(-)-Epinephrine bitartrate

ID: ALA1256958

Cas Number: 51-42-3

PubChem CID: 6852374

Max Phase: Approved

First Approval: 1965

Molecular Formula: C13H19NO9

Molecular Weight: 183.21

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Epinephrine Bitartrate | Adrenalin tartrate | Adrenaline (as tartrate) | Adrenaline acid tartrate | Adrenaline bitartate | Adrenaline bitartrate | Epinephrine hydrogen tartrate | Epinephrine tartrate | Epinephrini hydrogenotartras | L-epinephrine hydrogen tartrate | NSC-756755 | Adrenaline bitartrate|(-)-Epinephrine bitartrate|Epinephrine hydrogen tartrate|MLS000028381|SMR000058630|Adrenalin tartrate|SR-01000075267|51-42-3|NSC-756755|Opera_ID_1462|Epinephrini hydrogenotartras|Lopac0_000502|SShow More⌵

Trade Names(2): Bronitin mist | Medihaler-epi

Canonical SMILES:  CNC[C@H](O)c1ccc(O)c(O)c1.O=C(O)C(O)C(O)C(=O)O

Standard InChI:  InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;/m0./s1

Standard InChI Key:  YLXIPWWIOISBDD-FVGYRXGTSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  0  0  0  0  0  0999 V2000
   13.9917  -12.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4206  -12.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7063   -9.1695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1352   -8.3445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4207  -10.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7063  -11.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4206  -12.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7063  -10.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4207   -9.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1352  -10.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1352  -11.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1352   -9.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8498   -7.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4414  -11.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7270   -9.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8704  -10.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1559   -9.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2980  -10.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125  -11.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125  -10.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7270  -10.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4414  -10.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1559  -10.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  2  7  1  0
  9  3  1  1
  4 12  1  0
  4 13  1  0
  5  8  2  0
  5  9  1  0
  5 10  1  0
  6  7  2  0
  6  8  1  0
  7 11  1  0
  9 12  1  0
 10 11  2  0
 20 18  2  0
 21 15  1  0
 22 14  1  0
 20 19  1  0
 22 23  1  0
 21 22  1  0
 23 17  1  0
 20 21  1  0
 23 16  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 183.21

Molecular Weight (Monoisotopic): 183.0895

AlogP: 0.35

#Rotatable Bonds: 3

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.69

CX Basic pKa: 8.91

CX LogP: -0.43

CX LogD: -1.63

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.51

Np Likeness Score: 1.12

References

1. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

2. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Unpublished dataset, 

7. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

8. Smith HE, Burrows EP..  (1977)  Agonist effects of beta-phenethylamines on the noradrenergic cyclic adenosine 3',5'-monophosphate generating system in rat limbic forebrain. Stereoisomers of p-hydroxynorephedrine.,  20  (7): [PMID:195059] [10.1021/jm00217a028]

9. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

10. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

11. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21