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 data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00668
Name	Epinephrine
Groups	vet_approved 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	(−)-(R)-epinephrine Epinephrine hydrochloride 1,2-BENZENEDIOL, 4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)-, (R)- Epinephrine bitartrate (−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol Adrenaline Epinefrin L-Adrenaline 4-((1R)-1-HYDROXY-2-(METHYLAMINO)ETHYL)-1,2-BENZENEDIOL Epinephrine acetate Levoepinephrine Epinephrinum (R)-(-)-Adnephrine Epinefrina RACEPINEFRINE, (R)- Adrénaline 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol Epinephrin Epinephrine (R)-(-)-Epinephrine (R)-(-)-Adrenaline (R)-(-)-Epirenamine (R)-(−)-adrenaline (−)-adrenaline BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (-)-
Brand Names	Xylocaine with epinephrine Epinephrine Injection USP 1 mg/ml Orabloc 1:100,000 E-pilo-4 Oph Soln Sensorcaine Mpf Xylocaine 2% W Epinephrine 1:200000 Bupivacaine Hydrochloride and Epinephrine Primatene Mist E-pilo 6 Ophthalmic Solution Epinephrine Anapen Articaine Hydrochloride and Epinephrine Bitartrate Injection Lidocaine Hydrochloride 0.5% and Epinephrine 1:200000 Injection USP Octocaine 50 Lignospan Forte LIDOCAINE HCl AND EPINEPHRINE Minnerva II Bupivacaine Hci and Epinephrine Ephinephrine 4% Astracaine Dental With Epinephrine Forte 1:100,000 (0.01mg/ml) Numquick Analgesic Taro-epinephrine Auto-injector Xylocaine 1% W Epinephrine 1:200000 E-pilo-2 Oph Soln Posicaine Sp Septanest Sp Epinephrine Professional EMS Articaine HCl and Epinephrine Orabloc 1:200,000 EpinephrineSnap-V Adrenalin (epinephrine) Gingi Pak Cord No 1 Anakit Insect Sting Treatment Kit Taroclick Epinephrine Deluxe Dental Emergency Kit Epinephrine 1:1000 Inj 1mg/ml USP Epinephrinesnap-V Xylocaine Gingi-pak Max Soft-twist No 3 Sensorcaine With Epinephrine Lixtraxen 1% The Solution LIDOCAINE HCl AND EPI Marcaine 0.5% and Epinephrine 1:200,000 Liq D-Care 100X Twinject 0.3mg Auto-injector Pro Numb Xylocaine Dental Lidocaine HCl 2% and Epinephrine 1:100,000 2% Lidocaine and Epinephrine 1:100,000 Injection USP Adrenalin Vials Allerject Xylocaine Mpf 1.5% With Epinephrine Emerade Epinephrine Injection Ultracaine DS Forte Inj Adyphren Amp Kit Articadent Epinephrine Convenience Kit Ana-kit Scandonest 2% Special Inj Lidocaine Hci and Epinephrine Articaine Hydrochloride and Epinephrine Lidocaine 2% and Epinephrine 1:100,000 LIDOCAINE HCl and EPINEPHRINE Leep RediKit Octocaine HCl 2% Epinephrine 1:100000 Gingi-pak Max Z-twist No 00 Xylocaine(r) -mpf (lidocaine Hci and Epinephrine) Neffy Octocaine HCl 2% Epinephrine 1:50000 Epipen Jr Lidocaine 2% and Epinephrine 1:50,000 Dentsply 2% Lidocaine With Epinephrine 1:100,000 Gold Label Anorectal Numbing Spray Numbing Hemorrhoidal Label Zone 2 Epinephrine Inj 0.1mg/ml USP Spinal Anesthesia Tray Adrenalin (epinephrine in sodium chloride) Adrenaclick 0.30mg Auto-injector EpinephrineSnap-EMS Gingi-pak Max 2-ply Twinject 0.15mg Auto-injector Ultracaine DS Inj Xylocaine 1.5% W Epinephrine 1:200000 Epinephrine Pediatrics Dentsply 2% Lidocaine With Epinephrine 1:50,000 Adrenaclick 0.15mg Auto-injector Xylocaine MPF Citanest Forte DENTAL Epinephrine Chloride Solution Xylocaine 2% With Epinephrine 1:200000 Ultracaine D-S Injection Ultracaine D-S Forte Injection Marcaine E Lignospan Standard Lidocaine Hydrochloride 1.5% and Epinephrine 1:200000 Injection USP Symjepi Octocaine 100 Needleject Inj Epinephrine Professional E-pilo-6 Oph Soln QKit Procedure Tray Adyphren Kit Prilocaine Hydrochloride with Epinephrine Adrenalin Topical Solution Ana-kit (2mg/tab Orl, 1mg/ml Liq Sc Im) Ultacan Twinject 4% Astracaine Dental With Epinephrine 1:200,000 (0.005mg/ml) Marcaine Septocaine Crown-pak Max 4-ply E-pilo-1 Oph Soln Gingi-pak Max Z-twist No 1 Orostat 8% Taroclick Epinephrine Junior SENSORCAINE MPF with Epinephrine Certa Dose Epinephrine Convenience Kit Lidosite Numquick Topical Analgesic Septocaine and Epinephrine Xylocaine 2% W Epinephrine 1:100000 Citanest Forte E-pilo 1 Ophthalmic Solution Prilocaine HCl 4% Epineph 1:200000inj Marcaine with Epinephrine EPIsnap Epinephrine Convenience Kit EpiPen Jr Lidocaine and Epinephrine Inj.usp 2% 1:100000 Marcaine E Liq Prt 0.50% Orabloc Lidocaine Hydrochloride and Epinephrine Injection USP Vasocaine Dysne Inhal Lidocaine 2% and Epinephrine 1:100 000 Sensorcaine(r) (bupivacaine Hci and Epinephrine) 4% Citanest Forte Dental With Epinephrine 1:200,000 E-pilo 4 Ophthalmic Solution EpiPen CLIN-LIDO-Single Use Kit Ultacan Forte Xylocaine 0.5% W Epinephrine 1:200000 Adrenalin Gingi-pak Pellets Gingi-pak Max Z-twist No 3 Marcaine With Epinephrine Epinephrine Injection USP Dentsply 4% Prilocaine and Epinephrine Injection 1:200,000 Basic Dental Emergency Kit Epi E-Z Pen - Liquid - 0.3mg/0.3ml Lidocaine 2% and Epinephrine 1:50 000 Xylocaine 1.5% W Epinephrine 1:200000 Test Dose Gingi-pak Cotton Coil Adyphren II Kit Septanest N Marcaine E 0.25% Liq Prt Prime Asthma Relief EPY II Kit Posicaine N Epinephrine 0.15 Pediatrics Gingi-pak Max Soft-twist No 1 Auvi-Q Bronkaid Mistometer Aem 0.5% Epinephrine 0.3 Adults Medihaler-Epi Xylocaine 1% W Epinephrine 1:100000 Xylocaine Dental Lidocaine Hydrochloride 2% and Epinephrine 1:50,000 Bupivacaine Hydrochloride with Epinephrine Lignospan Speciale Inj Xylocaine-mpf With Epi Octocaine 100 Adyphren Amp II Kit Adrenalin(r) Lidocaine Hydrochloride 1.5% and Epinephrine 1:200000 Injection USP Test Dose Primatene Mist Refill Spinal Anaesthesia Tray Zorcaine Gingi-pak Max Soft-twist No 2 Sensorcaine Forte Articaine EPY Kit The Solution Anorectal Spray Temporary Pain Relief Lidocaine Gingi-pak Max Z-twist No 2 Blue Gel Anesthetic Sensorcaine Vivacaine Lidocaine Hci LIDOCAINE HCl Epipen Anapen Junior Bupivacaine HCl 0.5% and Epinephrine 1:200,000 Injection Lidocaine Hydrochloride and Epinephrine Lidocaine Hydrochloride and Epinephrine Bitartrate Adrenaclick Xylocaine 0.5% W Epinephrine 1:100000 E-pilo 2 Ophthalmic Solution Lidocaine Hci and Epinephrine With Epinephrine
Indication	Epinephrine injection and nasal spray are indicated in the emergency treatment of type I allergic reactions, including anaphylaxis.[L41260, L51798] Epinephrine injection 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 so 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 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

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

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	MFRQEQPLAEGSFAPMGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLT...	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