Pidotimod

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Pidotimod
Accession Number
DB11364
Type
Small Molecule
Groups
Experimental
Description

Pidotimod is a synthetic dipeptide with immunomodulatory properties.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Pilimod
Categories
UNII
785363R681
CAS number
121808-62-6
Weight
Average: 244.27
Monoisotopic: 244.051778048
Chemical Formula
C9H12N2O4S
InChI Key
UUTKICFRNVKFRG-WDSKDSINSA-N
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
IUPAC Name
(4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
SMILES
OC(=O)[C@@H]1CSCN1C(=O)[C@@H]1CCC(=O)N1

Pharmacology

Indication

For use as immunostimulant therapy for treatment of cell-mediated immunosuppression with respiratory or urinary infections [5].

Pharmacodynamics

Pidotimod modulates the immune system to induce an immune response against bacterial or viral pathogens [4]

Mechanism of action

Pidotimod inhibits tumor necrosis factor α (TNF-α) induced increases in extracellular signal-related kinase (ERK) phosphorylation [2]. 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 [4]. 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 [3, 4]. Lastly, pidotimod appears to increase antigen-specific antibody titer and cytotoxic response with antigen exposure [4]. The precise mechanism and timeline of events leading to these effects is unknown.

Absorption

Bioavailability of 45% [5].

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

95% of intravenous dose is eliminated in the urine as the parent compound [5].

Half life

Half life of 4 h [5].

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Pidotimod which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Pidotimod which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Pidotimod which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Ferrario BE, Garuti S, Braido F, Canonica GW: Pidotimod: the state of art. Clin Mol Allergy. 2015 May 21;13(1):8. doi: 10.1186/s12948-015-0012-1. eCollection 2015. [PubMed:25999796]
  2. Carta S, Silvestri M, Rossi GA: Modulation of airway epithelial cell functions by Pidotimod: NF-kB cytoplasmatic expression and its nuclear translocation are associated with an increased TLR-2 expression. Ital J Pediatr. 2013 May 10;39:29. doi: 10.1186/1824-7288-39-29. [PubMed:23663325]
  3. Kidd P: Th1/Th2 balance: the hypothesis, its limitations, and implications for health and disease. Altern Med Rev. 2003 Aug;8(3):223-46. [PubMed:12946237]
  4. Giagulli C, Noerder M, Avolio M, Becker PD, Fiorentini S, Guzman CA, Caruso A: Pidotimod promotes functional maturation of dendritic cells and displays adjuvant properties at the nasal mucosa level. Int Immunopharmacol. 2009 Nov;9(12):1366-73. doi: 10.1016/j.intimp.2009.08.010. Epub 2009 Aug 25. [PubMed:19712757]
  5. AIFA: Pidotimod Summary of Product Characteristics [Link]
External Links
KEGG Drug
D07261
PubChem Compound
65944
PubChem Substance
310265231
ChemSpider
59348
ChEBI
94618
ChEMBL
CHEMBL1488165
Wikipedia
Pidotimod
ATC Codes
L03AX05 — Pidotimod

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility19.5 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.3ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.83 m3·mol-1ChemAxon
Polarizability22.47 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
N-acyl-L-alpha-amino acids / Alpha amino acid amides / Pyrrolidinecarboxamides / Pyrrolidine-2-ones / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams / Thiohemiaminal derivatives / Azacyclic compounds
show 8 more
Substituents
Alpha-dipeptide / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Pyrrolidone / 2-pyrrolidone / Pyrrolidine / Thiazolidine
show 20 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on February 09, 2016 09:16 / Updated on November 02, 2018 07:09