Basic information
- CAS
121808-62-6- Standard SMILES
O=C1CC[C@@H](C(=O)N2CSC[C@H]2C(=O)O)N1- InChIKey
UUTKICFRNVKFRG-WDSKDSINSA-N- Molecular formula
- C9H12N2O4S
- Average molar mass
- 244.27 g/mol
- Monoisotopic mass
- 244.05177804
Overview
(4R)-3-[oxo-[(2S)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic acid is a peptide.
Names & identifiers
- Preferred name
- Pidotimod
- IUPAC
- (4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
- English name
- Pidotimod
- Molecular formula
- C9H12N2O4S
- Molecular weight
- 244.27
Names & synonyms
Pidotimod121808-62-6PidotimodumPilimodDTXSID0046199NSC-759841(4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acidDTXCID8026199785363R681Pgt-1A(4R)-3-((2S)-5-oxopyrrolidine-2-carbonyl)-1,3-thiazolidine-4-carboxylic acidRefChem:174211
Show more names
AdimodPidomod3-L-pyroglutaMyl-L-thiazolidine-4-carboxylic acidAxilOnakapiduomodPidomomod
3-((5-Oxo-2-pyrrolidinyl)carbonyl)-4-thiazolidinecarboxylic acidL03AX053-Pyroglutamylthiazolidine-4-carboxylic acidPidotomod(R)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acidPGT/1APolimodPidotimod [INN]
Database identifiers
- CAS
121808-62-6- PubChem CID
- 65944
- DTXSID
DTXSID0046199- ChEMBL
CHEMBL1488165- ChEBI
CHEBI:94618- UNII
- 785363R681
- EC Number
- 629-822-3
- Nikkaji
- J623.605G
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 346
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility>36.6 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- Melting point
- 194 · 194-198°C (dec.)
- alpha
- 25 · D25 -150° (c = 2 in 5N HCl)
- Boiling point
- 663 · 663.0±55.0 °C(Predicted)
- Density
- 1.53 · 1.53
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- 5 N · DMSO (Slightly, Heated), Methanol (Slightly, Heated), 5N HCl (Slightly)
- pka
- 3.03 · 3.03(at 25℃)
- form
- powder
- color
- white to beige
- optical activity
- -135 to · [α]/D -135 to -155°, c = 1 in 6 M HCl
- Water Solubility
- 2 O: · H2O: 2mg/mL, clear (warmed)
- Merck
- 14 · 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 · 121808-62-6(CAS DataBase Reference)
- FDA UNII
- 785363 R681 · 785363R681
- ATC code
- 3 AX05 · L03AX05
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- WGK Germany
- 3 · WGK 3
- RTECS
- 5426675 · XJ5426675
- HS Code
- 2934.1 · 2934.10.9000
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 in · LD50 in mice and rats (mg/kg): >4000 i.v.; >4000 i.m.; >8000 i.p.; >8000 orally (Coppi)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- WGK 3
- 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)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
PharmacodynamicsPidotimod modulates the immune system to induce an immune response against bacterial or viral pathogens
Mechanism of Action
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.
Biological Half-LifeHalf life of 4 h.
MeSH Pharmacological Classification
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.
Biologically active substances whose activities affect or play a role in the functioning of the immune system.
Absorption, Distribution and Excretion
Bioavailability of 45%.
95% of intravenous dose is eliminated in the urine as the parent compound.
Applications
DescriptionPidotimod, 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.
UsesImmunostimulant used in patients with cell-mediated immunodepression.
Usesimmune stimulant
Upstream & downstream products
Upstream raw materials
Suppliers100 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
北京迈索化学技术有限公司010-57862036 18811083386 · [email protected]
天津宜维盛科技有限公司+86 (22) 2989-4595 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
上海微巨实业有限公司021-34628682 18918069061 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
济南健丰化工有限公司0531-88110457; 18954159893 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海遐瑞医药科技有限公司+86 21 61551611
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
峨眉山鸿森生物医药股份有限公司0833-6186278 19162541913 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
武汉五方伟业药化有限公司027-85838075
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
四川美域高生物医药科技有限公司028-86136736 19130631884 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
潍坊鲁泽新材料有限公司0536-7971999 17176128999 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
上海拓目化工有限公司13391076197 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
成都百事兴科技实业有限公司18111554528 19544347486 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试（上海）科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
重庆朗天制药有限公司023-68980308 · [email protected]
铜陵恒优生物科技有限公司021-50426030 13856289449;13124863828 · [email protected]
南京熙泽医药科技有限公司025-66023220 15250997978 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
南京伶亚生物医药科技有限公司18068075658 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
南京励合化学新材料有限公司025-87787262
上海皓之翔生物科技有限公司（原上海拓青化工有限公司）526763801 13301653310 · [email protected]
斯派螺（武汉）药物研发有限公司[email protected]
珠海柏瑞医药科技有限公司0756-8699456 13427714006 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18049756717 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
苏州科源医药科技有限公司13656237714 13656237714 · [email protected]
济南元泰化工有限公司0531-69959492 18366108822 · [email protected]
Additional notes
DefinitionChEBI: (4R)-3-[oxo-[(2S)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic acid is a peptide.
Related reactions
0 records
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Compound notes
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