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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:49 UTC
HMDB IDHMDB0015023
Secondary Accession Numbers
  • HMDB15023
Metabolite Identification
Common NamePemirolast
DescriptionPemirolast, also known as pemirox or alamast, belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines 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. Pemirolast (INN) is a mast cell stabilizer used as an anti-allergic drug therapy. Pemirolast is a drug which is used for the prevention of itching of the eyes caused by allergies such as hay fever, and allergic conjunctivitis. Pemirolast is an extremely weak basic (essentially neutral) compound (based on its pKa). It is marketed under the tradenames Alegysal and Alamast. It has also been studied for the treatment of asthma. Clinical trials studying treatments for allergic conjunctivitis have found that an ophthalmic solution containing levocabastine with pemirolast potassium may be more effective in alleviating symptoms than levocabastine alone.
Structure
Data?1582753249
Synonyms
ValueSource
PemiroxKegg
Pemirolast potassiumHMDB
Pemiroplast potassiumHMDB
Pemirolast potassium saltHMDB
AlamastHMDB
9-TBXHMDB
9-Methyl-3-(1H-tetrazol-5-yl)-4H-pyrido(1,2-a)pyrimidin-4-oneHMDB
Chemical FormulaC10H8N6O
Average Molecular Weight228.2101
Monoisotopic Molecular Weight228.075958908
IUPAC Name9-methyl-3-(2H-1,2,3,4-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one
Traditional Namepemirolast
CAS Registry Number100299-08-9
SMILES
CC1=CC=CN2C(=O)C(=CN=C12)C1=NNN=N1
InChI Identifier
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)
InChI KeyHIANJWSAHKJQTH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridopyrimidines
Sub ClassNot Available
Direct ParentPyridopyrimidines
Alternative Parents
Substituents
  • Pyridopyrimidine
  • Pyrimidone
  • Methylpyridine
  • Pyridine
  • Pyrimidine
  • Azole
  • Tetrazole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.46 g/LNot Available
LogP0Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity63.35 m³·mol⁻¹ChemAxon
Polarizability21.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available152.1831661259
DarkChem[M-H]-PredictedNot Available151.29231661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kbf-3950000000-c347e87f936efcb3141d2017-08-28View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-f8717a6e5c5265d8a9102017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-9fbba7ed158f319c9e7e2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07g0-8980000000-fc446ac2f3c1579f18b22017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-5e06e7caaa1121a311132017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-6ae73c19cd8dada68ee22017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1590000000-bfb953dc73e97398b0662017-07-26View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00885 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00885 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00885
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID51990
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPemirolast
METLIN IDNot Available
PubChem Compound57697
PDB IDNot Available
ChEBI ID775149
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Yanni JM, Miller ST, Gamache DA, Spellman JM, Xu S, Sharif NA: Comparative effects of topical ocular anti-allergy drugs on human conjunctival mast cells. Ann Allergy Asthma Immunol. 1997 Dec;79(6):541-5. [PubMed:9433371 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Kobayashi K, Hiroi J, Kishi S, Sawase K, Hirayama Y, Chihara S, Imai T, Shigi Y, Shimomura K, Kohsaka M: Effects of quinotolast, a new orally active antiallergic drug, on experimental allergic models. Jpn J Pharmacol. 1993 Sep;63(1):73-81. [PubMed:7505860 ]