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