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Details

Stereochemistry ACHIRAL
Molecular Formula C27H23N5O4
Molecular Weight 481.5026
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRANLUKAST

SMILES

O=C(NC1=CC=CC2=C1OC(=CC2=O)C3=NN=NN3)C4=CC=C(OCCCCC5=CC=CC=C5)C=C4

InChI

InChIKey=NBQKINXMPLXUET-UHFFFAOYSA-N
InChI=1S/C27H23N5O4/c33-23-17-24(26-29-31-32-30-26)36-25-21(23)10-6-11-22(25)28-27(34)19-12-14-20(15-13-19)35-16-5-4-9-18-7-2-1-3-8-18/h1-3,6-8,10-15,17H,4-5,9,16H2,(H,28,34)(H,29,30,31,32)

HIDE SMILES / InChI

Molecular Formula C27H23N5O4
Molecular Weight 481.5026
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.e-search.ne.jp/~jpr/PDF/ONO04.PDF

Pranlukast is an antagonist of cysteinyl leukotriene receptor-1 antagonist. It is marketed in Japan by Ono Pharmaceuticals under trademark ONON for the treatment of bronchial asthma and allergic rhinitis as capsules and dry syrup for pediatric use.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
23.0 nM [IC50]
3620.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ONON

Approved Use

ONON capsules are indicated for treatment of bronchial asthma
Primary
ONON

Approved Use

ONON capsules are indicated for treatment of allergic rhinitis
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cysteinyl leukotrienes induce P-selectin expression in human endothelial cells via a non-CysLT1 receptor-mediated mechanism.
1997 May
Therapeutic effect of pranlukast, a selective cysteinyl leukotriene receptor antagonist, on bronchial asthma.
1997 Sep
Development of 2,2-dimethylchromanol cysteinyl LT1 receptor antagonists.
1998 Dec 15
Effects of the cysteinyl leukotriene receptor antagonists pranlukast and zafirlukast on tracheal mucus secretion in ovalbumin-sensitized guinea-pigs in vitro.
1998 Jun
Pharmacology of leukotriene receptor antagonists.
1998 Jun
Inhibition of 5-lipoxygenase diminishes neurally evoked tachykinergic contraction of guinea pig isolated airway.
1998 May
Leukotriene C4 is a tight-binding inhibitor of microsomal glutathione transferase-1. Effects of leukotriene pathway modifiers.
1999 Jan 22
Characterization of the human cysteinyl leukotriene CysLT1 receptor.
1999 Jun 24
Churg-Strauss syndrome after corticosteroid withdrawal in an asthmatic patient treated with pranlukast.
1999 Mar
Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor.
1999 Sep
Discovery of CP-199,330 and CP-199,331: two potent and orally efficacious cysteinyl LT1 receptor antagonists devoid of liver toxicity.
1999 Sep 20
A kinetic binding study to evaluate the pharmacological profile of a specific leukotriene C(4) binding site not coupled to contraction in human lung parenchyma.
2000 Jun
Characterization of the human cysteinyl leukotriene 2 receptor.
2000 Sep 29
Effects of pranlukast, a leukotriene receptor antagonist, on airway inflammation in mild asthmatics.
2001 Feb
Churg-Strauss syndrome after reduction of inhaled corticosteroid in a patient treated with pranlukast for asthma.
2001 May
Cysteinyl leukotriene receptor 1 is involved in N-methyl-D-aspartate-mediated neuronal injury in mice.
2006 Dec
Over-expression of the LTC4 synthase gene in mice reproduces human aspirin-induced asthma.
2011 Aug
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
Patents

Sample Use Guides

The usual adult dosage for oral use is 450 mg of pranlukast hydrate (4 capsules) daily in two divided doses after each meal in the morning and evening. The dosage may be adjusted according to the patient's age and symptoms.
Route of Administration: Oral
The activity of pranlukast was measured using calcium mobilization assay. HEK 293 cells stably expressing CysLT1 receptor and Gα16 protein were loaded with 2 uM Fluo-4 AM in Hanks balanced salt solution buffer. The compound was added to a solution, and after 10 min incubation at room temperature, 25 uL LTD4 was dispensed into the well using a FlexStation II microplate reader, and intracellular calcium change was recorded with an excitation wavelength of 485 nm and an emission wavelength of 525 nm. The IC50 for pranlukast was 23 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:48 GMT 2023
Record UNII
TB8Z891092
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRANLUKAST
INN   MART.   MI   WHO-DD  
INN  
Official Name English
PRANLUKAST [MART.]
Common Name English
ONO-1078
Code English
RS-411
Code English
SB-205312
Code English
pranlukast [INN]
Common Name English
RS 411
Code English
Pranlukast [WHO-DD]
Common Name English
BENZAMIDE, N-(4-OXO-2-(2H-TETRAZOL-5-YL)-4H-1-BENZOPYRAN-8-YL)-4-(4-PHENYLBUTOXY)-
Systematic Name English
SB 205312
Code English
PRANLUKAST [MI]
Common Name English
ONO 1078
Code English
AZLAIRE
Brand Name English
CCN-00401
Code English
ONON
Brand Name English
CCN 00401
Code English
N-(4-OXO-2-(1H-TETRAZOL-5-YL)-4H-1-BENZOPYRAN-8-YL)-P-(4-PHENYLBUTOXY)BENZAMIDE
Common Name English
Classification Tree Code System Code
WHO-VATC QR03DC02
Created by admin on Fri Dec 15 15:34:48 GMT 2023 , Edited by admin on Fri Dec 15 15:34:48 GMT 2023
NCI_THESAURUS C29712
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WHO-ATC R03DC02
Created by admin on Fri Dec 15 15:34:48 GMT 2023 , Edited by admin on Fri Dec 15 15:34:48 GMT 2023
Code System Code Type Description
FDA UNII
TB8Z891092
Created by admin on Fri Dec 15 15:34:48 GMT 2023 , Edited by admin on Fri Dec 15 15:34:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL21333
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PRIMARY
MERCK INDEX
m9100
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PRIMARY Merck Index
EPA CompTox
DTXSID3043782
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PRIMARY
PUBCHEM
4887
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PRIMARY
WIKIPEDIA
PRANLUKAST
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PRIMARY
SMS_ID
100000091523
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PRIMARY
DRUG CENTRAL
2237
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PRIMARY
INN
6943
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PRIMARY
NCI_THESAURUS
C96712
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PRIMARY
EVMPD
SUB09998MIG
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PRIMARY
MESH
C047681
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PRIMARY
IUPHAR
3634
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PRIMARY
DRUG BANK
DB01411
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PRIMARY
CAS
103177-37-3
Created by admin on Fri Dec 15 15:34:48 GMT 2023 , Edited by admin on Fri Dec 15 15:34:48 GMT 2023
PRIMARY
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