Identification

Generic Name
Picolinic acid
DrugBank Accession Number
DB05483
Background

PCL-016 or Picolinic acid drug substance is a pyridine carboxylate metabolite of tryptophan. It acts as an anti-infective and immunomodulator and is produced in approximately 25-50 mg quantities by the body on a daily basis through the breakdown of tryptophan. PCL-016 plays a key role in zinc transport. As a therapeutic agent, the molecule works by binding to zinc finger proteins (ZFPs) in a way that changes their structures and disrupts zinc binding, inhibiting function. ZFPs are involved in viral replication and packaging as well as normal cell homeostatic functions. Picolinic acid has been shown to be an anti-viral in vitro and in vivo, and sometimes works in conjunction with other cytokines such as interferon gamma to affect immune responses. Acne vulgaris, herpes and other viral infections therefore pose potential therapeutic targets of PCL-016.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 123.111
Monoisotopic: 123.032028405
Chemical Formula
C6H5NO2
Synonyms
  • 2-Carboxypyridine
  • Acide picolique
External IDs
  • PCL-016

Pharmacology

Indication

Investigated for use/treatment in acne, herpes labialis infections (cold sores), and venereal disease.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

PCL-016 or Picolinic acid drug substance is a pyridine carboxylate metabolite of tryptophan. It acts as an anti-infective and immunomodulator through its role in zinc transport. ZFPs are involved in viral replication and packaging as well as normal cell homeostatic functions. Picolinic acid has been shown to be an anti-viral in vitro and in vivo.

Mechanism of action

As a therapeutic agent, the molecule works by binding to zinc finger proteins (ZFPs) in a way that changes their structures and disrupts zinc binding, inhibiting function.

TargetActionsOrganism
UE3 ubiquitin-protein ligase UBR4Not AvailableHumans
UZinc finger Y-chromosomal proteinNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
QZV2W997JQ
CAS number
98-98-6
InChI Key
SIOXPEMLGUPBBT-UHFFFAOYSA-N
InChI
InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
IUPAC Name
pyridine-2-carboxylic acid
SMILES
OC(=O)C1=CC=CC=N1

References

General References
  1. Heffernan MP, Nelson MM, Anadkat MJ: A pilot study of the safety and efficacy of picolinic acid gel in the treatment of acne vulgaris. Br J Dermatol. 2007 Mar;156(3):548-52. [Article]
Human Metabolome Database
HMDB0002243
KEGG Compound
C10164
PubChem Substance
347910165
ChemSpider
993
BindingDB
50000407
RxNav
33684
ChEBI
28747
ChEMBL
CHEMBL72628
ZINC
ZINC000000039905
PDBe Ligand
6PC
Wikipedia
Picolinic_acid
PDB Entries
2oln / 2olo / 3hzl / 4hsj / 4m1e / 4yic / 4yzz / 5gja / 5wol / 6o4d
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility61.1 mg/mLALOGPS
logP0.22ALOGPS
logP-0.65Chemaxon
logS-0.3ALOGPS
pKa (Strongest Acidic)1Chemaxon
pKa (Strongest Basic)5.52Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area50.19 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity30.79 m3·mol-1Chemaxon
Polarizability11.38 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
E3 ubiquitin-protein ligase which is a component of the N-end rule pathway. Recognizes and binds to proteins bearing specific N-terminal residues that are destabilizing according to the N-end rule,...
Gene Name
UBR4
Uniprot ID
Q5T4S7
Uniprot Name
E3 ubiquitin-protein ligase UBR4
Molecular Weight
573835.26 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Probable transcriptional activator. Binds to the consensus sequence 5'-AGGCCY-3'.
Gene Name
ZFY
Uniprot ID
P08048
Uniprot Name
Zinc finger Y-chromosomal protein
Molecular Weight
90504.29 Da

Drug created at November 18, 2007 18:25 / Updated at August 26, 2022 21:50