VORTIOXETINE HYDROBROMIDE

ID: ALA2107387

Cas Number: 960203-27-4

PubChem CID: 56843850

Product Number: V129787, Order Now?

Max Phase: Approved

First Approval: 2013

Molecular Formula: C18H23BrN2S

Molecular Weight: 298.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lu aa21004 hbr | Lu-aa21004 hydrobromide | Lu AA21004 (HBr) | Vortioxetine hydrobromide|960203-27-4|Vortioxetine HBr|Brintellix|Trintellix|Vortioxetine (Lu AA21004) HBr|Vortioxetine (hydrobromide)|UNII-TKS641KOAY|Lu AA 21004 hydrobromide|Lu aa21004 hbr|TKS641KOAY|Lu-aa21004 hydrobromide|CHEBI:76015|Vortioxetine hydrobromide [USAN]|Voltiocetin hydrobromide|vortioxetine monohydrobromide|LU-AA21004 HBR|Lu AA21004 (HBr)|Vortioxetine.HBr|1-(2-((2,4-Dimethylphenyl)thio)phenyl)piperazine hydrobromide|9Show More⌵

Trade Names(2): Brintellix | Trintellix

Canonical SMILES:  Br.Cc1ccc(Sc2ccccc2N2CCNCC2)c(C)c1

Standard InChI:  InChI=1S/C18H22N2S.BrH/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20;/h3-8,13,19H,9-12H2,1-2H3;1H

Standard InChI Key:  VNGRUFUIHGGOOM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
  -14.5259  -16.5589    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  -20.3009  -14.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -21.0154  -15.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -21.0154  -16.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.3009  -16.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.5864  -16.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.5864  -15.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -21.7299  -16.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8719  -16.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8719  -14.9384    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8719  -14.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1574  -13.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1574  -12.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8719  -12.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.5864  -12.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.5864  -13.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4430  -14.1134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4430  -14.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7285  -15.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0140  -14.9384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0140  -14.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7285  -13.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  2  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  4  8  1  0
  6  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 16  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 22 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
M  END

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: Yes

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 298.46

Molecular Weight (Monoisotopic): 298.1504

AlogP: 3.86

#Rotatable Bonds: 3

Polar Surface Area: 15.27

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.85

CX LogP: 4.76

CX LogD: 3.31

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.93

Np Likeness Score: -1.11

References

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

2. Unpublished dataset, 

3. Hvenegaard MG, Bang-Andersen B, Pedersen H, Jørgensen M, Püschl A, Dalgaard L..  (2012)  Identification of the cytochrome P450 and other enzymes involved in the in vitro oxidative metabolism of a novel antidepressant, Lu AA21004.,  40  (7): [PMID:22496396] [10.1124/dmd.112.044610]

4. Hvenegaard MG, Bang-Andersen B, Pedersen H, Jørgensen M, Püschl A, Dalgaard L..  (2012)  Identification of the cytochrome P450 and other enzymes involved in the in vitro oxidative metabolism of a novel antidepressant, Lu AA21004.,  40  (7): [PMID:22496396] [10.1124/dmd.112.044610]

5. 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]

6. 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]

7. 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]

8. European Medicines Agency, 

Source

Source(5):

• Scientific Literature
• 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
• European Medicines Agency