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