Pidotimod

Base Information

• Chemical Name: Pidotimod
• CAS No.: 121808-62-6
• Molecular Formula: C9H12N2O4S
• Molecular Weight: 244.271
• Hs Code.: 2934999090
• European Community (EC) Number: 629-822-3
• NSC Number: 759841
• UNII: 785363R681
• DSSTox Substance ID: DTXSID0046199
• Nikkaji Number: J623.605G
• Wikipedia: Pidotimod
• Wikidata: Q3902720
• NCI Thesaurus Code: C76686
• Metabolomics Workbench ID: 152576
• ChEMBL ID: CHEMBL1488165
• Mol file: 121808-62-6.mol

Synonyms:3-((5-oxo-2-pyrrolidinyl)carbonyl)-4-thiazolidinecarboxylic acid;3-pyroglutamylthiazolidine-4-carboxylic acid;3-pyroglutamylthiazolidine-4-carboxylic acid, (R-(R*,S*))-isomer;Adimod;PGT-1A;pidotimod

Chemical Property of Pidotimod

Chemical Property:

• Appearance/Colour: Almost white to white crystalline powder
• Melting Point: 194-198 °C
• Boiling Point: 663 °C at 760 mmHg
• PKA: 3.03(at 25℃)
• Flash Point: 354.8 °C
• PSA: 112.01000
• Density: 1.53 g/cm³
• LogP: -0.48220
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated), 5N HCl (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 244.05177804
• Heavy Atom Count: 16
• Complexity: 346

Purity/Quality:

99%, ^*data from raw suppliers

Pidotimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1C(=O)N2CSCC2C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@@H]1C(=O)N2CSC[C@H]2C(=O)O
• Recent ClinicalTrials: Study of Pidotimod in Children With Recurrent Respiratory Tract Infections (RRI)
• Recent EU Clinical Trials: Clinical and immunomodulatory effects of antibiotic therapy + pidotimod versus antibiotic therapy alone in patients with community-acquired pneumonia (CAP)
• Drug Interactions: Avoid taking this drug when taking meals. It can be taken either before meals or 2 hours after the meal.
• Description: Pidotimod, a dipeptide immunomodulating agent, has been introduced as immunostimulant therapy in patients with cell-mediated immunosuppression during respiratory or urinary tract infections. Its mode of action on the immune system is by activation of T-lymphocytes via interleukin (IL)-2 stimulation and macrophages via activation of superoxide dismutase and chemotaxis. In mice, treatment with pidotimod causes significant increase in the natural killer cell activity that may play an important role in immunosurveillance against tumors and in physiological homeostasis. Pidotimod can reverse the immunosuppression caused by surgical stress and has antiinflammatory, antioxidant, and antiaging properties. It has also been reported to provide protection from bacterial infections in mice.
• Uses: Immunostimulant used in patients with cell-mediated immunodepression. immune stimulant

Technology Process of Pidotimod

There total 3 articles about Pidotimod 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: 80.0%

ethyl-(R)-3-<(S)-(5-oxo-2-pyrrolidinyl)carbonyl>-thiazolidine-4-carboxylate (135124-63-9) → pidotimod (121808-62-6,162148-17-6,117241-40-4,162148-16-5)

Guidance literature:

With sodium hydroxide; for 1h;

Reference yield: 76.0%

pentachlorophenyl ester of L-pyroglutamic acid (28990-85-4) + L-thioproline (34592-47-7,2756-91-4,6070-92-4,60731-25-1) → pidotimod (121808-62-6,162148-17-6,117241-40-4,162148-16-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

Reference yield:

L-Pyroglutamic acid (98-79-3) → pidotimod (121808-62-6,162148-17-6,117241-40-4,162148-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) r.t., 4 h

2: 80 percent / 1 N NaOH / 1 h

With sodium hydroxide; dicyclohexyl-carbodiimide; In dichloromethane;

upstream raw materials:

ethyl-(R)-3-<(S)-(5-oxo-2-pyrrolidinyl)carbonyl>-thiazolidine-4-carboxylate

pentachlorophenyl ester of L-pyroglutamic acid

L-thioproline

L-Pyroglutamic acid

Refernces

• 1、 Magni,Signorelli,Bocchiola. "Synthesis and preliminary pharmacological evaluation of pidotimod, its enantiomer, diastereomers and carboxamido derivatives". . p. 1402 - 1404. Retrieved 2007/10/02.