Identification

Name
Tranilast
Accession Number
DB07615
Type
Small Molecule
Groups
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
  • N-(3,4-Dimethoxycinnamoyl)anthranilic acid
  • tranilast
  • tranilastum
External IDs
MK 341 / MK-341 / MK341
International/Other Brands
Rizaben
Categories
UNII
HVF50SMY6E
CAS number
53902-12-8
Weight
Average: 327.3313
Monoisotopic: 327.110672659
Chemical Formula
C18H17NO5
InChI Key
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

Pharmacology

Indication

For the treatment of bronchial asthma, keloid and hypertrophic scar, and allergic disorders such as asthma, allergic rhinitis and atopic dermatitis.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHematopoietic prostaglandin D synthase
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Tranilast is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Tranilast is combined with (S)-Warfarin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Tranilast is combined with 2,4-thiazolidinedione.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Tranilast.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Tranilast.
5-androstenedioneThe metabolism of Tranilast can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Tranilast can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Tranilast.
AbafunginThe therapeutic efficacy of Abafungin can be increased when used in combination with Tranilast.
AbciximabTranilast may increase the anticoagulant activities of Abciximab.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D02027
PubChem Compound
5282230
PubChem Substance
99444086
ChemSpider
4445411
BindingDB
21613
ChEBI
77572
ChEMBL
CHEMBL415324
HET
D27
Wikipedia
Tranilast
PDB Entries
2vd0

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentMucinoses1
0Not Yet RecruitingTreatmentSarcoidosis1
0Not Yet RecruitingTreatmentScleredema Adultorum1
1WithdrawnTreatmentRheumatoid Arthritis1
2CompletedTreatmentActive Rheumatoid Arthritis1
2CompletedTreatmentAcute Gouty Arthritis / Hyperuricemia2
3CompletedTreatmentPterygium1
4CompletedTreatmentConjunctivitis, Seasonal Allergic1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-1900000000-7541d25405a74d897cf6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-2900000000-d54b9ceefe589f6ddc0b

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-cinnamoylanthranilic acids. These are aromatic compounds containing a cinnamic acid conjugated to an anthranilic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Cinnamic acid amides
Direct Parent
N-cinnamoylanthranilic acids
Alternative Parents
Acylaminobenzoic acid and derivatives / Dimethoxybenzenes / Anilides / Benzoic acids / Styrenes / Phenoxy compounds / N-arylamides / Anisoles / Benzoyl derivatives / Alkyl aryl ethers
show 8 more
Substituents
N-cinnamoylanthranilic acid / Acylaminobenzoic acid or derivatives / O-dimethoxybenzene / Dimethoxybenzene / Benzoic acid or derivatives / Benzoic acid / Anilide / Phenoxy compound / Anisole / Phenol ether
show 23 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dimethoxybenzene, cinnamamides, amidobenzoic acid (CHEBI:77572)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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 con...
Gene Name
HPGDS
Uniprot ID
O60760
Uniprot Name
Hematopoietic prostaglandin D synthase
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]
  2. Ikai K, Ujihara M, Fujii K, Urade Y: Inhibitory effect of tranilast on prostaglandin D synthetase. Biochem Pharmacol. 1989 Aug 15;38(16):2673-6. [PubMed:2475113]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Drug created on September 15, 2010 15:24 / Updated on November 02, 2018 06:35