CP-91149 | CAS#186392-40-5 | GP Inhibitor

CP-91149
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 524881

CAS#: 186392-40-5

Description: CP-91149 is a selective glycogen phosphorylase (GP) inhibitor with IC50 of 0.13 μM in the presence of glucose, 5- to 10-fold less potent in the absence of glucose.

Chemical Structure

CP-91149

CAS# 186392-40-5

Instruction

Theoretical Analysis

MedKoo Cat#: 524881
Name: CP-91149
CAS#: 186392-40-5
Chemical Formula: C21H22ClN3O3
Exact Mass: 399.13
Molecular Weight: 399.870
Elemental Analysis: C, 63.08; H, 5.55; Cl, 8.87; N, 10.51; O, 12.00

Price and Availability

Size	Price	Availability
10mg	USD 240	2 Weeks
25mg	USD 465	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: CP-91149; CP 91149; CP91149; UNII-O8EV00W45A.

IUPAC/Chemical Name: 1H-Indole-2-carboxamide, 5-chloro-N-((1S,2R)-3-(dimethylamino)-2-hydroxy-3-oxo-1-(phenylmethyl)propyl)-

InChi Key: HINJNZFCMLSBCI-PKOBYXMFSA-N

InChi Code: InChI=1S/C21H22ClN3O3/c1-25(2)21(28)19(26)17(10-13-6-4-3-5-7-13)24-20(27)18-12-14-11-15(22)8-9-16(14)23-18/h3-9,11-12,17,19,23,26H,10H2,1-2H3,(H,24,27)/t17-,19+/m0/s1

SMILES Code: CN(C)C(=O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)c2cc3cc(Cl)ccc3[nH]2

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, not in water

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 399.87 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.

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:
In vitro protocol:
In vivo protocol:

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1: Gao N, Shang J, Huynh D, Manthati VL, Arias C, Harding HP, Kaufman RJ, Mohr I, Ron D, Falck JR, Lehrman MA. Mannose-6-phosphate regulates destruction of lipid-linked oligosaccharides. Mol Biol Cell. 2011 Sep;22(17):2994-3009. doi: 10.1091/mbc.E11-04-0286. Epub 2011 Jul 7. PubMed PMID: 21737679; PubMed Central PMCID: PMC3164449.

2: Yoshida T, Okuno A, Takahashi K, Ogawa J, Hagisawa Y, Kanda S, Fujiwara T. Contributions of hepatic gluconeogenesis suppression and compensative glycogenolysis on the glucose-lowering effect of CS-917, a fructose 1,6-bisphosphatase inhibitor, in non-obese type 2 diabetes Goto-Kakizaki rats. J Pharmacol Sci. 2011;115(3):329-35. Epub 2011 Feb 22. PubMed PMID: 21350313.

3: Hampson LJ, Mackin P, Agius L. Stimulation of glycogen synthesis and inactivation of phosphorylase in hepatocytes by serotonergic mechanisms, and counter-regulation by atypical antipsychotic drugs. Diabetologia. 2007 Aug;50(8):1743-51. Epub 2007 Jun 20. PubMed PMID: 17579833.

4: Schnier JB, Nishi K, Gumerlock PH, Gorin FA, Bradbury EM. Glycogen synthesis correlates with androgen-dependent growth arrest in prostate cancer. BMC Urol. 2005 Mar 24;5:6. PubMed PMID: 15790394; PubMed Central PMCID: PMC1079895.

5: Hampson LJ, Agius L. Increased potency and efficacy of combined phosphorylase inactivation and glucokinase activation in control of hepatocyte glycogen metabolism. Diabetes. 2005 Mar;54(3):617-23. PubMed PMID: 15734835.

6: Boer P, Sperling O. Modulation of glycogen phosphorylase activity affects 5-phosphoribosyl-1-pyrophosphate availability in rat hepatocyte cultures. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1235-9. PubMed PMID: 15571236.

7: Green AR, Aiston S, Greenberg CC, Freeman S, Poucher SM, Brady MJ, Agius L. The glycogenic action of protein targeting to glycogen in hepatocytes involves multiple mechanisms including phosphorylase inactivation and glycogen synthase translocation. J Biol Chem. 2004 Nov 5;279(45):46474-82. Epub 2004 Aug 18. PubMed PMID: 15322104.

8: Shang J, Lehrman MA. Activation of glycogen phosphorylase with 5-aminoimidazole-4-carboxamide riboside (AICAR). Assessment of glycogen as a precursor of mannosyl residues in glycoconjugates. J Biol Chem. 2004 Mar 26;279(13):12076-80. Epub 2004 Jan 16. PubMed PMID: 14729664.

9: Lerín C, Montell E, Nolasco T, García-Rocha M, Guinovart JJ, Gómez-Foix AM. Regulation of glycogen metabolism in cultured human muscles by the glycogen phosphorylase inhibitor CP-91149. Biochem J. 2004 Mar 15;378(Pt 3):1073-7. PubMed PMID: 14651477; PubMed Central PMCID: PMC1224012.

10: Schnier JB, Nishi K, Monks A, Gorin FA, Bradbury EM. Inhibition of glycogen phosphorylase (GP) by CP-91,149 induces growth inhibition correlating with brain GP expression. Biochem Biophys Res Commun. 2003 Sep 12;309(1):126-34. PubMed PMID: 12943673.

11: Aiston S, Coghlan MP, Agius L. Inactivation of phosphorylase is a major component of the mechanism by which insulin stimulates hepatic glycogen synthesis. Eur J Biochem. 2003 Jul;270(13):2773-81. PubMed PMID: 12823547.

12: Halse R, Fryer LG, McCormack JG, Carling D, Yeaman SJ. Regulation of glycogen synthase by glucose and glycogen: a possible role for AMP-activated protein kinase. Diabetes. 2003 Jan;52(1):9-15. PubMed PMID: 12502487.

13: Latsis T, Andersen B, Agius L. Diverse effects of two allosteric inhibitors on the phosphorylation state of glycogen phosphorylase in hepatocytes. Biochem J. 2002 Nov 15;368(Pt 1):309-16. PubMed PMID: 12186629; PubMed Central PMCID: PMC1222981.

14: Aiston S, Hampson L, Gómez-Foix AM, Guinovart JJ, Agius L. Hepatic glycogen synthesis is highly sensitive to phosphorylase activity: evidence from metabolic control analysis. J Biol Chem. 2001 Jun 29;276(26):23858-66. Epub 2001 Apr 17. PubMed PMID: 11309391.

15: Oikonomakos NG, Skamnaki VT, Tsitsanou KE, Gavalas NG, Johnson LN. A new allosteric site in glycogen phosphorylase b as a target for drug interactions. Structure. 2000 Jun 15;8(6):575-84. PubMed PMID: 10873856.

16: Martin WH, Hoover DJ, Armento SJ, Stock IA, McPherson RK, Danley DE, Stevenson RW, Barrett EJ, Treadway JL. Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo. Proc Natl Acad Sci U S A. 1998 Feb 17;95(4):1776-81. PubMed PMID: 9465093; PubMed Central PMCID: PMC19188.

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