Pidotimod
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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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Recurrent upper respiratory tract infection •••••••••••• •••••••••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Pidotimod which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Pidotimod which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Pidotimod which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Pidotimod which could result in a higher serum level. Acetazolamide Acetazolamide 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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
- 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]
- 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]
- 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]
- 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]
- AIFA: Pidotimod Summary of Product Characteristics [Link]
- Vademecum: Broncotimod (pidotimod) for oral use [Link]
- External Links
- KEGG Drug
- D07261
- PubChem Compound
- 65944
- PubChem Substance
- 310265231
- ChemSpider
- 59348
- 40450
- ChEBI
- 94618
- ChEMBL
- CHEMBL1488165
- ZINC
- ZINC000003781245
- Wikipedia
- Pidotimod
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Recurrent Respiratory Tract Infections 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral 11.428 g Tablet Oral 400 mg Solution Oral 5.714 g Solution Oral 800 mg Solution Rectal 400.000 mg Granule, for solution Oral Injection, solution Solution Oral Tablet Oral Solution Oral 400 mg Solution Oral 5.71 g Solution Oral 800.00 mg Granule, for solution Oral 800 MG Solution Oral 200 MG Solution Oral 400.000 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 19.5 mg/mL ALOGPS logP -1.1 ALOGPS logP -1.3 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 3.57 Chemaxon pKa (Strongest Basic) -2.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 86.71 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 55.83 m3·mol-1 Chemaxon Polarizability 22.47 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-01qa-3930000000-9420ca3046023708e0c2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1590000000-54cbd9cd10b6669a6878 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-9620000000-26696fda8e868b2a6a4d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001c-7920000000-9f2a788c6b44377bc5d4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-015a-9400000000-377998e9ca171ee8e15a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9400000000-52aa1cbd547c15a5bddf Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.7723835 predictedDarkChem Lite v0.1.0 [M-H]- 147.5661 predictedDeepCCS 1.0 (2019) [M+H]+ 157.5742835 predictedDarkChem Lite v0.1.0 [M+H]+ 149.88237 predictedDeepCCS 1.0 (2019) [M+Na]+ 157.9330835 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.79488 predictedDeepCCS 1.0 (2019)
Drug created at February 09, 2016 16:16 / Updated at April 30, 2021 13:08