Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H23NO3S |
| Molecular Weight | 333.445 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC3(COC1=CC=C(CC2SC(=O)NC2=O)C=C1)CCCCC3
InChI
InChIKey=YZFWTZACSRHJQD-UHFFFAOYSA-N
InChI=1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)
| Molecular Formula | C18H23NO3S |
| Molecular Weight | 333.445 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Ciglitazone, 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2,4-dione, is a hypoglycemic agent and a thiazolidenedione derivative. Ciglitazone binds to the PPAR gamma receptor and possesses agonist activity. This drug was in clinical trials in Japan for the treatment Diabetes mellitus, but that study has been discontinued. Ciglitazone was able to decrease the production of vascular endothelial growth factor (VEGF) in an in vitro human granulosa cell model. That result together with the pivotal role of VEGF in ovarian hyperstimulation syndrome suggests that ciglitazone may have a high potential as a therapeutic agent.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sources: DOI: 10.1016/j.jtumed.2016.02.001 |
Primary | Unknown Approved UseUnknown |
||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3986302 |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIGLITAZONE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3986302 |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIGLITAZONE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
138 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3986302 |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIGLITAZONE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
93 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3986302 |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
CIGLITAZONE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of ciglitazone on blood pressure and intracellular calcium metabolism. | 1993 Jun |
|
| N-(2-Benzoylphenyl)-L-tyrosine PPARgamma agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents. | 1998 Dec 3 |
|
| Activation of NFkappaB represents the central event in the neoplastic progression associated with Barrett's esophagus: a possible link to the inflammation and overexpression of COX-2, PPARgamma and growth factors. | 2004 Aug |
|
| Implication of peroxisome proliferator-activated receptor gamma and proinflammatory cytokines in gastric carcinogenesis: link to Helicobacter pylori-infection. | 2004 Oct |
|
| Effect of peroxisome proliferator-activated receptor-gamma ligands on the expression of retinoic acid-inducible gene-I in endothelial cells stimulated with lipopolysaccharide. | 2005 Dec |
|
| Mechanism of the anti-inflammatory effect of thiazolidinediones: relationship with the glucocorticoid pathway. | 2005 May |
|
| Selective activation of PPARgamma in breast, colon, and lung cancer cell lines. | 2005 May 12 |
|
| Inhibitors of the arachidonic acid pathway and peroxisome proliferator-activated receptor ligands have superadditive effects on lung cancer growth inhibition. | 2005 May 15 |
|
| Gene expression profiling of potential peroxisome proliferator-activated receptor (PPAR) target genes in human hepatoblastoma cell lines inducibly expressing different PPAR isoforms. | 2005 Oct 3 |
|
| Peroxisome proliferator activated receptor-gamma (PPARgamma) represses thyroid hormone signaling in growth plate chondrocytes. | 2005 Sep |
|
| Troglitazone acutely inhibits protein synthesis in endothelial cells via a novel mechanism involving protein phosphatase 2A-dependent p70 S6 kinase inhibition. | 2006 Aug |
|
| Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways. | 2006 Feb 28 |
|
| Involvement of PPARgamma in oxidative stress-mediated prostaglandin E(2) production in SZ95 human sebaceous gland cells. | 2006 Jan |
|
| Thiazolidinediones and rexinoids induce peroxisome proliferator-activated receptor-coactivator (PGC)-1alpha gene transcription: an autoregulatory loop controls PGC-1alpha expression in adipocytes via peroxisome proliferator-activated receptor-gamma coactivation. | 2006 Jun |
|
| Mono(2-ethylhexyl)phthalate and mono-n-butyl phthalate activation of peroxisome proliferator activated-receptors alpha and gamma in breast. | 2006 Jun 1 |
|
| Type II nuclear hormone receptors, coactivator, and target gene repression in adipose tissue in the acute-phase response. | 2006 Oct |
|
| PPARgamma antagonists reverse the inhibition of neural antigen-specific Th1 response and experimental allergic encephalomyelitis by Ciglitazone and 15-deoxy-Delta12,14-prostaglandin J2. | 2006 Sep |
|
| Role of PPAR-gamma on the pathogenesis and vascular changes in glycerol-induced acute renal failure. | 2006 Sep |
|
| Activation of peroxisome proliferator-activated receptor-gamma (PPARgamma) induces cell death through MAPK-dependent mechanism in osteoblastic cells. | 2006 Sep 1 |
|
| Mitochondria, ciglitazone and liver: a neglected interaction in biochemical pharmacology. | 2007 Jul 12 |
|
| Mechanism of thiazolidinedione-dependent cell death in Jurkat T cells. | 2007 Jun |
|
| Glycogen synthase 2 is a novel target gene of peroxisome proliferator-activated receptors. | 2007 May |
|
| Peroxisome proliferator-activated receptor-gamma agonists inhibit respiratory syncytial virus-induced expression of intercellular adhesion molecule-1 in human lung epithelial cells. | 2007 May |
|
| Peroxisome proliferator-activated receptor gamma activation relieves expression of behavioral sensitization to methamphetamine in mice. | 2007 May |
|
| Delta5 desaturase mRNA levels are increased by simvastatin via SREBP-1 at early stages, not via PPARalpha, in THP-1 cells. | 2007 Oct 1 |
|
| Apoptotic action of peroxisome proliferator-activated receptor-gamma activation in human non small-cell lung cancer is mediated via proline oxidase-induced reactive oxygen species formation. | 2007 Sep |
|
| Nuclear receptor agonists improve insulin responsiveness in cultured cardiomyocytes through enhanced signaling and preserved cytoskeletal architecture. | 2008 Mar |
|
| Ciglitazone induces caspase-independent apoptosis through down-regulation of XIAP and survivin in human glioma cells. | 2008 Mar |
|
| PPAR-gamma agonists inhibit profibrotic phenotypes in human lung fibroblasts and bleomycin-induced pulmonary fibrosis. | 2008 May |
|
| Effects of the mango components mangiferin and quercetin and the putative mangiferin metabolite norathyriol on the transactivation of peroxisome proliferator-activated receptor isoforms. | 2008 May 14 |
|
| Troglitazone increases IL-1beta induced cyclooxygenase-2 and inducible nitric oxide synthase expression via enhanced phosphorylation of IkappaBalpha in vascular smooth muscle cells from Wistar-Kyoto rats and spontaneously hypertensive rats. | 2008 Oct |
|
| Keratinocyte-derived vascular endothelial growth factor biosynthesis represents a pleiotropic side effect of peroxisome proliferator-activated receptor-gamma agonist troglitazone but not rosiglitazone and involves activation of p38 mitogen-activated protein kinase: implications for diabetes-impaired skin repair. | 2008 Oct |
|
| Involvement of peroxisome proliferator-activated receptor gamma in gonadal steroidogenesis and steroidogenic acute regulatory protein expression. | 2009 |
|
| Type 2 deiodinase expression is induced by peroxisomal proliferator-activated receptor-gamma agonists in skeletal myocytes. | 2009 Apr |
|
| Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. | 2009 Jan 21 |
|
| Thiazolidinediones decrease vascular endothelial growth factor (VEGF) production by human luteinized granulosa cells in vitro. | 2010 Apr |
|
| Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. | 2010 Dec |
|
| Opposite effects of two thiazolidinediones, ciglitazone and troglitazone, on proteinase-activated receptor-1-triggered prostaglandin E(2) release. | 2010 Jan 31 |
|
| PPARgamma regulates LIF-induced growth and self-renewal of mouse ES cells through Tyk2-Stat3 pathway. | 2010 Mar |
|
| Steroid receptor coactivator 1 deficiency increases MMTV-neu mediated tumor latency and differentiation specific gene expression, decreases metastasis, and inhibits response to PPAR ligands. | 2010 Nov 16 |
|
| Combination of ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, and cisplatin enhances the inhibition of growth of human ovarian cancers. | 2011 Aug |
|
| Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. | 2011 Aug |
|
| Combined treatment with the Cox-2 inhibitor niflumic acid and PPARγ ligand ciglitazone induces ER stress/caspase-8-mediated apoptosis in human lung cancer cells. | 2011 Jan 28 |
|
| 15-Deoxy-delta12,14-prostaglandin J2-glycerol ester, a putative metabolite of 2-arachidonyl glycerol, activates peroxisome proliferator activated receptor gamma. | 2011 Jul |
|
| Stable reporter cell lines for peroxisome proliferator-activated receptor γ (PPARγ)-mediated modulation of gene expression. | 2011 Jul 1 |
|
| Synthesis and biological evaluation of novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase inhibitors. | 2011 Jul 28 |
|
| Troglitazone suppresses c-Myc levels in human prostate cancer cells via a PPARγ-independent mechanism. | 2011 Jun 15 |
|
| COM-1/p8 acts as a tumour growth enhancer in colorectal cancer cell lines. | 2012 Apr |
|
| The use of rat lens explant cultures to study the mechanism of drug-induced cataractogenesis. | 2012 Mar |
|
| Fenofibrate suppresses melanogenesis in B16-F10 melanoma cells via activation of the p38 mitogen-activated protein kinase pathway. | 2013 Oct 5 |
Patents
Sample Use Guides
Human middle ear epithelial cell lines (HMEECs) with or without ciglitazone pre-treatment were exposed to cigarette smoke solution (CSS) in order to induce the inflammatory response. The suppressive effect of inflammatory cytokines, such as tumor necrosis factor-alpha (TNF-α) and cyclooxygenase-2(COX-2), were evaluated using real-time polymerase chain reaction and Western blotting. Stimulation with CSS at 40 μg/ml for 6 h resulted in a 4.1-fold increase in the expression of TNF-α mRNA in the HMEECs. CSS-induced up-regulation of TNF-α mRNA was decreased by more than 2.8-fold in cells pre-treated with ciglitazone. The up-regulation of COX-2 mRNA and increased COX-2 protein expression induced by CSS were also inhibited by more than 3.7-fold with ciglitazone pre-treatment.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:55:50 GMT 2023
by
admin
on
Sat Dec 16 15:55:50 GMT 2023
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| Record UNII |
U8QXS1WU8G
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C98241
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DB09201
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U8QXS1WU8G
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CIGLITAZONE
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C039671
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DTXSID0040757
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C72726
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74772-77-3
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ENANTIOMER -> RACEMATE |
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TARGET -> AGONIST |
Binding Assay
IC50
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |
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