Inosine
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Inosine
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CAS No:
58-63-9
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Formula:
C10H12N4O5
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Chemical Name:
Inosine
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Synonyms:
Inosine;Hypoxanthine,9-β-D-ribofuranosyl-;Hypoxanthine riboside;Hypoxanthosine;9-β-D-Ribofuranosylhypoxanthine;Hypoxanthine ribonucleoside;Hypoxanthine 9-β-D-ribofuranoside;Atorel;HXR;Oxiamin;Panholic-L;Ribonosine;Selfer;Trophicardyl;Ino;Inosie;1,9-Dihydro-9-β-D-ribofuranosyl-6H-purin-6-one;6H-Purin-6-one,1,9-dihydro-9-β-D-ribofuranosyl-;NSC 20262;132953-54-9;4181-51-5;12712-98-0;28861-88-3;292853-81-7;691344-25-9;740029-83-8
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CAS No:
Description
Inosine, an endogenous purine nucleoside, has immunomodulatory, neuroprotective, and analgesic properties. 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.[1] Inosine dose-dependently stimulates cAMP production mediated through the A2AR. Inosine dose-dependently induces A2AR-mediated ERK1/2 phosphorylation.[2] In vivo: The reference for
Solid
Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines D-ribonucleoside and a member of inosines. It derives from a hypoxanthine and a ribofuranose.|A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed)
Inosine Basic Attributes
268.23
268.23
624889
200-390-4
5A614L51CT
DTXSID2045993
D - Dermatologicals|G - Genito urinary system and sex hormones|S - Sensory organs
2934999090
Characteristics
129
-2.1
White Crystalline Powder
1.613 g/cm3
218 °C (decomp)
226 C (dec.)
359.3±34.3 °C
1.879
H2O: 2.1 g/100 mL (20 ºC)
Store at RT.
LD50 oral in rat: > 10gm/kg
-49.2 º (c=1,H2O 18 ºC)
170.7 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|159.25 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|175.37 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|161.7 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|153 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|170.2 Ų [M+K]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|170.8 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|158.2 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|159.6 Ų [M-H]-
Safety Information
NONH for all modes of transport
2
36/37/38
24/25-36-26
NM7460000
Xi
Hygroscopic
P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
H302
Not Classified
Drug Information
The primary popular claim made for inosine, that it enhances exercise and athletic performance, is refuted by the available research data. There is some preliminary evidence that inosine may have some neurorestorative, anti-inflammatory, immunomodulatory and cardioprotective effects.
Inosine may have neuroprotective, cardioprotective, anti-inflammatory and immunomodulatory activities.
Ingested inosine is absorbed from the small intestine.
In the liver, inosine may be catabolized by a series of reactions culminating in the production of uric acid and also may be metabolized to adenine- and guanine-containing nucleotides. Inosine not metabolized in the liver is transported via the systemic circulation and distributed to various tissues of the body, where it is metabolized in similar fashion as in the liver. Uric acid, the purine end-product of inosine catabolism, is excreted in the urine.
Inosine has been found to have potent axon-promoting effects in vivo following unilateral transection of the corticospinal tract of rats. The mechanism of this action is unclear. Possibilities include serving as an agonist of a nerve growth factor-activated protein kinase (N-Kinase), conversion to cyclic nucleotides that enable advancing nerve endings to overcome the inhibitory effects of myelin, stimulation of differentiation in rat sympathetic neurons, augmentation of nerve growth factor-induced neuritogenesis and promotion of the survival of astrocytes, among others. The mechanism of inosine's possible cardioprotective effect is similarly unclear. Inosine has been reported to have a positive inotropic effect and also to have mild coronary vasodilation activity. Exogenous inosine may contribute to the high-energy phosphate pool of cardiac muscle cells and favorably affect bioenergetics generally. Inosine has also been reported to enhance the myocardial uptake of carbohydrates relative to free fatty acids as well as glycolysis. In cell culture studies, inosine has been found to inhibit the production, in immunostimulated macrophages and spleen cells, of the proinflammatory cytokines, tumor necrosis factor (TNF)-alpha, interleukin (IL)-1, interleukin (IL)-12, macrophage-inflammatory protein-1 alpha and interferon (IFN)-gamma. It also suppressed proinflammatory cytokine production and mortality in a mouse endotoxemic model. These actions might account for the possible immunomodulatory, anti-inflammatory and anti-ischemic actions of inosine.
Inosine
Inosine Use and Manufacturing
Method 1: Preparation of inosinate disodium inosinate dephosphorylation Corynebacterium 269 is fermented, the fermentation broth is decellularized, adsorbed, eluted, concentrated, added with ethanol, and crystallized under pH 7-7.5 to obtain disodium inosinate . Corynebacterium 269 [fermentation] → fermentation broth [debacteria, adsorption, elution, concentration] → concentrated solution [ethanol] → [pH7-7.5] Preparation of crude inosine disodium inosinate in acetic acid buffer, adjusted pH5.4-5.6, pressurized 137-147kPa, dephosphorylation for 5h, can get crude inosine. Disodium inosinate [acetic acid, pressurized] → dissolved inosine purified distilled water, pH=6, recrystallized to obtain high-quality products. Method two: One-step fermentation strain selection Bacillus mutans 7171-9-1 was transferred to slant medium and cultured at 30-32℃ for 48h. The components of the slant medium are glucose 1%, peptone 0.4%, yeast extract 0.7%, beef extract 1.4%, agar 2%, and sterilized at pH 7, 120°C for 20 min. Bacillus mutans 7171-9-1[Bevel culture]→[30-32℃, 48h] Bacterial seed bevel seed culture first-level seed: medium composition is glucose 2%, peptone 1%, yeast extract 1%, corn steep liquor 0.5%, urea 0.5%, sodium chloride 0.25%. Before sterilization, the pH was 7, and 150ml of medium was filled in a 1L triangular bottle and sterilized at 115°C for 15min. Put platinum earring fungus into each Erlenmeyer flask and incubate on a reciprocating shaker at 32℃±1℃ for 18h. Second-level seed: medium-level seed, enlarged 50L fermentor, fixed volume 25L, inoculation volume 3%, culture at 32℃±1℃ for 12-15h, stirring speed 320r/min, ventilation volume 1: 0.25V/(V ·Min), growth bacteria index A(650nm)=0.78, pH=6.4-6.6. Bacterial slant [shaker shaking]→[pH7, 32℃±1℃, 18h] first-level seed culture [50L fermentation tank]→[pH6.4-6.6, 32℃±1℃, 12-15h] second-level The seed culture broth is fermented in a 50L stainless steel standard fermenter with a fixed volume of 35L. The medium composition is starch hydrolyzed sugar 10%, dry yeast hydrolysate 1.5%, soybean cake hydrolysate 0.5%, urea 0.4%, magnesium sulfate 0.1%, potassium chloride 0.2%, disodium hydrogen phosphate 0.5%, ammonium sulfate 1.5%, Silicone oil 0.05%. pH=7, inoculation volume 0.9%, incubation at 32℃±1℃ for 93h, stirring speed 320r/min, ventilation volume 1: 0.5V/(V·min). 500L fermentation tank, constant volume 350L. The medium composition is starch hydrolyzed sugar 10%, dry yeast hydrolysate 1.5%, soybean cake hydrolysate 0.5%, ammonium sulfate 1.5%, magnesium sulfate 0.1%, potassium chloride 0.2%, disodium hydrogen phosphate 0.5%, calcium carbonate 1% , Silicone oil is less than 0.3%. pH=7, inoculation volume 7%, culture at 32℃±1℃ for 75h, stirring speed 230r/min, ventilation volume 1: 0.25V/(V·min). 20000L fermentor, the culture medium is the same as above, the inoculation volume is 2.5%, and the culture is 35℃±5℃ for 83h. Secondary seed culture [50L fermentation tank]→[pH7, 32℃±1℃, 93h] fermentation broth[500L fermentation tank]→[pH7, 32℃±1℃, 75h] fermentation broth[20000L fermentation tank]→[ pH7, 35℃±1℃, 83h] fermentation broth extraction, adsorption, elution The fermentation broth 30-40L was adjusted to pH=2.5-3, and the bacteria were adsorbed by two 3.5kg 732H resin columns connected in series. Wash once with pH 3 water equivalent to 3 times the total volume of the resin, separate the two columns, elute the inosine with pH 3 water, absorb the inosine through the 769 activated carbon column, and wash with 2-3 times the volume of water , Then wash with 70-80℃, 70-80℃, soak in 1mol/L sodium hydroxide solution for 30min, and finally elute inosine with 0.01mol/L sodium hydroxide solution, collect the eluent, concentrate in vacuum, pH11 or 6 Place and filter to get crude product. Fermentation broth [732 resin column] → [pH2.5-3] adsorbate [water] → [pH2.5-3] eluent [769 activated carbon column] → adsorbate [distilled water, sodium hydroxide] → [70- 80℃][Sodium hydroxide]→[70-80℃] Eluent [Concentrated crystal]→[pH11 or 6]Purification of crude inosine The crude product is formulated into 5%-10% solution, heated to dissolve, suction filtered, After cooling, filtering, washing with a small amount of water, and drying, the inosine refined product is obtained. Crude inosine [distilled water] → [recrystallization] finished inosine.
cell function activator, cardiotonic.Participate in energy metabolism and protein synthesis in the body.Used as coenzyme drugs.Biochemical research. Medicine is used to promote the growth of white blood cells.Inosine is a potential stimulator of nerve production factor (NGF).
Inosine: ACTIVE
Computed Properties
Molecular Weight:268.23
XLogP3:-1.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:268.08076950
Monoisotopic Mass:268.08076950
Topological Polar Surface Area:129
Heavy Atom Count:19
Complexity:405
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It participates in cellular energy metabolism and protein synthesis in the body, increases the activity of related metabolic enzymes, improves liver function, and promotes the recovery of damaged liver.
Registered Holders
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Jinan MINGXIN Pharmaceutical Co., Ltd.
Active
China
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Xinxiang Pharmaceutical Co., Ltd.
Active
China
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Henan Xinxiang Huaxing Pharmaceutical FACTORY
Active
China
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