ALE

L-EPINEPHRINE

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