ALE

L-EPINEPHRINE

Created:	1999-07-08
Last modified:	2021-03-01

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Chemical Details
Formal Charge	0
Atom Count	26
Chiral Atom Count	1
Bond Count	26
Aromatic Bond Count	6

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Chemical Component Summary
Name	L-EPINEPHRINE
Synonyms	ADRENALINE
Systematic Name (OpenEye OEToolkits)	4-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol
Formula	C₉ H₁₃ N O₃
Molecular Weight	183.204
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Oc1ccc(cc1O)C(O)CNC
SMILES	CACTVS	3.370	CNC[CH](O)c1ccc(O)c(O)c1
SMILES	OpenEye OEToolkits	1.7.6	CNCC(c1ccc(c(c1)O)O)O
Canonical SMILES	CACTVS	3.370	CNC[C@H](O)c1ccc(O)c(O)c1
Canonical SMILES	OpenEye OEToolkits	1.7.6	CNC[C@@H](c1ccc(c(c1)O)O)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	UCTWMZQNUQWSLP-VIFPVBQESA-N

Drug Info: DrugBank

DrugBank ID	DB00668
Name	Epinephrine
Groups	approved vet_approved
Description	Epinephrine, also known as _adrenaline_, is a hormone and neurotransmitter and produced by the adrenal glands that can also be used as a drug due to its various important functions. Though it has long been used in the treatment of hypersensitivity reactions, epinephrine in the auto-injector form (EpiPen) has been available since 1987 in the USA. Many new products/biosimilars and dosage routes have been approved under various names over the last several decades [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	4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol Adrénaline (R)-(-)-Epinephrine Epinefrina (−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol Adrenaline Epinefrin Epinephrine acetate (−)-adrenaline Epinephrine (R)-(-)-Adnephrine (R)-(-)-Epirenamine (−)-(R)-epinephrine Epinephrine hydrochloride (R)-(-)-Adrenaline Levoepinephrine Epinephrine bitartrate Epinephrinum (R)-(−)-adrenaline Epinephrin L-Adrenaline
Brand Names	Epinephrine Chloride Solution Ultracaine D-S Injection Epinephrine Injection USP 1 mg/ml Anapen Junior Gingi Pak Cord No 1 Lidocaine Hydrochloride and Epinephrine Injection USP Primatene Mist Septocaine and Epinephrine Adrenalin Octocaine 50 EpinephrineSnap-V Lidocaine E-pilo-1 Oph Soln Lidocaine and Epinephrine Inj.usp 2% 1:100000 Xylocaine Dental Lidocaine Hydrochloride 2% and Epinephrine 1:50,000 Marcaine with Epinephrine Gingi-pak Pellets Xylocaine 2% With Epinephrine 1:200000 Articaine HCl and Epinephrine Gingi-pak Max 2-ply Xylocaine 0.5% W Epinephrine 1:200000 EPY Kit Auvi-Q Adyphren II Kit Ana-kit Epi E-Z Pen - Liquid - 0.3mg/0.3ml Octocaine HCl 2% Epinephrine 1:50000 Symjepi Xylocaine Mpf 1.5% With Epinephrine Adrenalin (epinephrine) SENSORCAINE MPF with Epinephrine Octocaine 100 Needleject Inj Minnerva II Citanest Forte Lidocaine Hydrochloride 1.5% and Epinephrine 1:200000 Injection USP Test Dose Orabloc 1:100,000 2% Lidocaine and Epinephrine 1:100,000 Injection USP Xylocaine Dental Lidocaine HCl 2% and Epinephrine 1:100,000 Orostat 8% Epinephrine Injection Sensorcaine Forte LIDOCAINE HCl AND EPI Zone 2 Marcaine With Epinephrine Spinal Anaesthesia Tray EpiPen Jr Lidocaine Hci Taroclick Epinephrine Blue Gel Anesthetic Xylocaine 1.5% W Epinephrine 1:200000 Test Dose Articaine Hydrochloride and Epinephrine CLIN-LIDO-Single Use Kit LIDOCAINE HCl AND EPINEPHRINE Bupivacaine HCl 0.5% and Epinephrine 1:200,000 Injection Gingi-pak Max Soft-twist No 3 Xylocaine with epinephrine QKit Procedure Tray Lidocaine 2% and Epinephrine 1:100,000 Epipen Prilocaine HCl 4% Epineph 1:200000inj Bronkaid Mistometer Aem 0.5% Dentsply 2% Lidocaine With Epinephrine 1:100,000 Septocaine Gingi-pak Max Z-twist No 00 Ephinephrine Lignospan Speciale Inj Adyphren Amp Kit Ultracaine DS Inj Epinephrine Inj 0.1mg/ml USP Xylocaine 2% W Epinephrine 1:100000 Xylocaine MPF Lidocaine 2% and Epinephrine 1:50,000 Adrenalin(r) LIDOCAINE HCl and EPINEPHRINE Lidosite Lidocaine Hydrochloride and Epinephrine Octocaine HCl 2% Epinephrine 1:100000 Lidocaine Hydrochloride 0.5% and Epinephrine 1:200000 Injection USP Lidocaine Hydrochloride and Epinephrine Bitartrate Adrenaclick 0.15mg Auto-injector Ultracaine DS Forte Inj Epinephrine Epinephrine Professional EMS Xylocaine(r) -mpf (lidocaine Hci and Epinephrine) Lidocaine 2% and Epinephrine 1:50 000 Sensorcaine(r) (bupivacaine Hci and Epinephrine) Prilocaine Hydrochloride with Epinephrine Basic Dental Emergency Kit Gingi-pak Max Soft-twist No 2 Primatene Mist Refill Lignospan Standard Adrenaclick Sensorcaine Numquick Topical Analgesic Septanest N Marcaine E 0.25% Liq Prt Bupivacaine Hydrochloride with Epinephrine Taroclick Epinephrine Junior Crown-pak Max 4-ply Deluxe Dental Emergency Kit Septanest Sp D-Care 100X Spinal Anesthesia Tray Pro Numb Epinephrine Injection USP Articaine Hydrochloride and Epinephrine Bitartrate Injection Lidocaine Hydrochloride 1.5% and Epinephrine 1:200000 Injection USP Lidocaine 2% and Epinephrine 1:100 000 Numbing Hemorrhoidal Label The Solution Anorectal Spray Temporary Pain Relief 4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml) Gingi-pak Max Z-twist No 2 Xylocaine 1% W Epinephrine 1:200000 LIDOCAINE HCl Xylocaine-mpf With Epi Xylocaine 1% W Epinephrine 1:100000 Twinject Xylocaine 2% W Epinephrine 1:200000 Citanest Forte DENTAL Lidocaine Hci and Epinephrine With Epinephrine EpinephrineSnap-EMS Lignospan Forte Allerject E-pilo 1 Ophthalmic Solution Taro-epinephrine Auto-injector Gingi-pak Max Soft-twist No 1 Zorcaine Twinject 0.15mg Auto-injector The Solution Certa Dose Epinephrine Convenience Kit Emerade Sensorcaine With Epinephrine Ana-kit (2mg/tab Orl, 1mg/ml Liq Sc Im) E-pilo 2 Ophthalmic Solution Epinephrine 1:1000 Inj 1mg/ml USP EPIsnap Epinephrine Convenience Kit Leep RediKit Bupivacaine Hydrochloride and Epinephrine Dentsply 2% Lidocaine With Epinephrine 1:50,000 Orabloc 4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml) Marcaine E Lixtraxen 1% Posicaine N Anapen Anakit Insect Sting Treatment Kit Xylocaine 1.5% W Epinephrine 1:200000 Marcaine 0.5% and Epinephrine 1:200,000 Liq Dysne Inhal E-pilo-2 Oph Soln Numquick Analgesic Octocaine 100 Prime Asthma Relief Adrenaclick 0.30mg Auto-injector Sensorcaine Mpf Xylocaine 0.5% W Epinephrine 1:100000 Epinephrinesnap-V Articaine 4% Citanest Forte Dental With Epinephrine 1:200,000 Twinject 0.3mg Auto-injector Gingi-pak Max Z-twist No 1 EPY II Kit Adyphren Kit Scandonest 2% Special Inj Epipen Jr Ultacan Forte Gingi-pak Cotton Coil Adyphren Amp II Kit E-pilo-6 Oph Soln E-pilo 6 Ophthalmic Solution Gingi-pak Max Z-twist No 3 Medihaler-Epi Orabloc 1:200,000 E-pilo-4 Oph Soln Adrenalin Topical Solution Articadent Ultracaine D-S Forte Injection Vivacaine EpiPen Epinephrine Professional Marcaine Posicaine Sp Ultacan Lidocaine Hci and Epinephrine Epinephrine Convenience Kit Vasocaine Marcaine E Liq Prt 0.50% Bupivacaine Hci and Epinephrine Dentsply 4% Prilocaine and Epinephrine Injection 1:200,000 E-pilo 4 Ophthalmic Solution Xylocaine
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.[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 Adrenergic and Dopaminergic Agents Adrenergic beta-1 Receptor Agonists Adrenergic beta-2 Receptor Agonists Adrenergic beta-3 Receptor Agonists Adrenergic beta-Agonists Adrenergics, Inhalants Agents producing tachycardia Agents that produce hypertension Alpha-and Beta-adrenergic Agonists Amines Anti-Asthmatic Agents Antiglaucoma Preparations and Miotics Autonomic Agents Benzene Derivatives Biogenic Amines Biogenic Monoamines Bronchodilator Agents Cardiac Stimulants Excl. Cardiac Glycosides Cardiac Therapy Cardiovascular Agents Catecholamines Catechols COMT Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Dental Agents Drugs for Obstructive Airway Diseases Epinephrine and similars Hemostatics Hyperglycemia-Associated Agents Local Hemostatics Mydriatics Nasal Preparations Neurotransmitter Agents OCT1 substrates OCT2 Inhibitors OCT2 Substrates Ophthalmologicals Peripheral Nervous System Agents Phenols Respiratory System Agents Stomatological Preparations Sympathomimetic (Adrenergic) Agents Sympathomimetics Sympathomimetics in Glaucoma Therapy Sympathomimetics, Plain Vasoconstrictor Agents
ATC-Code	A01AD01 R03AK01 B02BC09 C01CA24 S01EA01 R01AA14 R03AA01 S01EA51
CAS number	51-43-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Alpha-1A adrenergic receptor	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	agonist
Alpha-1B adrenergic receptor	MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...	unknown	agonist
Beta-1 adrenergic receptor	MGAGVLVLGASEPGNLSSAAPLPDGAATAARLLVPASPPASLLPPASESP...	unknown	agonist
Beta-2 adrenergic receptor	MGQPGNGSAFLLAPNGSHAPDHDVTQERDEVWVVGMGIVMSLIVLAIVFG...	unknown	agonist
Alpha-2A adrenergic receptor	MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...	unknown	agonist
Alpha-2B adrenergic receptor	MDHQDPYSVQATAAIAAAITFLILFTIFGNALVILAVLTSRSLRAPQNLF...	unknown	agonist
Alpha-1D adrenergic receptor	MTFRDLLSVSFEGPRPDSSAGGSSAGGGGGSAGGAAPSEGPAVGGVPGGA...	unknown	antagonist
Tumor necrosis factor	MSTESMIRDVELAEEALPKKTGGPQGSRRCLFLSLFSFLIVAGATTLFCL...	unknown	antagonist,agonist
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Catechol O-methyltransferase	MPEAPPLLLAAVLLGLVLLVVLLLLLRHWGWGLCLIGWNEFILQPIHNLL...	unknown	substrate
Monoamine oxidase	MENQEKASIAGHMFDVVVIGGGISGLSAAKLLTEYGVSVLVLEARDRVGG...	unknown	substrate
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	substrate
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	substrate
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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