NAV

Ciglitazone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ciglitazone
DrugBank Accession Number
DB09201
Background

Developed by Takeda Pharmaceuticals in the early 1980s, it is considered the prototypical compound for the thiazolidinedione class.

Ciglitazone was never used as a medication, but it sparked interest in the effects of thiazolidinediones. Several analogues were later developed, some of which—such as pioglitazone and troglitazone—made it to the market.

Ciglitazone significantly decreases VEGF production by human granulosa cells in an in vitro study, and may potentially be used in ovarian hyperstimulation syndrome. Ciglitazone is a potent and selective PPARγ ligand with an EC50 of 3.0 µM. It is also an anti-hyperglycemic agent in the ob/ob murine model in vivo. Ciglitazone increases adipogenesis, decreases differentiation and angiogenesis in human umbilical vein endothelial cell (HUVEC), and osteoblastogenesis in human mesenchymal stem cells.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 333.45
Monoisotopic: 333.139864779
Chemical Formula
C18H23NO3S
Synonyms
  • ciglitazona
  • Ciglitazone
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
APeroxisome proliferator-activated receptor gamma
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AbametapirThe serum concentration of Ciglitazone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ciglitazone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Ciglitazone can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Ciglitazone.
AcebutololThe therapeutic efficacy of Ciglitazone can be increased when used in combination with Acebutolol.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Thiazolidinediones / Alkyl aryl ethers / Dicarboximides / Thiocarbamic acid derivatives / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Alkyl aryl ether / Aromatic heteromonocyclic compound / Azacycle / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Ether / Hydrocarbon derivative / Monocyclic benzene moiety
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, thiazolidinone (CHEBI:64227)
Affected organisms
Not Available

Chemical Identifiers

UNII
U8QXS1WU8G
CAS number
74772-77-3
InChI Key
YZFWTZACSRHJQD-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-({4-[(1-methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
SMILES
CC1(COC2=CC=C(CC3SC(=O)NC3=O)C=C2)CCCCC1

References

General References
  1. Pershadsingh HA, Szollosi J, Benson S, Hyun WC, Feuerstein BG, Kurtz TW: Effects of ciglitazone on blood pressure and intracellular calcium metabolism. Hypertension. 1993 Jun;21(6 Pt 2):1020-3. [Article]
  2. Imoto H, Imamiya E, Momose Y, Sugiyama Y, Kimura H, Sohda T: Studies on non-thiazolidinedione antidiabetic agents. 1. Discovery of novel oxyiminoacetic acid derivatives. Chem Pharm Bull (Tokyo). 2002 Oct;50(10):1349-57. [Article]
  3. Sohda T, Kawamatsu Y, Fujita T, Meguro K, Ikeda H: [Discovery and development of a new insulin sensitizing agent, pioglitazone]. Yakugaku Zasshi. 2002 Nov;122(11):909-18. [Article]
  4. Shah DK, Menon KM, Cabrera LM, Vahratian A, Kavoussi SK, Lebovic DI: Thiazolidinediones decrease vascular endothelial growth factor (VEGF) production by human luteinized granulosa cells in vitro. Fertil Steril. 2010 Apr;93(6):2042-7. doi: 10.1016/j.fertnstert.2009.02.059. Epub 2009 Apr 1. [Article]
  5. Xin X, Yang S, Kowalski J, Gerritsen ME: Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo. J Biol Chem. 1999 Mar 26;274(13):9116-21. [Article]
KEGG Drug
D03493
PubChem Compound
2750
PubChem Substance
310265109
ChemSpider
2648
BindingDB
50103636
ChEBI
64227
ChEMBL
CHEMBL7002
Wikipedia
Ciglitazone

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00534 mg/mLALOGPS
logP3.93ALOGPS
logP4.28Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)6.61Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area55.4 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity91.26 m3·mol-1Chemaxon
Polarizability36.36 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1209000000-50f9c7c859b43c1a5f5e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1019000000-f1f3976772bd6f328397
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0092000000-5f73c44cdb8813af2f2b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0il3-7195000000-5b48b8575d5f1a3e382e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-07bb-9110000000-139ba879f25f4247e058
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-4900000000-8a1657fedaa1486054c0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-173.44812
predicted
DeepCCS 1.0 (2019)
[M+H]+175.80632
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.91971
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Wick M, Hurteau G, Dessev C, Chan D, Geraci MW, Winn RA, Heasley LE, Nemenoff RA: Peroxisome proliferator-activated receptor-gamma is a target of nonsteroidal anti-inflammatory drugs mediating cyclooxygenase-independent inhibition of lung cancer cell growth. Mol Pharmacol. 2002 Nov;62(5):1207-14. [Article]
  2. Hinz B, Brune K, Pahl A: 15-Deoxy-Delta(12,14)-prostaglandin J2 inhibits the expression of proinflammatory genes in human blood monocytes via a PPAR-gamma-independent mechanism. Biochem Biophys Res Commun. 2003 Mar 7;302(2):415-20. doi: 10.1016/s0006-291x(03)00195-5. [Article]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Jaakkola T, Backman JT, Neuvonen M, Neuvonen PJ: Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14. doi: 10.1016/j.clpt.2004.12.266. [Article]
Details2. Cytochrome P450 2C8
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Jaakkola T, Backman JT, Neuvonen M, Neuvonen PJ: Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14. doi: 10.1016/j.clpt.2004.12.266. [Article]
  2. Sahi J, Black CB, Hamilton GA, Zheng X, Jolley S, Rose KA, Gilbert D, LeCluyse EL, Sinz MW: Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46. [Article]

Drug created at October 16, 2015 22:20 / Updated at May 05, 2022 18:09