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MCC-555

Item № 70735
CAS № 161600-01-7
Purity ≥98%
product image
                (CAS 161600-01-7)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $78.00 0.00
     5 mg $351.00 0.00
     10 mg $624.00 0.00
     25 mg Contact us

Pricing updated 2019-07-23. Prices are subject to change without notice.

Description
Synonyms
  • Isaglitazone
  • Netoglitazone
  • RWJ 241947

The peroxisome proliferator-activated receptor-γ (PPARγ) is the nuclear receptor responsible for transducing the therapeutic activity of the thiazolidinediones (TZDs), a group of structurally related synthetic agonists with antidiabetic actions in vivo.1,2 Rosiglitazone (BRL49653) is a prototypical TZD and has served as a reference compound for this class.3 MCC-555 is a structural homolog of rosiglitazone and the other TZDs. MCC-555 binds with about 1/10 the affinity of rosiglitazone to PPARγ.4 Despite this, MCC-555 is a more potent antidiabetic agent in whole animal experiments than rosiglitazone and several other prototypic TZDs; the ED50 value in these experiments was 2.7 mg/kg for MCC-555 compared with 7.1 mg/kg for rosiglitazone. MCC-555 is therefore a unique new member of the TZD class and may be useful in differentiating some of the multiple activities attributed to this class of compounds.

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Technical Information
Formal Name
5-[[6-[(2-fluorophenyl)methoxy]-2-naphthalenyl]methyl]-2,4-thiazolidinedione
CAS Number
161600-01-7
Synonyms
  • Isaglitazone
  • Netoglitazone
  • RWJ 241947
Molecular Formula
C21H16FNO3S
Formula Weight
381.4
Purity
≥98%
Formulation
A crystalline solid
SMILES
FC1=CC=CC=C1COC2=CC(C=CC(CC3SC(NC3=O)=O)=C4)=C4C=C2
InChI Code
InChI=1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25)
InChI Key
PKWDZWYVIHVNKS-UHFFFAOYSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
WET ICE in continental US; may vary elsewhere
Stability
≥ 1 year
Downloads & Resources
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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Product Citations
Product Description References

1. Willson, T.M., Cobb, J.E., Cowan, D.J., et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones J. Med. Chem. 39, 665-668 (1996).

2. Cantello, B.C.C., Cawthorne, M.A., Cottam, G.P., et al. [[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents J. Med. Chem. 37, 3977-3985 (1994).

3. Lehmann, J.M., Moore, L.B., Smith-Oliver, T.A., et al. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor γ (PPARγ) J. Biol. Chem. 270(22), 12953-12956 (1995).

4. Reginato, M.J., Bailey, S.T., Krakow, S.L., et al. A potent antidiabetic thiazolidinedione with unique peroxisome proliferator-activated receptor g -activating properties The Journal of Biological Chemisty 273, 32679-32684 (1998).

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