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

pka

2.09±0.10(Predicted)

color 

White to Light Brown

InChI

InChI=1S/C6H13NO3S/c7-5(6(9)10)4-11-3-1-2-8/h5,8H,1-4,7H2,(H,9,10)/t5-/m0/s1

InChIKey

KINWYTAUPKOPCQ-YFKPBYRVSA-N

SMILES

C(O)(=O)[C@H](CSCCCO)N

CAS DataBase Reference

13189-98-5(CAS DataBase Reference)

Safety Information

RTECS 

HA2350000

Fudosteine Usage And Synthesis

Description

Fudosteine 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.

Description

Fudostein 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 Properties

Off-White Powder

Originator

SS Pharmaceutical/Mitsubishi Pharma (Japan)

Uses

An antiinflammatory expectorant MUC5 mucin obstructive pulmonary disease.

Uses

An antiinflammatory expectorant used in the treatment of MUC5 mucin obstructive pulmonary disease.

Uses

Fudosteine 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

Uses

A demonstrated antiinflammatory

Uses

Fudosteine 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.

Definition

ChEBI: Fudosteine is an organic molecular entity.

brand name

Cleanal, Spelear (Mitsubishi Pharma)

Hazard

A reproductive hazard.

Synthesis

Fudosteine 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

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