ID: ALA2104993

Max Phase: Approved

First Approval: 2013

Molecular Formula: C18H22N2S

Molecular Weight: 298.46

Molecule Type: Small molecule

Representations

Synonyms (4): Vortioxetine | LU AA21004 | LU-AA21004 | LUAA21004
Synonyms from Alternative Forms(4):

Trade Names(1): Brintellix

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

Standard InChI:  InChI=1S/C18H22N2S/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

Standard InChI Key:  YQNWZWMKLDQSAC-UHFFFAOYSA-N

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

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: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

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. WHO Anatomical Therapeutic Chemical Classification, 

3. British National Formulary (72nd edition), 

4. Gu ZS, Xiao Y, Zhang QW, Li JQ..  (2017)  Synthesis and antidepressant activity of a series of arylalkanol and aralkyl piperazine derivatives targeting SSRI/5-HT1A/5-HT7.,  27  (24): [PMID:29138029] [10.1016/j.bmcl.2017.11.007]

5. Gu ZS, Zhou AN, Xiao Y, Zhang QW, Li JQ..  (2018)  Synthesis and antidepressant-like activity of novel aralkyl piperazine derivatives targeting SSRI/5-HT1A/5-HT7.,  144  [PMID:29291438] [10.1016/j.ejmech.2017.12.063]

6. Unpublished dataset, 

7. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

8. Gu ZS, Wang WT, Qian H, Zhou AN, Sun HB, Zhang QW, Li JQ..  (2019)  Synthesis and antidepressant effect of novel aralkyl piperazine and piperidine derivatives targeting SSRI/5-HT1A/5-HT7.,  29  (23): [PMID:31627993] [10.1016/j.bmcl.2019.126703]

9. Wang WT, Qian H, Wu JW, Chen XW, Li JQ..  (2019)  Synthesis and antidepressant-like activity of novel alkoxy-piperidine derivatives targeting SSRI/5-HT1A/5-HT7.,  29  (24): [PMID:31699607] [10.1016/j.bmcl.2019.126769]

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. 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]

12. 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]

13. 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]

14. 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]

15. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

16. Kucwaj-Brysz K, Baltrukevich H, Czarnota K, Handzlik J..  (2021)  Chemical update on the potential for serotonin 5-HT₆ and 5-HT₇ receptor agents in the treatment of Alzheimer's disease.,  49  [PMID:34311086] [10.1016/j.bmcl.2021.128275]

17. Yuan RX, Jiang KY, Wu JW, Zhang ZX, Li MS, Li JQ, Ni F..  (2022)  Synthesis and antidepressant activity of novel 1-(1-benzoylpiperidin-4-yl) methanamine derivatives selectively targeting SSRI/5-HT_1A.,  76  [PMID:36202190] [10.1016/j.bmcl.2022.129006]

18. Talmon M, Chaudhari RD, Suryavanshi H, Chowdhury N, Quaregna M, Pin A, Bagchi A, Biswas G, Fresu LG..  (2020)  Design, synthesis and biological evaluation of vortioxetine derivatives as new COX-1/2 inhibitors in human monocytes.,  28  (23.0): [PMID:32992247] [10.1016/j.bmc.2020.115760]

19. Institute for Molecular Medicine Finland - High Throughput Biomedicine Unit.  (2023)  ECBD screening data for assay EOS300108,  [10.6019/EOS300108]

Source

Source(8):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset