Details of the Drug

General Information of Drug (ID: DM3KJBC)

Drug Name

Epinephrine

Synonyms

ADROP; Adnephrine; Adrenal; Adrenalin; Adrenalina; Adrenaline; Adrenalinum; Adrenamine; Adrenan; Adrenapax; Adrenasol; Adrenatrate; Adrenine; Adrenodis; Adrenohorma; Adrenosan; Adrenutol; Adrin; Adrine; Antiasthmatique; Asthmanefrin; Astmahalin; Astminhal; Balmadren; Bernarenin; Biorenine; Bosmin; Brevirenin; Bronkaid; Chelafrin; Corisol; Drenamist; Dylephrin; Epifrin; Epiglaufrin; Epinefrin; Epinefrina; Epinephran; Epinephrin; Epinephrinum; Epipen; Epirenamine; Epirenan; Epirenin; Epitrate; Eppy; Esphygmogenina; Exadrin; Glaucon; Glaucosan; Glauposine; Glycirenan; Haemostasin; Haemostatin; Hektalin; Hemisine; Hemostasin; Hemostatin; Hypernephrin; Hyporenin; IOP; Intranefrin; Iontocaine; Isoptoepinal; Kidoline; Levoadrenaline; Levoepinephrine; Levorenen; Levorenin; Levorenine; Lyophrin; Metanephrin; Methylaminoethanolcatechol; Methylarterenol; Micronefrin; Micronephrine; Mucidrina; Myosthenine; Mytrate; Nephridine; Nieraline; Paranephrin; Primatene; Racepinephrine; Renagladin; Renaglandin; Renaglandulin; Renaleptine; Renalina; Renoform; Renostypricin; Renostypticin; Renostyptin; Scurenaline; Septocaine; Simplene; Sindrenina; Soladren; Sphygmogenin; Stryptirenal; Styptirenal; Supracapsulin; Supradin; Supranefran; Supranephrane; Supranephrine; Supranol; Suprarenaline; Suprarenin; Suprel; Surenine; Surrenine; Susphrine; Takamina; Takamine; Tokamina; Tonogen; Twinject; Vaponefrin; Vasoconstrictine; Vasoconstrictor; Vasodrine; Vasoton; Vasotonin; ADR ADRENALINE; Adrenalin in Oil; Adrenalina [DCIT]; Asmatane Mist; Asthma meter mist; Asthmahaler Mist; Bronkaid Mist; Bronkaid Suspension Mist; Bupivacaine Hcl and Epinephrine; Citanest Forte; EPI E Z PEN JR; EPIPEN E Z PEN; EPIPEN JR; Epi EZ Pen Jr; Epinefrin [Czech]; Epinephrine hydrochloride; Epipen EZ Pen; Primatene Mist; Racemic Epinephrine; Sympathin I; Adrenalin (TN); Adrenalin-Medihaler; Adrenaline (JP15); Adrenaline/Epinephrine; Ana-Guard; Asthma-nefrin; D-Adrenaline; D-Epifrin; D-Epinephrine; Dyspne-Inhal; Epinefrina [INN-Spanish]; Epinephrine (USP); Epinephrinum [INN-Latin]; Epipen (TN); Epipen Auto-Injector; Epipen Jr.; L-Adrenalin; L-Adrenaline; L-Adrenaline Base; L-Epinehphrine; L-Epinephine; L-Epirenamine; L-Methylaminoethanolcatechol; L-epinephrine; Levo-Methylaminoethanolcatechol; Medihaler-Epi; R-Adrenaline; Sus-Phrine; Twinject 0.15; Twinject 0.3; Twinject 0.30; Epinephrine (USP/INN); Epinephrine [USAN:INN:JAN]; Epipen Jr. Auto-Injector; L-Epinephrine (synthetic); SUS-PHRINE SULFITE-FREE; R-(-)-Epinephrine; L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol; (-)-(R)-Epinephrine; (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol; (-)-Adrenalin; (-)-Adrenaline; (-)-R-Epinephrine; (R)-(-)-Adnephrine; (R)-(-)-Adrenaline; (R)-(-)-Epinephrine; (R)-(-)-Epirenamine; (R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (R)-Adrenaline; (R)-Epinephrine; 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol; 1-Adrenalin; 1-Epinephrine; 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol; 4-(1-hydroxy-2-methylamino-ethyl)benzene-1,2-diol; 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

Indication

Disease Entry	ICD 11	Status	REF
Acute asthma	CA23	Approved	[1]
Allergy	4A80-4A85	Approved	[2]
Anaphylaxis	N.A.	Approved	[1]
Bronchiectasis	CA24	Approved	[1]
Bronchitis	CA20	Approved	[1]
Periodontitis	DA0C	Approved	[1]
Pulmonary emphysema	CA21.Z	Approved	[1]
Severe asthma	CA23	Approved	[1]
Asthma	CA23	Investigative	[1]
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Therapeutic Class

Vasoconstrictor Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

183.2

Logarithm of the Partition Coefficient (xlogp)

-1.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Elimination: About 40% of a parenteral dose of epinephrine is excreted in urine as metanephrine, 40% as VMA, 7% as 3-methoxy-4-hydroxyphenoglycol, 2% as 3,4-dihydroxymandelic acid, and the rest as acetylated derivatives [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 2 - 3 minutes [3]
Metabolism: The drug is metabolized via the enzymic transformation to metanephrine or normetanephrine []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.09116 micromolar/kg/day [4]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Cell-mediated cytotoxicity	Not Available	GSR	OTM2TUYM	[5]
Drug ineffective	Not Available	LEP	OT5Q7ODW	[5]
Inflammation	Not Available	CXCL8	OTS7T5VH	[5]
Platelet aggregation	Not Available	ADRA2A	OTZFGOTP	[5]
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Chemical Identifiers

Formula: C9H13NO3
IUPAC Name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Canonical SMILES: CNC[C@@H](C1=CC(=C(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

Cross-matching ID

PubChem CID: 5816
ChEBI ID: CHEBI:28918
CAS Number: 51-43-4
DrugBank ID: DB00668
TTD ID: D04PHC
VARIDT ID: DR00076
INTEDE ID: DR0590
ACDINA ID: D00234

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Agonist	[6]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 3 (SLC22A3)	DT6201N	S22A3_HUMAN	Substrate	[7]
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[8]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[9]
Sulfotransferase 1A1 (SULT1A1)	DEYWLRK	ST1A1_HUMAN	Substrate	[10]
Monoamine oxidase type A (MAO-A)	DERE4TU	AOFA_HUMAN	Substrate	[11]
Catechol O-methyltransferase (COMT)	DEV3T4A	COMT_HUMAN	Substrate	[12]
Thiopurine methyltransferase (TPMT)	DEFQ8VO	TPMT_HUMAN	Substrate	[13]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Alpha-1A adrenergic receptor (ADRA1A)	OTUIWCL5	ADA1A_HUMAN	Gene/Protein Processing	[14]
Alpha-1B adrenergic receptor (ADRA1B)	OTSAYAFD	ADA1B_HUMAN	Gene/Protein Processing	[14]
Alpha-1D adrenergic receptor (ADRA1D)	OTW2CD1O	ADA1D_HUMAN	Gene/Protein Processing	[14]
Alpha-2A adrenergic receptor (ADRA2A)	OTZFGOTP	ADA2A_HUMAN	Drug Response	[5]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[15]
Beta-2 adrenergic receptor (ADRB2)	OTSDOX4Q	ADRB2_HUMAN	Gene/Protein Processing	[16]
Carbonic anhydrase 2 (CA2)	OTJRMUAG	CAH2_HUMAN	Gene/Protein Processing	[17]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[18]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Drug Response	[19]
Catechol O-methyltransferase (COMT)	OTPWKTQG	COMT_HUMAN	Biotransformations	[20]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Epinephrine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Moderate	Additive hypertensive effects by the combination of Epinephrine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[21]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Epinephrine and Droxidopa.	Autonomic nervous system disorder [8D87]	[22]
Levomilnacipran	DMV26S8	Moderate	Increased risk of rapid heart rate by the combination of Epinephrine and Levomilnacipran.	Chronic pain [MG30]	[23]
Selegiline	DM6034S	Moderate	Additive hypertensive effects by the combination of Epinephrine and Selegiline.	Depression [6A70-6A7Z]	[21]
Isocarboxazid	DMAF1NB	Moderate	Additive hypertensive effects by the combination of Epinephrine and Isocarboxazid.	Depression [6A70-6A7Z]	[21]
Milnacipran	DMBFE74	Moderate	Additive hypertensive effects by the combination of Epinephrine and Milnacipran.	Depression [6A70-6A7Z]	[24]
Tranylcypromine	DMGB5RE	Moderate	Additive hypertensive effects by the combination of Epinephrine and Tranylcypromine.	Depression [6A70-6A7Z]	[21]
Desvenlafaxine	DMHD4PE	Moderate	Increased risk of rapid heart rate by the combination of Epinephrine and Desvenlafaxine.	Depression [6A70-6A7Z]	[23]
Phenelzine	DMHIDUE	Moderate	Additive hypertensive effects by the combination of Epinephrine and Phenelzine.	Depression [6A70-6A7Z]	[21]
Ergotamine	DMKR3C5	Major	Additive hypertensive effects by the combination of Epinephrine and Ergotamine.	Headache [8A80-8A84]	[25]
Procarbazine	DMIK367	Moderate	Additive hypertensive effects by the combination of Epinephrine and Procarbazine.	Hodgkin lymphoma [2B30]	[21]
Ozanimod	DMT6AM2	Moderate	Additive hypertensive effects by the combination of Epinephrine and Ozanimod.	Multiple sclerosis [8A40]	[21]
Sibutramine	DMFJTDI	Moderate	Additive hypertensive effects by the combination of Epinephrine and Sibutramine.	Obesity [5B80-5B81]	[26]
Safinamide	DM0YWJC	Moderate	Decreased metabolism of Epinephrine caused by Safinamide mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[27]
Opicapone	DM1BKA6	Moderate	Decreased metabolism of Epinephrine caused by Opicapone mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[28]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Epinephrine and Rasagiline.	Parkinsonism [8A00]	[21]
Ergonovine	DM0VEC1	Major	Additive hypertensive effects by the combination of Epinephrine and Ergonovine.	Postpartum haemorrhage [JA43]	[25]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Epinephrine 0.22 mg powder	0.22 mg	Inhalant Powder	Oral

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References

1	Epinephrine FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 509).
3	Medicines UK document
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
6	Adrenergic activation of electrogenic K+ secretion in guinea pig distal colonic epithelium: involvement of beta1- and beta2-adrenergic receptors. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G269-77.
7	Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain. Neuropharmacology. 2006 Jun;50(8):941-52.
8	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
9	Steroid glucuronides: human circulatory levels and formation by LNCaP cells. J Steroid Biochem Mol Biol. 1991;40(4-6):593-8.
10	Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3'-phosphoadenosine 5'-phosphate. Biochem Biophys Res Commun. 2005 Sep 23;335(2):417-23.
11	Role of monoamine-oxidase-A-gene variation in the development of glioblastoma in males: a case control study. J Neurooncol. 2019 Nov;145(2):287-294.
12	Different metabolism of norepinephrine and epinephrine by catechol-O-methyltransferase and monoamine oxidase in rats. J Pharmacol Exp Ther. 1994 Mar;268(3):1242-51.
13	Adrenal catecholamines and their metabolism in the vitamin A deficient rat. Ann Nutr Metab. 1983;27(3):220-7.
14	Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. doi: 10.1016/j.cardiores.2004.05.014.
15	Epinephrine facilitates the growth of T cell lymphoma by altering cell proliferation, apoptosis, and glucose metabolism. Chem Biol Interact. 2023 Jan 5;369:110278. doi: 10.1016/j.cbi.2022.110278. Epub 2022 Nov 22.
16	Myocardial ischaemia and ventricular arrhthymias precipitated by physiological concentrations of adrenaline in patients with coronary artery disease. Br Heart J. 1992 May;67(5):419-20. doi: 10.1136/hrt.67.5.419-b.
17	Effects of beta-adrenergic agonists on bone-resorbing activity in human osteoclast-like cells. Biochim Biophys Acta. 2003 May 12;1640(2-3):137-42.
18	Carvedilol prevents epinephrine-induced apoptosis in human coronary artery endothelial cells: modulation of Fas/Fas ligand and caspase-3 pathway. Cardiovasc Res. 2000 Feb;45(3):788-94. doi: 10.1016/s0008-6363(99)00369-7.
19	Evaluation of cytogenetic and DNA damage in human lymphocytes treated with adrenaline in vitro. Toxicol In Vitro. 2015 Feb;29(1):27-33. doi: 10.1016/j.tiv.2014.08.001. Epub 2014 Aug 27.
20	Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. Mol Pharmacol. 2001 Feb;59(2):393-402. doi: 10.1124/mol.59.2.393.
21	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
22	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
23	Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
24	Cerner Multum, Inc. "Australian Product Information.".
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26	Product Information. Meridia (sibutramine). Knoll Pharmaceutical Company, Whippany, NJ.
27	Cusson JR, Goldenberg E, Larochelle P "Effect of a novel monoamine-oxidase inhibitor, moclobemide on the sensitivity to intravenous tyramine and norepinephrine in humans." J Clin Pharmacol 31 (1991): 462-7. [PMID: 2050833]
28	Illi A, Sundberg S, Ojala-Karlsson P, Korhonen P, Scheinin M, Gordin A "The effect of entacapone on the disposition and hemodynamic effects of intravenous isoproterenol and epinephrine." Clin Pharmacol Ther 58 (1995): 221-7. [PMID: 7648772]