ALE

L-EPINEPHRINE

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is present as a standalone ligand in 8 entries

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Chemical Component Summary
Name	L-EPINEPHRINE
Synonyms	ADRENALINE
Identifiers	4-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol
Formula	C₉ H₁₃ N O₃
Molecular Weight	183.204
Type	NON-POLYMER
Isomeric SMILES	CNC[C@@H](c1ccc(c(c1)O)O)O
InChI	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	UCTWMZQNUQWSLP-VIFPVBQESA-N

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

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