Natural Product (NP) Details

General Information of the NP (ID: NP7685)
Name
Epinephrine
Synonyms
epinephrine; l-Adrenaline; L-epinephrine; 51-43-4; Adrenalin; adrenaline; Levoepinephrine; Adnephrine; Chelafrin; Epinefrina; Epinephran; Epirenan; (-)-Adrenaline; Nephridine; Adrenal; Epifrin; Renoform; Epipen; Vasoconstrictine; Hypernephrin; Renostypticin; Supracapsulin; Supranephrane; Suprarenaline; Adrenine; Hemisine; Hemostasin; Hemostatin; Levorenin; Levorenine; Lyophrin; Mucidrina; Nieraline; Paranephrin; Renaglandin; Renaleptine; Renalina; Scurenaline; Simplene; Styptirenal; Takamina; Vasotonin; Bosmin; Exadrin; (R)-Adrenaline; Adrin; l-Epirenamine; Bronkaid Mist; Primatene Mist; Sus-Phrine; Antiasthmatique; Esphygmogenina; Methylarterenol; Supranephrine; Adrenamine; Adrenapax; Adrenasol; Adrenodis; Adrenohorma; Adrenosan; Adrenutol; Astmahalin; Astminhal; Balmadren; Bernarenin; Biorenine; Brevirenin; Bronkaid; Drenamist; Dylephrin; Glaucosan; Glycirenan; Haemostasin; Haemostatin; Hektalin; Hyporenin; Intranefrin; Isoptoepinal; Kidoline; Myosthenine; Sindrenina; Soladren; Sphygmogenin; Stryptirenal; Supradin; Supranefran; Supranol; Takamine; Tokamina; Twinject; Vasodrine; (-)-Epinephrine; Corisol; Glaucon; Mytrate; Suprel; Tonogen; Asthma-nefrin; Asmatane Mist; L(-)-Epinephrine; Sympathin I; (-)-(R)-Epinephrine; (R)-Epinephrine; Asthma meter mist; Adrenalinum; Epiglaufrin; Glauposine; Adrenalin-Medihaler; Levorenen; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol; Eppy; Dyspne-Inhal; R-(-)-Epinephrine; Adrenalin in Oil; Epinefrin [Czech]; Epinefrin; Renostyptin; Surrenine; Citanest Forte; 1-Epinephrine; 1-Adrenalin; Epipen Jr.; Vaponefrin; (R)-(-)-Adrenaline; Rcra waste number P042; l-Epinephrine (synthetic); Adrenalina [DCIT]; Adrenatrate; Epinefrina [INN-Spanish]; Epinephrinum; Epinephrinum [INN-Latin]; Metanephrin; Renaglandulin; Renostypricin; Vasoconstrictor; Epirenin; Renagladin; Surenine; Vasoton; l-Adrenalin; R-Adrenaline; Suprarenin; Methylaminoethanolcatechol; Auvi-q; (R)-(-)-Epinephrine; l-Methylaminoethanolcatechol; d-Adrenaline; Medihaler-Epi; C9H13NO3; Lyodrin; (R)-(-)-Adnephrine; L-Epinehphrine; (R)-(-)-Epirenamine; l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol; 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol; RCRA waste no. P042; UNII-YKH834O4BH; Adrenalin (TN); Epirenamine; Micronefrin; Epitrate; Levo-Methylaminoethanolcatechol; Epinephrine hydrochloride; (-)-R-Epinephrine; 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-; 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol; AI3-19015; Adrenalin chloride; Lopac-E-4642; 1,2-Benzenediol, 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-; 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol; CHEMBL679; YKH834O4BH; Adrenan; Susphrine; Adrine; D-Epinephrine; (R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; D-Epifrin; CHEBI:28918; Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)-; Asthmanefrin; MFCD00002204; NCGC00015417-01; NCGC00142615-03; NCGC00142615-08; Adrenalina; 1,2-Benzenediol, 4-((1R)-1-hydroxy-2-(methylamino)ethyl)-; 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (theta)-; DSSTox_CID_2986; Adrenaline (L-Adrenaline); DSSTox_RID_76819; L(-)-Epinephrine, 99%; DSSTox_GSID_22986; (-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol; Adrenaclick; Exadri; 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-, (R)-; EPIPEN E Z PEN; l-Epinephine; Asthmahaler Mist; EPI E Z PEN JR; Ana-Guard; Ana-Kit; (+/-)-Epinephrine; CAS-51-43-4; Epipen EZ Pen; L-Adrenaline Base; Twinject 0.3; Epi EZ Pen Jr; ADROP; Epinephrine [USAN:INN:JAN]; Epipen Auto-Injector; SUS-PHRINE SULFITE-FREE; CCRIS 4812; Twinject 0.15; Auvi-Q auto-injector; EPIPEN JR; HSDB 4289; (+/-)-Adrenalin; Bronkaid Suspension Mist; EINECS 200-098-7; NSC 62786; 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; Epipen Jr. Auto-Injector; (r)-4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol; Epinephrin; Levoreninum; Primatene; Symjepi; NSC62786; Bupivacaine Hcl and Epinephrine; NSC-62786; Epinephrine [USP:INN:BAN:JAN]; ALE; IOP; (-)-Adrenalin; Epinephrine (USP); Epipen (TN); nchembio747-comp9; Twinject 0.30; Adrenaline/Epinephrine; Adrenaline (JP15); Adrenaline (JP17); Epitrate (Salt/Mix); Auvi-q (TN); Epinephrine (USP/INN); bmse000316; 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol #; Citanest Forte (Salt/Mix); L-Adrenaline (Epinephrine); SCHEMBL3814; 3,4-Dihydroxy-.alpha.-((methylamino)methyl)benzyl alcohol; GTPL479; BIDD:GT0119; E4250_SIGMA; DTXSID5022986; BDBM44818; cid_6852374; HY-B0447B; ZINC39089; component of E-Pilo (Salt/Mix); HMS3884H06; (R)-(-)-3,4-Dihydroxy-alpha-(methylaminomethyl)benzyl alcohol; 104655-05-2; BCP09042; Tox21_111562; BDBM50029050; HSCI1_000215; MFCD00063027; PDSP1_001120; PDSP2_001104; s2522; SBB012384; 51-43-4 (FREE BASE); AKOS024283500; Tox21_111562_1; CCG-204593; D29A657; DB00668; MCULE-9462717294; NE58416; SDCCGSBI-0050486.P002; SMP1_000227; (-)-Epinephrine, >=97.0% (NT); NCGC00142615-01; NCGC00142615-04; NCGC00142615-05; NCGC00142615-06; NCGC00142615-07; NCGC00142615-09; NCGC00142615-18; AC-13188; AC-31211; AS-13813; L926; ST069368; 4,5-beta-trihydroxy-N-methylphenethylamine; A0173; SW219274-1; 1401-EP2270011A1; 1401-EP2298735A1; 1401-EP2301934A1; 1401-EP2305677A1; 1401-EP2308562A2; 1401-EP2308861A1; 1401-EP2311464A1; 1401-EP2311823A1; 1401-EP2314571A2; 6367-EP2272841A1; 6367-EP2277861A1; 6367-EP2301934A1; 6367-EP2301936A1; 6367-EP2314571A2; C00788; D00095; J10365; 91382-EP2284149A1; 91382-EP2305636A1; AB00573227-11; AB00573227-12; AB00573227-13; AB00573227_14; AB00573227_15; 204017-EP2277867A2; 204017-EP2280003A2; Q132621; 4-(1-hydroxy-2-methylamino-ethyl)benzene-1,2-diol; Q-200601; SR-01000075267-8; 3,4-Dihydroxy-alpha-(methylaminomethyl)benzyl alcohol; 4-[(1R)-1-hydroxy-2-methylaminoethyl]benzene-1,2-diol; Z2686405805; (-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcohol; Adrenaline, European Pharmacopoeia (EP) Reference Standard; UNII-GR0L9S3J0F component UCTWMZQNUQWSLP-VIFPVBQESA-N; (+/-)-3,4-Dihydroxy-alpha-(methylaminomethyl)benzyl alcohol; (-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcohol; (-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]pyrocatechol;tartaric acid; Adrenaline with impurity F, European Pharmacopoeia (EP) Reference Standard; Benzyl alcohol, 3,4-dihydroxy-.alpha.-[(methylamino)methyl]-, (-)-; 2,3-dihydroxybutanedioic acid;4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol; 2,3-bis(oxidanyl)butanedioic acid;4-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol
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Species Origin Ephedra sinica ...     Click to Show/Hide
Ephedra sinica
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Gnetopsida
Order: Ephedrales
Family: Ephedraceae
Genus: Ephedra
Species: Ephedra sinica
Disease Allergic/hypersensitivity disorder [ICD-11: 4A80-4A85] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.685
 
MDCK Permeability
 -4.895
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 0.283
 
PPB
 54.3%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - - -
 
Excretion
CLplasma
 18.397
 
T1/2
 2.266
Toxicity
DILI
 - - -
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 +
 
Respiratory
 ++
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 - -
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 - -
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C9H13NO3
PubChem CID
5816
Canonical SMILES
CNCC(C1=CC(=C(C=C1)O)O)O
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
CAS Number
CAS 51-43-4
ChEBI ID
CHEBI:28918
TTD Drug ID
D04PHC
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Esmolol      Supraventricular tachyarrhythmia     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression TNNI3  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Increase 24-hour survival rate
Down-regulation Lactate level
Up-regulation Mean aortic pressure
Up-regulation Oxygen consumption
Up-regulation Oxygen delivery
                    In-vivo Model Twenty-four inbred Wuzhishan miniature pigs (12-14 months of age, 30+/-2 kg) were used in this study.
                    Experimental
                    Result(s)		 Combination of epinephrine with esmolol attenuates post-resuscitation myocardial dysfunction in a porcine model of cardiac arrest.
Target and Pathway
Target(s) Adrenergic receptor beta-1 (ADRB1)  Molecule Info  [3]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 cGMP-PKG signaling pathway
3 cAMP signaling pathway
4 Neuroactive ligand-receptor interaction
5 Endocytosis
6 Adrenergic signaling in cardiomyocytes
7 Gap junction
8 Salivary secretion
9 Dilated cardiomyopathy
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Beta1 adrenergic receptor signaling pathway
Pathwhiz Pathway Muscle/Heart Contraction Click to Show/Hide
Reactome Adrenoceptors Click to Show/Hide
2 G alpha (s) signalling events
WikiPathways Monoamine GPCRs Click to Show/Hide
2 Calcium Regulation in the Cardiac Cell
3 GPCRs, Class A Rhodopsin-like
4 Endothelin Pathways
5 GPCR ligand binding
6 GPCR downstream signaling
References
Reference 1 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).
Reference 2 Combination of epinephrine with esmolol attenuates post-resuscitation myocardial dysfunction in a porcine model of cardiac arrest. PLoS One. 2013 Dec 18;8(12):e82677.
Reference 3 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.
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