Ciglitazone

HCID 2750
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Basic information

CAS
74772-77-3
Standard SMILES
CC1(COc2ccc(CC3SC(=O)NC3=O)cc2)CCCCC1
InChIKey
YZFWTZACSRHJQD-UHFFFAOYSA-N
Molecular formula
C18H23NO3S
Average molar mass
333.4 g/mol
Monoisotopic mass
333.13986477

Names & identifiers

Preferred name
Ciglitazone
IUPAC
5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
English name
CIGLITAZONE
Molecular formula
C18H23NO3S
Molecular weight
333.45

Names & synonyms

ciglitazone74772-77-3CiglitizoneADD-3878CiglitazonaCiglitazonumU-63287DTXSID0040757U8QXS1WU8GCHEBI:64227DTXCID8020757U-63,287
Show more names
AD-4533CIGLITLZONECIGLITAZONE USP/EP/BPCiglitazone (Standard)Ciglitazone Solution, 100ppm
5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione5-(4-((1-methylcyclohexyl)methoxy)benzyl)-1,3-thiazolidine-2,4-dione5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-1,3-thiazolidine-2,4-dione5-(4-(1-methylcyclohexylmethoxy)benzyl)thiazolidine-2,4-dioneRefChem:577129ADD 3878

Database identifiers

CAS
74772-77-3
PubChem CID
2750
DTXSID
DTXSID0040757
ChEMBL
CHEMBL7002
ChEBI
CHEBI:64227
UNII
U8QXS1WU8G
EC Number
692-459-4
Nikkaji
J20.561C

Properties

Computed structural properties

XLogP
4.8
Topological polar surface area
80.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
23

Physicochemical properties

Melting point
130 · 130-131°C
Boiling point
504.5 · 504.5±23.0 °C(Predicted)
Density
1.189 · 1.189±0.06 g/cm3(Predicted)
storage temp.
Store at RT
solubility
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
form
Tan solid

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesRepr. 2 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

ciglitazone

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
3
rtecs
XJ5813700
hs_code
29341000
Signal word
Warning
Symbol(GHS)
GHS08

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Applications · 4 items

DescriptionCiglitazone (74772-77-3) is a PPARγ agonist (EC50=3 μM). Stimulates adipogenesis in human mesenchymal stem cells. Ciglitazone inhibits HUVEC differentiation and angiogenesis. Cell permeable.

UsesDisplays antihyperglycemic activity in genetically obese mice. It is a selective PPARg agonist.

UsesCiglitizone has been used as a proliferator-activated receptor γ (PPARγ) agonist:to study its effects on cell proliferation in human melanocytesto study its effects on pigmentation and migration of human melanocytesIt also may be used to study its effects on cell cycle and apoptosis in monocytic cells.

General DescriptionA potent thiazolinedione (TDZ) type anti-hyperglycemic agent and a selective PPARγ agonist (EC50 = 3 μM).

Suppliers57 total

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]

Additional notes

DefinitionChEBI: An aromatic ether that consists of 1,3-thiazolidine-2,4-dione with position 5 substituted by a 4-[(1-methylcyclohexyl)methoxy]benzyl group. A selective PPARgamma agonist.

Related reactions

4 records
New reaction record

Compound notes

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