Pidotimod

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

Identification

Summary

Pidotimod is a synthetic agent with immunomodulatory properties used in patients with documented cell-mediated immunosuppression to stimulate their immunity during lung and urinary tract infections.

Generic Name
Pidotimod
DrugBank Accession Number
DB11364
Background

Pidotimod is a synthetic dipeptide with immunomodulatory properties.1

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 244.27
Monoisotopic: 244.051778048
Chemical Formula
C9H12N2O4S
Synonyms
  • Pidotimod

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofRecurrent upper respiratory tract infection••••••••••••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir 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.
AcetazolamideAcetazolamide may increase the excretion rate of Pidotimod which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
Not Available

Products

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International/Other Brands
Pilimod

Categories

ATC Codes
L03AX05 — Pidotimod
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-pyrrolidone / Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid / Dialkylthioether
show 20 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
785363R681
CAS number
121808-62-6
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. AIFA: Pidotimod Summary of Product Characteristics [Link]
  6. Vademecum: Broncotimod (pidotimod) for oral use [Link]
KEGG Drug
D07261
PubChem Compound
65944
PubChem Substance
310265231
ChemSpider
59348
RxNav
40450
ChEBI
94618
ChEMBL
CHEMBL1488165
ZINC
ZINC000003781245
Wikipedia
Pidotimod

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedTreatmentRecurrent Respiratory Tract Infections1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral11.428 g
TabletOral400 mg
SolutionOral5.714 g
SolutionOral800 mg
SolutionRectal400.000 mg
Granule, for solutionOral
Injection, solution
SolutionOral
TabletOral
SolutionOral400 mg
SolutionOral5.71 g
Granule, for solutionOral800 MG
SolutionOral200 MG
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/MSsplash10-01qa-3930000000-9420ca3046023708e0c2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-1590000000-54cbd9cd10b6669a6878
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9620000000-26696fda8e868b2a6a4d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001c-7920000000-9f2a788c6b44377bc5d4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-015a-9400000000-377998e9ca171ee8e15a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9400000000-52aa1cbd547c15a5bddf
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.7723835
predicted
DarkChem Lite v0.1.0
[M-H]-147.5661
predicted
DeepCCS 1.0 (2019)
[M+H]+157.5742835
predicted
DarkChem Lite v0.1.0
[M+H]+149.88237
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.9330835
predicted
DarkChem Lite v0.1.0
[M+Na]+155.79488
predicted
DeepCCS 1.0 (2019)

Drug created at February 09, 2016 16:16 / Updated at April 30, 2021 13:08