ID: ALA3989559

Max Phase: Approved

First Approval: 2000

Molecular Formula: C16H16F2N3NaO5S

Molecular Weight: 383.38

Molecule Type: Small molecule

Representations

Synonyms (7): Controloc control | Pantoprazole (as sodium) | Pantoprazole sodium | Pantoprazole sodium hydrate | Pantoprazole sodium sesquihydrate | Pantozol control | Somac control
Synonyms from Alternative Forms(7):

Trade Names(4): Pantoprazole sodium | Pantozol control | Protonix | Protonix iv

Canonical SMILES:  COc1ccnc(C[S+]([O-])c2nc3cc(OC(F)F)ccc3[n-]2)c1OC.O.[Na+]

Standard InChI:  InChI=1S/C16H14F2N3O4S.Na.H2O/c1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16;;/h3-7,15H,8H2,1-2H3;;1H2/q-1;+1;

Standard InChI Key:  CGJRLPRCWSHOFU-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 383.38

Molecular Weight (Monoisotopic): 383.0751

AlogP: 2.88

#Rotatable Bonds: 7

Polar Surface Area: 92.32

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.54

CX Basic pKa: 3.55

CX LogP: 2.18

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.88

References

1. Unpublished dataset, 

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

3. PubChem BioAssay data set, 

4. Shea TA, Burburan PJ, Matubia VN, Ramcharan SS, Rosario I, Parkin DW, Stockman BJ..  (2014)  Identification of proton-pump inhibitor drugs that inhibit Trichomonas vaginalis uridine nucleoside ribohydrolase.,  24  (4): [PMID:24468412] [10.1016/j.bmcl.2014.01.014]

5. PubChem BioAssay data set, 

6. Wang L, McNamara PJ..  (2012)  Stereoselective interaction of pantoprazole with ABCG2. I. Drug accumulation in rat milk.,  40  (5): [PMID:22344699] [10.1124/dmd.111.041608]

7. Wang L, McNamara PJ..  (2012)  Stereoselective interaction of pantoprazole with ABCG2. I. Drug accumulation in rat milk.,  40  (5): [PMID:22344699] [10.1124/dmd.111.041608]

8. Wang L, McNamara PJ..  (2012)  Stereoselective interaction of pantoprazole with ABCG2. I. Drug accumulation in rat milk.,  40  (5): [PMID:22344699] [10.1124/dmd.111.041608]

9. Bi Y, Might M, Vankayalapati H, Kuberan B..  (2017)  Repurposing of Proton Pump Inhibitors as first identified small molecule inhibitors of endo-β-N-acetylglucosaminidase (ENGase) for the treatment of NGLY1 deficiency, a rare genetic disease.,  27  (13): [PMID:28512024] [10.1016/j.bmcl.2017.05.010]

10. Unpublished dataset, 

11. 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]

12. 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]

13.  (2018)  INHIBITORS OF SARM1 NADase ACTIVITY AND USES THEREOF, 

14. 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]

15. 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]

16. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

17. European Medicines Agency, 

Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21
• European Medicines Agency