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