Tiopronin

Base Information

• Chemical Name: Tiopronin
• CAS No.: 1953-02-2
• Molecular Formula: C5H9NO3S
• Molecular Weight: 163.197
• Hs Code.: 2942000000
• European Community (EC) Number: 217-778-4
• NSC Number: 760416
• UNII: C5W04GO61S
• DSSTox Substance ID: DTXSID4023678
• Nikkaji Number: J3.692G
• Wikipedia: Tiopronin
• Wikidata: Q414456
• NCI Thesaurus Code: C47758
• RXCUI: 6765
• Metabolomics Workbench ID: 67502
• ChEMBL ID: CHEMBL1314
• Mol file: 1953-02-2.mol

Synonyms:2 Mercaptopropionylglycine;2 Thiol propionamido acetic Acid;2 Thiolpropionamidoacetic Acid;2-Mercaptopropionylglycine;2-Thiol-propionamido-acetic Acid;2-Thiolpropionamidoacetic Acid;Acadione;Acid, 2-Thiol-propionamido-acetic;Acid, 2-Thiolpropionamidoacetic;alpha Mercaptopropionylglycine;alpha-Mercaptopropionylglycine;Captimer;Meprin;Mercaptopropionylglycine;Thiola;Thiopronine;Tiopronin;Tiopronine

Chemical Property of Tiopronin

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.6E-08mmHg at 25°C
• Melting Point: 93-98 °C
• Refractive Index: 1.518
• Boiling Point: 418.3 °C at 760 mmHg
• PKA: 3.36±0.10(Predicted)
• Flash Point: 206.8 °C
• PSA: 105.20000
• Density: 1.294 g/cm³
• LogP: -0.10360
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 163.03031432
• Heavy Atom Count: 10
• Complexity: 148

Purity/Quality:

98.5%min, ^*data from raw suppliers

Tiopronin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)NCC(=O)O)S
• Recent ClinicalTrials: Effect of Increasing Doses of Tiopronin on Cystine Capacity in Patients With Cystinuria
• Recent EU Clinical Trials: High dose antioxidant treatment of patients with cystic fibrosis evaluated by measuring desmosine/isodesmosine in urine
• Description: Tiopronin is a sulfiydryl derivative of N-propylglycine useful in the treatment of cystine urolithiasis in children. It is also reportedly effective in the management of rheumatoid polyarthritis, possibly due to its inhibitory effect on the free oxygen radicals produced by inflammatory macrophages and granulocytes. Tiopronin is an antioxidant that has diverse biological activities. It reduces free radical production by murine macrophages and granulocytes in vitro in a dose-dependent manner. Tiopronin induces expression of hypoxia-inducible factor 1α (HIF-1α) and increases VEGF secretion in human colon carcinoma cells. Rectal administration (500 μL of a 10 mM solution) reduces myeloperoxidase activity and reduces pro-inflammatory cytokine production in the colon in a rat model of colitis. Tiopronin (80-320 mg/kg per day) reduces the incidence of cleft palate in fetuses born to female mice orally exposed to teratogenic methylmercury chloride. Tiopronin (100 mg/kg) reduces heme oxygenase 1 mRNA expression, lipid peroxidation, and transverse aortic constriction in a mouse model of cardiac hypertrophy. Tiopronin (20 mg/kg) is hepatoprotective, increasing activity of the antioxidant enzymes superoxide dismutase and glutathione peroxidase and reversing hepatocyte degeneration in a rat model of high-fat diet-induced non-alcoholic steatohepatitis.
• Uses: It is used as antidote against heavy metal poisoning; hepatoprotectant; mucolytic. N-(2-Mercaptopropionyl)glycine or Tiopronin has been used:in the preparation of polyethylenimine (PEI)-coated gold microparticles (PEI-gold) for biolistic delivery of nucleic acidsto study the role of reactive oxygen species (ROS) at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotectionas a ROS inhibitor to study its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation
• Therapeutic Function: Antidote (heavy metal)

Technology Process of Tiopronin

There total 10 articles about Tiopronin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.5%

2-chloropropionylglycine (85038-45-5) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Guidance literature:

2-chloropropionylglycine; With sodium disulfide; sulfuric acid; sodium carbonate; In water; at 45 ℃; for 0.05h; Large scale;

With sulfuric acid; zinc; at 5 - 20 ℃; for 1.05h; Temperature; Large scale;

Reference yield:

2-methylmercaptoacetyl chloride (144122-68-9) + glycine (56-40-6,18875-39-3,25718-94-9) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Guidance literature:

With sodium carbonate; at 0 ℃; for 5h;

Reference yield:

C35H23F12NO5S3 → N-(2-mercaptopropionyl)glycine (1953-02-2) + C30H16F12O3S2

Guidance literature:

With water-d2; In aq. phosphate buffer; [D₃]acetonitrile; for 0.0833333h; pH=7;

DOI:10.1021/jacs.1c09958

upstream raw materials:

N-(2-bromo-propionyl)-glycine

α-Ethylxanthogenpropionylglycin

bis-2,2-mercaptopropionylglycine

α-Benzoylmercaptopropionylglycin

Downstream raw materials:

{2-[5-(Benzoyl-hydrazono)-3-hydroxy-1-methyl-6-oxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl]-propionylamino}-acetic acid

S-(2-phenylcarbamoyl-phenylselenyl)-DL-2-mercaptopropionylglycine

S-(2-phenylcarbamoyl-6-methoxy-phenylselenyl)-DL-2-mercaptopropionylglycine

bis-2,2-mercaptopropionylglycine

Refernces

• 1、 -. "Preparation method of tiopronin". Paragraph 0009. . Retrieved 2020/06/17.
• 2、 -. "Carotenoid ester analogs or derivatives for controlling C-reactive protein levels". . . Retrieved 2008/06/13.