4-Ethyl-5-(pyridine-4-carbonyl)-1,3-dihydro-imidazol-2-one

ID: ALA58355

Chembl Id: CHEMBL58355

Cas Number: 84490-12-0

PubChem CID: 55263

Max Phase: Phase

Molecular Formula: C11H11N3O2

Molecular Weight: 217.23

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MDL 19,205 | MDL-19205 | Piroximone|84490-12-0|MDL-19205|MDL 19,205|4-Ethyl-5-isonicotinoyl-4-imidazolin-2-one|4-ethyl-5-(pyridine-4-carbonyl)-1,3-dihydroimidazol-2-one|2VSD0380YB|Piroximone (USAN)|Piroximonum|2H-Imidazol-2-one, 4-ethyl-1,3-dihydro-5-(4-pyridinylcarbonyl)-|PIROXIMONE [USAN]|Piroximonum [Latin]|Piroximona [Spanish]|Piroximona|UNII-2VSD0380YB|Piroximone [USAN:INN:BAN]|PIROXIMONE [INN]|PIROXIMONE [MART.]|CHEMBL58355|SCHEMBL119758|DTXSID20233479|BDBM50225502|AKOS027201112|NS00123455Show More⌵

Canonical SMILES:  CCc1[nH]c(=O)[nH]c1C(=O)c1ccncc1

Standard InChI:  InChI=1S/C11H11N3O2/c1-2-8-9(14-11(16)13-8)10(15)7-3-5-12-6-4-7/h3-6H,2H2,1H3,(H2,13,14,16)

Standard InChI Key:  OQGWJZOWLHWFME-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA58355

   PIROXIMONE

Molecule Features

Natural Product: No

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: 217.23

Molecular Weight (Monoisotopic): 217.0851

AlogP: 0.89

#Rotatable Bonds: 3

Polar Surface Area: 78.61

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.67

CX Basic pKa: 2.96

CX LogP: 0.52

CX LogD: 0.52

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.75

Np Likeness Score: -0.76

References

1. Moos WH, Humblet CC, Sircar I, Rithner C, Weishaar RE, Bristol JA, McPhail AT..  (1987)  Cardiotonic agents. 8. Selective inhibitors of adenosine 3',5'-cyclic phosphate phosphodiesterase III. Elaboration of a five-point model for positive inotropic activity.,  30  (11): [PMID:2822927] [10.1021/jm00394a006]

2. Venuti MC, Stephenson RA, Alvarez R, Bruno JJ, Strosberg AM..  (1988)  Inhibitors of cyclic AMP phosphodiesterase. 3. Synthesis and biological evaluation of pyrido and imidazolyl analogues of 1,2,3,5-tetrahydro-2-oxoimidazo[2,1-b]quinazoline.,  31  (11): [PMID:2846839] [10.1021/jm00119a014]

3. Erhardt PW..  (1987)  In search of the digitalis replacement.,  30  (2): [PMID:3027335] [10.1021/jm00385a001]

4. Sircar I, Steffen RP, Bobowski G, Burke SE, Newton RS, Weishaar RE, Bristol JA, Evans DB..  (1989)  Cardiotonic agents. 9. Synthesis and biological evaluation of a series of (E)-4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]ethenyl]-3 (2H)-pyridazinones: a novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure.,  32  (2): [PMID:2536438] [10.1021/jm00122a011]

5. Weishaar RE, Cain MH, Bristol JA..  (1985)  A new generation of phosphodiesterase inhibitors: multiple molecular forms of phosphodiesterase and the potential for drug selectivity.,  28  (5): [PMID:2985781] [10.1021/jm50001a001]

6. Schnettler RA, Dage RC, Palopoli FP..  (1986)  4-Aroyl-1,3-dihydro-2H-imidazol-2-ones: a new class of cardiotonic agents. 2. Effect of 4-pyridoyl substituents and related compounds.,  29  (5): [PMID:3701794] [10.1021/jm00155a043]

7. 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]

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

9. 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]

10. 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]

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

14. 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]

Source

Source(5):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6