| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg | |||
| Other Sizes |
| Targets |
PGD2/rostaglandin D2 ( IC50 = 0.1 mM ); Angiotensin II
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| ADME/Pharmacokinetics |
Following oral administration in humans, peak plasma concentrations of Tranilast are achieved within 2 to 3 hours. The elimination half-life is approximately 8.6 hours. Drug levels are significantly reduced by 24 hours and fall below the detection limit after 48 hours .
Tranilast is primarily eliminated via urine, with the majority of the dose excreted within 96 hours of administration . The main metabolic pathway is the formation of a glucuronide conjugate. The principal metabolite is the 4-O-demethylated product conjugated with sulfate and glucuronic acid . In vitro studies using human liver microsomes and recombinant enzymes indicate that the oxidative metabolism of Tranilast involves multiple cytochrome P450 (CYP) isoforms. These include CYP2C9, CYP2C18, CYP2C8, CYP1A2, CYP3A4, and CYP2D6, with CYP2C9 being identified as a primary contributor . In vitro studies have elucidated the glucuronidation pathway of Tranilast. The glucuronidation is primarily catalyzed by the UGT1A1 enzyme in both human liver and intestine. The kinetic parameters (Km) for this activity were determined to be 51.5 μM in human liver microsomes, 50.6 μM in human jejunum microsomes, and 38.0 μM for recombinant UGT1A1. The corresponding Vmax values were 10.4, 42.9, and 19.7 pmol/min/mg protein, respectively. Calculated intrinsic clearance suggested that glucuronidation activity is 2.5-fold higher in the liver than in the intestine . In vitro metabolism studies also determined the kinetics for the formation of the phase I metabolite, 4-demethyltranilast (N-3). In human liver microsomes, the Km and Vmax for N-3 formation were 37.1 μM and 27.6 pmol/min/mg protein, respectively . Tranilast glucuronosyltransferase activity was found to be strongly inhibited by its phase I metabolite (N-3), suggesting a potential for the metabolite to affect the parent drug's metabolism . |
| Toxicity/Toxicokinetics |
In animal studies, Tranilast has been shown to have teratogenic effects, and therefore it is contraindicated in pregnant women .
Clinically, Tranilast can cause hepatic and renal adverse reactions. Hepatic effects may include jaundice and significant elevations in liver enzymes such as AST, ALT, and AL-P, potentially leading to liver dysfunction or hepatitis. Renal effects can include increases in blood urea nitrogen (BUN) and serum creatinine . Other observed adverse reactions include urinary system effects (e.g., frequency, dysuria, hematuria), hematological effects (e.g., decreased red blood cell count and hemoglobin, leukopenia, thrombocytopenia), gastrointestinal disturbances (e.g., anorexia, nausea, vomiting, abdominal pain), and central nervous system effects (e.g., headache, drowsiness, dizziness) . In vitro studies show that Tranilast and its phase I metabolite (N-3) strongly inhibit bilirubin glucuronosyltransferase (UGT1A1) activity. This inhibition is suggested as the mechanism for the hyperbilirubinemia observed in some patients during clinical trials, potentially linked to UGT1A1 genotype . In a clinical safety study involving patients with advanced heart failure and muscular dystrophy, Tranilast administered orally at 100 mg three times daily for 6 months was reported to have no serious adverse events related to the drug, aside from diarrhea, a known side effect . The material safety data sheet for Tranilast classifies it as an oral acute toxin (Category 4) and advises caution to avoid inhalation, skin contact, and eye contact . Standard first aid measures include rinsing skin or eyes with large amounts of water and seeking medical attention if necessary . The toxicological effects have not been thoroughly studied . |
| References | |
| Additional Infomation |
Tranilast is an aminobenzoic acid compound with a structure similar to anthranilic acid, except that one aniline hydrogen atom is replaced by a 3,4-dimethoxycinnamoyl group. It possesses various pharmacological effects, including anti-asthmatic, nephroprotective, anti-allergic, calcium channel blocker, antitumor, aryl hydrocarbon receptor agonist, and hepatoprotective agent. Tranilast belongs to the cinnamicamide, dimethoxybenzene, aminobenzoic acid, and secondary amide classes. Its function is related to that of anthranilic acid. Tranilast is an anti-allergic drug developed by Gisele Pharmaceuticals. In 1982, it was approved in Japan and South Korea for the treatment of bronchial asthma. In 1993, its indication for the treatment of keloids and hypertrophic scars was added. It has also been used to treat allergic diseases such as asthma, allergic rhinitis, and atopic dermatitis.
Drug Indications For the treatment of bronchial asthma, keloids and hypertrophic scars, as well as allergic diseases such as asthma, allergic rhinitis and atopic dermatitis. |
| Molecular Formula |
C18H17NO5
|
|---|---|
| Molecular Weight |
327.331285238266
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| Exact Mass |
327.111
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| Elemental Analysis |
C, 66.05; H, 5.23; N, 4.28; O, 24.44
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| CAS # |
70806-55-2
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| Related CAS # |
Tranilast; 53902-12-8; Tranilast sodium; 104931-56-8
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| PubChem CID |
5282230
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| Appearance |
White to off-white solid powder
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| LogP |
3.703
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
24
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| Complexity |
464
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(O)C1=CC=CC=C1NC(/C=C/C2=CC(OC)=C(OC)C=C2)=O
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| InChi Key |
NZHGWWWHIYHZNX-CSKARUKUSA-N
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| InChi Code |
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+
|
| Chemical Name |
2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid
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| Synonyms |
Tranilast; SB252218; SB-252218; SB 252218; MK 341; MK341; MK-341; trans-Tranilast; brand name: Rizaben; Tranilastum; Tranpro
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 65~100 mg/mL (198.6~305.5 mM)
Ethanol: ~4 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0550 mL | 15.2751 mL | 30.5502 mL | |
| 5 mM | 0.6110 mL | 3.0550 mL | 6.1100 mL | |
| 10 mM | 0.3055 mL | 1.5275 mL | 3.0550 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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