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Fudosteine

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CAS:13189-98-5
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CAS:13189-98-5
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CAS:13189-98-5
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CAS:13189-98-5
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Fudosteine Basic information
Product Name:Fudosteine
Synonyms:FUDESTEINE;Fudosteine (R)-2-Amino-3-(3-hydroxypropylthio)propionic acid;(2R)-2-amino-3-(3-hydroxypropylsulfanyl)propanoic acid;(2R)-2-amino-3-(3-hydroxypropylthio)propionic acid;(2R)-2-azanyl-3-(3-hydroxypropylsulfanyl)propanoic acid;3-[(3-Hydroxypropyl)thio]alanine;(r)-2-amino-3-(3-hydroxypropylthio)propionic acid;S-(3-HYDROXYPROPYL)CYSTEINE
CAS:13189-98-5
MF:C6H13NO3S
MW:179.24
EINECS:1592732-453-0
Product Categories:Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Other APIs;Sulfur & Selenium Compounds
Mol File:13189-98-5.mol
Fudosteine Structure
Fudosteine Chemical Properties
Melting point 200-202°C (dec.)
Boiling point 354.5±42.0 °C(Predicted)
density 1.301±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility Water (Slightly)
form Solid
pka2.09±0.10(Predicted)
color White to Light Brown
InChIInChI=1S/C6H13NO3S/c7-5(6(9)10)4-11-3-1-2-8/h5,8H,1-4,7H2,(H,9,10)/t5-/m0/s1
InChIKeyKINWYTAUPKOPCQ-YFKPBYRVSA-N
SMILESC(O)(=O)[C@H](CSCCCO)N
CAS DataBase Reference13189-98-5(CAS DataBase Reference)
Safety Information
RTECS HA2350000
MSDS Information
Fudosteine Usage And Synthesis
DescriptionFudosteine is a cysteine derivative that interferes with the increase in goblet cell number, expression of the mucin MUC5AC, and subsequent mucin secretion, in airways agonized with tobacco smoke, isoproterenol, lipopolysaccharide, TNF-α, or oxidants. Fudosteine, which is a thiol compound with antioxidant properties, limits NF-κB signaling and reduces inflammatory gene expression. It has greater bioavailability than N-acetyl-cysteine and increases cysteine levels in cells.
DescriptionFudostein was launched in Japan as a new mucoactive agent for the treatment of bronchitis and respiratory congestion. This cysteine derivative was obtained from L-cysteine by condensation with either allylic alcohol in the presence of potassium persulfate or the corresponding bromoalcohol in the presence of a base. Fudostein was shown to significantly reduce mucus glycoprotein hypersecretion and inhibit infiltration of airway mucosa by lymphocytes and inflammatory cells in bronchitic rats. When given to bronchitic rabbits, an oral dose of 500 mg/kg daily potently decreased the fucose/ N-acetylneuraminic acid in sputa, so exhibiting mucoregulatory properties. In another study with SO2-exposed rabbits, fudostein suppressed blood flow of tracheal microvasculature increased by SO2, partly due to scavenging of superoxide anion.
Chemical PropertiesOff-White Powder
OriginatorSS Pharmaceutical/Mitsubishi Pharma (Japan)
UsesAn antiinflammatory expectorant MUC5 mucin obstructive pulmonary disease.
UsesFudosteine is a novel mucoactive agent and a MUC5AC mucin hypersecretion inhibitor. MUC5AC mucin synthesis and the expression of the MUC5AC gene were increased by LPS in rats or TNF-α in NCI-H292 cells; these effects were inhibited by fudosteine treatment
UsesAn antiinflammatory expectorant used in the treatment of MUC5 mucin obstructive pulmonary disease.
UsesA demonstrated antiinflammatory
UsesFudosteine is a cysteine derivative that interferes with the increase in goblet cell number, expression of the mucin MUC5AC, and subsequent mucin secretion, in airways agonized with tobacco smoke, isoproterenol, lipopolysaccharide, TNF-α, or oxidants. Fudosteine, which is a thiol compound with antioxidant properties, limits NF-κB signaling and reduces inflammatory gene expression. It has greater bioavailability than N-acetyl-cysteine and increases cysteine levels in cells.
DefinitionChEBI: Fudosteine is an organic molecular entity.
Brand nameCleanal, Spelear (Mitsubishi Pharma)
HazardA reproductive hazard.
SynthesisFudosteine is synthesized by condensation of L-cysteine with 3-bromopropyl alcohol in aqueous NaOH, or by condensation of L-cysteine with allyl alcohol by means of aqueous potassium persulfate.
References[1] KOICHI TAKAHASHI . Effects of SS320A, a New Cysteine Derivative, on the Change in the Number of Goblet Cells Induced by Isoproterenol in Rat Tracheal Epithelium[J]. Japanese journal of pharmacology, 1998, 77 1: Pages 71-78. DOI: 10.1254/jjp.77.71
[2] C K RHEE. Effect of fudosteine on mucin production.[J]. European Respiratory Journal, 2008: 1195-1202. DOI: 10.1183/09031936.00018508
[3] RAHMAN I. Pharmacological antioxidant strategies as therapeutic interventions for COPD[J]. Biochimica et biophysica acta. Molecular basis of disease, 2012, 1822 5: Pages 714-728. DOI: 10.1016/j.bbadis.2011.11.004
Fudosteine Preparation Products And Raw materials
Tag:Fudosteine(13189-98-5) Related Product Information
Dilauryl thiodipropionate β-Alanine ALTRENOGEST Glycine 6-Aminocaproic acid N-Aminothiourea Propionic acid Dithiooxamide S-Carboxymethyl-L-cysteine Erdosteine L-ALANINE, 3-[(3-HYDROXYPROPYL)SULFINYL]- Fudosteine Impurity 5 Fudosteine Impurity 2 Tris(hydroxymethyl)aminomethane Fudosteine Impurity 1 Fudosteine Impurity 3 Fudosteine Impurity 2 Fudosteine Impurity 4

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