Pemirolast

HCID 57697CAS 100299-08-9

Grundinformationen

Standard-SMILES
Cc1cccn2c(=O)c(-c3nn[nH]n3)cnc12
InChIKey
HIANJWSAHKJQTH-UHFFFAOYSA-N
Summenformel
C10H8N6O
Durchschnittliche Molmasse
228,21 g/mol
Monoisotopische Masse
228,07595888

Überblick

Pemirolast is a pyridopyrimidine.

Namen und Bezeichner

Bevorzugter Name
Pemirolast
IUPAC
9-methyl-3-(2H-tetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one
Englischer Name
PEMIROLAST
Summenformel
C10H8N6O
Molmasse
228.21

Namen und Synonyme

Pemirolast69372-19-6PemirolastumPemiroxPermirolast2C09NV773M9-Methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-oneDTXSID1048338BMY-265174H-Pyrido(1,2-a)pyrimidin-4-one, 9-methyl-3-(1H-tetrazol-5-yl)-9-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido(1,2-a)pyrimidin-4-one9-methyl-3-(2H-1,2,3,4-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one
Weitere Namen anzeigen
4H-Pyrido[1,2-a]pyrimidin-4-one,9-methyl-3-(2H-tetrazol-5-yl)-Hsdb 7291PemilastonUnii-2C09nv773mPemiroplastpotassiumPEMIROLAST USP/EP/BP
9-methyl-3-(2H-1,2,3,4-tetrazol-5-yl)-4H-pyrido(1,2-a)pyrimidin-4-oneRefChem:859193DTXCID6028313Pemirolast [INN]Pemirolastum [INN-Latin]9-methyl-3-(2H-tetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-onePemirolast (INN)9-Methyl-3-(2H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one

Datenbank-Bezeichner

CAS
100299-08-9、69372-19-6
PubChem CID
57697
DTXSID
DTXSID1048338
ChEMBL
CHEMBL1201198
ChEBI
CHEBI:134936
UNII
2C09NV773M
Nikkaji
J227.675E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,3
Polarare Oberfläche (TPSA)
87,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
1
Schwere Atome
17

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogPlog Kow = 0.36 /Estimated/
Color/FormCrystals from dimethylformamide
Solubility · 2 Einträge

In water, 1.9X10+4 mg/L at 25 °C /Estimated/

4.62e-01 g/L

Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Allergic Agents; Histamine Antagonists
Melting Point310-311 °C (decomposes)

Physikochemische Eigenschaften

Schmelzpunkt
310 · 310-311° (dec)
Siedepunkt
454.8 · 454.8±55.0 °C(Predicted)
Dichte
1 · 1+-.0.1 g/cm3(Predicted)
pka
4 · 4.00±0.50(Predicted)
CAS Datenbank
69372 · 69372-19-6(CAS DataBase Reference)

Sicherheit und Regulatorisches

Gefahrenhinweise

FDA Requirements · 1 Eintrag

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pemirolast potassium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Pemirolast Potassium/

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Toxikologische Informationen

Interactions · 1 Eintrag

The effect of a newly developed anti-allergic drug, pemirolast potassium (TBX), on the pharmacokinetics and metabolism of theophylline was investigated under steady-state conditions in seven healthy male volunteers. A sustained-release theophylline formulation (100 mg twice daily at 12 h intervals) was given as monotherapy and coadministered with TBX (10 mg twice daily at 12 h). Plasma concentration-time curves and the urinary excretion of theophylline and its major metabolites after administration of theophylline alone and after coadministration with TBX were compared. No significant adverse effects from this study were observed. There were no significant differences in the total body clearance, renal clearance and maximum concentration of theophylline between the two treatments, although coadministration of TBX significantly delayed the time to reach maximum concentration of theophylline. In the case of urinary excretion, no significant changes in the fraction of urinary excretion of theophylline and its metabolites were observed. These results indicate that TBX has little or no effect on the pharmacokinetics and metabolism of theophylline and suggest that TBX is safe for asthma patients receiving theophylline therapy for treatment of chronic obstructive airway diseases.

Milk ConcentrationsPemirolast potassium is excreted in the milk of lactating rats at concentrations higher than those in plasma. It is not known whether pemirolast potassium is excreted in human milk. /Pemirolast potassium/
Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Pemirolast potassium was not teratogenic in rabbits given oral doses up to 150 mg/kg ... /Pemirolast potassium/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Pemirolast potassium caused an increased incidence of thymic remnant in the neck, interventricular septal defect, fetuses with wavy rib, splitting of thoracic vertebral body, and reduced numbers of ossified sternebrae, sacral and caudal vertebrae, and metatarsi when rats were given oral doses >/= 250 mg/kg during organogenesis. Increased incidence of dilation of renal pelvis/ureter in the fetuses and neonates was also noted when rats were given an oral dose of 400 mg/kg pemirolast potassium. /Pemirolast potassium/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Pemirolast potassium produced increased pre- and post-implantation losses, reduced embryo/fetal and neonatal survival, decreased neonatal body weight, and delayed neonatal development in rats receiving an oral dose at 400 mg/kg. Pemirolast potassium also caused a reduction in the number of corpus lutea, the number of implantations, and number of live fetuses in the F1 generation in rats when F0 dams were given oral doses >/= 250 mg/kg during late gestation and the lactation period. /Pemirolast potassium/

/GENOTOXICITY/ Pemirolast potassium was not mutagenic or clastogenic when tested in a series of bacterial and mammalian tests for gene mutation and chromosomal injury in vitro nor was it clastogenic when tested in vivo in rats. /Pemirolast potassium/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Pemirolast potassium had no effect on mating and fertility in rats at oral doses up to 250 mg/kg ... A reduced fertility and pregnancy index occurred in the F 1 generation when F 0 dams were treated with 400 mg/kg pemirolast potassium during late pregnancy and lactation period. /Pemirolast potassium/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Regulatorische Informationen

FDA Requirements · 1 Eintrag

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pemirolast potassium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Pemirolast Potassium/

Sicherheitsdaten

Giftige Stoffe Daten
69372-19-6(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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 <i>in vivo</i> 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 H<sub>1</sub>-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 H<sub>1</sub>-receptor sites on effector cells of blood vessels to provide effective, temporary relief of watery and itchy eyes.

Mechanism of Action · 3 Einträge

Pemirolast binds to the histamine H<sub>1</sub> 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.

To determine whether pemirolast, a new antiallergic drug, inhibits the activation of eosinophils, we investigated the effect of pemirolast on the release of leukotriene C4 (LTC4) and eosinophil cationic protein (ECP) from human eosinophils. Calcium ionophore A23187 caused both LTC4 and ECP release from human eosinophils, whereas PAF and FMLP induced only ECP release from the eosinophils. Pemirolast (10(-6) to 10(-3) M) inhibited A23187-induced LTC4 release from the eosinophils in a dose-dependent fashion with 77% inhibition at 10(-3) M. Pemirolast (10(-5) to 10(-3) M) inhibited A23187-induced ECP release from the eosinophils in a dose-dependent fashion with 42% inhibition at 10(-3) M. Pemirolast (10(-4) and 10(-3) M) also inhibited PAF-induced and FMLP-induced ECP release from the eosinophils. We conclude that pemirolast prevents the activation of human eosinophils to inhibit LTC4 and ECP release. These results suggest that pemirolast might be useful in controlling allergic diseases by inhibiting eosinophil activation. /Pemirolast potassium/

Pemirolast is a mast cell stabilizer and inhibits the release of inflammatory mediators from cells associated with Type I immediate hypersensitivity reactions. The drug has been observed to block antigen-stimulated calcium ion influx into mast cells. Pemirolast also inhibits the chemotaxis of eosinophils into ocular tissue, and prevents inflammatory mediator release from human eosinophils. /Pemirolast potassium/

Biological Half-Life · 2 Einträge

4.5 hours (Ophthalmic)

...Mean half-life was 4.5 +/- 0.2 hours. /Pemirolast potassium/

Metabolism/MetabolitesHepatic (Ophthalmic)
FDA Pharmacological Classification · 5 Einträge

2C09NV773M

PEMIROLAST

Physiologic Effects [PE] - Decreased Histamine Release

Established Pharmacologic Class [EPC] - Mast Cell Stabilizer

Pemirolast is a Mast Cell Stabilizer. The physiologic effect of pemirolast is by means of Decreased Histamine Release.

MeSH Pharmacological ClassificationDrugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only.

Verwendung und Herstellung

UsesMedication: antiallergic
Formulations/PreparationsOphthalmic: Solution 0.1% Alamast (with lauralkonium chloride), (Santen)
General Manufacturing Information · 2 Einträge

Preparation: P.F. Juby, US 4122274 (1978 to Bristol-Myers)

Information available in 2004 indicated that Pemirolast potassium was used in the manufacture of pharmaceutical preparations in the following countries: Japan, USA (1,2)

Anwendungen

VerwendenAnti-allergic; inhibitor (mediator release).

Anbieter23 Anbieter

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Hangzhou Sage Chemical Co., Ltd.+86057186818502 13588463833 · [email protected]

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