Synonym
Linogliride fumarate; McN-3935; McN 3935; McN3935;
IUPAC/Chemical Name
(E)-N-((E)-1-methylpyrrolidin-2-ylidene)-N'-phenylmorpholine-4-carboximidamide fumarate
InChi Key
ZSAMTXUUUFXIII-CZKNSKRSSA-N
InChi Code
InChI=1S/C16H22N4O.C4H4O4/c1-19-9-5-8-15(19)18-16(20-10-12-21-13-11-20)17-14-6-3-2-4-7-14;5-3(6)1-2-4(7)8/h2-4,6-7H,5,8-13H2,1H3;1-2H,(H,5,6)(H,7,8)/b17-16-,18-15+;2-1+
SMILES Code
CN1/C(CCC1)=N/C(N2CCOCC2)=N/C3=CC=CC=C3.O=C(O)/C=C/C(O)=O
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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
402.45
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 |
1: Levin PA, Jovanovic L, Chalew SA, Martin L, Pitarra DK, Kim F, Kowarski AA. Linogliride fumarate, representing a new class of oral hypoglycemic agent for diabetes. Clin Pharmacol Ther. 1987 Nov;42(5):498-503. PubMed PMID: 3315390.
2: Ronner P, Cheong E, Khalid P, Tuman RW, Matschinsky FM. Effect of linogliride on hormone release from perfused rat pancreas. Fuel dependence and desensitization by tolbutamide. Diabetes. 1991 Jul;40(7):878-84. PubMed PMID: 2060724.
3: Ronner P, Higgins TJ, Kimmich GA. Inhibition of ATP-sensitive K+ channels in pancreatic beta-cells by nonsulfonylurea drug linogliride. Diabetes. 1991 Jul;40(7):885-92. PubMed PMID: 2060725.
4: Salhanick AI, Leighty SJ, Amatruda JM. Postreceptor regulation of insulin action in primary cultures of rat hepatocytes by oral hypoglycemic agents: effects of linogliride and chlorpropamide. Horm Metab Res. 1989 Nov;21(11):596-601. PubMed PMID: 2687145.
5: Wu WN, Mutter MS. Biotransformation of linogliride, a hypoglycemic agent in laboratory animals and humans. J Pharm Biomed Anal. 1995 Jun;13(7):857-67. PubMed PMID: 8562609.
6: Zawalich WS, Rasmussen G, Tuman RW, Tutwiler GF. Influence of the oral hypoglycemic agent linogliride (McN-3935) on insulin secretion from isolated rat islets of Langerhans. Endocrinology. 1987 Mar;120(3):880-5. PubMed PMID: 3542516.
7: Woodfork KA, Wonderlin WF, Peterson VA, Strobl JS. Inhibition of ATP-sensitive potassium channels causes reversible cell-cycle arrest of human breast cancer cells in tissue culture. J Cell Physiol. 1995 Feb;162(2):163-71. PubMed PMID: 7822427.
8: Ng KT, Holland ML, Plutte JA. Determination of linogliride in biological fluids by high-performance liquid chromatography. J Chromatogr. 1984 Nov 28;311(2):418-23. PubMed PMID: 6520190.
9: Klimatcheva E, Wonderlin WF. An ATP-sensitive K(+) current that regulates progression through early G1 phase of the cell cycle in MCF-7 human breast cancer cells. J Membr Biol. 1999 Sep 1;171(1):35-46. PubMed PMID: 10485992.
10: Chrzanowski FA, Ahmad K. The preparation and evaluation of salt forms of linogliride with reduced solubilities as candidates for extended release. Drug Dev Ind Pharm. 2017 Mar;43(3):421-431. doi: 10.1080/03639045.2016.1257019. Epub 2016 Nov 21. PubMed PMID: 27808569.
11: Doi K. [New oral antidiabetic agents]. Nihon Rinsho. 1990 Dec;48 Suppl:962-73. Japanese. PubMed PMID: 2128351.
12: Wiener CM, Banta MR, Dowless MS, Flavahan NA, Sylvester JT. Mechanisms of hypoxic vasodilation in ferret pulmonary arteries. Am J Physiol. 1995 Sep;269(3 Pt 1):L351-7. PubMed PMID: 7573469.
13: Breslin HJ, Kukla MJ, Tuman RW, Rebarchak MC, Bowden CR. A novel series of N-(1-aminoalkylidene)carboximidamides as potential hypoglycemic agents. J Med Chem. 1993 May 28;36(11):1597-603. PubMed PMID: 8496927.
