Managlinat dialanetil

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MedKoo CAT#: 501202

CAS#: 280782-97-0

Description: Managlinat dialanetil, also known as MB06322 and CS-917, is a novel inhibitor of fructose 1,6-bisphphosphatase (FBPase) which is one of the rate-limiting enzymes of gluconeogenesis. CS-917 suppressed plasma glucose elevation after meal loading in a dose-dependent manner at doses ranging from 10 to 40 mg/kg.

Chemical Structure

Managlinat dialanetil
CAS# 280782-97-0

Theoretical Analysis

MedKoo Cat#: 501202
Name: Managlinat dialanetil
CAS#: 280782-97-0
Chemical Formula: C21H33N4O5PS
Exact Mass: 484.19093
Molecular Weight: 484.55
Elemental Analysis: C, 52.05; H, 6.86; N, 11.56; O, 16.51; P, 6.39; S, 6.62

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Synonym: MB-06322, MB 06322, MB06322, CS-917, CS 917, CS917; Managlinat dialanetil

IUPAC/Chemical Name: (2S,2'S)-diethyl 2,2'-(((5-(2-amino-5-isobutylthiazol-4-yl)furan-2-yl)phosphinediyl)bis(azanediyl))dipropanoate


InChi Code: InChI=1S/C21H33N4O5PS/c1-7-28-19(26)13(5)24-31(25-14(6)20(27)29-8-2)17-10-9-15(30-17)18-16(11-12(3)4)32-21(22)23-18/h9-10,12-14,24-25H,7-8,11H2,1-6H3,(H2,22,23)/t13-,14-/m0/s1

SMILES Code: CC(C)CC1=C(C2=CC=C(P(N[C@@H](C)C(OCC)=O)N[C@@H](C)C(OCC)=O)O2)N=C(N)S1

Appearance: Solid powder

Purity: >98%

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 sort term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 484.55 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

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1: van Poelje PD, Potter SC, Erion MD. Fructose-1, 6-bisphosphatase inhibitors for reducing excessive endogenous glucose production in type 2 diabetes. Handb Exp Pharmacol. 2011;(203):279-301. Review. PubMed PMID: 21484576.

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: Dang Q, Liu Y, Cashion DK, Kasibhatla SR, Jiang T, Taplin F, Jacintho JD, Li H, Sun Z, Fan Y, DaRe J, Tian F, Li W, Gibson T, Lemus R, van Poelje PD, Potter SC, Erion MD. Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase. J Med Chem. 2011 Jan 13;54(1):153-65. Epub 2010 Dec 2. PubMed PMID: 21126019.

4: Zhang Y, Xie Z, Zhou G, Zhang H, Lu J, Zhang WJ. Fructose-1,6-bisphosphatase regulates glucose-stimulated insulin secretion of mouse pancreatic beta-cells. Endocrinology. 2010 Oct;151(10):4688-95. Epub 2010 Aug 18. PubMed PMID: 20719858.

5: Yoshida T, Okuno A, Tanaka J, Takahashi K, Nakashima R, Kanda S, Ogawa J, Hagisawa Y, Fujiwara T. Metformin primarily decreases plasma glucose not by gluconeogenesis suppression but by activating glucose utilization in a non-obese type 2 diabetes Goto-Kakizaki rats. Eur J Pharmacol. 2009 Nov 25;623(1-3):141-7. Epub 2009 Sep 15. PubMed PMID: 19765581.

6: Yoshida T, Okuno A, Izumi M, Takahashi K, Hagisawa Y, Ohsumi J, Fujiwara T. CS-917, a fructose 1,6-bisphosphatase inhibitor, improves postprandial hyperglycemia after meal loading in non-obese type 2 diabetic Goto-Kakizaki rats. Eur J Pharmacol. 2008 Dec 28;601(1-3):192-7. Epub 2008 Nov 6. PubMed PMID: 19014931.

7: Dang Q, Kasibhatla SR, Jiang T, Fan K, Liu Y, Taplin F, Schulz W, Cashion DK, Reddy KR, van Poelje PD, Fujitaki JM, Potter SC, Erion MD. Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors. J Med Chem. 2008 Jul 24;51(14):4331-9. Epub 2008 Jun 21. PubMed PMID: 18570362.

8: Dang Q, Kasibhatla SR, Reddy KR, Jiang T, Reddy MR, Potter SC, Fujitaki JM, van Poelje PD, Huang J, Lipscomb WN, Erion MD. Discovery of potent and specific fructose-1,6-bisphosphatase inhibitors and a series of orally-bioavailable phosphoramidase-sensitive prodrugs for the treatment of type 2 diabetes. J Am Chem Soc. 2007 Dec 19;129(50):15491-502. Epub 2007 Nov 28. PubMed PMID: 18041834.

9: Wang Y, Tomlinson B. Managlinat dialanetil, a fructose-1,6-bisphosphatase inhibitor for the treatment of type 2 diabetes. Curr Opin Investig Drugs. 2007 Oct;8(10):849-58. Review. PubMed PMID: 17907062.

10: van Poelje PD, Potter SC, Chandramouli VC, Landau BR, Dang Q, Erion MD. Inhibition of fructose 1,6-bisphosphatase reduces excessive endogenous glucose production and attenuates hyperglycemia in Zucker diabetic fatty rats. Diabetes. 2006 Jun;55(6):1747-54. PubMed PMID: 16731838.

11: Erion MD, van Poelje PD, Dang Q, Kasibhatla SR, Potter SC, Reddy MR, Reddy KR, Jiang T, Lipscomb WN. MB06322 (CS-917): A potent and selective inhibitor of fructose 1,6-bisphosphatase for controlling gluconeogenesis in type 2 diabetes. Proc Natl Acad Sci U S A. 2005 May 31;102(22):7970-5. Epub 2005 May 23. PubMed PMID: 15911772; PubMed Central PMCID: PMC1138262.

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