ID: ALA1201022

Max Phase: Approved

First Approval: 1987

Molecular Formula: C11H12ClN5

Molecular Weight: 213.24

Molecule Type: Small molecule

Representations

Synonyms (7): Phenazopyridine hcl | Phenazopyridine hydrochloride | NC 150 | NC-150 | NSC-1879 | W 1655 | W-1655
Synonyms from Alternative Forms(7):

Trade Names(2): Pyridium | Uropyrine

Canonical SMILES:  Cl.Nc1ccc(/N=N/c2ccccc2)c(N)n1

Standard InChI:  InChI=1S/C11H11N5.ClH/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8;/h1-7H,(H4,12,13,14);1H/b16-15+;

Standard InChI Key:  QQBPIHBUCMDKFG-GEEYTBSJSA-N

Molecule Features

Natural Product: No

Oral: Yes

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: 213.24

Molecular Weight (Monoisotopic): 213.1014

AlogP: 2.66

#Rotatable Bonds: 2

Polar Surface Area: 89.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 6.86

CX LogP: 2.69

CX LogD: 2.58

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.75

Np Likeness Score: -0.56

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

5. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

6. Unpublished dataset, 

7. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

8. Villalta-Romero F, Gortat A, Herrera AE, Arguedas R, Quesada J, de Melo RL, Calvete JJ, Montero M, Murillo R, Rucavado A, Gutiérrez JM, Pérez-Payá E..  (2012)  Identification of new snake venom metalloproteinase inhibitors using compound screening and rational Peptide design.,  3  (7): [PMID:24900507] [10.1021/ml300068r]

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

10. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

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. Rana P, Will Y, Nadanaciva S, Jones LH..  (2016)  Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.,  26  (16): [PMID:27397500] [10.1016/j.bmcl.2016.06.088]

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. Loring HS,Parelkar SS,Mondal S,Thompson PR.  (2020)  Identification of the first noncompetitive SARM1 inhibitors.,  28  (18): [PMID:32828421] [10.1016/j.bmc.2020.115644]

Source

Source(7):

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