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