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MedKoo Cat#: 540075 | Name: Ciglitazone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ciglitazone is a PPARγ agonist. It is known to decrease insulin levels, VEGF production and blood pressure and induces cell cycle arrest in stomach cancer cells.

Chemical Structure

Ciglitazone
Ciglitazone
CAS#74772-77-3

Theoretical Analysis

MedKoo Cat#: 540075

Name: Ciglitazone

CAS#: 74772-77-3

Chemical Formula: C18H23NO3S

Exact Mass: 333.1399

Molecular Weight: 333.44

Elemental Analysis: C, 64.84; H, 6.95; N, 4.20; O, 14.39; S, 9.61

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
25mg USD 650.00 2 Weeks
100mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
ADD 3878; ADD-3878; ADD3878; Ciglitazona; U 63287; U-63287; U63287;
IUPAC/Chemical Name
5-(4-((1-methylcyclohexyl)methoxy)benzyl)thiazolidine-2,4-dione
InChi Key
YZFWTZACSRHJQD-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(N1)SC(CC2=CC=C(OCC3(C)CCCCC3)C=C2)C1=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ciglitazone is a selective agonist at PPARγ (peroxisome proliferator-activated receptor γ).
In vitro activity:
Ciglitazone effectively attenuated Th17 cell differentiation and offset the enhancement of Th17 differentiation induced by IL-1β (Fig. 2A). IL-22 and IL-17 levels, which are enhanced by IL-1β, were attenuated by ciglitazone (Fig. 2B). Reference: Biomol Ther (Seoul). 2015 Jan; 23(1): 71–76. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4286752/
In vivo activity:
In vivo study using NOD-scid IL2Rgamma(null) mice confirmed that ciglitazone significantly decreased ovarian cancer mass transplanted onto the back of the mice. Reference: Eur J Pharmacol. 2014 Nov 15;743:17-23. https://pubmed.ncbi.nlm.nih.gov/25240713/
Solvent mg/mL mM comments
Solubility
DMSO 21.0 62.98
DMF 16.0 47.98
Ethanol 29.0 86.97
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 333.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Kim DH, Ihn HJ, Moon C, Oh SS, Park S, Kim S, Lee KW, Kim KD. Ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, inhibits proliferation and differentiation of th17 cells. Biomol Ther (Seoul). 2015 Jan;23(1):71-6. doi: 10.4062/biomolther.2014.042. Epub 2015 Jan 1. PMID: 25593646; PMCID: PMC4286752. 2. Xu L, Wang S, Li B, Sun A, Zou Y, Ge J. A protective role of ciglitazone in ox-LDL-induced rat microvascular endothelial cells via modulating PPARγ-dependent AMPK/eNOS pathway. J Cell Mol Med. 2015 Jan;19(1):92-102. doi: 10.1111/jcmm.12463. Epub 2014 Nov 11. PMID: 25388834; PMCID: PMC4288353. 3. Shin SJ, Kim JY, Kwon SY, Mun KC, Cho CH, Ha E. Ciglitazone enhances ovarian cancer cell death via inhibition of glucose transporter-1. Eur J Pharmacol. 2014 Nov 15;743:17-23. doi: 10.1016/j.ejphar.2014.09.013. Epub 2014 Sep 21. PMID: 25240713. 4. Plissonnier ML, Fauconnet S, Bittard H, Lascombe I. The antidiabetic drug ciglitazone induces high grade bladder cancer cells apoptosis through the up-regulation of TRAIL. PLoS One. 2011;6(12):e28354. doi: 10.1371/journal.pone.0028354. Epub 2011 Dec 12. PMID: 22174792; PMCID: PMC3236187.
In vitro protocol:
1. Kim DH, Ihn HJ, Moon C, Oh SS, Park S, Kim S, Lee KW, Kim KD. Ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, inhibits proliferation and differentiation of th17 cells. Biomol Ther (Seoul). 2015 Jan;23(1):71-6. doi: 10.4062/biomolther.2014.042. Epub 2015 Jan 1. PMID: 25593646; PMCID: PMC4286752. 2. Xu L, Wang S, Li B, Sun A, Zou Y, Ge J. A protective role of ciglitazone in ox-LDL-induced rat microvascular endothelial cells via modulating PPARγ-dependent AMPK/eNOS pathway. J Cell Mol Med. 2015 Jan;19(1):92-102. doi: 10.1111/jcmm.12463. Epub 2014 Nov 11. PMID: 25388834; PMCID: PMC4288353.
In vivo protocol:
1. Shin SJ, Kim JY, Kwon SY, Mun KC, Cho CH, Ha E. Ciglitazone enhances ovarian cancer cell death via inhibition of glucose transporter-1. Eur J Pharmacol. 2014 Nov 15;743:17-23. doi: 10.1016/j.ejphar.2014.09.013. Epub 2014 Sep 21. PMID: 25240713. 2. Plissonnier ML, Fauconnet S, Bittard H, Lascombe I. The antidiabetic drug ciglitazone induces high grade bladder cancer cells apoptosis through the up-regulation of TRAIL. PLoS One. 2011;6(12):e28354. doi: 10.1371/journal.pone.0028354. Epub 2011 Dec 12. PMID: 22174792; PMCID: PMC3236187.
1: Shin SJ, Kim JY, Kwon SY, Mun KC, Cho CH, Ha E. Ciglitazone enhances ovarian cancer cell death via inhibition of glucose transporter-1. Eur J Pharmacol. 2014 Nov 15;743:17-23. doi: 10.1016/j.ejphar.2014.09.013. Epub 2014 Sep 21. PubMed PMID: 25240713. 2: Xu L, Wang S, Li B, Sun A, Zou Y, Ge J. A protective role of ciglitazone in ox-LDL-induced rat microvascular endothelial cells via modulating PPARγ-dependent AMPK/eNOS pathway. J Cell Mol Med. 2015 Jan;19(1):92-102. doi: 10.1111/jcmm.12463. Epub 2014 Nov 11. PubMed PMID: 25388834; PubMed Central PMCID: PMC4288353. 3: Hann SS, Tang Q, Zheng F, Zhao S, Chen J, Wang Z. Repression of phosphoinositide-dependent protein kinase 1 expression by ciglitazone via Egr-1 represents a new approach for inhibition of lung cancer cell growth. Mol Cancer. 2014 Jun 13;13:149. doi: 10.1186/1476-4598-13-149. PubMed PMID: 24925061; PubMed Central PMCID: PMC4061523. 4: Otto S, Jaeger K, Kolodgie FD, Muehlstaedt D, Franz M, Bischoff S, Schubert H, Figulla HR, Virmani R, Poerner TC. A novel polymer-free ciglitazone-coated vascular stent: in vivo and ex vivo analysis of stent endothelialization in a rabbit iliac artery model. Oncotarget. 2016 Sep 6;7(36):57571-57580. doi: 10.18632/oncotarget.11584. PubMed PMID: 27613845; PubMed Central PMCID: PMC5295373. 5: Huang CD, Hsiung TC, Ho SC, Lee KY, Chan YF, Kuo LW, Lin SM, Wang CH, Lin HC, Kuo HP. PPARγ ligand ciglitazone inhibits TNFα-induced ICAM-1 in human airway smooth muscle cells. Biomed J. 2014 Jul-Aug;37(4):191-8. doi: 10.4103/2319-4170.132890. PubMed PMID: 25116714. 6: Yokoyama Y, Xin B, Shigeto T, Mizunuma H. Combination of ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, and cisplatin enhances the inhibition of growth of human ovarian cancers. J Cancer Res Clin Oncol. 2011 Aug;137(8):1219-28. doi: 10.1007/s00432-011-0993-1. Epub 2011 Jun 17. PubMed PMID: 21681689. 7: Plissonnier ML, Fauconnet S, Bittard H, Lascombe I. The antidiabetic drug ciglitazone induces high grade bladder cancer cells apoptosis through the up-regulation of TRAIL. PLoS One. 2011;6(12):e28354. doi: 10.1371/journal.pone.0028354. Epub 2011 Dec 12. PubMed PMID: 22174792; PubMed Central PMCID: PMC3236187. 8: Jun HJ, Lim HW, Choi J, Jung HH, Chae SW. Ciglitazone inhibits cigarette smoke solution-induced inflammatory responses in human middle ear epithelial cells. Int J Pediatr Otorhinolaryngol. 2012 Aug;76(8):1136-9. doi: 10.1016/j.ijporl.2012.04.017. Epub 2012 May 18. PubMed PMID: 22609261. 9: Kim BM, Maeng K, Lee KH, Hong SH. 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. Cancer Lett. 2011 Jan 28;300(2):134-44. doi: 10.1016/j.canlet.2010.09.014. Epub 2010 Nov 9. PubMed PMID: 21067863. 10: Botton T, Puissant A, Cheli Y, Tomic T, Giuliano S, Fajas L, Deckert M, Ortonne JP, Bertolotto C, Tartare-Deckert S, Ballotti R, Rocchi S. Ciglitazone negatively regulates CXCL1 signaling through MITF to suppress melanoma growth. Cell Death Differ. 2011 Jan;18(1):109-21. doi: 10.1038/cdd.2010.75. Epub 2010 Jul 2. PubMed PMID: 20596077; PubMed Central PMCID: PMC3131866. 11: Botton T, Puissant A, Bahadoran P, Annicotte JS, Fajas L, Ortonne JP, Gozzerino G, Zamoum T, Tartare-Deckert S, Bertolotto C, Ballotti R, Rocchi S. In vitro and in vivo anti-melanoma effects of ciglitazone. J Invest Dermatol. 2009 May;129(5):1208-18. doi: 10.1038/jid.2008.346. Epub 2009 Jan 29. PubMed PMID: 19177142. 12: Stegenga ME, Florquin S, de Vos AF, van der Poll T. The thiazolidinedione ciglitazone reduces bacterial outgrowth and early inflammation during Streptococcus pneumoniae pneumonia in mice. Crit Care Med. 2009 Feb;37(2):614-8. doi: 10.1097/CCM.0b013e31819599b6. PubMed PMID: 19114898. 13: Moss PE, Lyles BE, Stewart LV. The PPARγ ligand ciglitazone regulates androgen receptor activation differently in androgen-dependent versus androgen-independent human prostate cancer cells. Exp Cell Res. 2010 Dec 10;316(20):3478-88. doi: 10.1016/j.yexcr.2010.09.015. Epub 2010 Oct 13. PubMed PMID: 20932825; PubMed Central PMCID: PMC2977976. 14: Takaoka K, Sekiguchi F, Shigi H, Maeda Y, Nishikawa H, Kawabata A. Opposite effects of two thiazolidinediones, ciglitazone and troglitazone, on proteinase-activated receptor-1-triggered prostaglandin E(2) release. Toxicology. 2010 Jan 31;268(1-2):40-5. doi: 10.1016/j.tox.2009.11.020. Epub 2009 Nov 30. PubMed PMID: 19954759. 15: Kwon CH, Park JY, Kim TH, Woo JS, Kim YK. Ciglitazone induces apoptosis via activation of p38 MAPK and AIF nuclear translocation mediated by reactive oxygen species and Ca(2+) in opossum kidney cells. Toxicology. 2009 Mar 4;257(1-2):1-9. doi: 10.1016/j.tox.2008.11.019. Epub 2008 Dec 3. PubMed PMID: 19110029. 16: Cheon CW, Kim DH, Kim DH, Cho YH, Kim JH. Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20. PubMed PMID: 19140230; PubMed Central PMCID: PMC2653327. 17: Chima RS, Hake PW, Piraino G, Mangeshkar P, Denenberg A, Zingarelli B. Ciglitazone ameliorates lung inflammation by modulating the inhibitor kappaB protein kinase/nuclear factor-kappaB pathway after hemorrhagic shock. Crit Care Med. 2008 Oct;36(10):2849-57. PubMed PMID: 18828195; PubMed Central PMCID: PMC3709447. 18: Lin TH, Tang CH, Wu K, Fong YC, Yang RS, Fu WM. 15-deoxy-Δ(12,14) -prostaglandin-J2 and ciglitazone inhibit TNF-α-induced matrix metalloproteinase 13 production via the antagonism of NF-κB activation in human synovial fibroblasts. J Cell Physiol. 2011 Dec;226(12):3242-50. doi: 10.1002/jcp.22685. PubMed PMID: 21344384. 19: Mo ZC, Chen X, Long ZF, Zeng Y, Zhang QH, Yi GH. [Effect of ciglitazone on THP-1 macrophage CD36 expression and cholesterol influx]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2011 Jun;27(6):685-7. Chinese. PubMed PMID: 21882481. 20: Kang DW, Choi CH, Park JY, Kang SK, Kim YK. Ciglitazone induces caspase-independent apoptosis through down-regulation of XIAP and survivin in human glioma cells. Neurochem Res. 2008 Mar;33(3):551-61. Epub 2007 Oct 17. PubMed PMID: 17940898.