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Cimicoxib

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Also known as: 265114-23-6, Cimalgex, Cimicoxib [inn], Ur-8880, 4-(4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl)benzenesulfonamide, W7fhj107mc

Molecular Formula

C₁₆H₁₃ClFN₃O₃S

Molecular Weight

381.8 g/mol

InChI Key

KYXDNECMRLFQMZ-UHFFFAOYSA-N

FDA UNII

W7FHJ107MC

Cimicoxib is a selective COX-2 inhibitor being developed by Affectis as a treatment for depression and schizophrenia. If approved, Cimicoxib would be the first drug in decades to treat depression by a new mechanism of action.

1 2D Structure

Cimicoxib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide

2.1.2 InChI

InChI=1S/C16H13ClFN3O3S/c1-24-14-7-2-10(8-13(14)18)15-16(17)20-9-21(15)11-3-5-12(6-4-11)25(19,22)23/h2-9H,1H3,(H2,19,22,23)

2.1.3 InChI Key

KYXDNECMRLFQMZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)C2=C(N=CN2C3=CC=C(C=C3)S(=O)(=O)N)Cl)F

2.2 Other Identifiers

2.2.1 UNII

W7FHJ107MC

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 265114-23-6

2. Cimalgex

3. Cimicoxib [inn]

4. Ur-8880

5. 4-(4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl)benzenesulfonamide

6. W7fhj107mc

7. 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide

8. Chembl435381

9. Chebi:76127

10. Cimicoxib (ema Epar: Veterinary)

11. 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl]benzenesulfonamide

12. Ur 8880;ur-8880;ur8880

13. Benzenesulfonamide, 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl]-

14. Unii-w7fhj107mc

15. Cimicoxib [mi]

16. Schembl3123310

17. Dtxsid30181093

18. Bcp24933

19. Zinc1494105

20. Bdbm50131593

21. Db05095

22. Ncgc00531794-01

23. Hy-100516

24. Cs-0019655

25. Q5120133

26. 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonamide

27. 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)-imidazol-1-yl]-benzenesulfonamide

28. Cimicoxib;4-(4-chloro-5-(3-fluoro-4-methoxyphenyl)-1h-imidazol-1-yl)benzene Sulfonamide

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₃ClFN₃O₃S
Molecular Weight	381.8 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	381.0350183 g/mol
Monoisotopic Mass	381.0350183 g/mol
Topological Polar Surface Area	95.6 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	553
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in depression.

Relief of pain and inflammation associated with osteoarthritis .

Management of peri-operative pain due to orthopaedic or soft-tissue surgeries.

5 Pharmacology and Biochemistry

5.1 ATC Code

QM01AH93

5.2 Mechanism of Action

Depression and schizophrenia are inflammatory diseases. Increased levels of pro-inflammatory cytokines and prostaglandin E (PGE) have repeatedly been described in major depression. COX-2 inhibitors inhibit production of both. Cimicoxib is a selective COX-2 inhibitor. The mechanism by which some COX-2 inhibitors work in depression could be linked to their anti-inflammatory mechanisms.

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