Basic information
- CAS
103177-37-3- Standard SMILES
O=C(Nc1cccc2c(=O)cc(-c3nn[nH]n3)oc12)c1ccc(OCCCCc2ccccc2)cc1- InChIKey
NBQKINXMPLXUET-UHFFFAOYSA-N- Molecular formula
- C27H23N5O4
- Average molar mass
- 481.5 g/mol
- Monoisotopic mass
- 481.17500423
Overview
N-[4-oxo-2-(2H-tetrazol-5-yl)-1-benzopyran-8-yl]-4-(4-phenylbutoxy)benzamide is a member of chromones.
Names & identifiers
- Preferred name
- Pranlukast
- IUPAC
- N-[4-oxo-2-(2H-tetrazol-5-yl)chromen-8-yl]-4-(4-phenylbutoxy)benzamide
- English name
- Pranlukast
- Molecular formula
- C27H23N5O4
- Molecular weight
- 481.5
Names & synonyms
Pranlukast103177-37-3AzlaireOno-1078ONO 1078Ono-RS-411N-[4-oxo-2-(2H-tetrazol-5-yl)chromen-8-yl]-4-(4-phenylbutoxy)benzamideCCN 00401RS 411SB 205312pranlukastumONO-RS 411
Show more names
Ononrs411Ultairono1078PrenastPrandtlPranlukasemihydrate
DTXSID3043782CCN-00401RS-411SB-205312TB8Z891092DTXCID1023782N-(4-Oxo-2-(1H-tetrazol-5-yl)-4H-1-benzopyran-8-yl)-p-(4-phenylbutoxy)benzamide8-(4 (4-phenylbutoxy)benzoyl)amino-2-(tetrazol-5'-yl)-4-oxo-4H-1-benzopyran
Database identifiers
- CAS
103177-37-3- PubChem CID
- 4887
- DTXSID
DTXSID3043782- ChEMBL
CHEMBL11350、CHEMBL21333- ChEBI
CHEBI:94810- UNII
- TB8Z891092
- EC Number
- 808-178-9
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 9
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 778
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 236 · 236-238°C
- Density
- 1.374 · 1.374±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- Soluble in DMSO (up to 25 mg/ml)
- pka
- 4.96 · 4.96±0.10(Predicted)
- form
- solid
- color
- White
- Merck
- 14 · 14,7710
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- InChIKey
- NBQKINXMPLXUET-UHFFFAOYSA-N
- SMILES
- C(NC1=C2OC(C3=NNN=N3)=CC(=O)C2=CC=C1)(=O)C1=CC=C(OCCCCC2=CC=CC=C2)C=C1
- CAS DataBase Reference
- 103177 · 103177-37-3(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Pranlukast
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- rtecs
- CV5647500
- hs_code
- 2934.99.4400
- Toxicity
- LD50 in male mice (mg/kg): >1000 i.v. (Toda)
- risk_code
- 11-34
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- F,C
- safety_code
- 16-26-36/37/39-45
- Hazard statements
- H315-H319-H413
- Precautionary statements
- P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
PharmacodynamicsPranlukast is a cysteinyl leukotriene receptor-1 antagonist.
Mechanism of Action
Pranlukast selectively antagonizes leukotriene D<sub>4</sub> (LTD<sub>4</sub>) at the cysteinyl leukotriene receptor, CysLT<sub>1</sub>, in the human airway. Pranlukast inhibits the actions of LTD<sub>4</sub> at the CysLT<sub>1</sub> receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.
Metabolism/MetabolitesHepatic
MeSH Pharmacological Classification
Drugs that are used to treat asthma.
A class of drugs designed to prevent leukotriene synthesis or activity by blocking binding at the receptor level.
Applications
DescriptionPranlukast, a novel chromone derivative, was introduced in Japan for the treatment of bronchial asthma and allergic diseases. Pranlukast is a highly potent, selective and competitive antagonist of peptidoleukotrienes with high affinity for the LTD4 receptor. In patients with bronchial asthma, pranlukast was reported to induce significant improvement in both immediate and late asthmatic response induced by antigen. Pranlukast is also being evaluated clinically for the treatment of perennial allergic rhinitis, pediatric asthma, and cutaneous pruritus in dialysis patients. The therapeutic potential of pranlukast in managing irritable bowel syndrome has been suggested.
UsesA potent, selective and orally active CysLT receptor antagonist. Leukotriene antagonist. Used as an antiasthmatic
Usesantiasthmatic;leukotriene receptor-1 antagonist
UsesLabeled Pranlukast, intended for use as an internal standard for the quantification of Pranlukast by GC- or LC-mass spectrometry.
Related reactions
1 records
Compound notes
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