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