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Identification
NameTranilast
Accession NumberDB07615
TypeSmall Molecule
GroupsApproved, Investigational
Description

Tranilast is an antiallergic drug developed by Kissei Pharmaceuticals. It was approved in 1982 for use in Japan and South Korea for bronchial asthma. Indications for keloid and hypertrophic scar were added in 1993. It has been used for the treatment of allergic disorders such as asthma, allergic rhinitis and atopic dermatitis.

Structure
Thumb
Synonyms
2-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid
External Identifiers
  • MK 341
  • MK-341
  • MK341
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
RizabenNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIHVF50SMY6E
CAS number53902-12-8
WeightAverage: 327.3313
Monoisotopic: 327.110672659
Chemical FormulaC18H17NO5
InChI KeyInChIKey=NZHGWWWHIYHZNX-CSKARUKUSA-N
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+
IUPAC Name
2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
SMILES
COC1=CC=C(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)C=C1OC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid amides
Direct ParentCinnamic acid amides
Alternative Parents
Substituents
  • Cinnamic acid amide
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • N-arylamide
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Phenylpropene
  • Benzoic acid
  • Benzoic acid or derivatives
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of bronchial asthma, keloid and hypertrophic scar, and allergic disorders such as asthma, allergic rhinitis and atopic dermatitis.
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5905
Blood Brain Barrier-0.58
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.6922
P-glycoprotein inhibitor INon-inhibitor0.7716
P-glycoprotein inhibitor IINon-inhibitor0.5842
Renal organic cation transporterNon-inhibitor0.9433
CYP450 2C9 substrateNon-substrate0.6853
CYP450 2D6 substrateNon-substrate0.8054
CYP450 3A4 substrateSubstrate0.5548
CYP450 1A2 substrateNon-inhibitor0.9137
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9451
CYP450 2C19 inhibitorNon-inhibitor0.9167
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7384
Ames testNon AMES toxic0.6665
CarcinogenicityNon-carcinogens0.871
BiodegradationNot ready biodegradable0.8218
Rat acute toxicity2.4428 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9921
hERG inhibition (predictor II)Non-inhibitor0.8008
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0084 mg/mLALOGPS
logP2.89ALOGPS
logP3.56ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.52 m3·mol-1ChemAxon
Polarizability34.2 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
WarfarinThe risk or severity of adverse effects can be increased when Tranilast is combined with Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the conjugation of glutathione with a wide range of aryl halides and organic isothiocyanates. Also exhibits low glutathione-peroxidase activity towards cumene hydroperoxide.
Gene Name:
HPGDS
Uniprot ID:
O60760
Molecular Weight:
23343.65 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on September 15, 2010 15:24 / Updated on October 29, 2015 14:33