salmeterol xinafoate

ID: ALA1082607

Chembl Id: CHEMBL1082607

Cas Number: 94749-08-3

PubChem CID: 56801

Product Number: S121754

Max Phase: Approved

First Approval: 1994

Molecular Formula: C36H45NO7

Molecular Weight: 415.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Salmeterol xinafoate | GR 33343 G | GR-33343 G | GR-33343X | LIPO-202 | salmeterol xinafoate|94749-08-3|Salmetedur|Arial|Serevent diskus|Asmerole|Betamican|Ultrabeta|Beglan|Dilamax|Inaspir|Salmeterol 1-hydroxy-2-naphthoate|GR 33343X xinafoate|GR 33343 G|Serevent Inhaler and Disks|SALMETEROLO|Salmeterol (xinafoate)|4-(1-Hydroxy-2-((6-(4-phenylbutoxy)hexyl)amino)ethyl)-2-(hydroxymethyl)phenol 1-hydroxy-2-naphthoate|UNII-6EW8Q962A5|DTXSID1045798|6EW8Q962A5|GR-33343X|GR-33343 G|2-(hydroxymethyl)-4-[Show More⌵

Trade Names(1): Serevent

Canonical SMILES:  O=C(O)c1ccc2ccccc2c1O.OCc1cc(C(O)CNCCCCCCOCCCCc2ccccc2)ccc1O

Standard InChI:  InChI=1S/C25H37NO4.C11H8O3/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2;1-6,12H,(H,13,14)

Standard InChI Key:  XTZNCVSCVHTPAI-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: No

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 415.57

Molecular Weight (Monoisotopic): 415.2723

AlogP: 4.11

#Rotatable Bonds: 16

Polar Surface Area: 81.95

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.12

CX Basic pKa: 9.40

CX LogP: 3.61

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: 0.20

References

1. Procopiou PA, Barrett VJ, Bevan NJ, Biggadike K, Box PC, Butchers PR, Coe DM, Conroy R, Emmons A, Ford AJ, Holmes DS, Horsley H, Kerr F, Li-Kwai-Cheung AM, Looker BE, Mann IS, McLay IM, Morrison VS, Mutch PJ, Smith CE, Tomlin P..  (2010)  Synthesis and structure-activity relationships of long-acting beta2 adrenergic receptor agonists incorporating metabolic inactivation: an antedrug approach.,  53  (11): [PMID:20462258] [10.1021/jm100326d]

2. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Unpublished dataset, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

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

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. 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]

15. Unpublished dataset, 

16. 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]

17. 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]

18. 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]

Source

Source(6):

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