Identification

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

Epinephrine injection is used for emergency treatment of severe allergic reactions (including anaphylaxis) to insect bites or stings, medicines, foods, or other substances. It can also be used in the treatment of idiopathic anaphylaxis (unknown cause) or exercise-induced anaphylaxis. When given intramuscularly or subcutaneously it has a rapid onset and short duration of action [Label].

In addition to the above function, epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest [3], [4].

This drug has been available since 1987 in the USA, however many new products have been approved under various names over the last several decades [9], [10], [11]. 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 [7].

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
  • 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
AdrenaclickInjection0.3 mg/0.3mLSubcutaneousAmedra Pharmaceuticals LLC2009-11-252014-11-01Us
AdrenaclickInjection1 mg/1mLIntramuscular; SubcutaneousSciele Pharma, Inc.2009-12-152013-08-19Us
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-injectorSolution0.15 mgIntramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada
Adrenaclick 0.30mg Auto-injectorSolution0.30 mgIntramuscularAmedra Pharmaceuticals LLCNot applicableNot applicableCanada
AdrenalinInjection1 mg/1mLIntramuscular; Intraocular; SubcutaneousRemedy Repack2015-03-242017-03-20Us
AdrenalinInjection1 mg/1mLIntramuscular; SubcutaneousRemedy Repack2018-08-03Not applicableUs
AdrenalinInjection1 mg/1mLIntramuscular; SubcutaneousPar Pharmaceutical2014-03-01Not applicableUs
AdrenalinInjection1 mg/1mLIntramuscular; SubcutaneousPar Pharmaceutical2013-07-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EpinephrineInjection0.15 mg/1SubcutaneousGreenstone, Llc2010-03-312012-09-30Us
EpinephrineInjection0.3 mg/0.3mLIntramuscularMedical Purchasing Solutions, Llc2016-12-15Not applicableUs
EpinephrineInjection0.15 mg/0.15mLSubcutaneousMedical Purchasing Solutions, Llc2010-04-01Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousA-S Medication Solutions2010-04-01Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousLineage Therapeutics2010-04-012018-05-31Us
EpinephrineInjection0.3 mg/0.3mLSubcutaneousA-S Medication Solutions2010-04-01Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousImpax Generics2010-04-01Not applicableUs
EpinephrineInjection0.3 mg/0.3mLSubcutaneousPreferreed Pharmaceuticals Inc.2016-04-14Not applicableUs
EpinephrineInjection0.3 mg/1SubcutaneousRebel Distributors2010-03-31Not applicableUs
EpinephrineInjection0.15 mg/0.3mLIntramuscularMedical Purchasing Solutions, Llc2016-12-15Not applicableUs
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 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
Orostat 8%Solution1200 mg/15mLDental; Oral; PeriodontalGingi-Pak a Division of the Belport1990-04-04Not applicableUs
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 Pharmaceutical1997-02-262003-11-28Canada
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 Forte 1:100,000 (0.01mg/ml)Epinephrine (0.01 mg) + Articaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical2004-01-29Not applicableCanada
4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml)Epinephrine (0.01 mg) + Articaine hydrochloride (40 mg)SolutionInfiltrationDentsply Pharmaceutical1997-02-262003-11-28Canada
4% Citanest Forte Dental With Epinephrine 1:200,000Epinephrine (5 mcg) + Prilocaine Hydrochloride (40 mg)LiquidInfiltrationDentsply Pharmaceutical2011-01-18Not applicableCanada
Ana-kitEpinephrine hydrochloride (1 mg) + Chlorpheniramine maleate (2 mg)Liquid; TabletIntramuscular; Oral; SubcutaneousMiles 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)KitIntramuscular; Subcutaneous; TopicalAsclemed Usa, Inc.2016-10-27Not applicableUs
Adyphren Amp KitEpinephrine (1 mg/1mL) + Isopropyl Alcohol (70 mL/100mL)KitIntramuscular; Subcutaneous; TopicalAsclemed Usa, Inc.2016-10-27Not applicableUs
Adyphren II KitEpinephrine (1 mg/1mL) + Isopropyl Alcohol (70 mL/100mL)KitIntramuscular; Intraocular; SubcutaneousAsclemed Usa, Inc.2016-10-04Not applicableUs
Adyphren KitEpinephrine (1 mg/1mL) + Isopropyl Alcohol (70 mL/100mL)KitIntramuscular; Intraocular; SubcutaneousAsclemed Usa, Inc.2016-10-04Not applicableUs
EphinephrineEpinephrine (0.1 mg/1mL)Injection, solutionIntravenousGeneral Injectables & Vaccines2010-08-012017-01-01Us
EpinephrineEpinephrine (0.1 mg/1mL)Injection, solutionEndotracheal; Intracardiac; IntravenousHF Acquisition Co LLC, DBA HealthFirst2018-09-17Not applicableUs
EpinephrineEpinephrine (0.1 mg/1mL)Injection, solutionEndotracheal; Intracardiac; IntravenousCardinal Health1985-05-01Not applicableUs
EpinephrineEpinephrine (1 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousAmerican Regent1994-03-01Not applicableUs
International/Other Brands
Adrenalin / Epi EZ Pen JR / Medihaler-Epi / Twinject
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].

Its 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 [13].

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 [13].

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. Epinephrine acts on alpha and beta receptors and is the strongest alpha receptor activator. Epinephrine relaxes the smooth muscle of the bronchi and iris and is an antagonist of histamine. This drug also produces an increase in blood sugar and increases glycogenolysis in the liver [13].

Mechanism of action

Epinephrine acts on alpha and beta-adrenergic receptors. 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. 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. Epinephrine also alleviates pruritus, urticaria, and angioedema and may work 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].

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-1B adrenergic receptor
agonist
Human
ABeta-1 adrenergic receptor
agonist
Human
ABeta-2 adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
UAlpha-1D adrenergic receptor
antagonist
Human
UTumor necrosis factor
antagonist
agonist
Human
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 [13], [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 detectable in the urine [13]. Epinephrine is rapidly inactivated in the body mostly by the enzymes COMT (catechol-O-methyltransferase) and MAO (monoamine oxidase). The liver is rich in the above enzymes, and is a primary, although not essential, tissue in the degradation process [12].

Route of elimination

The majority of the dose of epinephrine is accounted for by excretion of metabolites in the urine [12], [Label].

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 [12].

Clearance
Not Available
Toxicity

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

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), or aortic rupture [Label].

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].

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Epinephrine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Epinephrine.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Epinephrine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
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.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Epinephrine.
3,5-DinitrocatecholThe metabolism of Epinephrine can be decreased when combined with 3,5-Dinitrocatechol.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Epinephrine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
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. Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths. [Link]
  8. Epinephrine, by Injection: NIH [Link]
  9. Symjepi Approval History [Link]
  10. FDA approves Auvi-Q [Link]
  11. Epipen.ca [Link]
  12. Medicines UK document [Link]
  13. Epinephrine FDA label [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
IUPHAR
479
Guide to Pharmacology
GtP Drug Page
HET
ALE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Epinephrine
ATC Codes
R01AA14 — EpinephrineR03AK01 — Epinephrine and other drugs for obstructive airway diseasesC01CA24 — EpinephrineS01EA51 — Epinephrine, combinationsB02BC09 — EpinephrineA01AD01 — EpinephrineR03AA01 — EpinephrineS01EA01 — Epinephrine
AHFS Codes
  • 12:12.12 — Alpha-and Beta-adrenergic Agonists
  • 34:00.00 — Dental Agents
  • 12:12.00 — Sympathomimetic (Adrenergic) Agents
  • 52:32.00 — Vasoconstrictors
PDB Entries
2hkk / 4a7u / 4ldo
FDA label
Download (459 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceMorton's neuralgia1
0CompletedHealth Services ResearchPain NOS1
0CompletedOtherKnee Prosthesis1
0Not Yet RecruitingPreventionPulpitis - Irreversible1
0RecruitingTreatmentDiabetes Complications1
1Active Not RecruitingOtherSurgery, Colorectal1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableImmune System1
1CompletedBasic ScienceDrug-induced QT Interval Prolongation / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceNociceptive Pain / Peripheral Neuropathic Pain1
1CompletedHealth Services ResearchAnaesthesia therapy1
1CompletedSupportive CareHealthy Volunteers1
1CompletedSupportive CarePostoperative pain1
1CompletedTreatmentCoughing1
1CompletedTreatmentFibromyalgia / Pain, Chronic1
1CompletedTreatmentNeoplasms, Cystic, Mucinous, and Serous1
1CompletedTreatmentPain Management / Pregnancy Termination1
1CompletedTreatmentRadicular syndrome / Sciatica1
1Not Yet RecruitingTreatmentPostoperative pain1
1TerminatedOtherAnaesthesia therapy / Analgesia / Local Anesthesia1
1TerminatedPreventionPostoperative pain1
1TerminatedTreatmentPain, Neuropathic1
1Unknown StatusPreventionPostoperative pain1
1Unknown StatusTreatmentCardiac Arrest / Cardio-respiratory arrest1
1, 2CompletedTreatmentAsthma Bronchial1
1, 2CompletedTreatmentAsthma Bronchial / Bronchospasm / Difficulty Breathing / Wheezing1
1, 2CompletedTreatmentLung Cancers / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2RecruitingTreatmentLung Cancers / Postoperative pain1
1, 2TerminatedTreatmentAsthma Bronchial2
1, 2Unknown StatusTreatmentAnaesthesia therapy1
1, 2WithdrawnTreatmentColorectal Disorders1
1, 2WithdrawnTreatmentPostoperative Pain Management After Total Hip Arthroplasty1
2Active Not RecruitingTreatmentAnaphylaxis / Angioedema / Arterial Hypotension / Bronchospasm1
2CompletedBasic ScienceDiabetic Neuropathic Pain1
2CompletedPreventionDysmenorrhea1
2CompletedPreventionHyperalgesia / Knee Joint Osteoarthrosis / Severe Movement Related Pain1
2CompletedPreventionRotator Cuff Syndrome1
2CompletedSupportive CareDiverticulitis / Inflammatory Bowel Diseases (IBD) / Malignant Neoplasm of Colon1
2CompletedTreatmentAcute Lung Injury (ALI)1
2CompletedTreatmentAllodynia / Central Neuropathic Pain / Spinal Cord Injuries (SCI)1
2CompletedTreatmentArthroplasty, Replacement, Hip1
2CompletedTreatmentCardiac Arrest1
2CompletedTreatmentChronic Pain Syndrome / Prostatitis1
2CompletedTreatmentDysmenorrhea / Endometriosis1
2CompletedTreatmentFascicular Block / Latency Period / Motor Activities / Postoperative pain1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentHeart Arrest1
2CompletedTreatmentHip Pain Etiology Unknown1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentLow Back Pain (LBP)1
2CompletedTreatmentPain NOS1
2CompletedTreatmentPain NOS / Postoperative1
2CompletedTreatmentPain, Neuropathic / Vasoocclusive Sickle Cell Crises Pains1
2CompletedTreatmentPostherpetic Neuralgia1
2CompletedTreatmentShock, Septic1
2CompletedTreatmentShoulder Pain1
2Not Yet RecruitingSupportive CareCancer, Breast1
2Not Yet RecruitingSupportive CareReferred Pain1
2Not Yet RecruitingTreatmentBronchiolitis1
2RecruitingBasic ScienceAutonomic Failure / Diabetes Mellitus (DM) / Hypoglycemia1
2RecruitingSupportive CareMenopausal Hot Flushes1
2RecruitingTreatmentAbdominal Pain (AP)1
2RecruitingTreatmentBladder Pain Syndrome / Interstitial Cystitis1
2RecruitingTreatmentIntraoperative Bleeding1
2RecruitingTreatmentPost-Operative Pain1
2RecruitingTreatmentShock, Cardiogenic1
2TerminatedTreatmentDry Macular Degeneration1
2TerminatedTreatmentPostoperative Hemorrhages / Postoperative pain1
2TerminatedTreatmentTraumatic Femur Fracture1
2Unknown StatusPreventionCancer, Breast1
2WithdrawnTreatmentCerebrovascular Accidents / Strokes1
2WithdrawnTreatmentNeoplasms / Pain NOS1
2WithdrawnTreatmentPain NOS1
2WithdrawnTreatmentPhantom Limb Pain (PLP) / Primary/Secondary Scar Hyperalgesia1
2, 3CompletedTreatmentPain and Anxiety1
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, 3RecruitingPreventionHaemorrhage / Hemoptysis / Lung Transplant; Complications / Lung Transplant; Complications, Mechanical1
2, 3RecruitingTreatmentAnaesthesia therapy1
2, 3RecruitingTreatmentEsotropia / Exotropia / Graves Diseases / Nystagmus / Strabismus1
2, 3RecruitingTreatmentPain NOS1
2, 3RecruitingTreatmentTotal Hip Arthroplasty (THA)1
2, 3SuspendedPreventionPost-operative Cognitive Dysfunction1
2, 3SuspendedSupportive CareCancer-related Pain1
2, 3TerminatedTreatmentBronchiolitis / Children1
2, 3Unknown StatusTreatmentAchilles Tendinopathy / Achilles Tendon Enthesopathy / Insertional Achilles Tendinopathy / Mid-Portion Achilles Tendinopathy / Non-Insertional Achilles Tendinopathy1
3Active Not RecruitingPreventionEpidural; Anesthesia / Spinal Anaesthesia1
3CompletedBasic ScienceBMI >30 kg/m2 / Post-gastrointestinal bypass surgery1
3CompletedPreventionBariatric Surgical Pain1
3CompletedPreventionPost-operative Pain for Total Knee Arthroplasty1
3CompletedTreatmentAbdominal Pain (AP) / Gastroesophageal Reflux Disease / Indigestion / Intestinal Malabsorption1
3CompletedTreatmentAnaesthesia therapy2
3CompletedTreatmentAnkle Sprains1
3CompletedTreatmentAsthma Bronchial2
3CompletedTreatmentBiceps Tendonitis1
3CompletedTreatmentCardiac Arrest3
3CompletedTreatmentCardiac Output, Low1
3CompletedTreatmentChronic Low Back Pain (CLBP)1
3CompletedTreatmentForearm and Arm Surgery1
3CompletedTreatmentIntraoperative Blood Loss1
3CompletedTreatmentIrreversible Pulpitis1
3CompletedTreatmentModerate or Severe Submental Fullness1
3CompletedTreatmentNeoplasms, Colorectal1
3CompletedTreatmentNonviable Pregnancy1
3CompletedTreatmentPain NOS2
3CompletedTreatmentPeripheral Neuropathy1
3CompletedTreatmentPostoperative Pain Intensity / Rescue Pain Requirements1
3CompletedTreatmentPostoperative pain1
3CompletedTreatmentSpinal Anaesthesia1
3CompletedTreatmentUterine Leiomyomas1
3Not Yet RecruitingTreatmentIntervertebral Disc Degeneration / Prolapsed Lumbar Disc / Spondylolisthesis1
3RecruitingPreventionLabour Pain1
3RecruitingSupportive CareMalignant Neoplasms of Male Genital Organs1
3RecruitingSupportive CarePain NOS1
3RecruitingTreatmentAcute Upper Gastrointestinal Bleeding1
3RecruitingTreatmentCancers / Pain With Neuropathic Component1
3RecruitingTreatmentInguinal Hernias / Local Anesthesia / Sedation, Conscious1
3RecruitingTreatmentKnee Replacement Surgery / Osteoarthritis (OA) / Pain Management1
3RecruitingTreatmentLow Back Pain (LBP) / Modic I Discopathy1
3RecruitingTreatmentPostoperative pain1
3TerminatedPreventionTransient Neurologic Syndrome1
3TerminatedTreatmentBursitis / Periarthritis1
3TerminatedTreatmentPostoperative pain1
3Unknown StatusTreatmentCancers / Pain NOS1
3Unknown StatusTreatmentFibromyalgia1
3Unknown StatusTreatmentHealthy Volunteers1
3WithdrawnSupportive CareCesarean Delivery1
3WithdrawnSupportive CareFracture of Lower Limb1
3WithdrawnTreatmentParathyroid Diseases1
4Active Not RecruitingSupportive CareNerve Monitoring / Thyroidectomy1
4CompletedNot AvailableAnaesthesia therapy1
4CompletedNot AvailableAnaesthesia / Caudal epidural block therapy / Orthopaedic Disorders1
4CompletedNot AvailableNeuromuscular Block1
4CompletedBasic SciencePain NOS1
4CompletedDiagnosticArterial Hypotension / Free Flap / Head and Neck Carcinoma / Oral Cancers1
4CompletedHealth Services ResearchBronchiolitis1
4CompletedOtherPain NOS1
4CompletedPreventionAnaesthesia / Toxicity1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedPreventionCardiovascular Morbidity / Intubation Complications1
4CompletedPreventionChildbirth / Parturients1
4CompletedPreventionEsophagogastroduodenoscopy1
4CompletedPreventionGeneral Surgery / Pain NOS1
4CompletedPreventionLaminectomy1
4CompletedPreventionPain on Injection of Propofol,Lidocaine, Alkalinized Lidocaine1
4CompletedPreventionPostoperative Hemorrhages / Postoperative pain1
4CompletedPreventionPostoperative pain2
4CompletedPreventionRetinal Detachment / Retinoschisis / Vitreoretinopathy, Proliferative1
4CompletedPreventionSpinal Anesthetics Causing Adverse Effects in Therapeutic Use1
4CompletedPreventionThroat Pain1
4CompletedScreeningPostoperative pain1
4CompletedSupportive CareAnaesthesia therapy1
4CompletedSupportive CareBMI >30 kg/m2 / General Surgery / Neuromuscular Inhibition / Pain NOS1
4CompletedSupportive CareCesarean Section / Spinal Anaesthesia1
4CompletedSupportive CareDiverticulitis / Malignant Neoplasm of Colon / Post-Operative Pain1
4CompletedSupportive CareHandling of Auto-injectors1
4CompletedSupportive CareLumbar Spine Disc Herniation1
4CompletedTreatmentArthroplasty, Knee Replacement / Postoperative pain1
4CompletedTreatmentArthroplasty, Replacement, Hip1
4CompletedTreatmentArthroplasty / Osteoarthritis (OA)1
4CompletedTreatmentBack Pain / Cervical Pain1
4CompletedTreatmentBronchiolitis Acute1
4CompletedTreatmentCanal Syndrome / Pudendal Neuralgia1
4CompletedTreatmentCardiac Arrest1
4CompletedTreatmentCardiopulmonary Bypass Graft1
4CompletedTreatmentCarpal Tunnel Syndrome (CTS) / Trigger Finger1
4CompletedTreatmentCervical Intraepithelial Neoplasia (CIN)1
4CompletedTreatmentChronic Cough (CC)1
4CompletedTreatmentChronic Migraine1
4CompletedTreatmentCoronary Artery Disease1
4CompletedTreatmentEpicondylitis, Lateral Humeral / Lateral Epicondylitis1
4CompletedTreatmentFeeling Anxious / Nausea / Pain NOS1
4CompletedTreatmentFemur Fractures / Postoperative pain1
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentGastroscopy1
4CompletedTreatmentHallux Valgus1
4CompletedTreatmentHigh Blood Pressure (Hypertension)1
4CompletedTreatmentInjection Site Irritation1
4CompletedTreatmentAdjunct to general anesthesia therapy / Intravenous Anesthesia1
4CompletedTreatmentIrreversible Pulpitis1
4CompletedTreatmentIrreversible Pulpitis / Pain NOS1
4CompletedTreatmentKnee Arthroplasty, Total1
4CompletedTreatmentKnee Osteoarthritis (Knee OA)4
4CompletedTreatmentLocal Anesthesia for Peripheral Intravenous Catheterization / Pain NOS1
4CompletedTreatmentLung Cancers1
4CompletedTreatmentMeniscus Lesion1
4CompletedTreatmentMigrainous Headache1
4CompletedTreatmentNeuromuscular Block1
4CompletedTreatmentOpen Reduction Internal Fixation(ORIF) of Lateral Malleolus1
4CompletedTreatmentNeurocostal neuralgia / Opioid-Related Disorders1
4CompletedTreatmentOsteoarthritis, Hip2
4CompletedTreatmentPain NOS4
4CompletedTreatmentPain NOS / Peripheral Nerve Blocks1
4CompletedTreatmentPain NOS / Post-Operative Nausea and Vomiting (PONV)1
4CompletedTreatmentPain NOS / Pregnancy1
4CompletedTreatmentCaudal epidural block therapy / Pain NOS / Total Knee Arthroplasty (TKA)1
4CompletedTreatmentPain on IV Injection of Propofol1
4CompletedTreatmentPain, Acute1
4CompletedTreatmentPain, Chronic1
4CompletedTreatmentOr Peripheral Nerve Injury (PNI) / Peripheral Neuropathic Pain (PNP) Due to Postherpetic Neuralgia (PHN)1
4CompletedTreatmentPostoperative pain5
4CompletedTreatmentAdjunct to general anesthesia therapy / Propofol Target-controlled Infusion / Thoracic Epidural Anesthesia1
4CompletedTreatmentScoliosis1
4CompletedTreatmentSedation, Conscious1
4CompletedTreatmentShock, Cardiogenic1
4CompletedTreatmentSnake Bites1
4CompletedTreatmentSpinal Anaesthesia1
4CompletedTreatmentSurgical Procedures, Operative1
4CompletedTreatmentThermal Burns1
4CompletedTreatmentToothache1
4CompletedTreatmentTopical Anesthesia1
4CompletedTreatmentTotal Hip Arthroplasty (THA)1
4CompletedTreatmentGallstone formation1
4Enrolling by InvitationOtherCataracts1
4Enrolling by InvitationSupportive CareHemodynamics Instability1
4Enrolling by InvitationTreatmentKnee Osteoarthritis (Knee OA)1
4Enrolling by InvitationTreatmentTotal Hip Arthroplasty (THA)1
4Not Yet RecruitingBasic ScienceCesarean Section / Pregnancy1
4Not Yet RecruitingHealth Services ResearchUpper Gastrointestinal Hemorrhage1
4Not Yet RecruitingPreventionCritical Illness1
4Not Yet RecruitingTreatmentAnesthesia, Dental / Postoperative pain1
4Not Yet RecruitingTreatmentKnee Replacement, Total1
4Not Yet RecruitingTreatmentLocal Anesthesia / Spinal Diseases1
4RecruitingOtherAdverse Drug Events / Cataracts / Mydriasis1
4RecruitingPreventionAnaesthesia therapy / Hip Fractures1
4RecruitingPreventionPost-ERCP Acute Pancreatitis1
4RecruitingPreventionPostoperative pain1
4RecruitingSupportive CarePregnancy1
4RecruitingTreatmentAcetabular Labrum Tear / Femoroacetabular Impingement / Hip Dysplasia1
4RecruitingTreatmentAnaesthesia therapy / Analgesia / Conscious Sedation Failure During Procedure1
4RecruitingTreatmentAnaphylaxis1
4RecruitingTreatmentCardiac Arrest1
4RecruitingTreatmentCervical incompetence1
4RecruitingTreatmentCroup / Epinephrine Neublizer Treatment / Epinephrine, Administration, Inhalation1
4RecruitingTreatmentFracture, Ankle / Postoperative pain1
4RecruitingTreatmentPain NOS1
4RecruitingTreatmentPain, Radiating1
4RecruitingTreatmentPost Operative Pain (Post Laparoscopic Hernia Repair)1
4RecruitingTreatmentSedation therapy1
4RecruitingTreatmentShock1
4RecruitingTreatmentPost-pancreatectomy1
4TerminatedPreventionNausea / Occasional Constipation / Pain NOS / Vomiting1
4TerminatedPreventionPain NOS1
4TerminatedTreatmentAbscesses1
4TerminatedTreatmentArthritis Multiple Joint / Basal Thumb Joint Arthritis / Basilar Joint Arthritis / Carpometacarpal Arthritis / Trapeziometacarpal Arthritis1
4TerminatedTreatmentArthroplasty, Replacement, Knee1
4TerminatedTreatmentDegenerative Joint Disease / Osteoarthritis (OA)1
4TerminatedTreatmentForearm Fractures1
4TerminatedTreatmentPostoperative pain1
4TerminatedTreatmentPulmonary Arterial Hypertension (PAH)1
4TerminatedTreatmentShoulder Pain1
4Unknown StatusNot AvailableChronic Rhinosinusitis1
4Unknown StatusNot AvailableEndophthalmitis / Vitreoretinal Surgery1
4Unknown StatusPreventionDrug Usage1
4Unknown StatusPreventionOral Hemorrhage1
4Unknown StatusSupportive CareInjection Site Irritation1
4Unknown StatusSupportive CareTonsillectomy1
4Unknown StatusTreatmentCholecystolithiasis1
4Unknown StatusTreatmentDilatation and Evacuation / Laminaria Placement / Pain Alleviation1
4Unknown StatusTreatmentIUD Insertion Complication / Pain Control1
4Unknown StatusTreatmentPlanned Abdominal Hysterectomy1
4WithdrawnNot AvailableAdjunct to general anesthesia therapy / Elderly / Surgeries Requiring A Minimum One Day Hospitalization1
4WithdrawnSupportive CarePain Management / Total Knee Arthroplasty (TKA)1
4WithdrawnTreatmentCataract Surgery Anesthesia1
4WithdrawnTreatmentKnee Osteoarthritis (Knee OA)1
4WithdrawnTreatmentPain NOS1
Not AvailableActive Not RecruitingNot AvailableAAT Deficiency / AATD / Alpha-1 Antitrypsin Deficiency / Fibrosis, Liver1
Not AvailableActive Not RecruitingPreventionArterial Hypotension1
Not AvailableActive Not RecruitingPreventionPost-Operative Nausea and Vomiting (PONV) / Postoperative pain1
Not AvailableActive Not RecruitingTreatmentHeel Fat Pad Atrophy1
Not AvailableActive Not RecruitingTreatmentLow Back Pain (LBP) / Osteoarthritis Nos, of Sacroiliac Joint / Sprain of Sacroiliac Ligament1
Not AvailableActive Not RecruitingTreatmentMotor Impairments / Neurological Conditions / Orthopaedic Injury1
Not AvailableActive Not RecruitingTreatmentPost-Operative Pain1
Not AvailableActive Not RecruitingTreatmentRib Fractures1
Not AvailableActive Not RecruitingTreatmentRotator Cuff / Subacromial Impingement Syndrome1
Not AvailableCompletedNot AvailableAcute Gouty Arthritis / Arthritis / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedNot AvailableCancer, Breast1
Not AvailableCompletedNot AvailableDeath, Sudden,Cardiac / Heart Arrest1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableHemodynamic Response1
Not AvailableCompletedNot AvailableKnee Replacement Surgery1
Not AvailableCompletedNot AvailablePain NOS2
Not AvailableCompletedNot AvailablePain, Neuropathic1
Not AvailableCompletedNot AvailableRhytidoplasty1
Not AvailableCompletedNot AvailableSpinal Anaesthesia1
Not AvailableCompletedNot AvailableSpinal Anaesthesia / Total Knee Replacement Arthroplasty1
Not AvailableCompletedNot AvailableThyroid Cancers1
Not AvailableCompletedBasic ScienceArterial Hypotension / Pain NOS1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedDiagnosticPain NOS1
Not AvailableCompletedDiagnosticParesis1
Not AvailableCompletedHealth Services ResearchCataracts1
Not AvailableCompletedOtherPain NOS1
Not AvailableCompletedOtherPain, Neuropathic1
Not AvailableCompletedOtherStress Urinary Incontinence (SUI)1
Not AvailableCompletedPreventionAdult Disease1
Not AvailableCompletedPreventionAgitation States as Acute Reaction to Gross Stress1
Not AvailableCompletedPreventionCognitive Decline1
Not AvailableCompletedPreventionHypoglycemia / Respiratory Distress1
Not AvailableCompletedPreventionHypotension After Reperfusion in Liver Transplantation1
Not AvailableCompletedPreventionOther Intraoperative Cardiac Functional Disturbances During Cardiac Surgery1
Not AvailableCompletedPreventionPain NOS1
Not AvailableCompletedPreventionPost-ERCP Acute Pancreatitis1
Not AvailableCompletedPreventionPostoperative pain1
Not AvailableCompletedSupportive CareColorectal Cancers1
Not AvailableCompletedSupportive CareLabour Pain1
Not AvailableCompletedSupportive CareLaparoscopic Gynecologic Surgery / Paracervical Block / Postoperative pain1
Not AvailableCompletedSupportive CareOsteoarthritis (OA) / Post-traumatic; Arthrosis1
Not AvailableCompletedSupportive CarePain Insensitivity, Congenital1
Not AvailableCompletedSupportive CarePain NOS3
Not AvailableCompletedSupportive CareTrigeminal Neuralgia (TN)1
Not AvailableCompletedTreatmentAdverse Reaction to Epinephrine / Blood, Injection, Injury Type Phobia / Gastrointestinal Ulcer Haemorrhage1
Not AvailableCompletedTreatmentAge-Related Macular Degeneration (AMD)1
Not AvailableCompletedTreatmentAge-Related Macular Degeneration (ARMD) / Central Retinal Vein Occlusion (CRVO) / Diabetic Macular Edema (DME)1
Not AvailableCompletedTreatmentAnaesthesia therapy2
Not AvailableCompletedTreatmentAnaphylaxis1
Not AvailableCompletedTreatmentAnesthetics, Local / Blood Levels of Buffered vs Non-buffered Lidocaine1
Not AvailableCompletedTreatmentArterial Hypotension / Shock1
Not AvailableCompletedTreatmentBronchiolitis2
Not AvailableCompletedTreatmentDiverticulitis / Inflammatory Bowel Diseases (IBD) / Malignant Neoplasm of Colon1
Not AvailableCompletedTreatmentFibromyalgia1
Not AvailableCompletedTreatmentFracture Bone / Pain NOS1
Not AvailableCompletedTreatmentGall Stone Pancreatitis / Gallbladder Inflammation1
Not AvailableCompletedTreatmentGall Stones1
Not AvailableCompletedTreatmentGoiter, Nodular / Graves' Disease / Hyperparathyroidism / Neoplasms, Thyroid / Thyroid Nodules1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis, Hip / Osteoarthritis, Shoulder1
Not AvailableCompletedTreatmentKnee Replacement Surgery / Pain NOS1
Not AvailableCompletedTreatmentLabour Pain1
Not AvailableCompletedTreatmentLateral Epicondylitis1
Not AvailableCompletedTreatmentLumbar Puncture / Topical Analgesia1
Not AvailableCompletedTreatmentMigrainous Headache1
Not AvailableCompletedTreatmentOpioid Consumption / Postoperative pain1
Not AvailableCompletedTreatmentPain Control for Intrauterine Device Insertions1
Not AvailableCompletedTreatmentPain Intensity1
Not AvailableCompletedTreatmentPain NOS8
Not AvailableCompletedTreatmentGallstone formation / Pain NOS1
Not AvailableCompletedTreatmentPartial Thickness Rotator Cuff Tear / Subacromial Impingement Syndrome1
Not AvailableCompletedTreatmentPeptic Ulcers1
Not AvailableCompletedTreatmentPlantar fascial fibromatosis1
Not AvailableCompletedTreatmentPost Operative Pain1
Not AvailableCompletedTreatmentPosterior Knee Infiltration1
Not AvailableCompletedTreatmentPostoperative pain3
Not AvailableCompletedTreatmentPregnancy Termination / Uterine Curettage1
Not AvailableCompletedTreatmentProstate Cancer1
Not AvailableCompletedTreatmentPulpitis dental1
Not AvailableCompletedTreatmentRadius Fractures1
Not AvailableCompletedTreatmentSpine Surgery1
Not AvailableCompletedTreatmentUltrasound Therapy; Complications1
Not AvailableCompletedTreatmentMinor burns1
Not AvailableEnrolling by InvitationNot AvailableBrain Diseases / Cardiovascular Disease (CVD) / Central Nervous System Diseases / Cerebrovascular Disorders / Cerebrovascular Stroke / Ischemia, Brain / Nervous System Diseases / Strokes / Vascular Diseases1
Not AvailableEnrolling by InvitationSupportive CareFemoral Fractures / Postoperative pain1
Not AvailableNot Yet RecruitingPreventionAnaesthesia therapy / Spinal Puncture1
Not AvailableNot Yet RecruitingTreatmentEfficacy and Safety of VATS Block1
Not AvailableNot Yet RecruitingTreatmentHypotension and Shock1
Not AvailableRecruitingNot AvailableCardiac Arrest1
Not AvailableRecruitingNot AvailablePain NOS1
Not AvailableRecruitingOtherUpper Extremity Injury1
Not AvailableRecruitingPreventionAcute Pancreatitis (AP)1
Not AvailableRecruitingPreventionNonvalvular Atrial Fibrillation1
Not AvailableRecruitingTreatmentAbdominal Pain (AP) / Gastro-esophageal Reflux Disease (GERD) / Swallowing Disorders1
Not AvailableRecruitingTreatmentAcute Upper Gastrointestinal Bleeding / Tumor Bleeding1
Not AvailableRecruitingTreatmentBlood Loss2
Not AvailableRecruitingTreatmentFracture of Neck of Femur1
Not AvailableRecruitingTreatmentHip Injuries1
Not AvailableRecruitingTreatmentIUD Insertion Complication1
Not AvailableRecruitingTreatmentPilonidal Sinus1
Not AvailableRecruitingTreatmentPostoperative pain1
Not AvailableRecruitingTreatmentShock, Septic1
Not AvailableRecruitingTreatmentVideo-assisted Thoracic Surgery (VATS) / Video-assisted Thoracoscopic Surgery (VATS)1
Not AvailableTerminatedBasic SciencePain NOS1
Not AvailableTerminatedHealth Services ResearchCongenital Disorders1
Not AvailableTerminatedOtherAbdominal Wall Relaxation After Rectus Sheath Block / Hernia / Postoperative pain1
Not AvailableTerminatedPreventionLaryngospasm1
Not AvailableTerminatedTreatmentHysterectomy1
Not AvailableTerminatedTreatmentInterstitial Cystitis / Painful Bladder Syndrome (PBS)1
Not AvailableTerminatedTreatmentLaparoscopic Colorectal Resection1
Not AvailableTerminatedTreatmentLumbar and Other Intervertebral Disc Disorders With Radiculopathy1
Not AvailableTerminatedTreatmentPain NOS1
Not AvailableUnknown StatusNot AvailablePain NOS1
Not AvailableUnknown StatusNot AvailableTotal Knee Arthroplasty (TKA)1
Not AvailableUnknown StatusBasic ScienceAnesthetics, Local1
Not AvailableUnknown StatusPreventionAsymptomatic Gallstones Without Cholecystitis / Gallbladder Polyps1
Not AvailableUnknown StatusPreventionContraception1
Not AvailableUnknown StatusPreventionIntravenous Injections1
Not AvailableUnknown StatusSupportive CareOverweight and Obesity1
Not AvailableUnknown StatusTreatmentArrythmias / Arterial Hypotension / Bradycardia / High Blood Pressure (Hypertension) / Tachycardia1
Not AvailableUnknown StatusTreatmentBronchiolitis1
Not AvailableUnknown StatusTreatmentHypospadias Repair1
Not AvailableUnknown StatusTreatmentMacular Degeneration1
Not AvailableUnknown StatusTreatmentOsteoarthritis (OA)1
Not AvailableUnknown StatusTreatmentPain During and After Endovenous Laser Obliteration of Large Saphenous Vein Based on Lidocaine Tumescent Concentration1
Not AvailableUnknown StatusTreatmentPain NOS2
Not AvailableUnknown StatusTreatmentPost Operative Pain1
Not AvailableUnknown StatusTreatmentPostoperative pain1
Not AvailableUnknown StatusTreatmentPregnancy1
Not AvailableUnknown StatusTreatmentRenal Stones / Ureteral Calculus1
Not AvailableWithdrawnNot AvailableAirway Complication of Anaesthesia1
Not AvailableWithdrawnNot AvailableDiabetes, Diabetes Mellitus Type 12
Not AvailableWithdrawnDiagnosticInterstitial Cystitis1
Not AvailableWithdrawnPreventionVaginal Delivery1
Not AvailableWithdrawnSupportive CarePelvic Organ Prolapse (POP)1
Not AvailableWithdrawnTreatmentAdhesive Capsulitis1
Not AvailableWithdrawnTreatmentNasolabial Folds Correction / Pain NOS1
Not AvailableWithdrawnTreatmentPlantar fascial fibromatosis1
Not AvailableWithdrawnTreatmentTotal Knee Arthroplasty (TKA)1

Pharmacoeconomics

Manufacturers
  • Sterling health div sterling winthrop inc
  • Armstrong pharmaceuticals inc
  • Wyeth consumer healthcare
  • Shionogi pharma inc
  • Meridian medical technologies inc
  • Forest laboratories inc
  • 3m pharmaceuticals inc
  • Astrazeneca lp
  • Pharmaton ltd
  • Dentsply pharmaceutical
Packagers
  • 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
SolutionIntramuscular0.15 mg
SolutionIntramuscular0.30 mg
InjectionIntracardiac; Intramuscular; Intraspinal; Intravenous; Subcutaneous1 mg/1mL
InjectionIntramuscular; Intraocular; Subcutaneous1 mg/1mL
SolutionNasal1 mg
SolutionIntramuscular; Intravenous; Subcutaneous1 mg
KitIntramuscular; Subcutaneous; Topical
SolutionIntramuscular0.3 mg
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
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)0.5 %
Injection, solutionEpidural; Infiltration; Intracaudal
Injection, solutionInfiltration; Other
Injection, solutionSubmucosal
Injection, solutionParenteral
KitInfiltration; Intramuscular; Intravenous
SprayRespiratory (inhalation)3.5 %
Solution / dropsOphthalmic
SolutionIntramuscular0.5 mg
Injection, solutionIntravenous0.1 mg/1mL
LiquidIntramuscular0.3 mg
InjectionIntracardiac; Intravenous0.1 mg/1mL
InjectionParenteral0.1 mg/1mL
InjectionParenteral1 mg/1mL
InjectionSubcutaneous0.15 mg/1
InjectionSubcutaneous0.3 mg/1
InjectionSubcutaneous0.3 mg/0.3mL
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
LiquidIntracardiac; Intravenous.1 mg
SolutionEndotracheal; Intracardiac; Intramuscular; Intravenous; Subcutaneous1 mg
SolutionIntracardiac; Intravenous1 mg
Kit1 mg/1mL
InjectionIntramuscular0.3 mg/0.3mL
InjectionIntramuscular0.15 mg/0.3mL
InjectionIntramuscular; Subcutaneous1 mg/1000mL
KitIntramuscular; Intraocular; Subcutaneous
PackingDental.5 mg
SolutionDental; Oral; Periodontal0.197 mg/10mm
Kit
SolutionEpidural; Infiltration
InjectionInfiltration
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
InjectionSubmucosal
SolutionDental; Oral; Periodontal1200 mg/15mL
InhalantOral0.22 mg/1
CapsuleRespiratory (inhalation)0.22 mg/1
Kit0.22 mg/1
Injection, solutionPerineural
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural
Injection, solutionEpidural; Intracaudal; Perineural
Injection, solutionEpidural; Retrobulbar
InjectionEpidural; Parenteral
InjectionEpidural; Parenteral; Retrobulbar
LiquidInfiltration
Injection, solutionSubcutaneous
KitInfiltration; Topical
LiquidParenteral; Topical
InjectionIntramuscular; Subcutaneous0.3 mg/0.3mL
SolutionIntramuscular; Subcutaneous0.15 mg
SolutionIntramuscular; Subcutaneous0.3 mg
SolutionInfiltration
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)
US5665071No1993-05-272013-05-27Us
US7794432No2005-09-112025-09-11Us
US8870827No2005-09-112025-09-11Us
US7449012No2005-09-112025-09-11Us
US8048035No2005-09-112025-09-11Us
US7297136No2005-01-182025-01-18Us
US7621891No2005-02-042025-02-04Us
US6629968No2000-06-302020-06-30Us
US6635045No2001-06-292021-06-29Us
US9149579No2005-07-192025-07-19Us
US8425462No2004-11-232024-11-23Us
US8231573No2008-11-252028-11-25Us
US8016788No2005-03-212025-03-21Us
US9259539No2006-02-012026-02-01Us
US8206360No2007-02-272027-02-27Us
US9238108No2007-01-222027-01-22Us
US8226610No2009-04-102029-04-10Us
US7918823No2004-11-232024-11-23Us
US8608698No2004-11-232024-11-23Us
US8021344No2009-11-022029-11-02Us
US8361029No2004-11-232024-11-23Us
US8313466No2004-11-232024-11-23Us
US7731690No2005-01-152025-01-15Us
US9278182No2006-02-012026-02-01Us
US8920377No2004-11-232024-11-23Us
US7731686No2006-06-012026-06-01Us
US8926594No2006-03-312026-03-31Us
US7749194No2008-10-302028-10-30Us
US9056170No2004-11-232024-11-23Us
US7947017No2008-03-122028-03-12Us
US9295657No2015-03-132035-03-13Us
US9119876No2015-03-132035-03-13Us
US9283197No2014-08-152034-08-15Us
US9586010No2005-09-112025-09-11Us
US7905352No2007-04-122027-04-12Us
US9724471No2007-05-232027-05-23Us
US9737669No2004-11-232024-11-23Us
US9833573No2004-11-232024-11-23Us
US10039728No2014-08-142034-08-14Us
US10004700No2014-08-142034-08-14Us

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
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Sanbe A, Tanaka Y, Fujiwara Y, Tsumura H, Yamauchi J, Cotecchia S, Koike K, Tsujimoto G, Tanoue A: Alpha1-adrenoceptors are required for normal male sexual function. Br J Pharmacol. 2007 Oct;152(3):332-40. Epub 2007 Jul 2. [PubMed:17603545]
  2. Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [PubMed:17658513]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040]
  4. Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [PubMed:20857090]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Cotecchia S: The alpha1-adrenergic receptors: diversity of signaling networks and regulation. J Recept Signal Transduct Res. 2010 Dec;30(6):410-9. doi: 10.3109/10799893.2010.518152. Epub 2010 Oct 18. [PubMed:20954794]
  2. Shieh JP, Chu CC, Wang JJ, Lin MT: Epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via alpha1-adrenoceptors in rats. Acta Pharmacol Sin. 2009 Sep;30(9):1227-36. doi: 10.1038/aps.2009.129. [PubMed:19730427]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040]
  4. Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [PubMed:20857090]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774]
  3. 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
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774]
  3. Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [PubMed:17417877]
  4. Lucin KM, Sanders VM, Jones TB, Malarkey WB, Popovich PG: Impaired antibody synthesis after spinal cord injury is level dependent and is due to sympathetic nervous system dysregulation. Exp Neurol. 2007 Sep;207(1):75-84. Epub 2007 Jun 2. [PubMed:17597612]
  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
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Nyronen T, Pihlavisto M, Peltonen JM, Hoffren AM, Varis M, Salminen T, Wurster S, Marjamaki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS: Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. Mol Pharmacol. 2001 May;59(5):1343-54. [PubMed:11306720]
  2. MacLennan SJ, Reynen PH, Martin RS, Eglen RM, Martin GR: Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using extracellular acidification rate changes. Br J Pharmacol. 2000 Apr;129(7):1333-8. [PubMed:10742288]
  3. Hieble JP, Hehr A, Li YO, Ruffolo RR Jr: Molecular basis for the stereoselective interactions of catecholamines with alpha-adrenoceptors. Proc West Pharmacol Soc. 1998;41:225-8. [PubMed:9836297]
  4. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236]
  5. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [PubMed:18680204]
  6. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417]
  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
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Gobbi M, Frittoli E, Mennini T: The modulation of [3H]noradrenaline and [3H]serotonin release from rat brain synaptosomes is not mediated by the alpha 2B-adrenoceptor subtype. Naunyn Schmiedebergs Arch Pharmacol. 1990 Oct;342(4):382-6. [PubMed:1979424]
  2. Vizi ES, Katona I, Freund TF: Evidence for presynaptic cannabinoid CB(1) receptor-mediated inhibition of noradrenaline release in the guinea pig lung. Eur J Pharmacol. 2001 Nov 16;431(2):237-44. [PubMed:11728431]
  3. Rudling JE, Richardson J, Evans PD: A comparison of agonist-specific coupling of cloned human alpha(2)-adrenoceptor subtypes. Br J Pharmacol. 2000 Nov;131(5):933-41. [PubMed:11053214]
  4. Nash DT: Alpha-adrenergic blockers: mechanism of action, blood pressure control, and effects of lipoprotein metabolism. Clin Cardiol. 1990 Nov;13(11):764-72. [PubMed:1980236]
  5. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417]
  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
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Cotecchia S: The alpha1-adrenergic receptors: diversity of signaling networks and regulation. J Recept Signal Transduct Res. 2010 Dec;30(6):410-9. doi: 10.3109/10799893.2010.518152. Epub 2010 Oct 18. [PubMed:20954794]
  2. Shieh JP, Chu CC, Wang JJ, Lin MT: Epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via alpha1-adrenoceptors in rats. Acta Pharmacol Sin. 2009 Sep;30(9):1227-36. doi: 10.1038/aps.2009.129. [PubMed:19730427]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040]
  4. Jensen BC, Swigart PM, Montgomery MD, Simpson PC: Functional alpha-1B adrenergic receptors on human epicardial coronary artery endothelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2010 Dec;382(5-6):475-82. doi: 10.1007/s00210-010-0558-x. Epub 2010 Sep 22. [PubMed:20857090]
Kind
Protein
Organism
Human
Pharmacological action
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
Human
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
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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
Human
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
Human
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
Human
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
Human
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 October 21, 2018 20:25