Epinephrine

Identification

Summary

Epinephrine is a hormone and neurotransmitter used to treat allergic reactions, to restore cardiac rhythm, and to control mucosal congestion, glaucoma, and asthma.

Brand Names
Adrenalin, Allerject, Anapen, Articadent, Astracaine, Auvi-Q, Citanest, Citanest Forte, Emerade, Epipen, Lignospan, Marcaine, Marcaine With Epinephrine, Octocaine, Octocaine With Epinephrine, Orabloc, Scandonest, Sensorcaine, Sensorcaine With Epinephrine, Septanest, Septocaine, Symjepi, Ultacan, Ultracaine, Vivacaine, Xylocaine, Xylocaine With Epinephrine, Zorcaine
Generic Name
Epinephrine
DrugBank Accession Number
DB00668
Background

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 20. 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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 183.2044
Monoisotopic: 183.089543287
Chemical Formula
C9H13NO3
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
  • Adrenaline
  • Adrénaline
  • Epinefrin
  • Epinefrina
  • Epinephrin
  • Epinephrine
  • Epinephrinum
  • L-Adrenaline
  • Levoepinephrine
External IDs
  • NSC-62786

Pharmacology

Indication

Epinephrine injection is indicated in the emergency treatment of type I allergic reactions, including anaphylaxis. It is also used to increase mean arterial blood pressure in adult patients with hypotension associated with septic shock.17

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 18.

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 18.

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 19. It is also used for the maintenance of mydriasis during intraocular surgery 15.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAnaphylaxis••••••••••••
Treatment ofAnaphylaxis•••••••••••••••••••••• •••••••••• ••••••••• •••••••••• ••••••••• •••••••••••
Treatment ofAngioneurotic edema••••••••••••
Induction ofBleeding••••••••••••
Treatment ofBronchospasm••• •••••••••••
Contraindications & Blackbox Warnings
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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 18.

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 18. 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 20. This drug also produces an increase in blood sugar and increases glycogenolysis in the liver 18. 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
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 18, 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 18. 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.

Hover over products below to view reaction partners

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 20.

Adverse Effects
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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 20.

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 20.

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.

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
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Epinephrine.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Epinephrine.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Epinephrine.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Epinephrine.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Epinephrine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Epinephrine acetateM1NJX34RVJ97289-42-4CEBXQLPKMNOIHN-FVGYRXGTSA-N
Epinephrine bitartrate30Q7KI53AK51-42-3YLXIPWWIOISBDD-NDAAPVSOSA-N
Epinephrine hydrochlorideWBB047OO3855-31-2ATADHKWKHYVBTJ-FVGYRXGTSA-N
International/Other Brands
Epi EZ Pen JR
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AdrenaclickInjection0.3 mg/0.3mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252014-11-01US flag
AdrenaclickInjection1 mg/1mLIntramuscular; SubcutaneousSciele Pharma, Inc.2009-12-152013-08-19US flag
AdrenaclickInjection0.15 mg/0.15mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252014-11-01US flag
AdrenaclickInjection1 mg/1mLIntramuscular; SubcutaneousSciele Pharma, Inc.2009-12-152013-08-19US flag
Adrenaclick 0.15mg Auto-injectorSolution0.15 mg / 0.15 mLIntramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EpinephrineInjection, solution1 mg/1mLIntramuscular; SubcutaneousAMERICAN REGENT, INC.2023-01-31Not applicableUS flag
EpinephrineInjection0.3 mg/0.3mLIntramuscularA-S Medication Solutions2016-12-152017-02-16US flag
EpinephrineInjection0.15 mg/0.3mLIntramuscularMedical Purchasing Solutions, Llc2016-12-15Not applicableUS flag
EpinephrineInjection0.15 mg/0.3mLIntramuscular; Subcutaneousbryant ranch prepack2019-08-19Not applicableUS flag
EpinephrineInjection0.3 mg/0.3mLSubcutaneousPreferreed Pharmaceuticals Inc.2016-04-14Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Crown-pak Max 4-plySolution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1984-03-29Not applicableUS flag
Gingi-pak Cotton CoilSolution1.18 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1987-06-26Not applicableUS flag
Gingi-pak Max 2-plySolution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1984-03-29Not applicableUS flag
Gingi-pak Max Soft-twist No 1Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1987-06-26Not applicableUS flag
Gingi-pak Max Soft-twist No 2Solution0.197 mg/10mmDental; Oral; PeriodontalGingi-Pak a Division of the Belport1985-01-11Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2% Lidocaine and Epinephrine 1:100,000 Injection USPEpinephrine (0.01 mg / mL) + Lidocaine hydrochloride (20 mg / mL)LiquidInfiltrationAlveda Pharmaceuticals Inc2008-12-01Not applicableCanada flag
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Epinephrine (0.005 mg / mL) + Articaine hydrochloride (40 mg / mL)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada flag
4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml)Epinephrine bitartrate (0.005 mg / mL) + Articaine hydrochloride (40 mg / mL)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada flag
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Epinephrine bitartrate (0.01 mg / mL) + Articaine hydrochloride (40 mg / mL)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada flag
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Epinephrine (0.01 mg / mL) + Articaine hydrochloride (40 mg / mL)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AdrenalinEpinephrine (1 mg/1mL)InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; SubcutaneousJHP Pharmaceuticals, LLC.2007-10-012013-07-31US flag
AdrenalinEpinephrine (1 mg/1mL)InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; SubcutaneousJHP Pharmaceuticals, LLC.2007-10-012013-07-31US flag
Adyphren Amp II KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitTopicalAsclemed Usa, Inc.2016-10-27Not applicableUS flag
Adyphren Amp KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitTopicalAsclemed Usa, Inc.2016-10-27Not applicableUS flag
Adyphren II KitEpinephrine (1 mg/1mL) + Isopropyl alcohol (70 mL/100mL)KitIntramuscular; Intraocular; SubcutaneousAsclemed Usa, Inc.2016-10-04Not applicableUS flag

Categories

ATC Codes
A01AD01 — EpinephrineR03AK01 — Epinephrine and other drugs for obstructive airway diseasesB02BC09 — EpinephrineC01CA24 — EpinephrineS01EA01 — EpinephrineR01AA14 — EpinephrineR03AA01 — EpinephrineS01EA51 — Epinephrine, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Catechol / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
adrenaline (CHEBI:28918) / Biogenic amines, Adrenalines (C00788)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
YKH834O4BH
CAS number
51-43-4
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

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. [Article]
  2. Bennett MR: One hundred years of adrenaline: the discovery of autoreceptors. Clin Auton Res. 1999 Jun;9(3):145-59. [Article]
  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. [Article]
  4. Callaway CW: Epinephrine for cardiac arrest. Curr Opin Cardiol. 2013 Jan;28(1):36-42. doi: 10.1097/HCO.0b013e32835b0979. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. FDA Approved Drug Products: ADRENALIN (epinephrine injection) 1 mg/mL, for intramuscular, subcutaneous, and intravenous use [Link]
  18. Epinephrine FDA label [File]
  19. Primatene Prescribing Info [File]
  20. Pfizer Monograph [File]
Human Metabolome Database
HMDB0000068
KEGG Drug
D00095
KEGG Compound
C00788
PubChem Compound
5816
PubChem Substance
46509097
ChemSpider
5611
BindingDB
44818
RxNav
3992
ChEBI
28918
ChEMBL
CHEMBL679
ZINC
ZINC000000039089
Therapeutic Targets Database
DAP000066
PharmGKB
PA449470
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
ALE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Adrenaline
PDB Entries
2hkk / 4a7u / 4ldo / 7brn / 7bts / 8thl
FDA label
Download (459 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionPostoperative pain1
4Active Not RecruitingTreatmentAnesthesia Morbidity / Anesthetics Adverse Reaction / Dental Implant Failed / Surgical Complications From Local Anesthesia1
4Active Not RecruitingTreatmentRotator Cuff Injuries / Rotator Cuff Tears / Subacromial Impingement / Subacromial Impingement Syndrome1
4Active Not RecruitingTreatmentTraumatic Rib Fracture(s)1
4CompletedNot AvailableAnaesthesia / Nerve Block / Orthopaedic Disorders1

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
SolutionIntramuscular0.15 mg / 0.15 mL
SolutionIntramuscular0.30 mg / 0.30 mL
InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous1 mg/1mL
InjectionIntramuscular; Intraocular; Subcutaneous1 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous1 mg/1mL
SolutionIntracardiac; Intramuscular; Intraspinal; Intravenous; Ophthalmic; Subcutaneous1 mg / mL
Injection, solution0.25 mg/1ml
Injection, solution0.5 mg/1ml
Injection, solution1 mg/1ml
Injection, solutionParenteral1 mg/10ml
Injection, solutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous0.25 mg/mL
Injection, solutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous0.25 mg/1ml
Injection, solutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous0.5 mg/mL
Injection, solutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous1 mg/mL
SolutionTopical1 mg / mL
SolutionIntravenous; Subcutaneous1 mg
SolutionIntravenous; Subcutaneous100000 mg
SolutionIntramuscular; Intravenous; Subcutaneous1 mg
Injection, solutionIntravenous
Injection, solutionParenteral0.5 MG/ML
Injection, solutionParenteral1 MG/ML
Injection, solution
InjectionIntramuscular; Intravenous; Subcutaneous1 mg/ml
KitIntramuscular; Intraocular; Subcutaneous
SolutionIntramuscular0.3 mg / 0.3 mL
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
Injection, solution0.3 ml
InjectionPercutaneous
SolutionDental
Injection, solutionDental
InjectionInfiltration; Submucosal
Injection, solutionDental; Infiltration
Injection, solutionBuccal
Injection, solutionSubmucosal0.01 mg
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, metered; injection; kit; tablet; tablet, chewableIntramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual
Aerosol, meteredRespiratory (inhalation)0.5 %
Injection, solutionEpidural; Infiltration; Intracaudal
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural
Injection, solutionParenteral150 MICROGRAMMI/0.3ML
Injection, solutionParenteral300 MICROGRAMMI/0.3ML
Injection, solutionParenteral500 MICROGRAMMI/0.3ML
Injection, solutionSubmucosal
Injection, solutionParenteral
KitIntravenous
Injection, solution; kit; solutionEpidural; Infiltration; Intracaudal; Perineural; Topical
Aerosol, metered; injection; kit; solution; tablet; tablet, chewableIntramuscular; Intravenous; Oral; Respiratory (inhalation); Subcutaneous; Sublingual
SolutionIntravenous
SprayRespiratory (inhalation)3.5 %
Solution / dropsOphthalmic
Injection, solutionIntragingival
Injection, solutionOphthalmic150 MICROGRAMMI
Injection, solutionOphthalmic300 MICROGRAMMI
Injection, solutionOphthalmic500 MICROGRAMMI
SolutionIntramuscular0.5 mg / 0.5 mL
Injection, solutionParenteral150 Mikrogramm
Injection, solutionParenteral300 Mikrogramm
Injection, solutionParenteral500 Mikrogramm
Injection, solutionIntravenous0.1 mg/1mL
LiquidIntramuscular0.3 mg / 0.3 mL
SolutionParenteral1 mg
SolutionIntramuscular; Intravenous; Subcutaneous100000 mg
Injection
InjectionIntracardiac; Intravenous0.1 mg/1mL
InjectionIntramuscular; Subcutaneous0.15 mg/0.3mL
InjectionIntravenous0.1 mg/1mL
InjectionIntravenous1 mg/1mL
InjectionParenteral0.1 mg/1mL
InjectionParenteral1 mg/1mL
InjectionSubcutaneous0.15 mg/0.15mL
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
LiquidIntramuscular1 mg / mL
SolutionNasal1 mg/1mL
Injection; kit; swabIntramuscular; Subcutaneous; Topical
LiquidIntracardiac; Intravenous.1 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg / mL
SolutionIntravenous1 mg / 10 mL
SolutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous1 mg / 1 mL
SolutionEndotracheal; Intramuscular; Intravenous; Subcutaneous1 mg / 1 mL
SolutionIntracardiac; Intravenous1 mg / 10 mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg / 1 mL
KitIntramuscular; Subcutaneous
Injection; kitIntramuscular; Subcutaneous; Topical
KitIntramuscular; Subcutaneous1 mg/1mL
InjectionIntramuscular0.3 mg/0.3mL
Injection, solutionIntramuscular
Injection0.3 mg
InjectionIntramuscular0.15 mg/0.3mL
SolutionIntramuscular0.15 mg / 0.3 mL
Injection0.15 mg
Solution0.5 mg/1ml
InjectionIntramuscular; Subcutaneous1 mg/1000mL
KitTopical
PackingDental.5 mg / 2.54 cm
SolutionDental; Oral; Periodontal1.18 mg/10mm
SolutionDental; Oral; Periodontal0.197 mg/10mm
SolutionDental; Oral; Periodontal0.7 mg/1
Solution0.25 mg/ml
Solution0.5 mg/ml
Solution1 mg/ml
Injection, solutionParenteral150 MICROGRAMMI
Injection, solutionParenteral300 MICROGRAMMI
SolutionEndotracheal; Intravenous2 mg/20ml
SolutionIntradermal; Perineural; Subcutaneous
SolutionParenteral
Injection, solutionSubcutaneous
InjectionEpidural; Infiltration; Intracaudal; Perineural
SolutionEpidural; Infiltration
Injection, solutionEpidural
Injection, solutionEpidural; Infiltration
Injection, solutionInfiltration
Injection, solution
PatchIontophoresis
SolutionIntramuscular
LiquidInfiltration
InjectionIntravascular; Intravenous
InjectionEpidural
LiquidEpidural; Infiltration
AerosolRespiratory (inhalation)0.16 ug/1
SolutionSubcutaneous
SolutionSubcutaneous0.0180 mg
SprayTopical
SolutionTopical
GelTopical
InjectionDental0.01 mg/mL
LiquidDental; Subcutaneous
LiquidSubcutaneous
Injection
SolutionDental; Oral; Periodontal1200 mg/15mL
Injection, solutionIntramuscular0.15 mg/0.3ml
Injection, solutionIntramuscular1 mg/ml
AerosolRespiratory (inhalation)125 ug/1
InhalantOral0.22 mg/1
CapsuleRespiratory (inhalation)0.22 mg/1
KitRespiratory (inhalation)0.22 mg/1
Injection, solution; kit; solutionInfiltration; Perineural; Topical
SolutionInfiltration
InjectionIntramuscular
Injection, solutionPerineural
Injection, solutionEpidural; Intracaudal; Perineural
Injection, solutionEpidural; Retrobulbar
InjectionEpidural; Parenteral
InjectionEpidural; Parenteral; Retrobulbar
Injection, solutionInfiltration; Submucosal
SolutionIntramuscular1.0 mg
KitInfiltration; Topical
LiquidParenteral; Topical
Injection, solutionEndotracheal; Intramuscular; Intravenous; Subcutaneous1 mg/ml
InjectionDental5 mg
InjectionIntramuscular; Subcutaneous0.3 mg/0.3mL
Injection, solutionIntramuscular; Subcutaneous0.15 mg/0.3mL
Injection, solutionIntramuscular; Subcutaneous0.3 mg/0.3mL
SolutionIntramuscular; Subcutaneous0.15 mg / 0.15 mL
SolutionIntramuscular; Subcutaneous0.3 mg / 0.3 mL
InjectionSubmucosal40 mg/ml
SolutionParenteral0.0225 mg
Solution
InjectionParenteral
Injection, solutionInterstitial
InjectionSubmucosal
InjectionInfiltration
Injection, solutionInfiltration; Perineural
SolutionEpidural
InjectionDental0.0125 mg/ml
LiquidEpidural
InjectionDental
Solution1 mg/1ml
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)Region
US5665071No1997-09-092013-05-27US flag
US7794432No2010-09-142025-09-11US flag
US8870827No2014-10-282025-09-11US flag
US7449012No2008-11-112025-09-11US flag
US8048035No2011-11-012025-09-11US flag
US7297136No2007-11-202025-01-18US flag
US7621891No2009-11-242025-02-04US flag
US6629968No2003-10-072020-06-30US flag
US6635045No2003-10-212021-06-29US flag
US9149579No2015-10-062025-07-19US flag
US8425462No2013-04-232024-11-23US flag
US8231573No2012-07-312028-11-25US flag
US8016788No2011-09-132025-03-21US flag
US9259539No2016-02-162026-02-01US flag
US8206360No2012-06-262027-02-27US flag
US9238108No2016-01-192027-01-22US flag
US8226610No2012-07-242029-04-10US flag
US7918823No2011-04-052024-11-23US flag
US8608698No2013-12-172024-11-23US flag
US8021344No2011-09-202029-11-02US flag
US8361029No2013-01-292024-11-23US flag
US8313466No2012-11-202024-11-23US flag
US7731690No2010-06-082025-01-15US flag
US9278182No2016-03-082026-02-01US flag
US8920377No2014-12-302024-11-23US flag
US7731686No2010-06-082026-06-01US flag
US8926594No2015-01-062026-03-31US flag
US7749194No2010-07-062028-10-30US flag
US9056170No2015-06-162024-11-23US flag
US7947017No2011-05-242028-03-12US flag
US9295657No2016-03-292035-03-13US flag
US9119876No2015-09-012035-03-13US flag
US9283197No2016-03-152034-08-15US flag
US9586010No2017-03-072025-09-11US flag
US7905352No2011-03-152027-04-12US flag
US9724471No2017-08-082027-05-23US flag
US9737669No2017-08-222024-11-23US flag
US9833573No2017-12-052024-11-23US flag
US10039728No2018-08-072034-08-14US flag
US10004700No2018-06-262034-08-14US flag
US10130592No2018-11-202035-03-13US flag
US8367734No2013-02-052026-01-26US flag
US10314977No2019-06-112024-11-23US flag
US10335549No2019-07-022025-04-30US flag
US10166344No2019-01-012025-01-21US flag
US10166334No2019-01-012025-01-21US flag
US10737028No2020-08-112024-11-23US flag
US10688244No2020-06-232037-12-21US flag
US10842938No2020-11-242037-12-21US flag
US10960155No2021-03-302026-06-25US flag
US11141540No2021-10-122036-10-20US flag
US11590286No2006-12-122026-12-12US flag
US11083698No2021-08-102039-03-21US flag
US11207280No2021-12-282039-03-21US flag
US10653646No2020-05-192039-03-21US flag
US11771830No2017-12-212037-12-21US flag

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-MSsplash10-0006-9600000000-584d6e44f2be8cb4eeb1
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-1900000000-0d399e6fad3a0ed6f6be
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-8bb84cd6cb6c52fad802
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01w0-2900000000-5db308cee2e3dfc05378
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-0900000000-f28c51358a4d3cb4afdf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-6900000000-4e97c890ddae01e1d7ea
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-3900000000-09e7a330fec840581444
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-146.3216228
predicted
DarkChem Lite v0.1.0
[M-H]-146.8614228
predicted
DarkChem Lite v0.1.0
[M-H]-146.2810228
predicted
DarkChem Lite v0.1.0
[M-H]-141.8482
predicted
DeepCCS 1.0 (2019)
[M+H]+147.3575228
predicted
DarkChem Lite v0.1.0
[M+H]+147.9436228
predicted
DarkChem Lite v0.1.0
[M+H]+146.9951228
predicted
DarkChem Lite v0.1.0
[M+H]+144.24377
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.4668228
predicted
DarkChem Lite v0.1.0
[M+Na]+147.3108228
predicted
DarkChem Lite v0.1.0
[M+Na]+146.4223228
predicted
DarkChem Lite v0.1.0
[M+Na]+150.45146
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. 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. [Article]
  2. Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [Article]
  3. 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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  4. Strosberg AD: Structure, function, and regulation of adrenergic receptors. Protein Sci. 1993 Aug;2(8):1198-209. doi: 10.1002/pro.5560020802. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [Article]
  7. Ariens EJ, Simonis AM: Physiological and pharmacological aspects of adrenergic receptor classification. Biochem Pharmacol. 1983 May 15;32(10):1539-45. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [Article]
  6. Ariens EJ, Simonis AM: Physiological and pharmacological aspects of adrenergic receptor classification. Biochem Pharmacol. 1983 May 15;32(10):1539-45. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]

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. [Article]
  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. [Article]
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54