Showing Compound Celecoxib (FDB023586)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:00 UTC

Update date

2018-05-28 18:36:46 UTC

Primary ID

FDB023586

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Celecoxib

Description

Celecoxib (INN) is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer under the brand name Celebrex. In some countries, it is branded Celebra.; Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs; Celecoxib is a highly selective COX-2 inhibitor and primarily inhibits this isoform of cyclooxygenase, whereas traditional NSAIDs inhibit both COX-1 and COX-2. Celecoxib is approximately 10-20 times more selective for COX-2 inhibition over COX-1. In theory, this specificity allows celecoxib and other COX-2 inhibitors to reduce inflammation (and pain) while minimizing gastrointestinal adverse drug reactions (e.g. stomach ulcers) that are common with non-selective NSAIDs. It also means that it has a reduced effect on platelet aggregation compared to traditional NSAIDs. [HMDB]

CAS Number

169590-42-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide	HMDB
Celebrex	ChEBI
Celecoxib	hmdb
Celecoxibum	ChEBI
Celocoxib	HMDB
Onsenal	Kegg
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide	ChEBI
P-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide	ChEBI
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamide	Generator
P-(5-P-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamide	Generator

Showing 1 to 10 of 10 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	3.99	ALOGPS
logP	4.01	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.7	ChemAxon
pKa (Strongest Basic)	-0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.23 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H14F3N3O2S

IUPAC name

4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide

InChI Identifier

InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)

InChI Key

RZEKVGVHFLEQIL-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F

Average Molecular Weight

381.372

Monoisotopic Molecular Weight

381.075882012

Classification

Description

Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
Benzenesulfonamide
Benzenesulfonyl group
Toluene
Monocyclic benzene moiety
Organosulfonic acid amide
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Azacycle
Organic oxide
Alkyl halide
Alkyl fluoride
Organopnictogen compound
Organosulfur compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:41423 )
pyrazoles (CHEBI:41423 )
sulfonamide (CHEBI:41423 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

General disorders and administration site conditions:

Pain

Gastrointestinal disorders:

Biofluid and excreta:

Blood

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Celecoxib, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uy0-0729000000-75ddea9acd30a029b25b	Spectrum
Predicted GC-MS	Celecoxib, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Celecoxib, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0aou-3960000000-2bd7d8539498dde5c2f5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0029000000-1a5ed66ff895eeb127ce	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0129000000-a967b7f9e88a461e3db4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-01q9-2598000000-f71f4f9eb7c83ddf79f4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0029000000-13ff69b3abd31dde6bae	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-014i-9100000000-9a8cd0b75d276f108651	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-41eaecd214cbc50e645e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-f2376e3bc87d5951988c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-02vi-9100000000-3b8e53549d02c7db5cba	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-014i-9220000000-e1d41283ce6235c1de0d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0gx0-0059000000-9e48db23da1b4b859e68	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0009000000-25406fbf853a86a41e2f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-016r-7292000000-0c298e1f9b51823232c7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-57c7836793a5363fda3d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-017j-0198000000-927a7c09840b934e4cea	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-e3bce1b4f36e339f9f39	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001i-0293000000-c8b94b6bd1da23395b78	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-001i-0009000000-72b8641321f8f9f0f2b3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0490000000-0b6fde7d96dea087de34	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-23d25f88a0e277e47c54	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-a933645e1cf7fb8edf4f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3289000000-7c03de47cb9bd124fa0c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-9d1a9c471dc123cee735	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-bdb3f0787c9e831e7530	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9125000000-ad5803f68fece8f76b2a	2016-08-03	View Spectrum