Immunomodulator Physical and Chemical Properties Synthesis Method Clinical Applications Pharmacokinetics Adverse Reactions Precautions Drug Interactions
ChemicalBook > CAS DataBase List > Pidotimod

Pidotimod

Immunomodulator Physical and Chemical Properties Synthesis Method Clinical Applications Pharmacokinetics Adverse Reactions Precautions Drug Interactions
Product Name
Pidotimod
CAS No.
121808-62-6
Chemical Name
Pidotimod
Synonyms
Adimod;3-L-pyroglutaMyl-L-thiazolidine-4-carboxylic acid;Axil;Onaka;pgt/1a;PoliMod;Pidomod;PIDOTIMOD;Pidomomod;Pidolimod
CBNumber
CB9745917
Molecular Formula
C9H12N2O4S
Formula Weight
244.27
MOL File
121808-62-6.mol
More
Less

Pidotimod Property

Melting point:
194-198°C (dec.)
alpha 
D25 -150° (c = 2 in 5N HCl)
Boiling point:
663.0±55.0 °C(Predicted)
Density 
1.53
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
DMSO (Slightly, Heated), Methanol (Slightly, Heated), 5N HCl (Slightly)
pka
3.03(at 25℃)
form 
powder
color 
white to beige
optical activity
[α]/D -135 to -155°, c = 1 in 6 M HCl
Merck 
14,7419
InChI
InChI=1S/C9H12N2O4S/c12-7-2-1-5(10-7)8(13)11-4-16-3-6(11)9(14)15/h5-6H,1-4H2,(H,10,12)(H,14,15)/t5-,6-/m0/s1
InChIKey
UUTKICFRNVKFRG-WDSKDSINSA-N
SMILES
S1C[C@@H](C(O)=O)N(C([C@@H]2CCC(=O)N2)=O)C1
CAS DataBase Reference
121808-62-6(CAS DataBase Reference)
More
Less

Safety

RTECS 
XJ5426675
HS Code 
2934.10.9000
Toxicity
LD50 in mice and rats (mg/kg): >4000 i.v.; >4000 i.m.; >8000 i.p.; >8000 orally (Coppi)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1335
Product name
Pidotimod
Purity
≥98% (HPLC)
Packaging
50mg
Price
$118
Updated
2024/03/01
Sigma-Aldrich
Product number
SML1335
Product name
Pidotimod
Purity
≥98% (HPLC)
Packaging
250mg
Price
$370
Updated
2024/03/01
TCI Chemical
Product number
P2147
Product name
Pidotimod
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$184
Updated
2024/03/01
TCI Chemical
Product number
P2147
Product name
Pidotimod
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$463
Updated
2024/03/01
Cayman Chemical
Product number
18725
Product name
Pidotimod
Purity
≥98%
Packaging
1g
Price
$32
Updated
2024/03/01
More
Less

Pidotimod Chemical Properties,Usage,Production

Immunomodulator

Pidotimod, chemical name (4R)-3-(5-oxo-L-prolyl)-1,3-thiazolidine-4-carboxylic acid, is a representative of synthetic immunostimulants, its structure is similar with dipeptide. Pidotimod has anti-toxicity, anti-oxidation, anti-irritation, anti-infectivity properties etc.; it can promote both innate immunity responses and adaptive immunity responses. Clinically it is mainly used to treat children with recurrent respiratory infections, chronic bronchitis, recurrent urinary tract infections, other chronic diseases caused by machine body with low immune function and to reduce the recurrence of tumor. Pidotimod can be rapidly absorbed, excreted with no accumulation in the body, with good tolerance and with no restriction on the age of patients.
Pidotimod was originally developed by Poli Industria Chimica S.p.A, Italy. It was listed in 1993 and put into clinical practice. In 2003 our country imported pidotimod oral solution. At present, there are few approved raw material manufacturers to produce pidotimod.
Immunomodulators are drugs that regulate the function of the immune system. Studies have found that some immunomodulators do not have effect on the normal immune system, but can enhance the function of the immune system and regulate the immune responses. Pidotimod is a synthetic immunosuppressive agent with dipeptide like structure, and promote both innate and adaptive immunity of the machine body. On the one hand, pidotimod can block phagocytosis of cyclophosphamide on phagocytic cells (monocyte/macrophage, neutrophils, and etc.) and the suppression effect of cyclophosphamide on the proliferation of lymphocyte, enhance the phagocytosis of phagocytic cells, increase the cell chemotaxis, enhance the sensitivity of B cells, produce more antibodies to against foreign bodies, especially increase the production of protective secretory IgA; activate the natural killer cell (NK) to regulate the balance of T cells in the immune system; stimulate the proliferation of B/T lymphocyte. On the other hand, by stimulating the production of cytokines, interleukin-2 and interferon-y, pidotimod can further promote the phagocytosis of phagocytic cells, the activation of lymphocyte and cellular immune response; correct the imbalance of CD4+/CD8+ ratio in pathological condition to regulate the body’s immune system to the steady state under normal physiological condition. Furthermore, pidotimod can enhance deficitary feedback mechanism between the hypothalamic-pituitary-adrenal (HPA) axis and interleukin-1 (IL-1). Further studies have shown that: pidotimod could reconstitute the cellularity of the pritoneum and of the spleens of mice immunodepressed by mPDN. Pidotimod stimulate production of cytokines and other effects, the mutual coordination and restraint of vary cytokines and immune cells to adjust the immune system disorder in pathological condition to the normal body immunity.

Figure 1: Function mechanism of pidotimod
①: Pidotimod activates natural killer cells.
②: Pidotimod can correct the imbalance of CD+4/Cd+8 ratio.
③: Pidotimod can increase the activity of T cells and enhance the ability of T cells to eliminate virus.
④: Pidotimod can increase the level of IL/2 and IFN-γ in the immune response, enhance the body immunity.   
⑤: Pidotimod can promote the activity of macrophage.
⑥: Pidotimod can quickly increase the chemotaxis of neutrophils.

Physical and Chemical Properties

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, almost insoluble in chloroform. Its melting point is: 192-198°C.

Synthesis Method

First L-cysteine (1) was reacted with formaldehyde to give L-thiazolidine-4-carboxylic acid (2). L-pyroglutamic acid (3) was reacted with pentachlorophenol in solvent N,N-dimethylformamide (DMF) and with the presence of a condensing agent dicyclohexylcarbodiimide (DCC) to give  L-pyroglutamic acid pentachlorophenyl ester (4). The compound (2) reacted with compound (4) in solvent DMF and with deacid agent triethylamine to give pidotimod after dehydration condensation.

Figure 2: Synthesis route of pidotimod.

Clinical Applications

Applicable to patients with low immune function. It can be used to treat recurrent respiratory tract infection; infection in ear, nose, and throat; as adjuvant therapy for urogenital system infection; to treat virus infection, malignancies, and other chronic diseases.

Pharmacokinetics

This product can be taken orally, the bioavailability is 35%. Food intake might affect the absorbance of this drug. 2 hours after oral administration the peak of pidotimod concentration in plasma is reached. The plasma protein binding rate of pidotimod is very low and it is barely metabolized in body, and almost excreted as unmodified drug in the urine. The half life of pidotimod is 4 hours.
The physical and chemical properties, synthesis method, clinical applications, adverse reactions etc. are edited by the editor Dongfang of Chemicalbook. (2016-01-13)

Adverse Reactions

Occasionally observed headaches, dizziness, nausea, vomiting, diarrhea, rash etc.
Toboos: Allergic to this product disabled.

Precautions

  • Highly susceptible individuals with caution.
  • There is no information about this drug concerning pregnant and lactating women, thus, it is not suitable for pregnant and lactating women.
  • Strictly abide by the usage and dosage in children. There are no reports on the application for children under 2 years old.
  • There are no systematic clinical data on elderly patients.
  • There are no reports on the overdose of this drug. In case of overdose, conventional methods could be used, such as vomiting, cathartic, infusion, and other drugs to promote excretion of excessive drug.

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.

Chemical Properties

White Solid

Originator

Poli (Italy)

Uses

Immunostimulant used in patients with cell-mediated immunodepression.

Uses

immune stimulant

Definition

ChEBI: (4R)-3-[oxo-[(2S)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic acid is a peptide.

brand name

Polimod; Pigitil; Axil; Onaka

Pidotimod Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Pidotimod Suppliers

Emei shan Hongsheng Pharmaceutical Co., LTD
Tel
0833-6186272、6186278、6170066 18990613291
Fax
0833-5590359
Email
sales@hongshengpharm.com
Country
China
ProdList
58
Advantage
60
Wuhan Ying Yuan Bei Biological Limited
Tel
13349903920; 13349903920
Email
1540154086@qq.com
Country
China
ProdList
2998
Advantage
58
Jinan zhongdaoanran chemical Co;Ltd
Tel
18678233466 18678233466
Email
122574856@qq.com
Country
China
ProdList
110
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chemvon Biotechnology Co., Ltd
Tel
021-50790412
Fax
+86-21-50790419
Email
info@chemvon.com
Country
China
ProdList
371
Advantage
57
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10194
Advantage
62
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
zhangsn@titansci.com
Country
China
ProdList
14113
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070 13913916777;
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
17840
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32344
Advantage
50
More
Less

View Lastest Price from Pidotimod manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Pidotimod 121808-62-6
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-11-02
Hebei Duling International Trade Co. LTD
Product
Pidotimod 121808-62-6
Price
US $50.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1
Release date
2022-09-19
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Pidotimod 121808-62-6
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
99%min HPLC;CP2015
Supply Ability
500kgs
Release date
2021-07-06

121808-62-6, PidotimodRelated Search:


  • (4R)-3-[(2S)-5-Oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
  • Adimod
  • (4S)-3-(5-Oxo-L-prolyl)thiazolidine-4-carboxylic acid
  • 3-Pyroglutamoylthiazolidine-4-carboxylic acid
  • (4R)-3-[(2S)-5-ketopyrrolidine-2-carbonyl]thiazolidine-4-carboxylic acid
  • (4R)-3-[(2S)-5-oxopyrrolidin-2-yl]carbonyl-1,3-thiazolidine-4-carboxylic acid
  • 3-L-pyroglutaMyl-L-thiazolidine-4-carboxylic acid
  • (R)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid
  • Axil
  • Onaka
  • PoliMod
  • 4-Thiazolidinecarboxylic acid, 3-[[(2S)-5-oxo-2-pyrrolidinyl]carbonyl]-, (4R)-
  • PidotiMod API
  • 3-(5-OXO-2-PYRROLIDINYL)CARBONYL-4-THIAZOLIDINECARBOXYLICACID
  • Pidotimod W S
  • (R)-3-((S)-2-oxopyrrolidine-5-carbonyl)thiazolidine-4-carboxylic acid
  • ((R)-3-[(S)-(5-oxo-2-pyrrolidinyl) carbonyl]-thiazolidine-4-carboxylic acid
  • (r-(r*,s*))-3-((5-oxo-2-pyrrolidinyl)carbonyl)-4-thiazolidinecarboxylicacid
  • (r)-3-((s)-(5-oxo-2-pyrrolidinyl)carbonyl)-thiazolidin-4-carbonsaeure
  • 4-thiazolidinecarboxylicacid,3-((5-oxo-2-pyrrolidinyl)carbonyl)-,(r-(r*,s*))
  • pgt/1a
  • (R)-3-[(S)-(5-OXO-2-PYRROLIDINYL)CARBOXYL]-THIAZOLIDINE-4-CARBOCYLIC ACID
  • PIDOTIMOD
  • (4r)-3-[[(2s)-5-oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic acid
  • (4R)-3-[oxo-[(2S)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic acid
  • Pidomomod
  • Pidotimod Pidotimod
  • Pidotimod&gt
  • Pidolimod
  • (R)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylicaci
  • top quality Pidotimod
  • (R)-3-[[(S)-5-Oxo-2-pyrrolidinyl]carbonyl]-1,3-thiazolidine-4-carboxylic Acid
  • Pidotimod USP/EP/BP
  • Pidotomod
  • Pidotimod impurities1191
  • PidotimodQ: What is Pidotimod Q: What is the CAS Number of Pidotimod Q: What is the storage condition of Pidotimod Q: What are the applications of Pidotimod
  • -5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid
  • Pidomod
  • Pidotimod IP Sec Std
  • 121808-62-6
  • 121808-92-6
  • POLIMOD
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • API
  • 121808-62-6