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Showing NP-Card for Celecoxib (NP0334572)

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Record Information
Version2.0
Created at2024-09-10 18:57:30 UTC
Updated at2024-09-10 18:57:31 UTC
NP-MRD IDNP0334572
Secondary Accession NumbersNone
Natural Product Identification
Common NameCelecoxib
DescriptionCelecoxib, also known as celebrex or onsenal, 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. Celecoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). Celecoxib can be converted into hydroxycelecoxib; which is catalyzed by the enzymes cytochrome P450 2C9 and cytochrome P450 3A4. In humans, celecoxib is involved in celecoxib action pathway. Celecoxib is a potentially toxic compound. Celecoxib was first documented in 2007 (PMID: 17983259). The increased risk is about 81% (PMID: 18405470) (PMID: 19137124) (PMID: 19203891) (PMID: 21955617) (PMID: 22141388) (PMID: 22419293).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334572 (Celecoxib)

482
  Mrv0541 02231214432D          

 26 28  0  0  0  0            999 V2000
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M  END
Download

3D MOL for NP0334572 (Celecoxib)

Download
3D SDF for NP0334572 (Celecoxib)
482
  Mrv0541 02231214432D          

 26 28  0  0  0  0            999 V2000
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    1.6500    2.3402    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849    3.3101    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325    3.4926    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3899   -2.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5475    1.3731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -3.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2801    1.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2363    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232    0.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    1.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175    2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0209    0.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0334572

> <DATABASE_NAME>
NP-MRD

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

> <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

> <FORMULA>
C17H14F3N3O2S

> <MOLECULAR_WEIGHT>
381.372

> <EXACT_MASS>
381.075882012

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.200201261435936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.009441774333333

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.70145080874998

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4187111614431479

> <JCHEM_POLAR_SURFACE_AREA>
77.98

> <JCHEM_REFRACTIVITY>
92.23420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
celecoxib

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334572 (Celecoxib)
Download
PDB for NP0334572 (Celecoxib)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 482                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.001  -4.502   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0       3.080   4.368   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       5.572   6.179   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       3.421   6.520   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       7.541  -4.502   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.461  -4.502   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       6.001   1.658   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.755   2.563   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.001  -6.042   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.247   2.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.001   0.118   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.712   2.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.771   4.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.231   4.028   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.335  -0.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.668  -0.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.001  -2.962   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.032   0.581   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.856   3.118   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.335  -2.192   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.668  -2.192   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.641   1.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.497   0.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.321   2.642   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.326   5.274   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.106   0.660   0.000  0.00  0.00           C+0
CONECT    1    5    6    9   17                                             
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8   10   11                                                  
CONECT    8    7   14                                                       
CONECT    9    1                                                            
CONECT   10    7   12   13                                                  
CONECT   11    7   15   16                                                  
CONECT   12   10   18   19                                                  
CONECT   13   10   14                                                       
CONECT   14    8   13   25                                                  
CONECT   15   11   20                                                       
CONECT   16   11   21                                                       
CONECT   17    1   20   21                                                  
CONECT   18   12   23                                                       
CONECT   19   12   24                                                       
CONECT   20   15   17                                                       
CONECT   21   16   17                                                       
CONECT   22   23   24   26                                                  
CONECT   23   18   22                                                       
CONECT   24   19   22                                                       
CONECT   25    2    3    4   14                                             
CONECT   26   22                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Download
3D PDB for NP0334572 (Celecoxib)
Download
SMILES for NP0334572 (Celecoxib)
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
Download
INCHI for NP0334572 (Celecoxib)
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)
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View in JSmol
Synonyms
ValueSource
CelebrexChEBI
CelecoxibumChEBI
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamideChEBI
OnsenalKegg
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamideGenerator
CelocoxibHMDB
4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamideHMDB
Chemical FormulaC17H14F3N3O2S
Average Mass381.3720 Da
Monoisotopic Mass381.07588 Da
IUPAC Name4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional Namecelecoxib
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
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 KeyRZEKVGVHFLEQIL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzoles  
Sub ClassPyrazoles  
Direct ParentPhenylpyrazoles  
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.99ALOGPS
logP4.01ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)10.7ChemAxon
pKa (Strongest Basic)-0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.23 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005014  
DrugBank IDDB00482  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023586  
KNApSAcK IDNot Available
Chemspider ID2562  
KEGG Compound IDC07589  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCelecoxib  
METLIN IDNot Available
PubChem Compound2662  
PDB IDNot Available
ChEBI ID41423  
Good Scents IDNot Available
References
General References
  1. Frampton JE, Keating GM: Celecoxib: a review of its use in the management of arthritis and acute pain. Drugs. 2007;67(16):2433-72. doi: 10.2165/00003495-200767160-00008. [PubMed:17983259  ] 
  2. Chen YF, Jobanputra P, Barton P, Bryan S, Fry-Smith A, Harris G, Taylor RS: Cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs (etodolac, meloxicam, celecoxib, rofecoxib, etoricoxib, valdecoxib and lumiracoxib) for osteoarthritis and rheumatoid arthritis: a systematic review and economic evaluation. Health Technol Assess. 2008 Apr;12(11):1-278, iii. doi: 10.3310/hta12110. [PubMed:18405470  ] 
  3. O'Connor JP, Lysz T: Celecoxib, NSAIDs and the skeleton. Drugs Today (Barc). 2008 Sep;44(9):693-709. doi: 10.1358/dot.2008.44.9.1251573. [PubMed:19137124  ] 
  4. Fakih MG, Rustum YM: Does celecoxib have a role in the treatment of patients with colorectal cancer? Clin Colorectal Cancer. 2009 Jan;8(1):11-4. doi: 10.3816/CCC.2009.n.002. [PubMed:19203891  ] 
  5. Zweers MC, de Boer TN, van Roon J, Bijlsma JW, Lafeber FP, Mastbergen SC: Celecoxib: considerations regarding its potential disease-modifying properties in osteoarthritis. Arthritis Res Ther. 2011;13(5):239. doi: 10.1186/ar3437. Epub 2011 Sep 21. [PubMed:21955617  ] 
  6. McCormack PL: Celecoxib: a review of its use for symptomatic relief in the treatment of osteoarthritis, rheumatoid arthritis and ankylosing spondylitis. Drugs. 2011 Dec 24;71(18):2457-89. doi: 10.2165/11208240-000000000-00000. [PubMed:22141388  ] 
  7. Derry S, Moore RA: Single dose oral celecoxib for acute postoperative pain in adults. Cochrane Database Syst Rev. 2012 Mar 14;3(3):CD004233. doi:  10.1002/14651858.CD004233.pub3. [PubMed:22419293  ] 
  8. Huelin R, Pokora T, Foster TS, Mould JF: Economic outcomes for celecoxib: a systematic review of pharmacoeconomic studies. Expert Rev Pharmacoecon Outcomes Res. 2012 Aug;12(4):505-23. doi:  10.1586/erp.12.36. [PubMed:22971036  ] 
  9. Sacchetti A: Cancer cell killing by Celecoxib: reality or just in vitro precipitation-related artifact? J Cell Biochem. 2013 Jun;114(6):1434-44. doi: 10.1002/jcb.24485. [PubMed:23296687  ] 
  10. Essex MN, Zhang RY, Berger MF, Upadhyay S, Park PW: Safety of celecoxib compared with placebo and non-selective NSAIDs: cumulative meta-analysis of 89 randomized controlled trials. Expert Opin Drug Saf. 2013 Jul;12(4):465-77. doi: 10.1517/14740338.2013.780595.  Epub 2013 Mar 19. [PubMed:23506230  ]