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 |
|---|---|---|
| Fenofibrate suppresses melanogenesis in B16-F10 melanoma cells via activation of the p38 mitogen-activated protein kinase pathway. | 2013-10-05 |
|
| COM-1/p8 acts as a tumour growth enhancer in colorectal cancer cell lines. | 2012-04 |
|
| The use of rat lens explant cultures to study the mechanism of drug-induced cataractogenesis. | 2012-03 |
|
| Combination of ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, and cisplatin enhances the inhibition of growth of human ovarian cancers. | 2011-08 |
|
| Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. | 2011-08 |
|
| Synthesis and biological evaluation of novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase inhibitors. | 2011-07-28 |
|
| Stable reporter cell lines for peroxisome proliferator-activated receptor γ (PPARγ)-mediated modulation of gene expression. | 2011-07-01 |
|
| 15-Deoxy-delta12,14-prostaglandin J2-glycerol ester, a putative metabolite of 2-arachidonyl glycerol, activates peroxisome proliferator activated receptor gamma. | 2011-07 |
|
| Troglitazone suppresses c-Myc levels in human prostate cancer cells via a PPARγ-independent mechanism. | 2011-06-15 |
|
| 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. | 2011-01-28 |
|
| Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. | 2010-12 |
|
| Steroid receptor coactivator 1 deficiency increases MMTV-neu mediated tumor latency and differentiation specific gene expression, decreases metastasis, and inhibits response to PPAR ligands. | 2010-11-16 |
|
| Thiazolidinediones decrease vascular endothelial growth factor (VEGF) production by human luteinized granulosa cells in vitro. | 2010-04 |
|
| PPARgamma regulates LIF-induced growth and self-renewal of mouse ES cells through Tyk2-Stat3 pathway. | 2010-03 |
|
| Opposite effects of two thiazolidinediones, ciglitazone and troglitazone, on proteinase-activated receptor-1-triggered prostaglandin E(2) release. | 2010-01-31 |
|
| Type 2 deiodinase expression is induced by peroxisomal proliferator-activated receptor-gamma agonists in skeletal myocytes. | 2009-04 |
|
| Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. | 2009-01-21 |
|
| Involvement of peroxisome proliferator-activated receptor gamma in gonadal steroidogenesis and steroidogenic acute regulatory protein expression. | 2009 |
|
| 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. | 2008-10 |
|
| 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. | 2008-10 |
|
| Effects of the mango components mangiferin and quercetin and the putative mangiferin metabolite norathyriol on the transactivation of peroxisome proliferator-activated receptor isoforms. | 2008-05-14 |
|
| PPAR-gamma agonists inhibit profibrotic phenotypes in human lung fibroblasts and bleomycin-induced pulmonary fibrosis. | 2008-05 |
|
| Nuclear receptor agonists improve insulin responsiveness in cultured cardiomyocytes through enhanced signaling and preserved cytoskeletal architecture. | 2008-03 |
|
| Ciglitazone induces caspase-independent apoptosis through down-regulation of XIAP and survivin in human glioma cells. | 2008-03 |
|
| Delta5 desaturase mRNA levels are increased by simvastatin via SREBP-1 at early stages, not via PPARalpha, in THP-1 cells. | 2007-10-01 |
|
| 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. | 2007-09 |
|
| Mitochondria, ciglitazone and liver: a neglected interaction in biochemical pharmacology. | 2007-07-12 |
|
| Mechanism of thiazolidinedione-dependent cell death in Jurkat T cells. | 2007-06 |
|
| Glycogen synthase 2 is a novel target gene of peroxisome proliferator-activated receptors. | 2007-05 |
|
| Peroxisome proliferator-activated receptor-gamma agonists inhibit respiratory syncytial virus-induced expression of intercellular adhesion molecule-1 in human lung epithelial cells. | 2007-05 |
|
| Peroxisome proliferator-activated receptor gamma activation relieves expression of behavioral sensitization to methamphetamine in mice. | 2007-05 |
|
| Type II nuclear hormone receptors, coactivator, and target gene repression in adipose tissue in the acute-phase response. | 2006-10 |
|
| Activation of peroxisome proliferator-activated receptor-gamma (PPARgamma) induces cell death through MAPK-dependent mechanism in osteoblastic cells. | 2006-09-01 |
|
| PPARgamma antagonists reverse the inhibition of neural antigen-specific Th1 response and experimental allergic encephalomyelitis by Ciglitazone and 15-deoxy-Delta12,14-prostaglandin J2. | 2006-09 |
|
| Role of PPAR-gamma on the pathogenesis and vascular changes in glycerol-induced acute renal failure. | 2006-09 |
|
| Troglitazone acutely inhibits protein synthesis in endothelial cells via a novel mechanism involving protein phosphatase 2A-dependent p70 S6 kinase inhibition. | 2006-08 |
|
| Mono(2-ethylhexyl)phthalate and mono-n-butyl phthalate activation of peroxisome proliferator activated-receptors alpha and gamma in breast. | 2006-06-01 |
|
| 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. | 2006-06 |
|
| Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways. | 2006-02-28 |
|
| Involvement of PPARgamma in oxidative stress-mediated prostaglandin E(2) production in SZ95 human sebaceous gland cells. | 2006-01 |
|
| Effect of peroxisome proliferator-activated receptor-gamma ligands on the expression of retinoic acid-inducible gene-I in endothelial cells stimulated with lipopolysaccharide. | 2005-12 |
|
| Gene expression profiling of potential peroxisome proliferator-activated receptor (PPAR) target genes in human hepatoblastoma cell lines inducibly expressing different PPAR isoforms. | 2005-10-03 |
|
| Peroxisome proliferator activated receptor-gamma (PPARgamma) represses thyroid hormone signaling in growth plate chondrocytes. | 2005-09 |
|
| Inhibitors of the arachidonic acid pathway and peroxisome proliferator-activated receptor ligands have superadditive effects on lung cancer growth inhibition. | 2005-05-15 |
|
| Selective activation of PPARgamma in breast, colon, and lung cancer cell lines. | 2005-05-12 |
|
| Mechanism of the anti-inflammatory effect of thiazolidinediones: relationship with the glucocorticoid pathway. | 2005-05 |
|
| Implication of peroxisome proliferator-activated receptor gamma and proinflammatory cytokines in gastric carcinogenesis: link to Helicobacter pylori-infection. | 2004-10 |
|
| 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. | 2004-08 |
|
| N-(2-Benzoylphenyl)-L-tyrosine PPARgamma agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents. | 1998-12-03 |
|
| Effects of ciglitazone on blood pressure and intracellular calcium metabolism. | 1993-06 |
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
Wed Apr 02 06:56:20 GMT 2025
by
admin
on
Wed Apr 02 06:56:20 GMT 2025
|
| Record UNII |
U8QXS1WU8G
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C98241
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DB09201
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
U8QXS1WU8G
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
SUB06260MIG
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
100000081290
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
CIGLITAZONE
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
T-124
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
2750
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
C039671
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
DTXSID0040757
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
C72726
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
5364
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
CHEMBL7002
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
64227
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY | |||
|
74772-77-3
Created by
admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ENANTIOMER -> RACEMATE |
|
||
|
TARGET -> AGONIST |
Binding Assay
IC50
|
||
|
|
ENANTIOMER -> RACEMATE |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|
