved
Nitrous oxideNitrous oxide may increase the arrhythmogenic activities of Epinephrine.Approved, Vet Approved
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Epinephrine.Approved
NortriptylineNortriptyline may decrease the antihypertensive activities of Epinephrine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Epinephrine is combined with Nylidrin.Approved
OpipramolOpipramol may decrease the antihypertensive activities of Epinephrine.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Orciprenaline.Approved
OxprenololEpinephrine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Oxymetazoline.Approved
PenbutololEpinephrine may increase the atrioventricular blocking (AV block) activities of Penbutolol.Approved, Investigational
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Epinephrine.Approved, Vet Approved, Withdrawn
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Epinephrine.Approved, Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Phenmetrazine.Approved, Illicit
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Epinephrine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Epinephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Epinephrine.Approved, Vet Approved, Withdrawn
PindololEpinephrine may increase the atrioventricular blocking (AV block) activities of Pindolol.Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Epinephrine.Approved, Investigational
PiretanideEpinephrine may increase the hypokalemic activities of Piretanide.Experimental
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Epinephrine.Approved
PolythiazideEpinephrine may increase the hypokalemic activities of Polythiazide.Approved
PractololEpinephrine may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Epinephrine.Approved, Investigational
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Epinephrine.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Epinephrine.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Prenalterol.Experimental
ProcaterolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Procaterol.Approved
PromethazinePromethazine may decrease the vasoconstricting activities of Epinephrine.Approved
PropranololEpinephrine may increase the atrioventricular blocking (AV block) activities of Propranolol.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of Epinephrine.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Pseudoephedrine.Approved
QuinethazoneEpinephrine may increase the hypokalemic activities of Quinethazone.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Racepinephrine.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Epinephrine.Approved, Investigational
RitodrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Ritodrine.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Epinephrine.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Epinephrine.Approved
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Epinephrine.Approved
SevofluraneSevoflurane may increase the arrhythmogenic activities of Epinephrine.Approved, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Epinephrine.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Epinephrine.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Epinephrine.Approved, Investigational
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Epinephrine.Investigational
SotalolEpinephrine may increase the atrioventricular blocking (AV block) activities of Sotalol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Epinephrine.Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Epinephrine.Approved, Investigational
SynephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Synephrine.Experimental
TalinololEpinephrine may increase the atrioventricular blocking (AV block) activities of Talinolol.Investigational
TamsulosinTamsulosin may decrease the vasoconstricting activities of Epinephrine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Epinephrine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Epinephrine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Terbutaline.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Epinephrine.Experimental
TertatololEpinephrine may increase the atrioventricular blocking (AV block) activities of Tertatolol.Experimental
TetryzolineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Tetryzoline.Approved
TianeptineTianeptine may decrease the antihypertensive activities of Epinephrine.Approved
TimololEpinephrine may increase the atrioventricular blocking (AV block) activities of Timolol.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Epinephrine.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Epinephrine.Approved
TorasemideEpinephrine may increase the hypokalemic activities of Torasemide.Approved
TramazolineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Tramazoline.Investigational
TretoquinolThe risk or severity of adverse effects can be increased when Epinephrine is combined with Tretoquinol.Experimental
TrichlormethiazideEpinephrine may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrichloroethyleneTrichloroethylene may increase the arrhythmogenic activities of Epinephrine.Experimental
TrimazosinTrimazosin may decrease the vasoconstricting activities of Epinephrine.Experimental
TrimipramineTrimipramine may decrease the antihypertensive activities of Epinephrine.Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Epinephrine.Withdrawn
TyramineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Tyramine.Investigational, Nutraceutical
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Epinephrine.Experimental
UrapidilUrapidil may decrease the vasoconstricting activities of Epinephrine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Epinephrine.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Epinephrine.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Epinephrine.Approved, Investigational
XenonXenon may increase the arrhythmogenic activities of Epinephrine.Experimental
Food Interactions
Not 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
Human Metabolome Database
HMDB00068
KEGG Drug
D00095
KEGG Compound
C00788
PubChem Compound
5816
PubChem Substance
46509097
ChemSpider
5611
BindingDB
50029050
ChEBI
28918
ChEMBL
CHEMBL679
Therapeutic Targets Database
DAP000066
PharmGKB
PA449470
IUPHAR
479
Guide to Pharmacology
GtP Drug Page
HET
ALE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Epinephrine
ATC Codes
R03AK01 — Epinephrine and other drugs for obstructive airway diseasesR01AA14 — EpinephrineC01CA24 — EpinephrineS01EA51 — Epinephrine, combinationsA01AD01 — EpinephrineS01EA01 — EpinephrineR03AA01 — EpinephrineB02BC09 — Epinephrine
AHFS Codes
  • 12:12.12 — Alpha-and Beta-adrenergic Agonists
  • 34:00.00 — Dental Agents
  • 12:12.00 — Sympathomimetic (Adrenergic) Agents
  • 52:32.00 — Vasoconstrictors
PDB Entries
2hkk / 4a7u / 4ldo
FDA label
Download (369 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceMorton's neuralgia1
0CompletedHealth Services ResearchPain1
0RecruitingNot AvailableKnee Prosthesis1
0RecruitingTreatmentDiabetes Complications1
1Active Not RecruitingNot AvailableAAT Deficiency / AATD / Alpha-1 Antitrypsin Deficiency / Fibrosis, Liver1
1Active Not RecruitingOtherSurgery, Colorectal1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableImmune System1
1CompletedBasic ScienceDrug-induced QT Interval Prolongation / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceNociceptive Pain / Peripheral Neuropathic Pain1
1CompletedHealth Services ResearchAnaesthesia therapy1
1CompletedSupportive CarePostoperative pain1
1CompletedTreatmentCoughing1
1CompletedTreatmentFibromyalgia / Pain, Chronic1
1CompletedTreatmentNeoplasms, Cystic, Mucinous, and Serous1
1CompletedTreatmentPain Management / Pregnancy Termination1
1Not Yet RecruitingTreatmentPostoperative pain1
1RecruitingTreatmentPompe's Disease1
1RecruitingTreatmentRadicular syndrome / Sciatica1
1TerminatedPreventionPostoperative pain1
1TerminatedTreatmentPain, Neuropathic1
1Unknown StatusPreventionPostoperative pain1
1Unknown StatusTreatmentCardiac Arrest / Cardio-respiratory arrest1
1, 2Unknown StatusTreatmentAnaesthesia therapy1
1, 2WithdrawnTreatmentColorectal Disorders1
1, 2WithdrawnTreatmentPostoperative Pain Management After Total Hip Arthroplasty1
2CompletedBasic ScienceDiabetic Neuropathic Pain1
2CompletedPreventionDysmenorrhea1
2CompletedPreventionHyperalgesia / Knee Joint Osteoarthrosis / Severe Movement Related Pain1
2CompletedPreventionRotator Cuff Syndrome1
2CompletedSupportive CareDiverticulitis / Inflammatory Bowel Diseases (IBD) / Malignant Neoplasm of Colon1
2CompletedTreatmentAcute Lung Injury (ALI)1
2CompletedTreatmentAllodynia / Central Neuropathic Pain / Spinal Cord Injuries (SCI)1
2CompletedTreatmentArthroplasty, Replacement, Hip1
2CompletedTreatmentCardiac Arrest1
2CompletedTreatmentChronic Pain Syndrome / Prostatitis1
2CompletedTreatmentDysmenorrhea / Endometriosis1
2CompletedTreatmentFascicular Block / Latency Period / Motor Activities / Postoperative pain1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentHeart Arrest1
2CompletedTreatmentHip Pain Etiology Unknown1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentLow Back Pain (LBP)1
2CompletedTreatmentPain1
2CompletedTreatmentPain, Neuropathic / Vasoocclusive Sickle Cell Crises Pains1
2CompletedTreatmentPain / Postoperative1
2CompletedTreatmentPostherpetic Neuralgia1
2CompletedTreatmentShock, Septic1
2Not Yet RecruitingTreatmentBronchiolitis1
2RecruitingSupportive CareMenopausal Hot Flushes1
2RecruitingTreatmentAbdominal Pain (AP)1
2RecruitingTreatmentAnaphylaxis / Angioedema / Arterial Hypotension / Bronchospasm1
2RecruitingTreatmentBladder Pain Syndrome / Interstitial Cystitis1
2RecruitingTreatmentIntraoperative Bleeding1
2RecruitingTreatmentPhantom Limb Pain (PLP) / Primary/Secondary Scar Hyperalgesia1
2RecruitingTreatmentPost-Operative Pain1
2RecruitingTreatmentShock, Cardiogenic1
2TerminatedTreatmentDry Macular Degeneration1
2TerminatedTreatmentPostoperative Hemorrhages / Postoperative pain1
2Unknown StatusPreventionCancer, Breast1
2Unknown StatusTreatmentShoulder Pain1
2WithdrawnTreatmentCerebrovascular Accidents / Strokes1
2WithdrawnTreatmentNeoplasms / Pain1
2WithdrawnTreatmentPain1
2, 3CompletedTreatmentPain and Anxiety1
2, 3Not Yet RecruitingPreventionSurgical Site Infections / Venous Thromboembolism1
2, 3Not Yet RecruitingTreatmentLocal Anesthetics Causing Adverse Effects in Therapeutic Use / Opioid Dependence / Postoperative pain / Thoracic Diseases1
2, 3RecruitingPreventionHaemorrhage / Hemoptysis / Lung Transplant; Complications / Lung Transplant; Complications, Mechanical1
2, 3RecruitingPreventionPost-operative Cognitive Dysfunction1
2, 3RecruitingSupportive CareCancer-related Pain1
2, 3RecruitingTreatmentAnaesthesia therapy1
2, 3RecruitingTreatmentEsotropia / Exotropia / Graves Diseases / Nystagmus / Strabismus1
2, 3RecruitingTreatmentPain1
2, 3TerminatedTreatmentBronchiolitis / Children1
2, 3Unknown StatusTreatmentAchilles Tendinopathy / Achilles Tendon Enthesopathy / Insertional Achilles Tendinopathy / Mid-Portion Achilles Tendinopathy / Non-Insertional Achilles Tendinopathy1
3CompletedBasic ScienceBMI >30 kg/m2 / Post-gastrointestinal bypass surgery1
3CompletedPreventionPost-operative Pain for Total Knee Arthroplasty1
3CompletedTreatmentAbdominal Pain (AP) / Gastroesophageal Reflux Disease / Indigestion / Intestinal Malabsorption1
3CompletedTreatmentAnaesthesia therapy2
3CompletedTreatmentAnkle Sprains1
3CompletedTreatmentBiceps Tendonitis1
3CompletedTreatmentCardiac Arrest3
3CompletedTreatmentCardiac Output, Low1
3CompletedTreatmentChronic Low Back Pain (CLBP)1
3CompletedTreatmentForearm and Arm Surgery1
3CompletedTreatmentIntraoperative Blood Loss1
3CompletedTreatmentIrreversible Pulpitis1
3CompletedTreatmentModerate or Severe Submental Fullness1
3CompletedTreatmentNeoplasms, Colorectal1
3CompletedTreatmentNonviable Pregnancy1
3CompletedTreatmentPain2
3CompletedTreatmentPostoperative Pain Intensity / Rescue Pain Requirements1
3CompletedTreatmentPostoperative pain1
3CompletedTreatmentSpinal Anaesthesia1
3CompletedTreatmentUterine Leiomyomas1
3RecruitingSupportive CareMalignant Neoplasms of Male Genital Organs1
3RecruitingSupportive CarePain1
3RecruitingTreatmentCancers / Pain With Neuropathic Component1
3RecruitingTreatmentInguinal Hernias / Local Anesthesia / Sedation, Conscious1
3RecruitingTreatmentKnee Replacement Surgery / Pain Management / Synovitis of osteoarthritis1
3RecruitingTreatmentLow Back Pain (LBP) / Modic I Discopathy1
3RecruitingTreatmentPostoperative pain1
3TerminatedPreventionTransient Neurologic Syndrome1
3TerminatedTreatmentBursitis / Periarthritis1
3TerminatedTreatmentPostoperative pain1
3Unknown StatusPreventionBariatric Surgical Pain1
3Unknown StatusTreatmentCancers / Pain1
3Unknown StatusTreatmentFibromyalgia1
3Unknown StatusTreatmentHealthy Volunteers1
3Unknown StatusTreatmentPeripheral Neuropathy1
3WithdrawnSupportive CareCesarean Delivery1
3WithdrawnSupportive CareFracture of Lower Limb1
3WithdrawnTreatmentParathyroid Diseases1
4Active Not RecruitingTreatmentPain1
4Active Not RecruitingTreatmentPostoperative pain1
4CompletedNot AvailableAnaesthesia therapy1
4CompletedNot AvailableAnaesthesia / Caudal epidural block therapy / Orthopaedic Disorders1
4CompletedNot AvailableNeuromuscular Block1
4CompletedBasic SciencePain1
4CompletedDiagnosticArterial Hypotension / Free Flap / Head and Neck Carcinoma / Oral Cancers1
4CompletedHealth Services ResearchBronchiolitis1
4CompletedOtherPain1
4CompletedPreventionAnaesthesia / Toxicity1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedPreventionCardiovascular Morbidity / Intubation Complications1
4CompletedPreventionChildbirth / Parturients1
4CompletedPreventionEsophagogastroduodenoscopy1
4CompletedPreventionGeneral Surgery / Pain1
4CompletedPreventionLaminectomy1
4CompletedPreventionPain on Injection of Propofol,Lidocaine, Alkalinized Lidocaine1
4CompletedPreventionPostoperative Hemorrhages / Postoperative pain1
4CompletedPreventionPostoperative pain2
4CompletedPreventionRetinal Detachment / Retinoschisis / Vitreoretinopathy, Proliferative1
4CompletedPreventionThroat Pain1
4CompletedScreeningPostoperative pain1
4CompletedSupportive CareBMI >30 kg/m2 / General Surgery / Neuromuscular Inhibition / Pain1
4CompletedSupportive CareCesarean Section / Spinal Anaesthesia1
4CompletedSupportive CareDiverticulitis / Malignant Neoplasm of Colon / Post-Operative Pain1
4CompletedSupportive CareHandling of Auto-injectors1
4CompletedSupportive CareLumbar Spine Disc Herniation1
4CompletedTreatmentAcute Bronchiolitis1
4CompletedTreatmentArthroplasty, Knee Replacement / Postoperative pain1
4CompletedTreatmentArthroplasty, Replacement, Hip1
4CompletedTreatmentBack Pain / Cervical Pain1
4CompletedTreatmentCanal Syndrome / Pudendal Neuralgia1
4CompletedTreatmentCardiac Arrest1
4CompletedTreatmentCardiopulmonary Bypass Graft1
4CompletedTreatmentCarpal Tunnel Syndrome (CTS) / Trigger Finger1
4CompletedTreatmentCervical Intraepithelial Neoplasia (CIN)1
4CompletedTreatmentChronic Cough (CC)1
4CompletedTreatmentChronic Migraine1
4CompletedTreatmentEpicondylitis, Lateral Humeral / Lateral Epicondylitis1
4CompletedTreatmentFeeling Anxious / Nausea / Pain1
4CompletedTreatmentFemur Fractures / Postoperative pain1
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentGastroscopy1
4CompletedTreatmentHallux Valgus1
4CompletedTreatmentHypertensive1
4CompletedTreatmentInjection Site Irritation1
4CompletedTreatmentAdjunct to general anesthesia therapy / Intravenous Anesthesia1
4CompletedTreatmentIrreversible Pulpitis1
4CompletedTreatmentIrreversible Pulpitis / Pain1
4CompletedTreatmentKnee Arthroplasty, Total1
4CompletedTreatmentLocal Anesthesia for Peripheral Intravenous Catheterization / Pain1
4CompletedTreatmentLung Cancers1
4CompletedTreatmentMeniscus Lesion1
4CompletedTreatmentMigrainous Headache1
4CompletedTreatmentNeuromuscular Block1
4CompletedTreatmentOpen Reduction Internal Fixation(ORIF) of Lateral Malleolus1
4CompletedTreatmentNeurocostal neuralgia / Opioid-Related Disorders1
4CompletedTreatmentOsteoarthritis of the Knees4
4CompletedTreatmentOsteoarthritis, Hip1
4CompletedTreatmentPain3
4CompletedTreatmentPain on IV Injection of Propofol1
4CompletedTreatmentPain, Acute1
4CompletedTreatmentPain, Chronic1
4CompletedTreatmentPain / Peripheral Nerve Blocks1
4CompletedTreatmentPain / Pregnancy1
4CompletedTreatmentPain / Prophylaxis against postoperative nausea and vomiting1
4CompletedTreatmentCaudal epidural block therapy / Pain / Total Knee Arthroplasty (TKA)1
4CompletedTreatmentOr Peripheral Nerve Injury (PNI) / Peripheral Neuropathic Pain (PNP) Due to Postherpetic Neuralgia (PHN)1
4CompletedTreatmentPostoperative pain4
4CompletedTreatmentAdjunct to general anesthesia therapy / Propofol Target-controlled Infusion / Thoracic Epidural Anesthesia1
4CompletedTreatmentScoliosis1
4CompletedTreatmentSedation, Conscious1
4CompletedTreatmentShock, Cardiogenic1
4CompletedTreatmentSnake Bites1
4CompletedTreatmentSpinal Anaesthesia1
4CompletedTreatmentSurgical Procedures, Operative1
4CompletedTreatmentThermal Burns1
4CompletedTreatmentToothache1
4CompletedTreatmentTopical Anesthesia1
4CompletedTreatmentGallstone formation1
4Enrolling by InvitationOtherCataracts1
4Enrolling by InvitationSupportive CareHemodynamics Instability1
4Enrolling by InvitationTreatmentOsteoarthritis of the Knees1
4Enrolling by InvitationTreatmentTotal Hip Arthroplasty (THA)1
4Not Yet RecruitingHealth Services ResearchUpper Gastrointestinal Hemorrhage1
4Not Yet RecruitingPreventionCritical Illness1
4Not Yet RecruitingPreventionPostoperative pain1
4Not Yet RecruitingTreatmentCervical incompetence1
4Not Yet RecruitingTreatmentKnee Replacement, Total1
4Not Yet RecruitingTreatmentLocal Anesthesia / Spinal Diseases1
4RecruitingNot AvailablePain1
4RecruitingPreventionAnaesthesia therapy / Hip Fractures1
4RecruitingPreventionPost-ERCP Acute Pancreatitis1
4RecruitingPreventionSpinal Anesthetics Causing Adverse Effects in Therapeutic Use1
4RecruitingSupportive CareAnaesthesia therapy1
4RecruitingSupportive CareNerve Monitoring / Thyroidectomy1
4RecruitingSupportive CarePregnancy1
4RecruitingTreatmentAcetabular Labrum Tear / Femoroacetabular Impingement / Hip Dysplasia1
4RecruitingTreatmentArthroplasty / Synovitis of osteoarthritis1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentFracture, Ankle / Postoperative pain1
4RecruitingTreatmentPain1
4RecruitingTreatmentPain, Radiating1
4RecruitingTreatmentPost Operative Pain (Post Laparoscopic Hernia Repair)1
4RecruitingTreatmentSedation therapy1
4RecruitingTreatmentShock1
4RecruitingTreatmentPost-pancreatectomy1
4TerminatedPreventionNausea / Occasional Constipation / Pain / Vomiting1
4TerminatedPreventionPain1
4TerminatedTreatmentAbscesses1
4TerminatedTreatmentArthritis Multiple Joint / Basal Thumb Joint Arthritis / Basilar Joint Arthritis / Carpometacarpal Arthritis / Trapeziometacarpal Arthritis1
4TerminatedTreatmentArthroplasty, Replacement, Knee1
4TerminatedTreatmentForearm Fractures1
4TerminatedTreatmentPostoperative pain1
4TerminatedTreatmentPulmonary Arterial Hypertension (PAH)1
4TerminatedTreatmentShoulder Pain1
4Unknown StatusNot AvailableChronic Rhinosinusitis1
4Unknown StatusNot AvailableEndophthalmitis / Vitreoretinal Surgery1
4Unknown StatusPreventionDrug Usage1
4Unknown StatusPreventionOral Hemorrhage1
4Unknown StatusSupportive CareInjection Site Irritation1
4Unknown StatusSupportive CareTonsillectomy1
4Unknown StatusTreatmentAnaesthesia therapy / Analgesia / Conscious Sedation Failure During Procedure1
4Unknown StatusTreatmentCholecystolithiasis1
4Unknown StatusTreatmentCroup / Epinephrine Neublizer Treatment1
4Unknown StatusTreatmentDilatation and Evacuation / Laminaria Placement / Pain Alleviation1
4Unknown StatusTreatmentIUD Insertion Complication / Pain Control1
4Unknown StatusTreatmentPlanned Abdominal Hysterectomy1
4WithdrawnNot AvailableAdjunct to general anesthesia therapy / Elderly / Surgeries Requiring A Minimum One Day Hospitalization1
4WithdrawnSupportive CarePain Management / Total Knee Arthroplasty (TKA)1
4WithdrawnTreatmentCataract Surgery Anesthesia1
4WithdrawnTreatmentOsteoarthritis of the Knees1
4WithdrawnTreatmentPain1
Not AvailableActive Not RecruitingPreventionPostoperative pain / Prophylaxis against postoperative nausea and vomiting1
Not AvailableActive Not RecruitingTreatmentAnaesthesia therapy2
Not AvailableActive Not RecruitingTreatmentLow Back Pain (LBP) / Osteoarthritis Nos, of Sacroiliac Joint / Sprain of Sacroiliac Ligament1
Not AvailableActive Not RecruitingTreatmentMotor Impairments / Neurological Conditions / Orthopaedic Injury1
Not AvailableActive Not RecruitingTreatmentPost-Operative Pain1
Not AvailableActive Not RecruitingTreatmentRib Fractures1
Not AvailableActive Not RecruitingTreatmentRotator Cuff / Subacromial Impingement Syndrome1
Not AvailableCompletedNot AvailableCancer, Breast1
Not AvailableCompletedNot AvailableDeath, Sudden,Cardiac / Heart Arrest1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableHemodynamic Response1
Not AvailableCompletedNot AvailableKnee Replacement Surgery1
Not AvailableCompletedNot AvailablePain2
Not AvailableCompletedNot AvailablePain, Neuropathic2
Not AvailableCompletedNot AvailableRhytidoplasty1
Not AvailableCompletedNot AvailableSpinal Anaesthesia1
Not AvailableCompletedNot AvailableSpinal Anaesthesia / Total Knee Replacement Arthroplasty1
Not AvailableCompletedNot AvailableStress Urinary Incontinence (SUI)1
Not AvailableCompletedNot AvailableThyroid Cancers1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedDiagnosticPain1
Not AvailableCompletedDiagnosticParesis1
Not AvailableCompletedHealth Services ResearchCataracts1
Not AvailableCompletedPreventionAdult Disease1
Not AvailableCompletedPreventionCognitive Decline1
Not AvailableCompletedPreventionHypoglycemia / Respiratory Distress1
Not AvailableCompletedPreventionHypotension After Reperfusion in Liver Transplantation1
Not AvailableCompletedPreventionOther Intraoperative Cardiac Functional Disturbances During Cardiac Surgery1
Not AvailableCompletedPreventionPain1
Not AvailableCompletedPreventionPost-ERCP Acute Pancreatitis1
Not AvailableCompletedPreventionPostoperative pain1
Not AvailableCompletedSupportive CareColorectal Cancers1
Not AvailableCompletedSupportive CareLabour Pain1
Not AvailableCompletedSupportive CareLaparoscopic Gynecologic Surgery / Paracervical Block / Postoperative pain1
Not AvailableCompletedSupportive CarePain3
Not AvailableCompletedSupportive CarePain Insensitivity, Congenital1
Not AvailableCompletedSupportive CarePost-traumatic; Arthrosis / Synovitis of osteoarthritis1
Not AvailableCompletedSupportive CareTrigeminal Neuralgia (TN)1
Not AvailableCompletedTreatmentAdverse Reaction to Epinephrine / Blood, Injection, Injury Type Phobia / Gastrointestinal Ulcer Haemorrhage1
Not AvailableCompletedTreatmentAge-Related Macular Degeneration (AMD)1
Not AvailableCompletedTreatmentAge-Related Macular Degeneration (ARMD) / Central Retinal Vein Occlusion (CRVO) / Diabetic Macular Edema (DME)1
Not AvailableCompletedTreatmentAnaphylaxis1
Not AvailableCompletedTreatmentAnesthetics, Local / Blood Levels of Buffered vs Non-buffered Lidocaine1
Not AvailableCompletedTreatmentArterial Hypotension / Shock1
Not AvailableCompletedTreatmentBronchiolitis1
Not AvailableCompletedTreatmentDiverticulitis / Inflammatory Bowel Diseases (IBD) / Malignant Neoplasm of Colon1
Not AvailableCompletedTreatmentFibromyalgia1
Not AvailableCompletedTreatmentFracture Bone / Pain1
Not AvailableCompletedTreatmentGall Stone Pancreatitis / Gallbladder Inflammation1
Not AvailableCompletedTreatmentGall Stones1
Not AvailableCompletedTreatmentLabour Pain1
Not AvailableCompletedTreatmentLateral Epicondylitis1
Not AvailableCompletedTreatmentLumbar Puncture / Topical Analgesia1
Not AvailableCompletedTreatmentLung Cancers / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedTreatmentMigrainous Headache1
Not AvailableCompletedTreatmentOpioid Consumption / Postoperative pain1
Not AvailableCompletedTreatmentOsteoarthritis of the Knees1
Not AvailableCompletedTreatmentOsteoarthritis of the Knees / Osteoarthritis, Hip / Osteoarthritis, Shoulder1
Not AvailableCompletedTreatmentPain8
Not AvailableCompletedTreatmentPain Control for Intrauterine Device Insertions1
Not AvailableCompletedTreatmentPain Intensity1
Not AvailableCompletedTreatmentGallstone formation / Pain1
Not AvailableCompletedTreatmentPartial Thickness Rotator Cuff Tear / Subacromial Impingement Syndrome1
Not AvailableCompletedTreatmentPedal Fat Pad Atrophy1
Not AvailableCompletedTreatmentPeptic Ulcers1
Not AvailableCompletedTreatmentPlantar fascial fibromatosis1
Not AvailableCompletedTreatmentPost Operative Pain1
Not AvailableCompletedTreatmentPosterior Knee Infiltration1
Not AvailableCompletedTreatmentPostoperative pain2
Not AvailableCompletedTreatmentPregnancy Termination / Uterine Curettage1
Not AvailableCompletedTreatmentProstate Cancer1
Not AvailableCompletedTreatmentPulpitis dental1
Not AvailableCompletedTreatmentSpine Surgery1
Not AvailableCompletedTreatmentMinor burns1
Not AvailableEnrolling by InvitationNot AvailableArthritis / Gout Acute / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableEnrolling by InvitationNot AvailableBrain Diseases / Cardiovascular Disease (CVD) / Central Nervous System Diseases / Cerebrovascular Disorders / Cerebrovascular Stroke / Ischemia, Brain / Nervous System Diseases / Strokes / Vascular Diseases1
Not AvailableEnrolling by InvitationSupportive CareFemoral Fractures / Postoperative pain1
Not AvailableEnrolling by InvitationTreatmentGoiter, Nodular / Graves' Disease / Hyperparathyroidism / Neoplasms, Thyroid / Thyroid Nodules1
Not AvailableNot Yet RecruitingNot AvailableKnee Replacement Surgery / Pain1
Not AvailableNot Yet RecruitingPreventionAnaesthesia therapy / Spinal Puncture1
Not AvailableNot Yet RecruitingTreatmentAcute Upper Gastrointestinal Bleeding / Tumor Bleeding1
Not AvailableNot Yet RecruitingTreatmentAnalgesia / Aspiration / Pain / Tibial Fractures1
Not AvailableNot Yet RecruitingTreatmentEfficacy and Safety of VATS Block1
Not AvailableRecruitingNot AvailableCardiac Arrest1
Not AvailableRecruitingNot AvailablePain1
Not AvailableRecruitingBasic ScienceArterial Hypotension / Pain1
Not AvailableRecruitingPreventionAcute Pancreatitis (AP)1
Not AvailableRecruitingPreventionAgitation States as Acute Reaction to Gross Stress1
Not AvailableRecruitingPreventionArterial Hypotension1
Not AvailableRecruitingPreventionNonvalvular Atrial Fibrillation1
Not AvailableRecruitingTreatmentAbdominal Pain (AP) / GERD / Swallowing Disorders1
Not AvailableRecruitingTreatmentAcute Upper Gastrointestinal Bleeding1
Not AvailableRecruitingTreatmentBlood Loss2
Not AvailableRecruitingTreatmentFracture of Neck of Femur1
Not AvailableRecruitingTreatmentHeel Fat Pad Atrophy1
Not AvailableRecruitingTreatmentHip Injuries1
Not AvailableRecruitingTreatmentIUD Insertion Complication1
Not AvailableRecruitingTreatmentInterstitial Cystitis / Painful Bladder Syndrome (PBS)1
Not AvailableRecruitingTreatmentPilonidal Sinus1
Not AvailableRecruitingTreatmentPostoperative pain2
Not AvailableRecruitingTreatmentRadius Fractures1
Not AvailableRecruitingTreatmentShock, Septic1
Not AvailableRecruitingTreatmentVideo-assisted Thoracic Surgery (VATS) / Video-assisted Thoracoscopic Surgery (VATS)1
Not AvailableTerminatedBasic SciencePain1
Not AvailableTerminatedHealth Services ResearchCongenital Disorders1
Not AvailableTerminatedOtherAbdominal Wall Relaxation After Rectus Sheath Block / Hernia / Postoperative pain1
Not AvailableTerminatedPreventionLaryngospasm1
Not AvailableTerminatedTreatmentHysterectomy1
Not AvailableTerminatedTreatmentLaparoscopic Colorectal Resection1
Not AvailableTerminatedTreatmentLumbar and Other Intervertebral Disc Disorders With Radiculopathy1
Not AvailableTerminatedTreatmentPain1
Not AvailableUnknown StatusNot AvailablePain1
Not AvailableUnknown StatusNot AvailableTotal Knee Arthroplasty (TKA)1
Not AvailableUnknown StatusBasic ScienceAnesthetics, Local1
Not AvailableUnknown StatusPreventionAsymptomatic Gallstones Without Cholecystitis / Gallbladder Polyps1
Not AvailableUnknown StatusPreventionContraception1
Not AvailableUnknown StatusPreventionIntravenous Injections1
Not AvailableUnknown StatusSupportive CareOverweight and Obesity1
Not AvailableUnknown StatusTreatmentArrythmias / Arterial Hypotension / Bradycardia / Hypertensive / Tachycardia1
Not AvailableUnknown StatusTreatmentBronchiolitis1
Not AvailableUnknown StatusTreatmentHypospadias Repair1
Not AvailableUnknown StatusTreatmentMacular Degeneration1
Not AvailableUnknown StatusTreatmentPain2
Not AvailableUnknown StatusTreatmentPain During and After Endovenous Laser Obliteration of Large Saphenous Vein Based on Lidocaine Tumescent Concentration1
Not AvailableUnknown StatusTreatmentPost Operative Pain1
Not AvailableUnknown StatusTreatmentPostoperative pain1
Not AvailableUnknown StatusTreatmentPregnancy1
Not AvailableUnknown StatusTreatmentRenal Stones / Ureteral Calculus1
Not AvailableUnknown StatusTreatmentSynovitis of osteoarthritis1
Not AvailableWithdrawnNot AvailableAirway Complication of Anaesthesia1
Not AvailableWithdrawnNot AvailableDiabetes, Diabetes Mellitus Type 12
Not AvailableWithdrawnDiagnosticInterstitial Cystitis1
Not AvailableWithdrawnPreventionVaginal Delivery1
Not AvailableWithdrawnSupportive CarePelvic Organ Prolapse (POP)1
Not AvailableWithdrawnTreatmentAdhesive Capsulitis1
Not AvailableWithdrawnTreatmentNasolabial Folds Correction / Pain1
Not AvailableWithdrawnTreatmentPlantar fascial fibromatosis1
Not AvailableWithdrawnTreatmentTotal Knee Arthroplasty (TKA)1

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
SolutionIntramuscular0.30 mg
InjectionIntramuscular; Intraocular; Subcutaneous1 mg/mL
InjectionIntramuscular; Subcutaneous1 mg/mL
SolutionNasal1 mg
SolutionIntramuscular; Intravenous; Subcutaneous1 mg
KitIntramuscular; Subcutaneous; Topical
KitIntramuscular; Intraocular; Subcutaneous
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
SolutionIntramuscular0.3 mg
SolutionIntramuscular0.15 mg
InjectionIntramuscular; Subcutaneous.15 mg/1
InjectionIntramuscular; Subcutaneous.3 mg/1
Injection, solutionIntramuscular.15 mg/.15mL
Injection, solutionIntramuscular.3 mg/.3mL
Aerosol, meteredRespiratory (inhalation)0.5 %
Injection, solutionEpidural; Infiltration; Intracaudal
Injection, solutionDental
SprayRespiratory (inhalation)3.5 %
Solution / dropsOphthalmic
SolutionIntramuscular0.5 mg
Injection, solutionIntravenous.1 mg/mL
LiquidIntramuscular0.3 mg
InjectionIntracardiac; Intravenous.1 mg/mL
InjectionParenteral.1 mg/mL
InjectionParenteral1 mg/mL
InjectionSubcutaneous.3 mg/1
InjectionSubcutaneous.3 mg/.3mL
Injection, solutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous1 mg/mL
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
SolutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous1 mg
InjectionIntramuscular.3 mg/.3mL
InjectionIntramuscular.15 mg/.3mL
InjectionIntramuscular; Subcutaneous1 mg/1000mL
PackingDental.5 mg
Kit
SolutionEpidural; Infiltration
Injection, solutionDental; Infiltration
Injection, solutionEpidural
Injection, solutionInfiltration
LiquidEpidural; Infiltration
SprayTopical
SolutionTopical
GelTopical
LiquidDental; Subcutaneous
Injection, solutionSubcutaneous
LiquidSubcutaneous
InjectionSubmucosal
CapsuleRespiratory (inhalation).22 mg/1
Kit
Injection, solutionPerineural
Injection, solutionEpidural; Intracaudal; Perineural
Injection, solutionEpidural; Retrobulbar
LiquidInfiltration
KitInfiltration; Topical
LiquidParenteral; Topical
SolutionIntramuscular1 mg
SolutionIntramuscular; Subcutaneous0.15 mg
SolutionIntramuscular; Subcutaneous0.3 mg
Injection, solutionSubmucosal
SolutionInfiltration
Injection, solutionInfiltration; Perineural
SolutionEpidural
Injection, solutionEpidural; Infiltration; Intracaudal; 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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5665071No1993-05-272013-05-27Us
US7794432No2005-09-112025-09-11Us
US8870827No2005-09-112025-09-11Us
US7449012No2005-09-112025-09-11Us
US8048035No2005-09-112025-09-11Us
US7297136No2005-01-182025-01-18Us
US7621891No2005-02-042025-02-04Us
US6629968No2000-06-302020-06-30Us
US6635045No2001-06-292021-06-29Us
US9149579No2005-07-192025-07-19Us
US8425462No2004-11-232024-11-23Us
US8231573No2008-11-252028-11-25Us
US8016788No2005-03-212025-03-21Us
US9259539No2006-02-012026-02-01Us
US8206360No2007-02-272027-02-27Us
US9238108No2007-01-222027-01-22Us
US8226610No2009-04-102029-04-10Us
US7918823No2004-11-232024-11-23Us
US8608698No2004-11-232024-11-23Us
US8021344No2009-11-022029-11-02Us
US8361029No2004-11-232024-11-23Us
US8313466No2004-11-232024-11-23Us
US7731690No2005-01-152025-01-15Us
US9278182No2006-02-012026-02-01Us
US8920377No2004-11-232024-11-23Us
US7731686No2006-06-012026-06-01Us
US8926594No2006-03-312026-03-31Us
US7749194No2008-10-302028-10-30Us
US9056170No2004-11-232024-11-23Us
US7947017No2008-03-122028-03-12Us
US9295657No2015-03-132035-03-13Us
US9119876No2015-03-132035-03-13Us
US9283197No2014-08-152034-08-15Us
US9586010No2005-09-112025-09-11Us
US7905352No2007-04-122027-04-12Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)211.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-0900000000-5ca773e378035e522e65
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0900000000-5ca773e378035e522e65
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-014i-0900000000-7718bec49c1a109083e5
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a4i-4900000000-ec5581e838e2a4a66139
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-9200000000-4572448ba3dadff2d2a6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0900000000-9da12d9c8551de2507be
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-03di-0900000000-12dd42d00be1feb2ea6f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-0900000000-57c9bc614d9bbbfeed6b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00dj-0900000000-375b0df9797eb0a3db5f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0fdk-1900000000-04c230e802b08770ccd4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-0900000000-b707acd2982b875d2b8a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-014i-0900000000-f3590054822872902032
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0a4i-1900000000-7d7916641e9f2b8c2a1d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0adi-8900000000-5bbc248c0ddc66e4fe40
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004i-9300000000-af8ce8ce2cdd535404e9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0159-0900000000-f2fafb87963f9f1c6960
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0uxr-2900000000-b54ca44315664cba912a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0udi-4900000000-881b25fed45874c66e13
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0ugi-9500000000-1fadd0dd0beb4816b39d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004j-9000000000-61011b8f179c08d62b62
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-QFT , negativeLC-MS/MSsplash10-03di-0900000000-32c82b77af021d75c50c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0900000000-01e028bfa6568f5b6c73
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03k9-0900000000-a6ef0d80ad589128e08c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0900000000-40299b1fe53fcb9eecd0
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dj-0900000000-86d7c17c9ef430bd35b3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dj-0900000000-1804022689692d453a61
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-9da12d9c8551de2507be
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-12dd42d00be1feb2ea6f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0900000000-c14c5838cb37fa872ab3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00dj-0900000000-375b0df9797eb0a3db5f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0fdk-1900000000-04c230e802b08770ccd4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-a6d3f1554e198f6a8f03
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-764cb0c1210c346e8bd3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-474addf762a49be24ee7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-1900000000-ac89b65a526c832307e0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ab9-3900000000-683ba244d13e2d75c306
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05i0-5900000000-5cdca096026d6d3b9207
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-b707acd2982b875d2b8a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-11cde2cb09790e4e65cf
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-1900000000-a1e4933b8de2ad37fc1a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0adi-8900000000-618cea43e6fe3e029eb0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9300000000-77667b55ec8b2d2f01a9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0159-0900000000-d6da72693f2867eafeeb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0uxr-2900000000-b54ca44315664cba912a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-4900000000-ddb658c2925f26d0d038
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ugi-9500000000-1fadd0dd0beb4816b39d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004j-9000000000-61011b8f179c08d62b62
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0900000000-501938a09fca0bf8890f
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Benzenediols
Direct Parent
Catechols
Alternative Parents
Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Secondary amine / Secondary aliphatic amine / Aromatic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
adrenaline (CHEBI:28918) / Biogenic amines, Adrenalines (C00788)

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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
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 e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
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 oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
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...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
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
Uniprot Name
Alpha-1D adrenergic receptor
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
Uniprot Name
Phenylalanine-4-hydroxylase
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
Uniprot Name
Alpha-2C adrenergic receptor
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]
Details
10. Beta-3 adrenergic receptor
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
Uniprot Name
Beta-3 adrenergic receptor
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 ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name
SOD1
Uniprot ID
P00441
Uniprot Name
Superoxide dismutase [Cu-Zn]
Molecular Weight
15935.685 Da
References
  1. Wright GS, Antonyuk SV, Kershaw NM, Strange RW, Samar Hasnain S: Ligand binding and aggregation of pathogenic SOD1. Nat Commun. 2013;4:1758. doi: 10.1038/ncomms2750. [PubMed:23612299]

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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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
Substrate
Inhibitor
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, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
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
Substrate
Inhibitor
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
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]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2017 14:13