ID: ALA1569487

Max Phase: Approved

Molecular Formula: C13H10ClN3O4S2

Molecular Weight: 371.83

Molecule Type: Small molecule

Representations

Synonyms (7): Lorcam | Lornoxicam | CTX | NSC-759620 | RO 13-9297 | RO-13-9297 | RO-139297
Synonyms from Alternative Forms(7):

Trade Names(1): Xefo

Canonical SMILES:  CN1C(C(=O)Nc2ccccn2)=C(O)c2sc(Cl)cc2S1(=O)=O

Standard InChI:  InChI=1S/C13H10ClN3O4S2/c1-17-10(13(19)16-9-4-2-3-5-15-9)11(18)12-7(23(17,20)21)6-8(14)22-12/h2-6,18H,1H3,(H,15,16,19)

Standard InChI Key:  WLHQHAUOOXYABV-UHFFFAOYSA-N

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

Properties

Molecular Weight: 371.83

Molecular Weight (Monoisotopic): 370.9801

AlogP: 2.30

#Rotatable Bonds: 2

Polar Surface Area: 99.60

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.82

CX Basic pKa: 4.22

CX LogP: 0.64

CX LogD: -1.14

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -1.42

References

1. Guerra A, Campillo NE, Páez JA..  (2010)  Neural computational prediction of oral drug absorption based on CODES 2D descriptors.,  45  (3): [PMID:20022146] [10.1016/j.ejmech.2009.11.034]

2. PubChem BioAssay data set, 

3. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

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

5. Unpublished dataset, 

6. Unpublished dataset, 

7. Unpublished dataset, 

8. WHO Anatomical Therapeutic Chemical Classification, 

9. British National Formulary (72nd edition), 

10. Open TG-GATES,  [10.6019/CHEMBL3885861]

11. Morgan RE, van Staden CJ, Chen Y, Kalyanaraman N, Kalanzi J, Dunn RT, Afshari CA, Hamadeh HK..  (2013)  A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.,  136  (1): [PMID:23956101] [10.1093/toxsci/kft176]

12. Unpublished dataset, 

13. 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]

14. 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]

15. Dargó G, Bajusz D, Simon K, Müller J, Balogh GT..  (2020)  Human Serum Albumin Binding in a Vial: A Novel UV-pH Titration Method To Assist Drug Design.,  63  (4): [PMID:31995375] [10.1021/acs.jmedchem.0c00046]

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. 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]

19. 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(10):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Open TG-GATEs
• USP Dictionary of USAN and International Drug Names
• Gene Expression Atlas Compounds
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6