Identification

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Name
Epinephrine
Accession Number
DB00668  (APRD00450, EXPT00496)
Type
Small Molecule
Groups
Approved, Vet approved
Description

Epinephrine, also known as adrenaline, is a hormone and neurotransmitter and produced by the adrenal glands that can also be used as a drug due to its various important functions. Though it has long been used in the treatment of hypersensitivity reactions, epinephrine in the auto-injector form (EpiPen) has been available since 1987 in the USA. Many new products/biosimilars and dosage routes have been approved under various names over the last several decades 10, 11, 12. On August 16, 2018, Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths 8. Dosage delivery routes for epinephrine include intravenous, inhalation, nebulization, intramuscular injection, and subcutaneous injection.

In general, the most common uses of parenteral epinephrine are to relieve respiratory distress due to bronchospasm, to provide rapid relief of hypersensitivity (anaphylactic or anaphylactoid) reactions to drugs, animal serums and other allergens, and to prolong the action of infiltration anesthetics 19. In addition to the above functions, epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest 3, 4. It can be used in severe cases of croup 14.

Structure
Thumb
Synonyms
  • (−)-(R)-epinephrine
  • (−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol
  • (−)-adrenaline
  • (R)-(-)-Adnephrine
  • (R)-(-)-Adrenaline
  • (R)-(-)-Epinephrine
  • (R)-(-)-Epirenamine
  • (R)-(−)-adrenaline
  • 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
  • Adrénaline
  • 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 hydrochlorideWBB047OO3855-31-2ATADHKWKHYVBTJ-FVGYRXGTSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdrenaclickInjection1 mg/1mLIntramuscular; SubcutaneousSciele Pharma, Inc.2009-12-152013-08-19Us
AdrenaclickInjection0.3 mg/0.3mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252014-11-01Us
AdrenaclickInjection0.15 mg/0.15mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252014-11-01Us
AdrenaclickInjection1 mg/1mLIntramuscular; SubcutaneousSciele Pharma, Inc.2009-12-152013-08-19Us
Adrenaclick 0.15mg Auto-injectorSolutionIntramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada
Adrenaclick 0.30mg Auto-injectorSolutionIntramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada
AdrenalinInjection1 mg/1mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables and Vaccines, Inc.2019-08-13Not applicableUs
AdrenalinInjection1 mg/1mLIntracardiac; Intramuscular; Intraspinal; Intravenous; SubcutaneousJHP Pharmaceuticals, LLC.2007-10-012013-07-31Us
AdrenalinInjection1 mg/1mLIntracardiac; Intramuscular; Intraspinal; Intravenous; SubcutaneousJHP Pharmaceuticals, LLC.2007-10-012013-07-31Us
AdrenalinInjection1 mg/1mLIntramuscular; Intraocular; SubcutaneousRemedy Repack2015-03-242017-03-20Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EpinephrineInjection0.3 mg/0.3mLSubcutaneousSina Health Inc2010-04-01Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousHF Acquisition Co LLC, DBA HealthFirst2018-09-14Not applicableUs
EpinephrineInjection0.15 mg/0.15mLSubcutaneousMedical Purchasing Solutions, Llc2010-04-01Not applicableUs
EpinephrineInjection0.15 mg/0.15mLSubcutaneousLineage Therapeutics2010-04-012018-04-30Us
EpinephrineInjection0.3 mg/0.3mLIntramuscular; SubcutaneousREMEDYREPACK INC.2019-08-26Not applicableUs
EpinephrineInjection0.15 mg/0.15mLSubcutaneousSina Health Inc2010-04-01Not applicableUs
EpinephrineInjection0.15 mg/0.15mLSubcutaneousHF Acquisition Co LLC, DBA HealthFirst2018-09-14Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousA-S Medication Solutions2010-04-01Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousPreferreed Pharmaceuticals Inc.2016-04-14Not applicableUs
EpinephrineInjection0.15 mg/0.3mLIntramuscular; SubcutaneousTeva Pharmaceuticals USA, Inc.2019-08-19Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Crown-pak Max 4-plySolution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1984-03-29Not applicableUs
Gingi-pak Cotton CoilSolution1.18 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1987-06-26Not applicableUs
Gingi-pak Max 2-plySolution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1984-03-29Not applicableUs
Gingi-pak Max Soft-twist No 1Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1987-06-26Not applicableUs
Gingi-pak Max Soft-twist No 2Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1985-01-11Not applicableUs
Gingi-pak Max Soft-twist No 3Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1985-01-11Not applicableUs
Gingi-pak Max Z-twist No 00Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1995-05-24Not applicableUs
Gingi-pak Max Z-twist No 1Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1995-05-24Not applicableUs
Gingi-pak Max Z-twist No 2Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1995-05-24Not applicableUs
Gingi-pak Max Z-twist No 3Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1995-05-24Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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 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% Citanest Forte Dental With Epinephrine 1:200,000Epinephrine (0.005 mg) + Prilocaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical2011-01-18Not applicableCanada
Ana-kitEpinephrine hydrochloride (1 mg) + Chlorpheniramine maleate (2 mg)Liquid; TabletIntramuscular; Oral; SubcutaneousMiles Canada Inc. Pharmaceutical Division1995-12-311998-09-25Canada
Ana-kit (2mg/tab Orl, 1mg/ml Liq Sc Im)Epinephrine (1 mg) + Chlorpheniramine maleate (2 mg)Liquid; TabletIntramuscular; Oral; SubcutaneousHollister Stier Laboratories Llc1997-05-132002-09-05Canada
Anakit Insect Sting Treatment KitEpinephrine (1 mg) + Chlorpheniramine maleate (2 mg)Liquid; TabletOral; ParenteralHollister Stier, Unit Pharm, Division Of Miles Canada Inc.1964-12-311998-09-25Canada
ArticadentEpinephrine bitartrate (0.005 mg/1mL) + Articaine hydrochloride (40 mg/1mL)Injection, solutionSubcutaneousDentsply Pharmaceutical2000-04-03Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AdrenalinEpinephrine (1 mg/1mL)InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; SubcutaneousJHP Pharmaceuticals, LLC.2007-10-012013-07-31Us
AdrenalinEpinephrine (1 mg/1mL)InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; SubcutaneousJHP Pharmaceuticals, LLC.2007-10-012013-07-31Us
Adyphren Amp II KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitTopicalAsclemed Usa, Inc.2016-10-27Not applicableUs
Adyphren Amp KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitTopicalAsclemed Usa, Inc.2016-10-27Not applicableUs
Adyphren II KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitTopicalAsclemed Usa, Inc.2016-10-04Not applicableUs
Adyphren KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitTopicalAsclemed Usa, Inc.2016-10-04Not applicableUs
Crown-pak Max 4-plyEpinephrine hydrochloride (0.197 mg/10mm)SolutionDental; Oral; PeriodontalGingi-Pak a Division of the Belport1984-03-29Not applicableUs
EphinephrineEpinephrine (0.1 mg/1mL)Injection, solutionIntravenousGeneral Injectables & Vaccines2010-08-012017-01-01Us
EpinephrineEpinephrine (0.1 mg/1mL)InjectionParenteralAmphastar Pharmaceuticals, Inc.1976-12-012010-09-02Us
EpinephrineEpinephrine (0.1 mg/1mL)Injection, solutionEndotracheal; Intracardiac; IntravenousHF Acquisition Co LLC, DBA HealthFirst2018-09-17Not applicableUs
International/Other Brands
Epi EZ Pen JR
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[C@H](O)C1=CC(O)=C(O)C=C1

Pharmacology

Indication

Epinephrine injection is indicated in the emergency treatment of allergic reactions (Type I) including anaphylaxis to stinging insects (e.g., order Hymenoptera, which include bees, wasps, hornets, yellow jackets and fire ants) and biting insects (e.g., triatoma, mosquitos), allergen immunotherapy, foods, drugs, diagnostic testing substances (e.g., radiocontrast media) and other allergens, as well as idiopathic anaphylaxis or exercise-induced anaphylaxis. Injectable epinephrine is intended for immediate/urgent administration in patients, who are found to be at increased risk for anaphylaxis, including individuals with a history of anaphylaxis. Selection of the appropriate dosage strength is determined according to body weight Label.

Epinephrine's cardiac effects may be of use in restoring cardiac rhythm in cardiac arrest due to various causes but is not used in cardiac failure or in hemorrhagic, traumatic, or cardiogenic shock 17.

Epinephrine is used as a hemostatic agent. It is also used in treating mucosal congestion of hay fever, rhinitis, and acute sinusitis; to relieve bronchial asthmatic paroxysms; in syncope due to complete heart block or carotid sinus hypersensitivity; for symptomatic relief of serum sickness, urticaria, angioneurotic edema; for resuscitation in cardiac arrest following anesthetic accidents; in simple (open angle) glaucoma; for relaxation of uterine musculature and to inhibit uterine contractions. Epinephrine injection can be utilized to prolong the action of local anesthetics 17.

In addition to the above, epinephrine is used as an over the counter (OTC) agent for the intermittent symptoms of asthma, such as wheezing, tightness of chest and shortness of breath 18. It is also used for the maintenance of mydriasis during intraocular surgery 15.

Associated Conditions
Pharmacodynamics

Epinephrine is a sympathomimetic drug. It causes an adrenergic receptive mechanism on effector cells and mimics all actions of the sympathetic nervous system except those on the facial arteries and sweat glands 17.

Important effects of epinephrine include increased heart rate, myocardial contractility, and renin release via beta-1 receptors. Beta-2 effects produce bronchodilation which may be useful as an adjunct treatment of asthma exacerbations as well as vasodilation, tocolysis, and increased aqueous humor production 15. In croup, nebulized epinephrine is associated with both clinically and statistically significant transient reduction of croup symptoms 30 minutes post-treatment 7. Epinephrine also alleviates pruritus, urticaria, and angioedema and may be helpful in relieving gastrointestinal and genitourinary symptoms associated with anaphylaxis because of its relaxing effects on the smooth muscle of the stomach, intestine, uterus, and urinary bladder Label.

Mechanism of action

Epinephrine acts on alpha and beta-adrenergic receptors. Epinephrine acts on alpha and beta receptors and is the strongest alpha receptor activator 17. Through its action on alpha-adrenergic receptors, epinephrine minimizes the vasodilation and increased the vascular permeability that occurs during anaphylaxis, which can cause the loss of intravascular fluid volume as well as hypotension. Epinephrine relaxes the smooth muscle of the bronchi and iris and is a histamine antagonist, rendering it useful in treating the manifestations of allergic reactions and associated conditions 19. This drug also produces an increase in blood sugar and increases glycogenolysis in the liver 17. Through its action on beta-adrenergic receptors, epinephrine leads to bronchial smooth muscle relaxation that helps to relieve bronchospasm, wheezing, and dyspnea that may occur during anaphylaxis Label.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Humans
AAlpha-1B adrenergic receptor
agonist
Humans
ABeta-1 adrenergic receptor
agonist
Humans
ABeta-2 adrenergic receptor
agonist
Humans
AAlpha-2A adrenergic receptor
agonist
Humans
AAlpha-2B adrenergic receptor
agonist
Humans
UAlpha-1D adrenergic receptor
antagonist
Humans
UTumor necrosis factor
antagonist
agonist
Humans
Additional Data Available
Adverse Effects

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Contraindications

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Blackbox Warnings

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Absorption

Following I.V. (intravenous) injection, epinephrine disappears rapidly from the blood stream. Subcutaneously or I.M. (intramuscular) administered epinephrine has a rapid onset and short duration of action. Subcutaneous (SC) administration during asthmatic attacks may produce bronchodilation within 5 to 10 minutes, and maximal effects may occur within 20 minutes. The drug becomes fixed in the tissues rapidly 17, Label.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Epinephrine is rapidly inactivated mainly by enzymic transformation to metanephrine or normetanephrine, either of which is then conjugated and excreted in the urine in the form of both sulfates and glucuronides. Either sequence results in the formation of 3-methoxy-4- hydroxy-mandelic acid(vanillylmandelic acid, VMA) which is shown to be detectable in the urine 17. Epinephrine is rapidly inactivated in the body mostly by the enzymes COMT (catechol-O-methyltransferase) and MAO (monoamine oxidase). The liver is abundant in the above enzymes, and is a primary, although not essential, tissue in the degradation process 13.

Route of elimination

The majority of the dose of epinephrine is seen excreted in the urine 13, Label. About 40% of a parenteral dose of epinephrine is excreted in urine as metanephrine, 40% as VMA, 7% as 3-methoxy-4-hydroxyphenoglycol, 2% as 3,4-dihydroxymandelic acid, and the rest as acetylated derivatives. These metabolites are excreted mainly as the sulfate conjugates and, to a lesser extent, the glucuronide conjugates. Only small amounts of the drug are excreted completely unchanged 16.

Half life

The plasma half-life is approximately 2-3 minutes. However, when administered by subcutaneous or intramuscular injection, local vasoconstriction may delay absorption so that epinephrine's effects may last longer than the half-life suggests 13.

Clearance

Intravenous injection produces an immediate and intensified response. Following intravenous injection, epinephrine disappears rapidly from the blood stream 19.

Toxicity

Skin, LD50 = 62 mg/kg (rat) MSDS

Pregnancy

Epinephrine is teratogenic in rats when given in doses about 25 times the human doses. It is unknown whether epinephrine can cause fetal harm when administered to a pregnant woman or can affect reproduction capacity. Epinephrine should be given to a pregnant woman only if clearly required in critical situations/emergencies 19.

Labor and Delivery Parenteral administration of epinephrine, if used as support for blood pressure during low or other spinal anesthesia for delivery, can lead to the acceleration of fetal heart rate and should not be used in obstetrics when maternal blood pressure is higher than 130/80. Epinephrine may delay the second stage of labour.

Common and generalized adverse effects: Transient and minor side effects of anxiety, headache, fear, and palpitations may occur with therapeutic doses of epinephrine, especially in hyperthyroid individuals. Repeated local injections may result in necrosis at sites of injection due to vascular constriction. Cerebral hemorrhage; hemiplegia; subarachnoid hemorrhage; anginal pain in patients with angina pectoris; anxiety; restlessness; throbbing headache; tremor; weakness; dizziness; pallor; respiratory difficulty; palpitation; apprehensiveness; sweating; nausea; vomiting Label.

Cardiovascular effects: Inadvertently induced high arterial blood pressure may result in angina pectoris (especially when coronary insufficiency is present), cardiac ischemia, or aortic rupture Label, 15. Epinephrine may cause serious cardiac arrhythmias in patients not suffering from heart disease and patients with organic heart disease receiving drugs that sensitize the cardiac muscle. With the injection of epinephrine 1:1,000, a paradoxical but transient lowering of blood pressure, bradycardia and apnea may occur immediately post-injection Label.

Cerebrovascular hemorrhage: Overdosage or accidental I.V. injection of epinephrine may lead to cerebrovascular hemorrhage resulting from the sharp rise in blood pressure Label.

Renal vasoconstriction: Parenterally administered epinephrine initially may produce constriction of renal blood vessels and decrease urine formation. High doses may cause complete renal shutdown 19.

Pulmonary edema: Fatality may also result from pulmonary edema due to the peripheral constriction and cardiac stimulation produced by epinephrine injection Label.

Digital vasoconstriction: Since epinephrine is a strong vasoconstrictor, accidental injection into the digits, hands or feet may lead to the loss of blood flow to the affected area. Treatment should be directed at vasodilation in addition to further treatment of anaphylaxis Label.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Aromatic L-Aminoacid Decarboxylase DeficiencyDisease
Tyrosine MetabolismMetabolic
Catecholamine BiosynthesisMetabolic
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
AlkaptonuriaDisease
HawkinsinuriaDisease
Tyrosinemia, Transient, of the NewbornDisease
Tyrosine Hydroxylase DeficiencyDisease
Dopamine beta-Hydroxylase DeficiencyDisease
Monoamine Oxidase-A Deficiency (MAO-A)Disease
Epinephrine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Epinephrine.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Epinephrine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Epinephrine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazole1-benzylimidazole may decrease the hypertensive activities of Epinephrine.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Epinephrine.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of 2,5-Dimethoxy-4-ethylamphetamine can be increased when used in combination with Epinephrine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of 2,5-Dimethoxy-4-ethylthioamphetamine can be increased when used in combination with Epinephrine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Epinephrine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe risk or severity of adverse effects can be increased when Epinephrine is combined with 3,5-diiodothyropropionic acid.
3,5-DiiodotyrosineThe risk or severity of adverse effects can be increased when Epinephrine is combined with 3,5-Diiodotyrosine.
Additional Data Available
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    Extended Description

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  • Severity
    Severity

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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]
  3. Otto CW, Yakaitis RW, Blitt CD: Mechanism of action of epinephrine in resuscitation from asphyxial arrest. Crit Care Med. 1981 Apr;9(4):321-4. [PubMed:7214942]
  4. Callaway CW: Epinephrine for cardiac arrest. Curr Opin Cardiol. 2013 Jan;28(1):36-42. doi: 10.1097/HCO.0b013e32835b0979. [PubMed:23196774]
  5. Shao H, Li CS: Epinephrine in Out-of-hospital Cardiac Arrest: Helpful or Harmful? Chin Med J (Engl). 2017 Sep 5;130(17):2112-2116. doi: 10.4103/0366-6999.213429. [PubMed:28836556]
  6. 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]
  7. Bjornson C, Russell K, Vandermeer B, Klassen TP, Johnson DW: Nebulized epinephrine for croup in children. Cochrane Database Syst Rev. 2013 Oct 10;(10):CD006619. doi: 10.1002/14651858.CD006619.pub3. [PubMed:24114291]
  8. Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths. [Link]
  9. Epinephrine, by Injection: NIH [Link]
  10. Symjepi Approval History [Link]
  11. FDA approves Auvi-Q [Link]
  12. Epipen.ca [Link]
  13. Medicines UK document [Link]
  14. Croup: American Family Physician Document [Link]
  15. NIH STAT pearls [Link]
  16. PubChem: Epinephrine [Link]
  17. Epinephrine FDA label [File]
  18. Primatene Prescribing Info [File]
  19. Pfizer Monograph [File]
External Links
Human Metabolome Database
HMDB0000068
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
Guide to Pharmacology
GtP Drug Page
HET
ALE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Epinephrine
ATC Codes
A01AD01 — EpinephrineR03AK01 — Epinephrine and other drugs for obstructive airway diseasesB02BC09 — EpinephrineC01CA24 — EpinephrineS01EA01 — EpinephrineR01AA14 — EpinephrineR03AA01 — EpinephrineS01EA51 — Epinephrine, combinations
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 (459 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentPain1
0Not Yet RecruitingBasic ScienceDepression1
0Not Yet RecruitingTreatmentParathyroid Adenomas / Thyroid1
0RecruitingTreatmentDiabetes Complications1
1CompletedNot AvailableImmune System1
1CompletedNot AvailableInfection NOS1
1CompletedNot AvailableSafety of Neosaxitoxin in Healthy Volunteers1
1CompletedHealth Services ResearchUnderdosing of Local Anesthetics, Initial Encounter1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentAnesthetics, Local / Hip Fracture / Perioperative Pain1
1CompletedTreatmentCardiac Arrest / Cardio Respiratory Arrest1
1CompletedTreatmentOvercoming the Failure of Anesthesia in the Mandibular Teeth1
1Not Yet RecruitingTreatmentPostoperative pain1
1TerminatedOtherAnaesthesia therapy / Analgesia / Local Anesthesia1
1, 2CompletedTreatmentAsthma1
1, 2CompletedTreatmentAsthma / Bronchospasm / Dyspnea / Wheezing1
1, 2CompletedTreatmentRadical Mastectomy1
1, 2RecruitingPreventionChronic Rhinosinusitis (Diagnosis)1
1, 2RecruitingTreatmentInjection Site Reactions / Systemic Reactions1
1, 2RecruitingTreatmentLung Cancers / Postoperative pain1
1, 2TerminatedTreatmentAsthma2
1, 2Unknown StatusTreatmentAnaesthesia therapy1
2CompletedNot AvailablePostoperative pain1
2CompletedPreventionIrreversible Pulpitis1
2CompletedPreventionPainful Irreversible Pulpitis1
2CompletedPreventionRotator Cuff Syndrome1
2CompletedTreatmentAbdominal Pain1
2CompletedTreatmentAcute Lung Injury (ALI)1
2CompletedTreatmentAnaphylaxis / Angioedema / Bronchospasm / Hypotension1
2CompletedTreatmentAsthma1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentCardiac Arrest1
2CompletedTreatmentHeart Arrest1
2CompletedTreatmentCaudal epidural block therapy / Herniorrhaphy / Regional Anesthesia1
2CompletedTreatmentHip Fracture / Local Anesthesia / Postoperative pain1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentLaceration1
2CompletedTreatmentPostoperative pain4
2CompletedTreatmentShock, Cardiogenic1
2CompletedTreatmentShock, Septic1
2Not Yet RecruitingTreatmentBronchiolitis1
2RecruitingBasic ScienceAutonomic Failure / Diabetes Mellitus (DM) / Hypoglycemia1
2RecruitingTreatmentCesarean Delivery1
2RecruitingTreatmentIntraoperative Bleeding1
2RecruitingTreatmentLocal Anesthesia / Wounds Injuries1
2RecruitingTreatmentPostoperative pain1
2SuspendedTreatmentApical Periodontitis / Caries,Dental3
2TerminatedSupportive CareReferred Pain1
2TerminatedTreatmentTraumatic Femur Fracture1
2, 3Active Not RecruitingTreatmentTotal Hip Arthroplasty (THA)1
2, 3CompletedOtherLocal Anesthesia1
2, 3CompletedPreventionHypospadias1
2, 3CompletedTreatmentIrreversible Pulpitis1
2, 3CompletedTreatmentPostoperative pain1
2, 3Not Yet RecruitingPreventionPostoperative pain1
2, 3Not Yet RecruitingPreventionSurgical Site Infections / Venous Thromboembolism (VTE)1
2, 3Not Yet RecruitingTreatmentLocal Anesthetics Causing Adverse Effects in Therapeutic Use / Opioid Dependence / Postoperative pain / Thoracic Diseases1
2, 3RecruitingPreventionBleeding / Hemoptysis / Lung Transplant; Complications / Lung Transplant; Complications, Mechanical1
2, 3RecruitingTreatmentAnaesthesia therapy1
2, 3SuspendedPreventionPost-operative Cognitive Dysfunction1
2, 3TerminatedTreatmentBronchiolitis / Children1
3CompletedNot AvailableLocal Anesthesia1
3CompletedSupportive CareHemorrhoids1
3CompletedTreatmentAcute Upper Gastrointestinal Bleeding1
3CompletedTreatmentAcute Viral Bronchiolitis1
3CompletedTreatmentAsthma4
3CompletedTreatmentBiceps Tendonitis1
3CompletedTreatmentCardiac Arrest2
3CompletedTreatmentCardiac Output, Low1
3CompletedTreatmentIntraoperative Blood Loss1
3CompletedTreatmentIrreversible Pulpitis1
3CompletedTreatmentModerate or Severe Submental Fullness1
3CompletedTreatmentPain1
3CompletedTreatmentPostoperative Pain Intensity / Rescue Pain Requirements1
3CompletedTreatmentRhinitis, Allergic, Nonseasonal / Rhinitis, Allergic, Perennial1
3CompletedTreatmentRhinitis, Allergic, Seasonal1
3CompletedTreatmentUterine Leiomyomas1
3Not Yet RecruitingTreatmentEarly Gastric Cancer / Neoplasm, Gastric1
3RecruitingSupportive CareMalignant Neoplasms of Male Genital Organs1
3RecruitingTreatmentBronchiolitis1
3RecruitingTreatmentIntervertebral Disc Degeneration / Prolapsed Lumbar Disc / Spondylolisthesis1
3RecruitingTreatmentKnee Replacement Surgery / Osteoarthritis (OA) / Pain Management1
3RecruitingTreatmentKnee Replacement Surgery / Pain Management1
3RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Stage 11
3TerminatedSupportive CarePain1
3Unknown StatusTreatmentChronic Rhinosinusitis1
3Unknown StatusTreatmentGoitre / Neoplasms, Thyroid1
4Active Not RecruitingTreatmentColorectal Cancers / Crohn's Disease (CD) / Digestive System Diseases / Gastrointestinal Cancers / Gastrointestinal Diseases / Inflammatory Bowel Diseases (IBD) / Intestinal Diseases / Pain / Pain, Neuropathic / Postoperative pain1
4Active Not RecruitingTreatmentEndoscopic Sinus Surgery / Polyps, Nasal1
4Active Not RecruitingTreatmentVaricosities of the great saphenous vein1
4CompletedNot AvailableAnaesthesia / Caudal epidural block therapy / Orthopaedic Disorders1
4CompletedBasic SciencePain1
4CompletedDiagnosticFree Flap / Head and Neck Carcinoma / Hypotension / Oral Cancers1
4CompletedHealth Services ResearchBronchiolitis1
4CompletedOtherPain1
4CompletedOtherPeriodontitis1
4CompletedPreventionAnaesthesia / Therapeutic Agent Toxicity1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedPreventionApplication Site Discomfort / Medical Device Discomfort1
4CompletedPreventionArthritis / Joint Dysfunction1
4CompletedPreventionArthrosis, Unspecified, Ankle and Foot1
4CompletedPreventionBacteremia / Tooth Extraction Status Nos1
4CompletedPreventionGeneral Surgery / Pain1
4CompletedPreventionHypotension / Maternal Hypotension1
4CompletedPreventionPostoperative Hemorrhages / Postoperative pain1
4CompletedPreventionSpinal Anaesthesia / Spinal Anesthetics Causing Adverse Effects in Therapeutic Use1
4CompletedScreeningPostoperative pain1
4CompletedSupportive CareAnaesthesia therapy1
4CompletedSupportive CareCesarean Section / Spinal Anaesthesia1
4CompletedSupportive CareHandling of Auto-injectors1
4CompletedSupportive CarePain2
4CompletedSupportive CareTransversus Abdominis Plane Block1
4CompletedTreatmentAcetabular Labrum Tear / Femoroacetabular Impingement / Hip Dysplasia1
4CompletedTreatmentAnaesthesia therapy / General Surgery / Pain / Varicosities of the great saphenous vein1
4CompletedTreatmentAnaphylaxis1
4CompletedTreatmentAnesthetics, Local / Hip Fracture / Postoperative pain1
4CompletedTreatmentArthroplasty, Replacement, Hip1
4CompletedTreatmentArthroplasty / Osteoarthritis (OA)1
4CompletedTreatmentAsthma1
4CompletedTreatmentBronchiolitis2
4CompletedTreatmentBronchiolitis Acute1
4CompletedTreatmentCardiac Arrest1
4CompletedTreatmentCardiac Dysrhythmia1
4CompletedTreatmentCardiac Output Change Following Ephedrine, Phenylephrine, Norepinephrine, Ondansetron / Cardiac Output, Low1
4CompletedTreatmentCardiopulmonary Bypass Graft1
4CompletedTreatmentCardiovascular Response to Epinephrine1
4CompletedTreatmentCervical Intraepithelial Neoplasia (CIN)1
4CompletedTreatmentFemur Fractures / Postoperative pain1
4CompletedTreatmentFracture Bone / Pain1
4CompletedTreatmentFracture, Ankle / Postoperative pain1
4CompletedTreatmentGastroscopy1
4CompletedTreatmentHip Injuries / Orthopaedic Related Pain (Musculoskeletal Pain)1
4CompletedTreatmentIrreversible Pulpitis1
4CompletedTreatmentIrreversible Pulpitis / Pain1
4CompletedTreatmentKnee Osteoarthritis (Knee OA)3
4CompletedTreatmentKnee Replacement, Total1
4CompletedTreatmentLocal Anesthesia of the Skin3
4CompletedTreatmentMigraine1
4CompletedTreatmentMolar, Third1
4CompletedTreatmentObturator Nerve Block / Total Hip Replacement1
4CompletedTreatmentOpen Reduction Internal Fixation(ORIF) of Lateral Malleolus1
4CompletedTreatmentOsteoarthritis, Hip2
4CompletedTreatmentOther Peripheral Nerve Disease1
4CompletedTreatmentPain2
4CompletedTreatmentPain, Acute1
4CompletedTreatmentCaudal epidural block therapy / Pain / Total Knee Arthroplasty (TKA)1
4CompletedTreatmentPopliteal Plexus Block / Total Knee Arthroplasty (TKA)1
4CompletedTreatmentPost Thoracic Surgery1
4CompletedTreatmentPostoperative pain3
4CompletedTreatmentRecession, Gingival1
4CompletedTreatmentShock, Cardiogenic1
4CompletedTreatmentSnake Bites1
4CompletedTreatmentTotal Hip Arthroplasty (THA)1
4CompletedTreatmentTotal Hip and Knee Arthroplasty / Total Hip Arthroplasty (THA)1
4CompletedTreatmentTotal Knee Arthroplasty (TKA)1
4CompletedTreatmentTrigger Finger1
4Enrolling by InvitationSupportive CareHemodynamics Instability1
4Enrolling by InvitationTreatmentKnee Osteoarthritis (Knee OA)1
4Not Yet RecruitingBasic ScienceCesarean Section / Pregnancy1
4Not Yet RecruitingHealth Services ResearchUpper Gastrointestinal Hemorrhage1
4Not Yet RecruitingOtherLocal Anesthetic Drug Adverse Reaction / Local Infiltration / Pulp Disease, Dental1
4Not Yet RecruitingPreventionPain / Supratentorial Brain Tumor1
4Not Yet RecruitingPreventionStress Urinary Incontinence (SUI)1
4Not Yet RecruitingSupportive CareTeeth, Impacted1
4Not Yet RecruitingTreatmentCardiac Arrest, Out-Of-Hospital / Sudden Cardiac Arrest / Ventricular Fibrillation / Ventricular Tachycardia-Pulseless1
4Not Yet RecruitingTreatmentCardiothoracic Surgery1
4Not Yet RecruitingTreatmentCerebral Palsy (CP) / Hip Dysplasia / Postoperative pain1
4Not Yet RecruitingTreatmentColorectal Polyps1
4RecruitingBasic ScienceDistribution of Ropivacaine in Erector Spinae Plane Block1
4RecruitingOtherAdverse Drug Events / Cataracts / Mydriasis1
4RecruitingOtherLocal Anesthesia / Pain1
4RecruitingPreventionPost-ERCP Acute Pancreatitis1
4RecruitingPreventionPostoperative pain1
4RecruitingTreatmentAnesthesia Complications / Anesthesia Morbidity / Dental Implant Failed / Surgical Complications From Local Anesthesia1
4RecruitingTreatmentAnesthesia; Regional / Postoperative pain1
4RecruitingTreatmentCardiac Arrest1
4RecruitingTreatmentCroup / Epinephrine Neublizer Treatment / Epinephrine, Administration, Inhalation1
4RecruitingTreatmentLaceration / Pain, Acute1
4RecruitingTreatmentOsteoarthritis of the Shoulder / Pain Management / Post-Operative Pain / Total Shoulder Arthroplasty1
4RecruitingTreatmentPostoperative pain1
4RecruitingTreatmentRobotic Lung Surgery1
4RecruitingTreatmentShock1
4RecruitingTreatmentVideo-assisted Thoracic Surgery (VATS) / Video-assisted Thoracoscopic Surgery (VATS)1
4SuspendedTreatmentPostoperative pain1
4TerminatedOtherCataracts1
4TerminatedTreatmentAbscesses1
4TerminatedTreatmentArthroplasty, Replacement, Knee1
4TerminatedTreatmentCicatrix1
4TerminatedTreatmentDegenerative Joint Disease / Osteoarthritis (OA)1
4TerminatedTreatmentHemorrhoids1
4TerminatedTreatmentRsv Bronchiolitis1
4TerminatedTreatmentShoulder Pain1
4Unknown StatusNot AvailableChronic Rhinosinusitis1
4Unknown StatusPreventionOral Hemorrhage1
4Unknown StatusTreatmentBronchiolitis1
4WithdrawnSupportive CarePain Management / Total Knee Arthroplasty (TKA)1
4WithdrawnTreatmentArthroplasty, Replacement, Knee / Knee Osteoarthritis (Knee OA)1
4WithdrawnTreatmentArthroplasty, Replacement, Knee / Osteoarthritis (OA) / Postoperative pain1
4WithdrawnTreatmentKnee Osteoarthritis (Knee OA)1
4WithdrawnTreatmentPain1
Not AvailableActive Not RecruitingPreventionPost-Operative Nausea and Vomiting (PONV) / Postoperative pain1
Not AvailableActive Not RecruitingTreatmentEdema / Pain / Trismus1
Not AvailableActive Not RecruitingTreatmentHeel Fat Pad Atrophy1
Not AvailableCompletedNot AvailableCardiac Arrest1
Not AvailableCompletedNot AvailableDeath, Sudden,Cardiac / Heart Arrest1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableKnee Replacement Surgery1
Not AvailableCompletedNot AvailableMethaemoglobinaemia1
Not AvailableCompletedNot AvailableRadius Fractures2
Not AvailableCompletedNot AvailableSpinal Anaesthesia1
Not AvailableCompletedNot AvailableSpinal Anaesthesia / Total Knee Replacement Arthroplasty1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedBasic ScienceHypotension / Pain1
Not AvailableCompletedBasic ScienceVascular Function in Healthy Volunteers1
Not AvailableCompletedHealth Services ResearchCataracts1
Not AvailableCompletedOtherAnesthetics, Local / Brachial Plexus Block1
Not AvailableCompletedOtherStress Urinary Incontinence (SUI)1
Not AvailableCompletedPreventionAgitation States as Acute Reaction to Gross Stress1
Not AvailableCompletedPreventionHypoglycemia / Respiratory Distress1
Not AvailableCompletedPreventionHypotension1
Not AvailableCompletedPreventionHypotension After Reperfusion in Liver Transplantation1
Not AvailableCompletedPreventionOphthalmic Artery / Peribulbar Block1
Not AvailableCompletedPreventionPost-ERCP Acute Pancreatitis1
Not AvailableCompletedPreventionPostoperative pain / Wisdom Tooth1
Not AvailableCompletedSupportive CareAnaesthesia therapy / Postoperative pain1
Not AvailableCompletedSupportive CareAnesthetics, Local1
Not AvailableCompletedSupportive CareOsteoarthritis (OA) / Post-traumatic; Arthrosis1
Not AvailableCompletedSupportive CarePosterior Spine Surgery1
Not AvailableCompletedSupportive CarePostoperative pain1
Not AvailableCompletedTreatmentAcute on Chronic Liver Failure1
Not AvailableCompletedTreatmentAdverse Reaction to Epinephrine / Blood, Injection, Injury Type Phobia / Gastrointestinal Ulcer Haemorrhage1
Not AvailableCompletedTreatmentAnaesthesia therapy1
Not AvailableCompletedTreatmentAnaphylaxis1
Not AvailableCompletedTreatmentBlood Pressures / Epistaxis1
Not AvailableCompletedTreatmentBrain Swelling / Craniotomy / Craniotomy [E04.525.190] / General Surgery / Intracranial Aneurysms / Neurosurgery / Scoliosis1
Not AvailableCompletedTreatmentBronchiolitis2
Not AvailableCompletedTreatmentBronchiolitis / Infections, Respiratory Syncytial Virus1
Not AvailableCompletedTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Postoperative pain1
Not AvailableCompletedTreatmentDental Anxiety / Local Anaesthetic1
Not AvailableCompletedTreatmentFracture of Neck of Femur1
Not AvailableCompletedTreatmentHypotension / Shock1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis of the Shoulder / Osteoarthritis, Hip1
Not AvailableCompletedTreatmentCaudal epidural block therapy / Mastectomy1
Not AvailableCompletedTreatmentPain1
Not AvailableCompletedTreatmentPeptic Ulcer1
Not AvailableCompletedTreatmentPost Surgical Pain1
Not AvailableCompletedTreatmentPosterior Knee Infiltration1
Not AvailableCompletedTreatmentPostoperative pain3
Not AvailableCompletedTreatmentPulpitis dental1
Not AvailableCompletedTreatmentSquamous Cell Carcinoma (SCC) / Superficial Basal Cell Carcinoma1
Not AvailableCompletedTreatmentTotal Knee Arthroplasty (TKA)1
Not AvailableCompletedTreatmentFace edema1
Not AvailableEnrolling by InvitationNot AvailableBlood Transfusions / Catecholamine Treatment / Fetal Myocardial Function / Maternal Obesity During Childbirth / Medical Closere of Arterial Duct / Newborn Myocardial Function1
Not AvailableNot Yet RecruitingNot AvailableCardiac Arrest1
Not AvailableNot Yet RecruitingPreventionChronic Rhinosinusitis (Diagnosis) / Nasal Septum Deviation / Polyps, Nasal / Postoperative Agitation: Impaired Awareness, Abnormal Cognitive Function, Confusion, and Verbal and Physical Agitation During Recovery From General Anesthesia1
Not AvailableNot Yet RecruitingPreventionDysphonia / Postoperative pain / Swallowing Disorders1
Not AvailableNot Yet RecruitingPreventionPostoperative pain1
Not AvailableNot Yet RecruitingTreatmentEfficacy and Safety of VATS Block1
Not AvailableNot Yet RecruitingTreatmentHypotension and Shock1
Not AvailableRecruitingBasic ScienceDental and gingival conditions / Oral Soft Tissue Conditions / Vasoconstriction1
Not AvailableRecruitingOtherUpper Extremity Injury1
Not AvailableRecruitingPreventionAcute Pancreatitis (AP)1
Not AvailableRecruitingSupportive CarePain Management1
Not AvailableRecruitingTreatmentAcute Upper Gastrointestinal Bleeding / Tumor Bleeding1
Not AvailableRecruitingTreatmentAnesthesia, Dental / Tooth Extractions1
Not AvailableRecruitingTreatmentBleeding Ulcers1
Not AvailableRecruitingTreatmentBlood Loss2
Not AvailableRecruitingTreatmentChronic Lung Diseases / Lung Cancers1
Not AvailableRecruitingTreatmentChronic Rhinosinusitis1
Not AvailableRecruitingTreatmentClavicle Fractures1
Not AvailableRecruitingTreatmentHeart Failure1
Not AvailableRecruitingTreatmentKnee Arthropathy1
Not AvailableRecruitingTreatmentPostoperative pain1
Not AvailableRecruitingTreatmentRespiratory Distress Score1
Not AvailableRecruitingTreatmentShock, Septic1
Not AvailableSuspendedPreventionEpisiotomy; Complications / Local Anesthesia / Second Degree Perineal Tear During Delivery - Delivered1
Not AvailableTerminatedHealth Services ResearchCongenital Disorders1
Not AvailableTerminatedOtherCataracts1
Not AvailableTerminatedPreventionEndoscopic Retrograde Cholangiopancreatography / Pancreatitis1
Not AvailableTerminatedTreatmentBreast Cancer / Postoperative pain1
Not AvailableTerminatedTreatmentLaparoscopic Colorectal Resection1
Not AvailableTerminatedTreatmentRenal Insufficiency,Chronic1
Not AvailableUnknown StatusNot AvailableBreastfeeding Outcomes / Neonatal Neurobehavior1
Not AvailableUnknown StatusPreventionIntravenous Injections1
Not AvailableUnknown StatusTreatmentAnaesthesia therapy1
Not AvailableUnknown StatusTreatmentArrhythmia / Bradycardia / High Blood Pressure (Hypertension) / Hypotension / Tachycardia1
Not AvailableUnknown StatusTreatmentBronchiolitis1
Not AvailableUnknown StatusTreatmentHypospadias Repair1
Not AvailableUnknown StatusTreatmentOsteoarthritis (OA)1
Not AvailableUnknown StatusTreatmentPain1
Not AvailableWithdrawnNot AvailableType 1 Insulin-Dependent Diabetes Mellitus2
Not AvailableWithdrawnPreventionVaginal Delivery1
Not AvailableWithdrawnSupportive CarePain1
Not AvailableWithdrawnTreatmentHepatorenal Syndrome1
Not AvailableWithdrawnTreatmentUpper Eyelid Surgery1

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
  • Adamis Laboratories
  • Amend
  • American Regent
  • Amphastar Pharmaceuticals
  • APP Pharmaceuticals
  • Armstrong Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Baroli
  • Bayer Healthcare
  • Belport Co. Inc.
  • Bioniche Pharma
  • Cardinal Health
  • Carestream Health Inc.
  • Catalent Pharma Solutions
  • Claris Lifesciences Inc.
  • Cura Pharmaceutical Co. Inc.
  • DENTSPLY International
  • Deproco Inc.
  • Dey Pharma LP
  • Eastman Kodak Co. Dental Products
  • General Injectables and Vaccines Inc.
  • Greenstone LLC
  • Henry Schein Inc.
  • Hikma Pharmaceuticals
  • Hollister-Stier Laboratories LLC
  • Hospira Inc.
  • JHP Pharmaceuticals LLC
  • Jordan Pharmaceuticals Inc.
  • Luitpold Pharmaceuticals Inc.
  • Mckesson Corp.
  • Medical Products Laboratories Inc.
  • Meridian Medical Technologies Inc.
  • Monarch Pharmacy
  • Nephro-Tech Inc.
  • North Safety Products
  • Novocol Pharmaceutical Canada
  • Pascal Co. Inc.
  • Pharmedium
  • Phillips Medical
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Professional Co.
  • Prometic Pharma Inc.
  • Sciele Pharma Inc.
  • Septodont Inc.
  • Shionogi Pharma Inc.
  • Sintetica SA
  • Smiths Medical ASD Inc.
  • Taylor Pharmaceuticals
  • Verus Pharmaceuticals Inc.
  • Walgreen Co.
  • West-Ward Pharmaceuticals
  • Wyeth Pharmaceuticals
Dosage forms
FormRouteStrength
InjectionIntramuscular; Subcutaneous1 mg/1mL
InjectionSubcutaneous0.15 mg/0.15mL
SolutionIntramuscular
InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous1 mg/1mL
InjectionIntramuscular; Intraocular; Subcutaneous1 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous1 mg/1mL
SolutionNasal
SolutionIntramuscular; Intravenous; Subcutaneous
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
InjectionSubmucosal
InjectionIntramuscular; Subcutaneous.15 mg/1
InjectionIntramuscular; Subcutaneous0.3 mg/1
Injection, solutionIntramuscular0.1 mg/0.1mL
Injection, solutionIntramuscular0.15 mg/0.15mL
Injection, solutionIntramuscular0.3 mg/0.3mL
Aerosol, meteredRespiratory (inhalation)
Injection, solutionEpidural; Infiltration; Intracaudal
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural
Injection, solutionEpidural; Intracaudal; Perineural
Injection, solutionPerineural
Injection, solutionInfiltration; Other
Injection, solutionSubmucosal
Injection, solutionParenteral
KitIntravenous
SprayRespiratory (inhalation)
Solution / dropsOphthalmic
Injection, solutionIntravenous0.1 mg/1mL
LiquidIntramuscular
InjectionIntracardiac; Intravenous0.1 mg/1mL
InjectionIntramuscular; Subcutaneous0.15 mg/0.3mL
InjectionParenteral0.1 mg/1mL
InjectionParenteral1 mg/1mL
InjectionSubcutaneous0.15 mg/1
InjectionSubcutaneous0.3 mg/0.3mL
InjectionSubcutaneous0.3 mg/1
Injection, solutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous1 mg/1mL
Injection, solutionEndotracheal; Intracardiac; Intravenous0.1 mg/1mL
Injection, solutionIntracardiac; Intramuscular; Intravenous; Subcutaneous1 mg/1mL
Injection, solutionIntracardiac; Intravenous0.1 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous1 mg/1mL
Injection, solutionIntramuscular; Subcutaneous1 mg/1mL
Injection, solutionSubcutaneous1 mg/1mL
Injection, solution, concentrateIntravenous1 mg/1mL
LiquidIntracardiac; Intravenous
SolutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous
SolutionIntracardiac; Intravenous
KitIntramuscular; Subcutaneous1 mg/1mL
InjectionIntramuscular0.3 mg/0.3mL
SolutionIntramuscular0.3 mg
InjectionIntramuscular0.15 mg/0.3mL
SolutionIntramuscular0.15 mg
InjectionIntramuscular; Subcutaneous1 mg/1000mL
KitTopical
PackingDental
SolutionDental; Oral; Periodontal1.18 mg/10mm
SolutionDental; Oral; Periodontal0.197 mg/10mm
SolutionDental; Oral; Periodontal0.7 mg/1
SolutionInfiltration
SolutionEpidural; Infiltration
Injection, solutionDental; Infiltration
Injection, solutionEpidural
Injection, solutionEpidural; Infiltration; Other
Injection, solutionInfiltration
PatchIontophoresis
LiquidEpidural; Infiltration
AerosolRespiratory (inhalation)0.16 ug/1
SprayTopical
SolutionTopical
GelTopical
LiquidDental; Subcutaneous
LiquidSubcutaneous
SolutionDental; Oral; Periodontal1200 mg/15mL
AerosolRespiratory (inhalation)125 ug/1
InhalantOral0.22 mg/1
CapsuleRespiratory (inhalation)0.22 mg/1
KitRespiratory (inhalation)0.22 mg/1
Injection, solutionEpidural; Retrobulbar
InjectionEpidural; Parenteral
InjectionEpidural; Parenteral; Retrobulbar
LiquidInfiltration
Injection, solutionSubcutaneous
KitInfiltration; Topical
LiquidParenteral; Topical
InjectionIntramuscular; Subcutaneous0.15 mg/0.15mL
InjectionIntramuscular; Subcutaneous0.3 mg/0.3mL
SolutionIntramuscular; Subcutaneous
InjectionInfiltration
Injection, solutionInfiltration; Perineural
SolutionEpidural
LiquidEpidural
InjectionDental
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)
US5665071No1997-09-092013-05-27Us
US7794432No2010-09-142025-09-11Us
US8870827No2014-10-282025-09-11Us
US7449012No2008-11-112025-09-11Us
US8048035No2011-11-012025-09-11Us
US7297136No2007-11-202025-01-18Us
US7621891No2009-11-242025-02-04Us
US6629968No2003-10-072020-06-30Us
US6635045No2003-10-212021-06-29Us
US9149579No2015-10-062025-07-19Us
US8425462No2013-04-232024-11-23Us
US8231573No2012-07-312028-11-25Us
US8016788No2011-09-132025-03-21Us
US9259539No2016-02-162026-02-01Us
US8206360No2012-06-262027-02-27Us
US9238108No2016-01-192027-01-22Us
US8226610No2012-07-242029-04-10Us
US7918823No2011-04-052024-11-23Us
US8608698No2013-12-172024-11-23Us
US8021344No2011-09-202029-11-02Us
US8361029No2013-01-292024-11-23Us
US8313466No2012-11-202024-11-23Us
US7731690No2010-06-082025-01-15Us
US9278182No2016-03-082026-02-01Us
US8920377No2014-12-302024-11-23Us
US7731686No2010-06-082026-06-01Us
US8926594No2015-01-062026-03-31Us
US7749194No2010-07-062028-10-30Us
US9056170No2015-06-162024-11-23Us
US7947017No2011-05-242028-03-12Us
US9295657No2016-03-292035-03-13Us
US9119876No2015-09-012035-03-13Us
US9283197No2016-03-152034-08-15Us
US9586010No2017-03-072025-09-11Us
US7905352No2011-03-152027-04-12Us
US9724471No2017-08-082027-05-23Us
US9737669No2017-08-222024-11-23Us
US9833573No2017-12-052024-11-23Us
US10039728No2018-08-072034-08-14Us
US10004700No2018-06-262034-08-14Us
US10130592No2018-11-202035-03-13Us
US8367734No2013-02-052026-01-26Us
US10314977No2004-11-232024-11-23Us
US10335549No2005-04-302025-04-30Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)211.5 https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine
boiling point (°C)215MSDS
water solubilityless than 0.1 mg/mL at 64° Fhttps://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Melting-Point
logP-1.37https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Vapor-Pressure
Caco2 permeability-6.02https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Stability
pKa8.59 (at 25 °C)https://pubchem.ncbi.nlm.nih.gov/compound/epinephrine#section=Stability
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
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. 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
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. 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
Humans
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. Khasar SG, McCarter G, Levine JD: Epinephrine produces a beta-adrenergic receptor-mediated mechanical hyperalgesia and in vitro sensitization of rat nociceptors. J Neurophysiol. 1999 Mar;81(3):1104-12. doi: 10.1152/jn.1999.81.3.1104. [PubMed:10085337]
  4. Strosberg AD: Structure, function, and regulation of adrenergic receptors. Protein Sci. 1993 Aug;2(8):1198-209. doi: 10.1002/pro.5560020802. [PubMed:8401205]
Kind
Protein
Organism
Humans
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]
  5. Reiner S, Ambrosio M, Hoffmann C, Lohse MJ: Differential signaling of the endogenous agonists at the beta2-adrenergic receptor. J Biol Chem. 2010 Nov 12;285(46):36188-98. doi: 10.1074/jbc.M110.175604. Epub 2010 Sep 13. [PubMed:20837485]
Kind
Protein
Organism
Humans
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]
  7. Ariens EJ, Simonis AM: Physiological and pharmacological aspects of adrenergic receptor classification. Biochem Pharmacol. 1983 May 15;32(10):1539-45. [PubMed:6134529]
Kind
Protein
Organism
Humans
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]
  6. Ariens EJ, Simonis AM: Physiological and pharmacological aspects of adrenergic receptor classification. Biochem Pharmacol. 1983 May 15;32(10):1539-45. [PubMed:6134529]
Kind
Protein
Organism
Humans
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
Humans
Pharmacological action
Unknown
Actions
Antagonist
Agonist
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]
  2. Liao J, Keiser JA, Scales WE, Kunkel SL, Kluger MJ: Role of epinephrine in TNF and IL-6 production from isolated perfused rat liver. Am J Physiol. 1995 Apr;268(4 Pt 2):R896-901. doi: 10.1152/ajpregu.1995.268.4.R896. [PubMed:7733399]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data based on findings of in vitro studies.
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. Gervasini G, Martinez C, Benitez J, Agundez JA: Effect of neurotransmitters on NADPH-cytochrome P450 reductase in vitro activity. Drug Metab Lett. 2007 Aug;1(3):172-5. [PubMed:19356039]
  2. Gervasini G, Martinez C, Agundez JA, Garcia-Gamito FJ, Benitez J: Inhibition of cytochrome P450 2C9 activity in vitro by 5-hydroxytryptamine and adrenaline. Pharmacogenetics. 2001 Feb;11(1):29-37. [PubMed:11207028]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Enzyme action supported only by one in vitro study.
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. Gervasini G, Martinez C, Benitez J, Agundez JA: Effect of neurotransmitters on NADPH-cytochrome P450 reductase in vitro activity. Drug Metab Lett. 2007 Aug;1(3):172-5. [PubMed:19356039]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Bryan-Lluka LJ, O'Donnell SR: Dopamine and adrenaline, but not isoprenaline, are substrates for uptake and metabolism in isolated perfused lungs of rats. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jul;346(1):20-6. [PubMed:1407001]
  2. Eisenhofer G, Finberg JP: Different metabolism of norepinephrine and epinephrine by catechol-O-methyltransferase and monoamine oxidase in rats. J Pharmacol Exp Ther. 1994 Mar;268(3):1242-51. [PubMed:8138937]
  3. Medicines UK document [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...

Components:
References
  1. Bryan-Lluka LJ, O'Donnell SR: Dopamine and adrenaline, but not isoprenaline, are substrates for uptake and metabolism in isolated perfused lungs of rats. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jul;346(1):20-6. [PubMed:1407001]
  2. Eisenhofer G, Finberg JP: Different metabolism of norepinephrine and epinephrine by catechol-O-methyltransferase and monoamine oxidase in rats. J Pharmacol Exp Ther. 1994 Mar;268(3):1242-51. [PubMed:8138937]
  3. Medicines UK document [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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]
  3. Jonker JW, Wagenaar E, Van Eijl S, Schinkel AH: Deficiency in the organic cation transporters 1 and 2 (Oct1/Oct2 [Slc22a1/Slc22a2]) in mice abolishes renal secretion of organic cations. Mol Cell Biol. 2003 Nov;23(21):7902-8. [PubMed:14560032]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2019 16:12