PRANLUKAST HEMIHYDRATE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C27H23N5O4.H2O
Molecular Weight	981.0205
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O=C(NC1=CC=CC2=C1OC(=CC2=O)C3=NN=NN3)C4=CC=C(OCCCCC5=CC=CC=C5)C=C4.O=C(NC6=C7OC(=CC(=O)C7=CC=C6)C8=NN=NN8)C9=CC=C(OCCCCC%10=CC=CC=C%10)C=C9

InChI

InChIKey=MSXTUBJFNBZPGC-UHFFFAOYSA-N

InChI=1S/2C27H23N5O4.H2O/c2*33-23-17-24(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;/h2*1-3,6-8,10-15,17H,4-5,9,16H2,(H,28,34)(H,29,30,31,32);1H2

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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB01411
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cysteinyl leukotriene receptor 1 18 Target ID: CHEMBL1798 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26985325	Antagonist 2849		23.0 nM [IC50]
Cysteinyl leukotriene receptor 2 3 Target ID: CHEMBL4330 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10851239	Antagonist 2849		3620.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bronchial asthma 50 Sources: http://www.e-search.ne.jp/~jpr/PDF/ONO04.PDF	Primary	Approved 8583	ONON Approved Use ONON capsules are indicated for treatment of bronchial asthma
Allergic rhinitis 104 Sources: http://www.e-search.ne.jp/~jpr/PDF/ONO04.PDF	Primary	Approved 8583	ONON Approved Use ONON capsules are indicated for treatment of allergic rhinitis
Chronic sinusitis 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00410735	Primary	Phase III 665	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Development of 2,2-dimethylchromanol cysteinyl LT1 receptor antagonists.	1998 Dec 15	9934474
Leukotriene C4 is a tight-binding inhibitor of microsomal glutathione transferase-1. Effects of leukotriene pathway modifiers.	1999 Jan 22	9890956
Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor.	1999 Sep	10462554
Characterization of the human cysteinyl leukotriene 2 receptor.	2000 Sep 29	10851239
Effects of pranlukast, a leukotriene receptor antagonist, on airway inflammation in mild asthmatics.	2001 Feb	11256554
Molecular cloning and functional characterization of murine cysteinyl-leukotriene 1 (CysLT(1)) receptors.	2001 Nov 1	11705452
[Clinical effects of long-term administration of pranlukast, a leukotriene receptor antagonist, on adult patients with bronchial asthma].	2003 Oct	14584388
Inhibitory effects of angiotensin II receptor antagonists and leukotriene receptor antagonists on the transport of human organic anion transporter 4.	2006 Nov	17132213
Protective effect of pranlukast, a cysteinyl-leukotriene receptor 1 antagonist, on indomethacin-induced small intestinal damage in rats.	2007 Dec	18236018
Pranlukast attenuates ischemia-like injury in endothelial cells via inhibiting reactive oxygen species production and nuclear factor-kappaB activation.	2009 Jan	19129732

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 19:13:21 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:21 GMT 2025`
Record UNII	FR702N558K
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PRANLUKAST HYDRATE

Preferred Name

English

PRANLUKAST HEMIHYDRATE

Common Name

English

PRANLUKAST HYDRATE [JAN]

Common Name

English

BENZAMIDE, N-(4-OXO-2-(2H-TETRAZOL-5-YL)-4H-1-BENZOPYRAN-8-YL)-4-(4-PHENYLBUTOXY)-, HYDRATE (2:1)

Common Name

English

Pranlukast hydrate [WHO-DD]

Common Name

English

N-(4-OXO-2-(1H-TETRAZOL-5-YL)-4H-1-BENZOPYRAN-8-YL)-P-(4-PHENYLBUTOXY)BENZAMIDE, HEMIHYDRATE

Common Name

English

SC-215745

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29712