Pemirolast

Identification

Name
Pemirolast
Accession Number
DB00885
Description

Pemirolast potassium is a slightly yellow powder that is soluble in water. It is a mast cell stabilizer that acts as an antiallergic agent. As an ophthalmic aqueous sterile solution, pemirolast is used for the prevention of itching of the eyes caused by allergies such as hay fever, and allergic conjunctivitis. Pemirolast is potentially useful for prophylaxis of pulmonary hypersensitivity reactions to drugs such as paclitaxel.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 228.2101
Monoisotopic: 228.075958908
Chemical Formula
C10H8N6O
Synonyms
  • Pemirolast
  • Pemirolastum
External IDs
  • BMY 26517
  • DE 068
  • TBX

Pharmacology

Pharmacology
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Indication

For the prevention of itching of the eyes caused by allergies such as hay fever, and allergic conjunctivitis

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics

Pemirolast is used for the prophylactic treatment of itching of the eye associated with allergic conjunctivitis. Pemirolast potassium is a mast cell stabilizer that inhibits the in vivo Type I immediate hypersensitivity reaction. Pemirolast inhibits the antigen-induced release of inflammatory mediators (e.g., histamine, leukotriene C4, D4, E4) from human mast cells. Allergic reactions lead to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis and vasodilatation (allowing blood fluids to enter the area to cause swelling). Pemirolast is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of blood vessels to provide effective, temporary relief of watery and itchy eyes.

Mechanism of action

Pemirolast binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Pemirolast has also been observed to inhibit antigen-stimulated calcium ion influx into mast cells through the blockage of calcium channels. Pemirolast inhibits the chemotaxis of eosinophils into ocular tissue, and prevents inflammatory mediator release from human eosinophils.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic (Ophthalmic)

Route of elimination

Following topical administration, about 10-15% of the dose was excreted unchanged in the urine.

Half-life

4.5 hours (Ophthalmic)

Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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.
No interactions found.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pemirolast potassium497A17OUUE100299-08-9NMMVKSMGBDRONO-UHFFFAOYSA-N
International/Other Brands
Alegysal (Santen Pharmaceutical Co.) / Pemirox
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlamastSolution1 mg/1mLOphthalmicVistakon Pharmaceuticals2000-05-012014-11-14US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridopyrimidines. These are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridopyrimidines
Sub Class
Not Available
Direct Parent
Pyridopyrimidines
Alternative Parents
Pyrimidones / Methylpyridines / Tetrazoles / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Methylpyridine / Organic nitrogen compound / Organic oxide / Organic oxygen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
2C09NV773M
CAS number
69372-19-6
InChI Key
HIANJWSAHKJQTH-UHFFFAOYSA-N
InChI
InChI=1S/C10H8N6O/c1-6-3-2-4-16-9(6)11-5-7(10(16)17)8-12-14-15-13-8/h2-5H,1H3,(H,12,13,14,15)
IUPAC Name
9-methyl-3-(2H-1,2,3,4-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one
SMILES
CC1=CC=CN2C(=O)C(=CN=C12)C1=NNN=N1

References

Synthesis Reference

Graziano Castaldi, "Process for the preparation of high purity pemirolast." U.S. Patent US20030032805, issued February 13, 2003.

US20030032805
General References
  1. Tinkelman DG, Berkowitz RB: A pilot study of pemirolast in patients with seasonal allergic rhinitis. Ann Allergy. 1991 Feb;66(2):162-5. [PubMed:1994787]
Human Metabolome Database
HMDB0015023
KEGG Drug
D01088
PubChem Compound
57697
PubChem Substance
46509034
ChemSpider
51990
BindingDB
50323686
RxNav
19551
ChEBI
134936
ChEMBL
CHEMBL1201198
ZINC
ZINC000005783214
Therapeutic Targets Database
DAP001064
PharmGKB
PA164781018
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pemirolast
FDA label
Download (372 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentAsthma, Allergic1
1CompletedNot AvailableHealthy Volunteers1

Pharmacoeconomics

Manufacturers
  • Santen inc
Packagers
  • Santen Inc.
  • Vistakon Pharmaceuticals LLC
Dosage Forms
FormRouteStrength
SolutionOphthalmic1 mg/1mL
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Alamast 0.1% drops11.39USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5034230No1991-07-232011-07-02US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.462 mg/mLALOGPS
logP0.13ALOGPS
logP1.46ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)5.8ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.13 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity63.35 m3·mol-1ChemAxon
Polarizability21.96 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9766
Caco-2 permeable+0.6032
P-glycoprotein substrateNon-substrate0.6874
P-glycoprotein inhibitor INon-inhibitor0.7029
P-glycoprotein inhibitor IINon-inhibitor0.9336
Renal organic cation transporterNon-inhibitor0.8165
CYP450 2C9 substrateNon-substrate0.7256
CYP450 2D6 substrateNon-substrate0.8314
CYP450 3A4 substrateSubstrate0.5485
CYP450 1A2 substrateInhibitor0.874
CYP450 2C9 inhibitorNon-inhibitor0.8783
CYP450 2D6 inhibitorNon-inhibitor0.8729
CYP450 2C19 inhibitorNon-inhibitor0.8134
CYP450 3A4 inhibitorNon-inhibitor0.543
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5112
Ames testAMES toxic0.5453
CarcinogenicityNon-carcinogens0.8916
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.3619 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9391
hERG inhibition (predictor II)Non-inhibitor0.8932
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Drug created on June 13, 2005 13:24 / Updated on April 03, 2021 09:40