Details of the Drug

General Information of Drug (ID: DME5Y64)

• Drug Name: Tranilast
• Synonyms: tranilast; 53902-12-8; Rizaben; trans-Tranilast; Tranilastum; 70806-55-2; MK 341; N-(3,4-Dimethoxycinnamoyl)anthranilic acid; Tranilastum [INN-Latin]; Tranilast [USAN:INN:JAN]; Tranpro; UNII-HVF50SMY6E; SB-252218; MK-341; Tranilast (SB 252218); 3,4-DAA; n-(3',4'-dimethoxycinnamoyl) anthranilic acid; HVF50SMY6E; MLS000028468; CHEBI:77572; C18H17NO5; Anthranilic acid, N-(3,4-dimethoxycinnamoyl)-; NZHGWWWHIYHZNX-CSKARUKUSA-N; 2-((3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid; MFCD00864787; T 0318; NU-3450; Rizaben (TN); Tranilast (JAN/USAN/INN); Rizaben, SB 252218, MK 341, Tranpro ,Tranilast; N-(3',4'-dimethoxycinnamoyl) anthranilic acid; N-(3′ -Dimethoxycinnamoyl)anthranilic Acid; 2-({(2E)-3-[3,4-bis(methyloxy)phenyl]prop-2-enoyl}amino)benzoic acid; 2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid; 2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino] benzoic acid; Molecule 20

Indication

Disease Entry	ICD 11	Status	REF
Allergic rhinitis	CA08.0	Approved	[1]
Ocular allergy	4A81	Approved	[2]
Asthma	CA23	Investigative	[3]
Keloid	EE60	Investigative	[4]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 327.3
  Logarithm of the Partition Coefficient (xlogp); 3.2
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 5
• Chemical Identifiers:
  Formula: C18H17NO5
  IUPAC Name: 2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid
  Canonical SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)NC2=CC=CC=C2C(=O)O)OC
  InChI: InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+
  InChIKey: NZHGWWWHIYHZNX-CSKARUKUSA-N
• Cross-matching ID:
  PubChem CID: 5282230
  ChEBI ID: CHEBI:77572
  CAS Number: 53902-12-8
  DrugBank ID: DB07615
  TTD ID: D0E6OC
  INTEDE ID: DR1628
• 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
Histamine H1 receptor (H1R)	TTTIBOJ	HRH1_HUMAN	Antagonist	[5]
Steryl-sulfatase (STS)	TTHM0R1	STS_HUMAN	Inhibitor	[6]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[7]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[8]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Gene/Protein Processing	[9]
C-X-C chemokine receptor type 4 (CXCR4)	OTUFSBX2	CXCR4_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 1B1 (CYP1B1)	OTYXFLSD	CP1B1_HUMAN	Gene/Protein Processing	[9]
Transient receptor potential cation channel subfamily V member 2 (TRPV2)	OT0A9AVD	TRPV2_HUMAN	Gene/Protein Processing	[10]

Molecular Expression Atlas of This Drug

• The Studied Disease: Allergic rhinitis
• ICD Disease Classification: CA08.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Steryl-sulfatase (STS)	DTT	STS	1.80E-38	-0.79	-1.15
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	1.07E-11	-1.16E-01	-2.53E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	1.87E-03	-6.67E-02	-2.12E-01

References

• [1] Seasonal facial erythema in a patient with allergic rhinitis treated using a combination of tranilast and roxithromycin. Immunopharmacol Immunotoxicol. 2023 Dec;45(4):508-510.
• [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: 6326).
• [3] Tranilast: a review of its therapeutic applications. Pharmacol Res. 2015 Jan;91:15-28.
• [4] Treatment of keloid and hypertrophic scars by iontophoretic transdermal delivery of tranilast. Scand J Plast Reconstr Surg Hand Surg. 1997 Jun;31(2):151-8.
• [5] Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20.
• [6] Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer. Curr Med Chem. 2002 Jan;9(2):263-73.
• [7] Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
• [8] Glucuronidation of antiallergic drug, Tranilast: identification of human UDP-glucuronosyltransferase isoforms and effect of its phase I metabolite. Drug Metab Dispos. 2007 Apr;35(4):583-9.
• [9] Omeprazole inhibits pancreatic cancer cell invasion through a nongenomic aryl hydrocarbon receptor pathway. Chem Res Toxicol. 2015 May 18;28(5):907-18.
• [10] Ca(2+) Signaling and IL-8 Secretion in Human Testicular Peritubular Cells Involve the Cation Channel TRPV2. Int J Mol Sci. 2018 Sep 19;19(9):2829. doi: 10.3390/ijms19092829.