Ciglitazone
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
- Weight
- Average: 333.45
Monoisotopic: 333.139864779 - Chemical Formula
- C18H23NO3S
- Synonyms
- ciglitazona
- Ciglitazone
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APeroxisome proliferator-activated receptor gamma agonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Ciglitazone can be increased when it is combined with Abametapir. Abatacept The metabolism of Ciglitazone can be increased when combined with Abatacept. Abiraterone The metabolism of Ciglitazone can be decreased when combined with Abiraterone. Acarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with Ciglitazone. Acebutolol The therapeutic efficacy of Ciglitazone can be increased when used in combination with Acebutolol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Blood Glucose Lowering Agents
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Sulfur Compounds
- Thiazoles
- Thiazolidinediones
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- 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);">
Phase Status Purpose Conditions Count
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
Property Value Source Water Solubility 0.00534 mg/mL ALOGPS logP 3.93 ALOGPS logP 4.28 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 6.61 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 55.4 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 91.26 m3·mol-1 Chemaxon Polarizability 36.36 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-1209000000-50f9c7c859b43c1a5f5e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-1019000000-f1f3976772bd6f328397 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0092000000-5f73c44cdb8813af2f2b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0il3-7195000000-5b48b8575d5f1a3e382e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-07bb-9110000000-139ba879f25f4247e058 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-4900000000-8a1657fedaa1486054c0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 173.44812 predictedDeepCCS 1.0 (2019) [M+H]+ 175.80632 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.91971 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
- 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]
- 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
- 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
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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