Inosine, 肌苷, 次黄苷

Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. Inosine derives from a hypoxanthine and a ribofuranose. Inosine plays a key role as a metabolite in bacteria, fungi, humans, and other animals. There is preliminary evidence that inosine may have neurorestorative, anti-inflammatory, immunomodulatory, and cardioprotective effects.

Purine nucleoside and adenosine metabolite. Cell-permeable. Displays neuroprotective and immunomodulatory effects. Potent vasodilator and axon growth stimulator.

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Inosine, an endogenous purine nucleoside, has immunomodulatory, neuroprotective, and analgesic properties. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing. In vitro: Inosine has been shown to stimulate axonal growth in cell culture and promote corticospinal tract axons to sprout collateral branches after stroke, spinal cord injury and TBI in rodent models. Incorporation of inosine in place of guanine modulates translational events. Inosine has antioxidant, anti-inflammatory and neuroprotective functionality. Inosine is prescribed as a therapeutic supplement for nerve injury, inflammation and oxidative stress. Inosine has been used as a medium supplement in nucleotide rescue experiments in pancreatic cancer cell lines.

Title: Inosine

CAS Registry Number: 58-63-9

Additional Names: Hypoxanthine riboside; 9-b-D-ribofuranosylhypoxanthine; hypoxanthosine

Trademarks: Inosie (Morishita); Oxiamine (Made); Ribonosine (Toyo Jozo); Trophicardyl

Molecular Formula: C10H12N4O5

Molecular Weight: 268.23

Percent Composition: C 44.78%, H 4.51%, N 20.89%, O 29.82%

Literature References: In meat and meat extracts, in sugar beets. Prepd from adenosine by incubation with purified adenosine deaminase from intestine: Kalckar, J. Biol. Chem. 167, 445 (1947); also by the action of sodium nitrite and acetic acid on adenosine: Levene, Jacobs, Ber. 43, 3161 (1910); by the use of barium nitrite and H2SO4: Reiff et al., US 3049536 (1962 to Zellstoff-Fabrik Waldhof). Fermentation method: Motozaki et al., US 3111459 (1963 to Ajinomoto). Structure: Bredereck, Ber. 66, 198 (1933); Z. Physiol. Chem. 223, 61 (1934); Gulland, Holiday, J. Chem. Soc. 1936, 765.

Derivative Type: Dihydrate

Properties: Long rectangular plates from water, mp 90°. Anhydrous needles from 80% alc, dec 218° (rapid heating). [a]D18 -49.2° (c = 0.9 in H2O). [a]20white -73° (0.5 g + 2 ml N NaOH + 3 ml H2O). 100 ml of the satd water soln at 20° contain 1.6 g inosine. Absorption spectrum: Kalckar, loc. cit. uv max (pH 6.0): 248.5 nm (e 12200). Boiling with 0.1N H2SO4 yields hypoxanthin and D-ribose.

Melting point: mp 90°

Optical Rotation: [a]D18 -49.2° (c = 0.9 in H2O); [a]20white -73° (0.5 g + 2 ml N NaOH + 3 ml H2O)

Absorption maximum: uv max (pH 6.0): 248.5 nm (e 12200) 

Therap-Cat: Activates cellular functions.