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
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=CC=CC7=C6OC(=CC7=O)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
| 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 |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.e-search.ne.jp/~jpr/PDF/ONO04.PDF
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1798 |
23.0 nM [IC50] | ||
Target ID: CHEMBL4330 |
3620.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ONON Approved UseONON capsules are indicated for treatment of bronchial asthma |
|||
| Primary | ONON Approved UseONON capsules are indicated for treatment of allergic rhinitis |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Cough-variant asthma successfully treated with a peptide leukotriene receptor antagonist]. | 1997 Jan |
|
| 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 |
|
| Pharmacological characterization of the cysteinyl-leukotriene antagonists CGP 45715A (iralukast) and CGP 57698 in human airways in vitro. | 1998 Feb |
|
| 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 |
|
| The protective effects of leukotriene modifiers in aspirin-induced asthma. | 2000 Sep 15 |
|
| Characterization of the human cysteinyl leukotriene 2 receptor. | 2000 Sep 29 |
|
| Effects of pranlukast, a cysteinyl leukotriene receptor 1 antagonist, combined with inhaled beclomethasone in patients with moderate or severe asthma. | 2001 Aug |
|
| 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 |
|
| Molecular cloning and functional characterization of murine cysteinyl-leukotriene 1 (CysLT(1)) receptors. | 2001 Nov 1 |
|
| Fulminant eosinophilic endomyocarditis in an asthmatic patient treated with pranlukast after corticosteroid withdrawal. | 2001 Sep |
|
| Evaluation of the combined effect of pranlukast during high-dose steroid inhalation. | 2002 |
|
| Pharmacological differences among CysLT(1) receptor antagonists with respect to LTC(4) and LTD(4) in human lung parenchyma. | 2002 Apr 15 |
|
| Leukotriene C4 synthase gene A(-444)C polymorphism and clinical response to a CYS-LT(1) antagonist, pranlukast, in Japanese patients with moderate asthma. | 2002 Oct |
|
| Long-term observations of the clinical course after step down of corticosteroid inhalation therapy in adult chronic asthmatics: correlation with serum levels of eosinophil cationic protein. | 2002 Sep |
|
| Clinical effects of long-term administration of pranlukast, a leukotriene receptor antagonist, on adult patients with bronchial asthma. | 2003 |
|
| [Clinical effects of long-term administration of pranlukast, a leukotriene receptor antagonist, on adult patients with bronchial asthma]. | 2003 Oct |
|
| Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. | 2004 May |
|
| Pranlukast, a leukotriene receptor antagonist, inhibits interleukin-5 production via a mechanism distinct from leukotriene receptor antagonism. | 2005 Feb |
|
| Evaluation of theophylline or pranlukast, a cysteinyl leukotriene receptor 1 antagonist, as add-on therapy in uncontrolled asthmatic patients with a medium dose of inhaled corticosteroids. | 2005 Jul-Aug |
|
| Cysteinyl leukotriene receptor 1 is involved in N-methyl-D-aspartate-mediated neuronal injury in mice. | 2006 Dec |
|
| Inhibitory effects of angiotensin II receptor antagonists and leukotriene receptor antagonists on the transport of human organic anion transporter 4. | 2006 Nov |
|
| Protective effect of pranlukast, a cysteinyl-leukotriene receptor 1 antagonist, on indomethacin-induced small intestinal damage in rats. | 2007 Dec |
|
| Role of regular treatment with inhaled corticosteroid or leukotriene receptor antagonist in mild intermittent asthma. | 2008 Mar-Apr |
|
| Pranlukast attenuates ischemia-like injury in endothelial cells via inhibiting reactive oxygen species production and nuclear factor-kappaB activation. | 2009 Jan |
|
| Antileukotriene drugs in the treatment of asthma. | 2010 Mar |
|
| 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 |
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
Edited
Fri Dec 15 18:29:16 GMT 2023
by
admin
on
Fri Dec 15 18:29:16 GMT 2023
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| Record UNII |
FR702N558K
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| Record Status |
Validated (UNII)
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| Record Version |
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C29712
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Pranlukast hydrate
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |