Natural Product (NP) Details

General Information of the NP (ID: NP7106)
Name
Rofecoxib
Synonyms
rofecoxib; 162011-90-7; Vioxx; Ceoxx; MK 966; 4-(4-(Methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one; 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one; MK-966; MK 0966; MK-0966; 4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone; MK0966; UNII-0QTW8Z7MCR; 3-(4-methylsulfonylphenyl)-4-phenyl-2H-furan-5-one; Rofecoxib (Vioxx); C17H14O4S; 3-phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone; 0QTW8Z7MCR; CHEMBL122; 4-(4-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone; 2(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl-; CHEBI:8887; TRM-201; refecoxib; NCGC00095118-01; Vioxx Dolor; 2(5H)-Furanone, 4-(4-(methylsulfonyl)phenyl)-3-phenyl-; Vioxx (trademark); SMR000466331; CCRIS 8967; Vioxx (TN); HSDB 7262; SR-01000762904; rofecoxibum; Rofecoxib (JAN/USAN/INN); Rofecoxib [USAN:INN:BAN]; 3-Phenyl-4-(4-(methylsulfonyl)phenyl))-2(5H)-furanone; MK966; 4-(4-methylsulfonylphenyl)-3-phenyl-5H-furan-2-one; 4-(p-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone; KS-1107; MK 0996; PubChem15028; Spectrum_000119; SpecPlus_000669; Spectrum2_000446; Spectrum3_001153; Spectrum4_000631; Spectrum5_001598; DSSTox_CID_3567; SCHEMBL3050; DSSTox_RID_77084; DSSTox_GSID_23567; BSPBio_002705; KBioGR_001242; KBioGR_002345; KBioSS_000559; KBioSS_002348; MLS000759440; MLS001165770; MLS001195623; MLS001424113; MLS006010091; BIDD:GT0399; DivK1c_006765; SPECTRUM1504235; SPBio_000492; 3-(4-methanesulfonylphenyl)-2-phenyl-2-buten-4-olide; GTPL2893; ZINC7455; DTXSID2023567; BDBM22369; KBio1_001709; KBio2_000559; KBio2_002345; KBio2_003127; KBio2_004913; KBio2_005695; KBio2_007481; KBio3_002205; KBio3_002825; AOB6956; EX-A708; M01AH02; cMAP_000024; HMS1922H11; HMS2051G16; HMS2089H20; HMS2093E04; HMS2232G21; HMS3371P11; HMS3393G16; HMS3651F16; HMS3713B07; HMS3750I17; HMS3885E05; Pharmakon1600-01504235; BCP03619; EBD34785; Tox21_111430; ANW-71936; CCG-40253; MFCD00935806; NSC720256; NSC758705; s3043; STK635144; AKOS000280931; AB07701; CS-0997; DB00533; MCULE-4806636118; NC00132; NSC 720256; NSC 758705; NSC-720256; NSC-758705; SB19518; VA11689; NCGC00095118-02; NCGC00095118-03; NCGC00095118-04; NCGC00095118-05; NCGC00095118-08; NCGC00095118-17; NCGC00095118-18; AC-28318; AK-60971; HY-17372; NCI60_041175; SBI-0206774.P001; AB0012045; CAS-162011-90-7; FT-0631192; R0206; SW219668-1; C07590; D00568; J10420; K-5064; AB00052090-06; AB00052090-08; AB00052090_09; AB00052090_10; 011R907; A810324; L000912; Q411412; Q-201676; SR-01000762904-3; SR-01000762904-5; BRD-K21733600-001-02-6; BRD-K21733600-001-06-7; 3-(4-methanesulfonyl-phenyl)-2-phenyl-2-buten-4-olide; 2(5H)-Furanone, 4-[4-(methyl-sulfonyl)phenyl]-3-phenyl-; 3-(Phenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone; 3-Phenyl-4-(4-(Methylsulfonyl)Phenyl)-2-(5H)-Furanone; 4-(4-METHANESULFONYL-PHENYL)-3-PHENYL-5H-FURAN-2-ONE; 4-(4-methanesulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one; 4-(4-methylsulfonylphenyl)-3-phenyl-2,5-dihydro-2-furanone; Vioxx; 4-[4-(Methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Osteoarthritis [ICD-11: FA00-FA05] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.716
 
MDCK Permeability
 -4.564
 
PAMPA
 ++
 
HIA
 - - -
 
Distribution
VDss
 -0.113
 
PPB
 93.5%
 
BBB
 ++
 
Metabolism
CYP1A2 inhibitor
 - -
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 ++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - - -
 
Excretion
CLplasma
 1.004
 
T1/2
 2.474
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 +
 
FDAMDD
 ++
 
Respiratory
 - - -
 
Human Hepatotoxicity
 +++
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 ++
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C17H14O4S
PubChem CID
5090
Canonical SMILES
CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
InChI
1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChIKey
RZJQGNCSTQAWON-UHFFFAOYSA-N
CAS Number
CAS 162011-90-7
ChEBI ID
CHEBI:8887
TTD Drug ID
D05VLS
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Ionizing radiation      Renal Insufficiency     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Cells isolated from T-75 Nunclon tissue Healthy Homo sapiens
                    Experimental
                    Result(s)		 Rofecoxib inhibited endothelial cell proliferation, migration, and tube formation (differentiation) at clinically relevant doses. In combination with radiation, inhibition of endothelial cell function further increased twofold.
Target and Pathway
Target(s) Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [3]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 NF-kappa B signaling pathway
4 VEGF signaling pathway
5 TNF signaling pathway
6 Retrograde endocannabinoid signaling
7 Serotonergic synapse
8 Ovarian steroidogenesis
9 Oxytocin signaling pathway
10 Regulation of lipolysis in adipocytes
11 Leishmaniasis
12 Pathways in cancer
13 Chemical carcinogenesis
14 MicroRNAs in cancer
15 Small cell lung cancer
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TSH Signaling Pathway
3 IL4 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL5 Signaling Pathway
Panther Pathway Endothelin signaling pathway Click to Show/Hide
2 Inflammation mediated by chemokine and cytokine signaling pathway
3 Toll receptor signaling pathway
4 CCKR signaling map ST
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
Pathway Interaction Database Calcineurin-regulated NFAT-dependent transcription in lymphocytes Click to Show/Hide
2 S1P1 pathway
3 C-MYB transcription factor network
4 Signaling mediated by p38-alpha and p38-beta
5 Calcium signaling in the CD4+ TCR pathway
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Arachidonic acid metabolism
3 Aryl Hydrocarbon Receptor
4 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
5 Spinal Cord Injury
6 Integrated Pancreatic Cancer Pathway
7 Eicosanoid Synthesis
8 Selenium Micronutrient Network
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2893).
Reference 2 Targeting angiogenic processes by combination rofecoxib and ionizing radiation. Am J Clin Oncol. 2001 Oct;24(5):438-42.
Reference 3 Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
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