Details of the Drug

General Information of Drug (ID: DMYHDCA)

Drug Name
Pranlukast
Synonyms Azlaire; Azlaire (TN); Pranlukast (INN); N-[4-oxo-2-(2H-tetrazol-5-yl)chromen-8-yl]-4-(4-phenylbutoxy)benzamide
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Asthma CA23 Approved [2]
Therapeutic Class
Antiasthmatic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 481.5
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C27H23N5O4
IUPAC Name
N-[4-oxo-2-(2H-tetrazol-5-yl)chromen-8-yl]-4-(4-phenylbutoxy)benzamide
Canonical SMILES
C1=CC=C(C=C1)CCCCOC2=CC=C(C=C2)C(=O)NC3=CC=CC4=C3OC(=CC4=O)C5=NNN=N5
InChI
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)
InChIKey
NBQKINXMPLXUET-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4887
ChEBI ID
CHEBI:94810
CAS Number
103177-37-3
DrugBank ID
DB01411
TTD ID
D08QIP
VARIDT ID
DR01179
INTEDE ID
DR1321
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Leukotriene CysLT1 receptor (CYSLTR1) TTGKOY9 CLTR1_HUMAN Antagonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [5]
Cysteinyl leukotriene receptor 1 (CYSLTR1) OT904HBN CLTR1_HUMAN Protein Interaction/Cellular Processes [6]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [7]
Interleukin-5 (IL5) OTAFPSCO IL5_HUMAN Gene/Protein Processing [8]
Leukotriene C4 synthase (LTC4S) OT3XNFJZ LTC4S_HUMAN Drug Response [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 The Effects of Combined Therapeutic Protocol on Allergic Rhinitis Symptoms and Molecular Determinants. Iran J Allergy Asthma Immunol. 2022 Apr 11;21(2):141-150.
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3634).
3 Beneficial effects of leukotriene receptor antagonists in the prevention of cedar pollinosis in a community setting. J Investig Allergol Clin Immunol. 2009;19(3):195-203.
4 Effect of clarithromycin on the pharmacokinetics of pranlukast in healthy volunteers. Drug Metab Pharmacokinet. 2008;23(6):428-33.;
5 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
6 A kinetic binding study to evaluate the pharmacological profile of a specific leukotriene C(4) binding site not coupled to contraction in human lun... Mol Pharmacol. 2000 Jun;57(6):1182-9.
7 Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. Xenobiotica. 2004 May;34(5):429-38.
8 Pranlukast, a leukotriene receptor antagonist, inhibits interleukin-5 production via a mechanism distinct from leukotriene receptor antagonism. Int Arch Allergy Immunol. 2005 Feb;136(2):165-72. doi: 10.1159/000083325. Epub 2005 Jan 12.
9 Leukotriene C4 synthase gene A(-444)C polymorphism and clinical response to a CYS-LT(1) antagonist, pranlukast, in Japanese patients with moderate asthma. Pharmacogenetics. 2002 Oct;12(7):565-70. doi: 10.1097/00008571-200210000-00009.