Chemical Component Summary

NameL-EPINEPHRINE
SynonymsADRENALINE
Identifiers4-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol
FormulaC9 H13 N O3
Molecular Weight183.204
TypeNON-POLYMER
Isomeric SMILESCNC[C@@H](c1ccc(c(c1)O)O)O
InChIInChI=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
InChIKeyUCTWMZQNUQWSLP-VIFPVBQESA-N

Chemical Details

Formal Charge0
Atom Count26
Chiral Atom Count1
Bond Count26
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00668 
NameEpinephrine
Groups
  • approved
  • vet_approved
DescriptionEpinephrine, 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 [L4355], [L4356], [L4358]. 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 [L4353]. 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 [F2136]. In addition to the above functions, epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest [A37697], [A37699]. It can be used in severe cases of croup [L4824].
Synonyms
  • (R)-(-)-Epinephrine
  • Epinephrin
  • (R)-(−)-adrenaline
  • (R)-(-)-Epirenamine
  • (−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol
Brand Names
  • Sensorcaine Forte
  • QKit Procedure Tray
  • Ana-kit (2mg/tab Orl, 1mg/ml Liq Sc Im)
  • Epinephrine 1:1000 Inj 1mg/ml USP
  • E-pilo 6 Ophthalmic Solution
IndicationEpinephrine 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.[L41260] 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 [F1247]. 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 [F1247]. 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 [F2131]. It is also used for the maintenance of mydriasis during intraocular surgery [L4825].
Categories
  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-1 Receptor Agonists
  • Adrenergic alpha-2 Receptor Agonists
  • Adrenergic alpha-Agonists
ATC-Code
  • A01AD01
  • R03AK01
  • B02BC09
  • C01CA24
  • S01EA01
CAS number51-43-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Alpha-1A adrenergic receptorMVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...unknownagonist
Alpha-1B adrenergic receptorMNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...unknownagonist
Beta-1 adrenergic receptorMGAGVLVLGASEPGNLSSAAPLPDGAATAARLLVPASPPASLLPPASESP...unknownagonist
Beta-2 adrenergic receptorMGQPGNGSAFLLAPNGSHAPDHDVTQERDEVWVVGMGIVMSLIVLAIVFG...unknownagonist
Alpha-2A adrenergic receptorMGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL679
PubChem 139148732, 5816
ChEMBL CHEMBL679
ChEBI CHEBI:28918
CCDC/CSD ADRTAR