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Showing metabocard for Hydroxycelecoxib (HMDB0013995)
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| Version | 4.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-09-06 15:00:46 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2017-09-25 12:09:30 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| HMDB ID | HMDB0013995 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Status | Expected but not Quantified | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolite Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common Name | Hydroxycelecoxib | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Hydroxycelecoxib is only found in individuals that have used or taken Celecoxib. Hydroxycelecoxib is a metabolite of Celecoxib. Hydroxycelecoxib belongs to the family of Phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula | C17H14F3N3O3S | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 397.372 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 397.070796634 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | 4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl}benzene-1-sulfonamide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional Name | 4-{5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl}benzenesulfonamide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES | NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(CO)C=C1)C(F)(F)F | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1S/C17H14F3N3O3S/c18-17(19,20)16-9-15(12-3-1-11(10-24)2-4-12)23(22-16)13-5-7-14(8-6-13)27(21,25)26/h1-9,24H,10H2,(H2,21,25,26) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | ICRSYPPLGADZKA-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | This compound belongs to the class of chemical entities known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Chemical entities | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Azoles | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Phenylpyrazoles | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Ontology | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Disposition |
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| Process |
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| Role |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Displaying all 2 entries | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Associated Disorders and Diseases | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Disease References | None | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Associated OMIM IDs | None | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank Metabolite ID | DBMET00165 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Metabolite ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FoodDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KNApSAcK ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemspider ID | 8084428 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BiGG ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| NuGOwiki Link | HMDB0013995 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| METLIN ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 9908776 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 139316 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| General References | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Involved in peroxidase activity
- Specific function:
- Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
- Gene Name:
- PTGS2
- Uniprot ID:
- P35354
- Molecular weight:
- 68995.625
References
- Sigthorsson G, Simpson RJ, Walley M, Anthony A, Foster R, Hotz-Behoftsitz C, Palizban A, Pombo J, Watts J, Morham SG, Bjarnason I: COX-1 and 2, intestinal integrity, and pathogenesis of nonsteroidal anti-inflammatory drug enteropathy in mice. Gastroenterology. 2002 Jun;122(7):1913-23. [PubMed:12055598 ]
- Scheiman JM: Outcomes studies of the gastrointestinal safety of cyclooxygenase-2 inhibitors. Cleve Clin J Med. 2002;69 Suppl 1:SI40-6. [PubMed:12086292 ]
- Reddy BS, Rao CV: Novel approaches for colon cancer prevention by cyclooxygenase-2 inhibitors. J Environ Pathol Toxicol Oncol. 2002;21(2):155-64. [PubMed:12086402 ]
- Ahmad SR, Kortepeter C, Brinker A, Chen M, Beitz J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Saf. 2002;25(7):537-44. [PubMed:12093311 ]
- Lu S, Zhang X, Badawi AF, El-Sohemy A, Archer MC: Cyclooxygenase-2 inhibitor celecoxib inhibits promotion of mammary tumorigenesis in rats fed a high fat diet rich in n-6 polyunsaturated fatty acids. Cancer Lett. 2002 Oct 8;184(1):7-12. [PubMed:12104042 ]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
- General function:
- Involved in monooxygenase activity
- Specific function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular weight:
- 57255.585
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
- General function:
- Involved in monooxygenase activity
- Specific function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular weight:
- 55627.365
References
- Davies NM, McLachlan AJ, Day RO, Williams KM: Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet. 2000 Mar;38(3):225-42. [PubMed:10749518 ]
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
- Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
- Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [PubMed:11259318 ]
- General function:
- Involved in protein kinase activity
- Specific function:
- Phosphorylates and activates not only PKB/AKT, but also PKA, PKC-zeta, RPS6KA1 and RPS6KB1. May play a general role in signaling processes and in development. Isoform 3 is catalytically inactive
- Gene Name:
- PDPK1
- Uniprot ID:
- O15530
- Molecular weight:
- 63151.3
References
- Kulp SK, Yang YT, Hung CC, Chen KF, Lai JP, Tseng PH, Fowble JW, Ward PJ, Chen CS: 3-phosphoinositide-dependent protein kinase-1/Akt signaling represents a major cyclooxygenase-2-independent target for celecoxib in prostate cancer cells. Cancer Res. 2004 Feb 15;64(4):1444-51. [PubMed:14973075 ]
- Zhu J, Huang JW, Tseng PH, Yang YT, Fowble J, Shiau CW, Shaw YJ, Kulp SK, Chen CS: From the cyclooxygenase-2 inhibitor celecoxib to a novel class of 3-phosphoinositide-dependent protein kinase-1 inhibitors. Cancer Res. 2004 Jun 15;64(12):4309-18. [PubMed:15205346 ]
- Tong Z, Wu X, Ovcharenko D, Zhu J, Chen CS, Kehrer JP: Neutrophil gelatinase-associated lipocalin as a survival factor. Biochem J. 2005 Oct 15;391(Pt 2):441-8. [PubMed:16060857 ]
- Li J, Zhu J, Melvin WS, Bekaii-Saab TS, Chen CS, Muscarella P: A structurally optimized celecoxib derivative inhibits human pancreatic cancer cell growth. J Gastrointest Surg. 2006 Feb;10(2):207-14. [PubMed:16455452 ]
- Tseng PH, Wang YC, Weng SC, Weng JR, Chen CS, Brueggemeier RW, Shapiro CL, Chen CY, Dunn SE, Pollak M, Chen CS: Overcoming trastuzumab resistance in HER2-overexpressing breast cancer cells by using a novel celecoxib-derived phosphoinositide-dependent kinase-1 inhibitor. Mol Pharmacol. 2006 Nov;70(5):1534-41. Epub 2006 Aug 3. [PubMed:16887935 ]
- General function:
- Involved in monooxygenase activity
- Specific function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular weight:
- 55768.94
References
- Werner U, Werner D, Rau T, Fromm MF, Hinz B, Brune K: Celecoxib inhibits metabolism of cytochrome P450 2D6 substrate metoprolol in humans. Clin Pharmacol Ther. 2003 Aug;74(2):130-7. [PubMed:12891223 ]
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
- General function:
- Involved in monooxygenase activity
- Specific function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
- Gene Name:
- CYP2C8
- Uniprot ID:
- P10632
- Molecular weight:
- 55824.275
References
- Rodrigues AD: Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75. Epub 2005 Aug 23. [PubMed:16118328 ]
- Martinez C, Blanco G, Garcia-Martin E, Agundez JA: [Clinical pharmacogenomics for CYP2C8 and CYP2C9: general concepts and application to the use of NSAIDs]. Farm Hosp. 2006 Jul-Aug;30(4):240-8. [PubMed:17022718 ]
Transporters
- General function:
- Involved in ATP binding
- Specific function:
- May be an organic anion pump relevant to cellular detoxification
- Gene Name:
- ABCC4
- Uniprot ID:
- O15439
- Molecular weight:
- 149525.3
References
- Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412 ]