1,4:3,6-Dianhydro-D-glucitol

二脱水-D-葡萄糖醇,异山梨醇

Isosorbide dinitrate is a drug that belongs to the class of nitrates. It is used in the treatment of angina pectoris, as well as congestive heart failure and chronic heart failure. Isosorbide dinitrate has been shown to cause caspase-independent cell death in human leukemia cells and breast cancer cells. This may be due to its ability to inhibit mitochondrial membrane potential and interfere with intracellular calcium mobilization. The optimum concentration for isosorbide dinitrate is 10 µM, which inhibits the growth of bacteria, including Mycobacterium tuberculosis and Salmonella enterica serovar Typhimurium. The drug also inhibits the production of proinflammatory cytokines such as IL-1β, IL-6, and TNF-α by inhibiting c-jun phosphorylation.

Isosorbide is a 1,4:3,6-dianhydrohexitol that can be derived from glucose. It has been used in the synthesis of the nitric oxide (NO) donors isosorbide mono- and dinitrate, which have vasodilatory activity. Isosorbide has also been used as a monomer or building block in the synthesis of various polymers and functional materials, respectively.

Isosorbide is an organic nitrate with vasodilator activity. Isosorbide relaxes vascular smooth muscle by formation of the free radical nitric oxide (NO), which is identical to the endothelium-derived relaxing factor (EDRF). NO activates guanylyl cyclase, thereby increasing the synthesis of cGMP within smooth muscle. Elevated cGMP levels in smooth muscle activate cGMP-dependent kinase activity that leads to release of sequestered Ca2+. In turn, free Ca+ triggers dephosphorylation of light chain myosin and relaxation of peripheral arteries and veins. In addition isosorbide relaxes coronary arteries, thereby increasing the blood circulation through the ischemic area.

Isosorbide is an organic molecular entity.

Isosorbide is an organic nitrate with vasodilatory properties on both arteries and veins.

Title: Isosorbide

CAS Registry Number: 652-67-5

CAS Name: 1,4:3,6-Dianhydro-D-glucitol

Additional Names: 1,4:3,6-dianhydrosorbitol

Manufacturers' Codes: AT-101; NSC-40725

Trademarks: Hydronol (Stuart); Ismotic (Alcon); Isobide (Nikken)

Molecular Formula: C6H10O4

Molecular Weight: 146.14

Percent Composition: C 49.31%, H 6.90%, O 43.79%

Literature References: Prepd by acid dehydration of D-glucitol: Haworth, Wiggins, GB 600870 (1948). Purification: Hartmann, US 3160641 (1964 to Atlas Chemical Industries). Review of prepn, structure, properties: Wiggins, Adv. Carbohydr. Chem. 5, 191-228 (1950). Stereochemistry: Cope, Shen, J. Am. Chem. Soc. 78, 3177 (1956). Conformation studies: Hopton, Thomas, Can. J. Chem. 47, 2395 (1969). Pharmacodynamics in man: Nodine et al., Clin. Pharmacol. Ther. 14, 196 (1973).

Properties: Crystals, mp 61-64°. [a]D +44°.

Melting point: mp 61-64°

Optical Rotation: [a]D +44°

Therap-Cat: Diuretic.

Keywords: Diuretic.