4-[4-(4-Bromo-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-fluoro-phenyl)-butan-1-one

ID: ALA28218

Chembl Id: CHEMBL28218

Cas Number: 10457-90-6

PubChem CID: 2448

Product Number: B134247

Max Phase: Approved

Molecular Formula: C21H23BrFNO2

Molecular Weight: 420.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bromperidol | NSC-759275 | R 11,333 | R-11333 | bromperidol|10457-90-6|Impromen|Bromoperidol|4-(4-(4-bromophenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one|R 11333|4-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one|NSC-759275|4-(4-(4-Bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone|4-(4-(p-Bromophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone|R 11,333|LYH6F7I22E|DTXSID0022690|Tesoprel|R-11333|1-Butanone, 4-(4-(4-bromophenyl)-4-hydroxy-1-piperidinyShow More⌵

Trade Names(1): Impromen

Canonical SMILES:  O=C(CCCN1CCC(O)(c2ccc(Br)cc2)CC1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C21H23BrFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

Standard InChI Key:  RKLNONIVDFXQRX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA28218

   BROMPERIDOL

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 420.32

Molecular Weight (Monoisotopic): 419.0896

AlogP: 4.53

#Rotatable Bonds: 6

Polar Surface Area: 40.54

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.97

CX Basic pKa: 8.07

CX LogP: 3.83

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.84

References

1. Moerlein SM, Stöcklin GL..  (1985)  Synthesis of high specific activity [75Br]- and [77Br]bromperidol and tissue distribution studies in the rat.,  28  (9): [PMID:4032434] [10.1021/jm00147a035]

2. Vincent SH, Shambhu MB, Digenis GA..  (1980)  Synthesis of [82Br]bromperidol and preliminary tissue distribution studies in the rat.,  23  (1): [PMID:7359515] [10.1021/jm00175a014]

3. Kornhuber J, Tripal P, Reichel M, Terfloth L, Bleich S, Wiltfang J, Gulbins E..  (2008)  Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.,  51  (2): [PMID:18027916] [10.1021/jm070524a]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

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

7. PubChem BioAssay data set, 

8. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

9. PubChem BioAssay data set, 

10. WHO Anatomical Therapeutic Chemical Classification, 

11. British National Formulary (72nd edition), 

12. Unpublished dataset, 

13. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

14. 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]

15. 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]

16. 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]

17. 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]

18. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

19. 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]

20. Punetha A, Green KD, Garzan A, Thamban Chandrika N, Willby MJ, Pang AH, Hou C, Holbrook SYL, Krieger K, Posey JE, Parish T, Tsodikov OV, Garneau-Tsodikova S..  (2021)  Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from Mycobacterium tuberculosis to overcome kanamycin resistance.,  12  (11.0): [PMID:34825186] [10.1039/D1MD00239B]

21. Holbrook SYL, Garzan A, Dennis EK, Shrestha SK, Garneau-Tsodikova S..  (2017)  Repurposing antipsychotic drugs into antifungal agents: Synergistic combinations of azoles and bromperidol derivatives in the treatment of various fungal infections.,  139  [PMID:28797882] [10.1016/j.ejmech.2017.07.030]

22. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• 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
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6