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MedKoo Cat#: 326899 | Name: Rivoglitazone HCl

Description:

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

Rivoglitazone, also known as CI-1037; CS-011; DE-101; R-119702; Rivo, is a peroxisome proliferator-activated receptor γ agonist (PARPγ agonist) potentially for the treatment of type 2 diabetes. Rivoglitazone has been shown, through small clinical studies, to decrease hemoglobin A(1c) (A1C) by 0.11-1.1% when compared with placebo and may provide greater A1C reduction than pioglitazone. Rivoglitazone reduces hyperglycemia, hyperinsulinemia, and hypertriglyceridemia by acting as an agonist of PPAR-γ. Rivoglitazone is the most potent PPAR-γ agonist.

Chemical Structure

Rivoglitazone HCl
Rivoglitazone HCl
CAS#299176-11-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 326899

Name: Rivoglitazone HCl

CAS#: 299176-11-7 (HCl)

Chemical Formula: C20H20ClN3O4S

Exact Mass:

Molecular Weight: 433.91

Elemental Analysis: C, 55.36; H, 4.65; Cl, 8.17; N, 9.68; O, 14.75; S, 7.39

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
185428-18-6 (free base) 299176-11-7 (HCl)
Synonym
CI-1037; CI 1037; CI1037; CS-011; CS011; CS011; DE-101; R-119702; Rivo; Rivoglitazone HCl; Rivoglitazone hydrochloride.
IUPAC/Chemical Name
5-(4-((6-methoxy-1-methyl-1H-benzo[d]imidazol-2-yl)methoxy)benzyl)thiazolidine-2,4-dione hydrochloride
InChi Key
LKKAMJRUPIIUTC-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H19N3O4S.ClH/c1-23-16-10-14(26-2)7-8-15(16)21-18(23)11-27-13-5-3-12(4-6-13)9-17-19(24)22-20(25)28-17;/h3-8,10,17H,9,11H2,1-2H3,(H,22,24,25);1H
SMILES Code
O=C(N1)SC(CC2=CC=C(OCC3=NC4=CC=C(OC)C=C4N3C)C=C2)C1=O.[H]Cl
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
Related CAS# 185428-18-6(Rivoglitazone) 299176-11-7(Rivoglitazone hydrochloride)

Preparing Stock Solutions

The following data is based on the product molecular weight 433.91 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
1: Izumi T, Tsuruta F, Ishizuka T, Nakamura K, Kothuma M, Takahashi M. Stereoselectivity in pharmacokinetics of rivoglitazone, a novel peroxisome proliferator-activated receptor γ agonist, in rats and monkeys: model-based pharmacokinetic analysis and in vitro-in vivo extrapolation approach. J Pharm Sci. 2013 Sep;102(9):3174-88. doi: 10.1002/jps.23586. Epub 2013 May 19. PubMed PMID: 23686684. 2: Koffarnus RL, Wargo KA, Phillippe HM. Rivoglitazone: a new thiazolidinedione for the treatment of type 2 diabetes mellitus. Ann Pharmacother. 2013 Jun;47(6):877-85. doi: 10.1345/aph.1R754. Epub 2013 Apr 30. Review. PubMed PMID: 23632280. 3: Chou HS, Truitt KE, Moberly JB, Merante D, Choi Y, Mun Y, Pfützner A. A 26-week, placebo- and pioglitazone-controlled monotherapy study of rivoglitazone in subjects with type 2 diabetes mellitus. Diabetes Obes Metab. 2012 Nov;14(11):1000-9. doi: 10.1111/j.1463-1326.2012.01631.x. Epub 2012 Jul 4. PubMed PMID: 22686944. 4: Uchiyama M, Koda H, Fischer T, Mueller J, Yamamura N, Oguchi M, Iwabuchi H, Okazaki O, Izumi T. In vitro metabolism of rivoglitazone, a novel peroxisome proliferator-activated receptor γ agonist, in rat, monkey, and human liver microsomes and freshly isolated hepatocytes. Drug Metab Dispos. 2011 Jul;39(7):1311-9. doi: 10.1124/dmd.111.038729. Epub 2011 Apr 21. PubMed PMID: 21511943. 5: Kong AP, Yamasaki A, Ozaki R, Saito H, Asami T, Ohwada S, Ko GT, Wong CK, Leung GT, Lee KF, Yeung CY, Chan JC. A randomized-controlled trial to investigate the effects of rivoglitazone, a novel PPAR gamma agonist on glucose-lipid control in type 2 diabetes. Diabetes Obes Metab. 2011 Sep;13(9):806-13. doi: 10.1111/j.1463-1326.2011.01411.x. PubMed PMID: 21492364. 6: Hiuge-Shimizu A, Maeda N, Hirata A, Nakatsuji H, Nakamura K, Okuno A, Kihara S, Funahashi T, Shimomura I. Dynamic changes of adiponectin and S100A8 levels by the selective peroxisome proliferator-activated receptor-gamma agonist rivoglitazone. Arterioscler Thromb Vasc Biol. 2011 Apr;31(4):792-9. doi: 10.1161/ATVBAHA.110.221747. Epub 2011 Jan 13. PubMed PMID: 21233451. 7: Uchiyama M, Iwabuchi H, Tsuruta F, Abe K, Takahashi M, Koda H, Oguchi M, Okazaki O, Izumi T. Pharmacokinetics, metabolism, and disposition of rivoglitazone, a novel peroxisome proliferator-activated receptor γ agonist, in rats and monkeys. Drug Metab Dispos. 2011 Apr;39(4):653-66. doi: 10.1124/dmd.110.036194. Epub 2010 Dec 21. PubMed PMID: 21177486. 8: Truitt KE, Goldberg RB, Rosenstock J, Chou HS, Merante D, Triscari J, Wang AC. A 26-week, placebo- and pioglitazone-controlled, dose-ranging study of rivoglitazone, a novel thiazolidinedione for the treatment of type 2 diabetes. Curr Med Res Opin. 2010 Jun;26(6):1321-31. doi: 10.1185/03007991003715079. PubMed PMID: 20370378. 9: Kanda S, Nakashima R, Takahashi K, Tanaka J, Ogawa J, Ogata T, Yachi M, Araki K, Ohsumi J. Potent antidiabetic effects of rivoglitazone, a novel peroxisome proliferator-activated receptor-gamma agonist, in obese diabetic rodent models. J Pharmacol Sci. 2009 Oct;111(2):155-66. Epub 2009 Oct 6. PubMed PMID: 19809220. 10: Origlieri C, Bielory L. Emerging drugs for conjunctivitis. Expert Opin Emerg Drugs. 2009 Sep;14(3):523-36. doi: 10.1517/14728210903103818. Review. PubMed PMID: 19708819. 11: Rohatagi S, Carrothers TJ, Jin J, Jusko WJ, Khariton T, Walker J, Truitt K, Salazar DE. Model-based development of a PPARgamma agonist, rivoglitazone, to aid dose selection and optimize clinical trial designs. J Clin Pharmacol. 2008 Dec;48(12):1420-9. doi: 10.1177/0091270008323260. Epub 2008 Oct 20. PubMed PMID: 18936283. 12: Schimke K, Davis TM. Drug evaluation: rivoglitazone, a new oral therapy for the treatment of type 2 diabetes. Curr Opin Investig Drugs. 2007 Apr;8(4):338-44. Review. PubMed PMID: 17458185.