CIGLITAZONE

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

Structure Search

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)

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6711015 | https://www.ncbi.nlm.nih.gov/pubmed/22609261 | https://www.ncbi.nlm.nih.gov/pubmed/19342033

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor gamma 111 Target ID: P37231\|\|\|Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22609261	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetes mellitus 91 Sources: DOI: 10.1016/j.jtumed.2016.02.001	Primary		Phase II 1132	Unknown Approved Use Unknown
Ovarian hyperstimulation syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19342033	Primary		Basic research	Unknown Approved Use Unknown

C_max

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

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY570066	https://www.001chemical.com/chem/74772-77-3
3B Scientific (Wuhan) Corp	3B2-1217	http://www.3bsc.com/index/pro_info.php?id=54933
AA Blocks	AA003OTQ	https://www.aablocks.com/goods/Goods/detail?id=AA003OTQ
AHH Chemical co.,ltd	MT-49257	http://www.ahhchemical.com/product/MT-49257.html
AK Scientific, Inc. (AKSCI)	Z3112	http://www.aksci.com/item_detail.php?cat=Z3112
Aaron Chemicals	AR003PLI	http://www.aaronchem.com/74772-77-3
Achemica	ACMC-20emv7	http://www.achemica.com/prodinfo/?id=146489
Alfa Chemistry	AP74772773-A	https://reagents.alfa-chemistry.com/product/ciglitazone-cas-74772-77-3-cas-74772-77-3-15936.html
Alfa Chemistry	AP74772773-B	https://reagents.alfa-chemistry.com/product/ciglitizone-cas-74772-77-3-15937.html
Alichem	59006461	http://www.alichem.com/en/products/74772-77-3.html
Angene	AGN-PC-0JK6C7	http://www.angenechemical.com/productshow/AGN-PC-0JK6C7.html
Aurora Fine Chemicals LLC	A17.913.116	http://online.aurorafinechemicals.com/info?ID=A17.913.116
AvaChem Scientific	6213	https://www.avachem.com/productSearch.asp?6213
Avantor Inc	100579-480	https://us.vwr.com/store/catalog/product.jsp?catalog_number=100579-480
BLD Pharm	BD121285	http://www.bldpharm.com/products/74772-77-3.html
BOC Sciences	74772-77-3	https://www.bocsci.com/ciglitazone-cas-74772-77-3-item-32058.html
BioCrick	BCC7014	http://www.biocrick.com/Ciglitazone-BCC7014.html
CSNpharm	CSN22759	https://www.csnpharm.com/products/ciglitazone.html
Calbiochem	230950	http://www.emdbiosciences.com/product/230950
Chem Scene	CS-W011936	http://www.chemscene.com/74772-77-3.html
ChemMol	97900667	http://www.chemmol.com/chemmol/97900667.html
ChemShuttle	113692	http://www.chemshuttle.com/catalogsearch/result/?q=74772-77-3&cat=
Chemspace	CSSB00000038955	https://chem-space.com/CSSB00000038955
DC Chemicals	DC33417	http://www.dcchemicals.com//product_show-ADD_3878.html
Debye Scientific	DB-055908	http://www.debyesci.com/cas_74772-77-3.html
EMD Millipore	230950	http://www.emdbiosciences.com/product/230950
Finetech	FT-0602959	http://www.finetechnology-ind.com/prod/detail/pub/74772-77-3.html
Glentham Life Sciences	GL8018	http://www.glentham.com/products/product/GL8018/
Lab Network	LN01264181	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01264181
Matrix Scientific	147786	https://www.matrixscientific.com/147786.html
MolPort	MolPort-003-845-947	https://www.molport.com/shop/molecule-link/MolPort-003-845-947
MolPort	MolPort-047-544-023	https://www.molport.com/shop/molecule-link/MolPort-047-544-023
Molcore	MC570066	https://www.molcore.com/product/74772-77-3
MuseChem	R000841	https://www.musechem.com/product/R000841.html
Parchem	43268	https://www.parchem.com/chemical-supplier-distributor/Ciglitazone-043268.aspx
Sigma-Aldrich	C3974_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c3974?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S523752	http://www.smolecule.com/products/s523752
THE BioTek	bt-264742	https://www.thebiotek.com/product/inhibitors/bt-264742
TimTec	ST079285	http://www.echemstore.com/st079285-ciglitizone.html
Tocris	1307	https://www.tocris.com/products/ciglitazone_1307
abcr GmbH	AB494370	http://www.abcr.com/shop/en/AB494370
eNovation Chemicals	D583112	https://www.enovationchem.com/ProductDetails.asp?ProductID=D583112
mcule	MCULE-4419123362	https://mcule.com/MCULE-4419123362/

PubMed

Title	Date	PubMed
N-(2-Benzoylphenyl)-L-tyrosine PPARgamma agonists. 1. Discovery of a novel series of potent antihyperglycemic and antihyperlipidemic agents.	1998 Dec 3	9836620
Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo.	1999 Mar 26	10085162
Bisphenol A diglycidyl ether (BADGE) is a PPARgamma agonist in an ECV304 cell line.	2000 Oct	11030710
Peroxisome proliferator-activated receptor gamma ligands suppress the transcriptional activation of cyclooxygenase-2. Evidence for involvement of activator protein-1 and CREB-binding protein/p300.	2001 Apr 13	11278336
Arylhydrocarbon receptor (AhR) is involved in negative regulation of adipose differentiation in 3T3-L1 cells: AhR inhibits adipose differentiation independently of dioxin.	2001 Aug	11683414
Cloning of the human cholesteryl ester hydrolase promoter: identification of functional peroxisomal proliferator-activated receptor responsive elements.	2001 Jun 22	11409902
Involvement of p21(WAF1/Cip1), p27(Kip1), and p18(INK4c) in troglitazone-induced cell-cycle arrest in human hepatoma cell lines.	2001 May	11343236
Nimesulide, a preferential cyclooxygenase 2 inhibitor, suppresses peroxisome proliferator-activated receptor induction of cyclooxygenase 2 gene expression in human synovial fibroblasts: evidence for receptor antagonism.	2002 Feb	11840453
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size.	2002 Jul	12087064
Superoxide anion-dependent Raf/MEK/ERK activation by peroxisome proliferator activated receptor gamma agonists 15-deoxy-delta(12,14)-prostaglandin J(2), ciglitazone, and GW1929.	2002 Jul 15	12083801
Induction of apoptosis in human and rat glioma by agonists of the nuclear receptor PPARgamma.	2002 Jun	12065618
Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2.	2002 Jun 21	12031542
Cyclooxygenase-2 expression by nonsteroidal anti-inflammatory drugs in human airway smooth muscle cells: role of peroxisome proliferator-activated receptors.	2003 Jan 15	12517972
PPARgamma ligand attenuates PDGF-induced mesangial cell proliferation: role of MAP kinase.	2003 Jul	12787395
15-Deoxy-Delta(12,14)-prostaglandin J2 inhibits the expression of proinflammatory genes in human blood monocytes via a PPAR-gamma-independent mechanism.	2003 Mar 7	12604364
Implication of peroxisome proliferator-activated receptor gamma and proinflammatory cytokines in gastric carcinogenesis: link to Helicobacter pylori-infection.	2004 Oct	15492468
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	16303604
Mechanism of the anti-inflammatory effect of thiazolidinediones: relationship with the glucocorticoid pathway.	2005 May	15684043
Selective activation of PPARgamma in breast, colon, and lung cancer cell lines.	2005 May 12	15866424
Inhibitors of the arachidonic acid pathway and peroxisome proliferator-activated receptor ligands have superadditive effects on lung cancer growth inhibition.	2005 May 15	15899809
Troglitazone acutely inhibits protein synthesis in endothelial cells via a novel mechanism involving protein phosphatase 2A-dependent p70 S6 kinase inhibition.	2006 Aug	16825603
Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways.	2006 Feb 28	16386710
Involvement of PPARgamma in oxidative stress-mediated prostaglandin E(2) production in SZ95 human sebaceous gland cells.	2006 Jan	16417216
Glycogen synthase 2 is a novel target gene of peroxisome proliferator-activated receptors.	2007 May	17437057
Peroxisome proliferator-activated receptor-gamma agonists inhibit respiratory syncytial virus-induced expression of intercellular adhesion molecule-1 in human lung epithelial cells.	2007 May	17425601
Peroxisome proliferator-activated receptor gamma activation relieves expression of behavioral sensitization to methamphetamine in mice.	2007 May	17019405
Delta5 desaturase mRNA levels are increased by simvastatin via SREBP-1 at early stages, not via PPARalpha, in THP-1 cells.	2007 Oct 1	17655842
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	17535976
Nuclear receptor agonists improve insulin responsiveness in cultured cardiomyocytes through enhanced signaling and preserved cytoskeletal architecture.	2008 Mar	18063688
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	18393431
Type 2 deiodinase expression is induced by peroxisomal proliferator-activated receptor-gamma agonists in skeletal myocytes.	2009 Apr	19036883
Thiazolidinediones decrease vascular endothelial growth factor (VEGF) production by human luteinized granulosa cells in vitro.	2010 Apr	19342033
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.	2010 Dec	20829430
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	21080969
Combination of ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, and cisplatin enhances the inhibition of growth of human ovarian cancers.	2011 Aug	21681689
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.	2011 Aug	21543282
The use of rat lens explant cultures to study the mechanism of drug-induced cataractogenesis.	2012 Mar	22193206
Fenofibrate suppresses melanogenesis in B16-F10 melanoma cells via activation of the p38 mitogen-activated protein kinase pathway.	2013 Oct 5	23872139

Patents

Sample Use Guides

In Vivo Use Guide

for Diabetes mellitus in Japan

Route of Administration: Oral

In Vitro Use Guide

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 `Sat Dec 16 15:55:50 UTC 2023` Edited by `admin` on `Sat Dec 16 15:55:50 UTC 2023`
Record UNII	U8QXS1WU8G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIGLITAZONE

Official Name

English

(±)-5-(P-((1-METHYLCYCLOHEXYL)METHOXY)BENZYL)-2,4-THIAZOLIDINEDIONE

Common Name

English

2,4-THIAZOLIDINEDIONE, 5-((4-((1-METHYLCYCLOHEXYL)METHOXY)PHENYL)METHYL)-, (±)-

Systematic Name

English

U-63287

Code

English

CIGLITAZONE [USAN]

Common Name

English

ADD-3878

Code

English

U-63,287

Code

English

ciglitazone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98241