Pidotimod
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Pidotimod
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CAS No:
121808-62-6
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Formula:
C9H12N2O4S
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Chemical Name:
Pidotimod
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Synonyms:
4-Thiazolidinecarboxylic acid,3-[[(2S)-5-oxo-2-pyrrolidinyl]carbonyl]-,(4R)-;4-Thiazolidinecarboxylic acid,3-[(5-oxo-2-pyrrolidinyl)carbonyl]-,[R-(R*,S*)]-;(4R)-3-[[(2S)-5-Oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic acid;Pidotimod;Adimod;Axil (pharmaceutical);Onaka;Pigitil;Polimod
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CAS No:
Description
White SolidPidotimod, a dipeptide immunomodulating agent, has been introduced as immunostimulant therapy in patients with cell-mediated immunosuppression during respiratory or urinary tract infections. It has also been reported to provide protection from bacterial infections in mice.The chemical name of pidotimod is: (4R)-3-(5-oxo-L-prolyl)-1,3-thiazolidine-4-carboxylic acid. Its formula is C9H13N2O4S, molecular mass is 244.26 g/mol. It is a white odorless crystalline powder, soluble in water
(4R)-3-[oxo-[(2S)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic acid is a peptide.|Pidotimod is a synthetic dipeptide with immunomodulatory properties.
Pidotimod Basic Attributes
244.27
244.27
2017-001-1
785363R681
759841
DTXSID0046199
L - Antineoplastic and immunomodulating agents
2934999090
Characteristics
112
-0.7
Almost white to white crystalline powder
1.53
194-198 °C (decomp)
663.0±55.0 °C(Predicted)
354.8±31.5 °C
1.619
>36.6 [ug/mL]
Hygroscopic, -20°C Freezer, Under Inert Atmosphere
LD50 in mice and rats (mg/kg): >4000 i.v.; >4000 i.m.; >8000 i.p.; >8000 orally (Coppi)
D25 -150° (c = 2 in 5N HCl)
Drug Information
For use as immunostimulant therapy for treatment of cell-mediated immunosuppression with respiratory or urinary infections.
Pidotimod modulates the immune system to induce an immune response against bacterial or viral pathogens
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Biologically active substances whose activities affect or play a role in the functioning of the immune system. (See all compounds classified as Immunologic Factors.)
Bioavailability of 45%.|95% of intravenous dose is eliminated in the urine as the parent compound.
Half life of 4 h.
Pidotimod inhibits tumor necrosis factor α (TNF-α) induced increases in extracellular signal-related kinase (ERK) phosphorylation. It also increases nuclear factor κB (NFκB) expression and translocation to the nucleus. It is these to modulatory effects on ERK and NFκB signalling which are thought to produce the increase in toll-like receptor expression seen with pidotimod. Pidotimod increase maturation of dendritic cells responsible for presenting antigens to naive Th-cells. It also appears to result in a greater population these cells diiferentiating to Th1 cells which are believed to mediate the immune response to pathogens like bacteria and viruses. Lastly, pidotimod appears to increase antigen-specific antibody titer and cytotoxic response with antigen exposure. The precise mechanism and timeline of events leading to these effects is unknown.
3-((5-oxo-2-pyrrolidinyl)carbonyl)-4-thiazolidinecarboxylic acid
Pidotimod Use and Manufacturing
The above-mentioned product L-thiazolidine-4-carboxylic acid was added to 500 ml of absolute ethanol, and 100 g of thionyl chloride was added dropwise thereto, which was produced as a white gas, and the mixture was heated to reflux for 5 hours. Ethanol was distilled off under reduced pressure, concentrated aqueous ammonia was added dropwise, pH was adjusted to 12, extracted twice with isopropyl acetate, and the ester layer was evaporated to dryness.500 ml of THF was added, and 82 g of L-pyroglutamic acid was added in portions, stirred and dissolved, and then cooled to 0 °C. 125 g of DCC in THF was added dropwise, and the mixture was warmed to room temperature overnight, and an insoluble solid cyclohexylurea appeared during the reaction.Filtration, filter cake washing, and evaporation of the filtrate. The temperature was lowered to 5 ° C, and the potassium hydroxide solution was slowly dropped, and the reaction was completed by TLC. The pH was adjusted to 1 with concentrated hydrochloric acid, and the temperature was lowered and a few pimodex seeds were added. After stirring for 2 hours, a large amount of solid was precipitated, and dried by filtration to obtain 47.2 g.
Immunostimulant used in patients with cell-mediated immunodepression.
Computed Properties
Molecular Weight:244.27
XLogP3:-0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:244.05177804
Monoisotopic Mass:244.05177804
Topological Polar Surface Area:112
Heavy Atom Count:16
Complexity:346
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
This product is a synthetic oral immunostimulant that works by stimulating and regulating cell-mediated immune responses.
Registered Holders
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Tianjin Zhongjin Pharmaceutical Co., Ltd.
Active![China]()
China
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Jilin Yimintang Pharmaceutical Co., Ltd.
Active![China]()
China
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China Resources Sanjiu (Tangshan) Pharmaceutical Co., Ltd.
Active![China]()
China
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