2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID
tranilast
CAS: 53902-12-8
Molecular Formula: C18H17NO5
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Names and Identifiers
| Name | tranilast |
| Synonyms | n-5' rizaben SB-252218 tranilast n-(3,4-dimethoxycinnamoyl)-anthranilicaci N-(3',4'-DIMETHOXYCINNAMOYL)ANTHRANILIC ACID 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)-benzoicaci 2-{[(2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid 2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID 2-({(2E)-3-[3,4-bis(methyloxy)phenyl]prop-2-enoyl}amino)benzoic acid benzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- Benzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]- |
| CAS | 53902-12-8 |
| InChI | InChI=1/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 |
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Physico-chemical Properties
| Molecular Formula | C18H17NO5 |
| Molar Mass | 327.33 |
| Density | 1.3185 (rough estimate) |
| Melting Point | 166.2-168.2 °C (lit.) |
| Boling Point | 465.23°C (rough estimate) |
| Flash Point | 307.9°C |
| Solubility | DMSO: 18mg/mL |
| Vapor Presure | 1.49E-14mmHg at 25°C |
| Appearance | powder |
| Color | white to beige |
| Merck | 14,9570 |
| pKa | 3.47±0.36(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| Refractive Index | 1.5100 (estimate) |
| Physical and Chemical Properties | Appearance: light yellow crystal Melting Point: 207-210 ℃ |
| Use | For the treatment of bronchial asthma and allergic rhinitis |
| In vitro study | Tranilast is an anti-allergic drug that inhibits the release of substances such as histamine and prostaglandins from mast cells, thereby inhibiting collagen synthesis by fibroblasts derived from keloid tissue. Tranilast(3-300 mM) inhibited collagen synthesis in hypertrophic scar tissue-derived fibroblasts, but healthy skin fibroblasts were not affected. Tranilast(30-300 mM) inhibits the release of transforming growth factor (TGF)-β1 from fibrocytes, which enhances collagen synthesis in keloid tissue-derived fibroblasts. Tranilast ameliorates abnormal proliferation of keloids and hypertrophic scars and excessive accumulation of collagen by fibroblasts. Tranilast inhibits the release of TGF-β1,IL-1β, and PGE2 from human monocyte-macrophages. Tranilast inhibited proliferation stimulated with fetal bovine serum (FBS),TGF-β1, and platelet-derived growth factor-BB(PDGF-BB), as well as PDGF-BB-induced migration. Tranilast inhibits spontaneous collagen synthesis and TGF-β1 induced collagen and glycosaminoglycan synthesis. |
| In vivo study | In diabetic hearts of rats, Tranilast reduced tgf-β1-induced 3[H] Hydroxyproline incorporation by 58%. In diabetic hearts of rats, Tranilast attenuated myocardial fibrosis by 37%, accompanied by a decrease in phosphorylated smad2. In dog carotid arteries, Tranilast completely prevented the increase in chymaselike activity, reduced chymase mRNA levels by 43% and reduced carotid intima/mediator ratio by 63%. |
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | DG8731000 |
| Toxicity | LD50 in male, female mice, male, female rats (mg/kg): 780, 680, 1600, 1100 orally; 410, 385, 405, 395 i.p.; 2630, 2820, 3630, 3060 s.c. (Nakazawa, p 385) |
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Standard
Authoritative Data Verified Data
This product is N-(3, 4-dimethoxycinnamoyl) anthranilic acid. Calculated as dried product, the content of C18H17N05 shall not be less than 98.5%.
Last Update：2024-01-02 23:10:35
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Trait
Authoritative Data Verified Data
- This product is light yellow or light yellow green crystal or crystalline powder; Odorless, tasteless.
- This product is soluble in N,N-dimethylformamide, slightly soluble in methanol, insoluble in water.
Last Update：2022-01-01 11:44:46
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Differential diagnosis
Authoritative Data Verified Data
- take about 10 mg of this product, add 1.5 of N,N-dimethylformamide, shake to dissolve, add 1ml of water, mix well, add several drops of potassium permanganate solution Dropwise, shake, the purple color will disappear.
- Take 10mg of this product, add an appropriate amount of methanol, ultrasonic to dissolve, add methanol to 100ml, shake, dilute with methanol to make a solution containing 5ug per lml, as determined by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at a wavelength of nm and a minimum absorption at a wavelength of Nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 1140).
Last Update：2022-01-01 11:44:46
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Exam
Authoritative Data Verified Data
chloride
take this product l.Og, heat 50ml of water and 1 ml of nitric acid, put them on a water bath for 5 minutes, shake fully, let them cool, filter, take 25ml of filtrate, and check according to law (General rule 0801), with standard sodium chloride solution 5.0ml of the control solution should not be more concentrated (0.01%).
Related substances
operation in the dark. Take about 50mg of this product, put it in a 50ml measuring flask, add an appropriate amount of methanol, ultrasonic to dissolve, cool, dilute with methanol to the scale, shake, as a test solution; take 1ml of precision, 100ml flask, diluted with methanol to scale, shake, as a control solution. According to the high performance liquid chromatography (General 0512) test, with the eighteen alkyl silane bonded silica gel as the filler, methanol-acetonitrile -0.02mol/ L ammonium acetate solution (1:1:2)(With acetic acid to adjust the pH value to 4.0 0.05) as mobile phase, the detection wavelength was 308nm. Take Tranilast 50mg, add methanol 50ml, sonicate to dissolve, shake well, irradiate with light intensity above 1500l for 2 hours, shake well, cool down, take 10ul to inject human liquid chromatograph, the chromatogram was recorded. The number of theoretical plates shall not be less than 4000 calculated by Tranilast peak, and the separation degree between Tranilast peak and adjacent impurity peaks shall meet the requirements. Take 10 u1 of the test solution and the control solution respectively, inject the human liquid chromatograph, record the chromatogram to 4 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than 0.5 times (0.5%) of the area of the main peak of the control solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (1.0%).
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the ignition residue item shall not contain more than 15 parts per million of heavy metals as inspected by law (General rule 0821, Law II).
Last Update：2022-01-01 11:44:47
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Content determination
Authoritative Data Verified Data
take this product about 0.4g, precision weighing, add N,N-dimethylformamide 40ml, shake to dissolve, add new boiling exothermic water 10ml and phenolphthalein indicator solution 3 drops, with sodium hydroxide titration solution (0.1 mol/L) titration until the solution is pink and does not fade within 30 seconds, and the results of the titration are corrected by a blank test. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 32.73mg of C18H17NO5.
Last Update：2022-01-01 11:44:48
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Category
Authoritative Data Verified Data
anti-allergic drugs.
Last Update：2022-01-01 11:44:48
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Storage
Authoritative Data Verified Data
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:44:48
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - TranilastTablets
Authoritative Data Verified Data
This product contains Tranilast (C18H17N05) should be 93.0% to 107.0% of the label.
trait
This product is light yellow or light yellow green tablets.
identification
- take an appropriate amount of fine powder of this product (about 50mg of Tranilast), add 5ml of N,N-dimethylformamide, shake to dissolve Tranilast, add 5ml of water, and mix well, filter, take filtrate 2ml, add potassium permanganate solution 1ml, shake, red disappeared, resulting in brown precipitate.
- take an appropriate amount of fine powder of this product, add an appropriate amount of anhydrous ethanol to dissolve Tranilast, filter, and take the filtrate, A solution containing 5ug of Tranilast per 1 ml was prepared by dilution with absolute ethanol and had an absorption maximum at a wavelength of 0401 nm as determined by UV-Vis spectrophotometry (general).
examination
- dissolution rate protected from light. Take this product, according to the dissolution and release determination method (General rule 0931 The first method), phosphate buffer (pH 6.8) ml as the dissolution medium, the rotation speed is 150 rpm, according to the law, after 25 minutes, take 5ml of the solution for filtration, take 1ml of the filtrate accurately, put it in a 25ml measuring flask, add 0.5ml of anhydrous ethanol, dilute it to the mark with dissolution medium, and shake well, as a test solution; Take 10mg of Tranilast reference substance with precision, put it in a 50ml measuring flask, dissolve it with absolute ethanol, dilute it to the scale, shake well, and take 1ml with precision, in a 50ml measuring flask, dilute the dissolution medium to the scale, shake well, and use as a reference solution. The absorbance of each of the above two Solutions was measured at a wavelength of 0401 nm by ultraviolet-visible spectrophotometry (general), and the elution amount of each tablet was calculated. The limit is 85% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
operation in the dark. Take 20 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (about equivalent to Tranilast 10 mg), 100ml brown measuring flask, add 0.Olmol/L sodium hydroxide solution about 50ml, shake for 5 minutes, with 0.Olmol/L sodium hydroxide solution diluted to the scale, shake, filter, precision take the filtrate to continue 5ml, 100ml brown flask, with 0. Dilute Olmol/L sodium hydroxide solution to the scale, shake well, measure absorbance at the wavelength of 333nm according to UV-Vis spectrophotometry (General rule 0401), precision weighing, add 0.Olmol/L sodium hydroxide solution was dissolved and diluted quantitatively to make a solution containing 5ug per lml, which was determined and calculated by the same method.
category
with Tranilast.
specification
0.lg
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:44:49
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Tranilast capsules
Authoritative Data Verified Data
This product contains Tranilast (C18H17N05) should be 90.0% to 110.0% of the label.
trait
The content of this product is light yellow or light yellow green granules or powder.
identification
- take an appropriate amount of the contents of this product (about 50mg of Tranilast), add 8ml of N,N-dimethylformamide, shake to dissolve Tranilast, add 5ml of water, mix well, filtered. Take 2ml of the filtrate, add several drops of potassium permanganate solution Dropwise, shake, and the purple color will disappear.
- take the test solution under the content determination item, according to UV-visible spectrophotometry (General 0401), there is a maximum absorption at the wavelength of 333nm, there is minimal absorption at a wavelength of 263nm.
examination
- the related substances were protected from light. Take an appropriate amount of the contents of this product (about 50mg equivalent to Tranilast), put it in a 50ml measuring flask, add an appropriate amount of methanol, sonicate the Tranilast to dissolve, cool, and dilute to the scale with methanol, shake well, filter, and take the continued filtrate as a test solution; Take 1ml accurately, put it in a 100ml measuring flask, dilute it to the scale with methanol, shake well, and use it as a control solution. Test according to the method under Tranilast related substances. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (1.0%).
- dissolution rate protected from light. Take this product, according to the dissolution and release determination method (General rule 0931 The first method), phosphate buffer (pH7.4)900ml as the dissolution medium, the rotation speed is 100 rpm, according to the law operation, after 30 minutes, 10ml of the solution was taken, filtered, and 2ml of the filtrate was accurately taken, placed in a 50ml measuring flask, diluted to the scale with dissolution medium, and shaken to serve as a test solution; another precision weigh Tranilast reference product lOmg, put it in a 100ml measuring flask, add appropriate amount of dissolution medium, ultrasonic dissolution, let it cool, dilute it to the scale with dissolution medium, and shake it well, an appropriate amount was taken in a precise amount and quantitatively diluted with a dissolution medium to prepare a solution containing about 5ug per 1 ml as a reference solution. The absorbance of each of the above two Solutions was measured at a wavelength of 0401 Mn by ultraviolet-visible spectrophotometry (general), and the elution amount of each particle was calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
operation in the dark. Take the contents under the difference of loading amount, mix evenly, weigh an appropriate amount (about 10mg equivalent to Tranilast), put it in a 100ml measuring flask, and add an appropriate amount of methanol, dissolve Tranilast by ultrasound, let it cool, dilute to scale with methanol, shake well, filter, Take 5ml of filtrate accurately, put it in a 100ml measuring flask, dilute to scale with methanol, as the test solution, measure the absorbance at the wavelength of 333mn by UV-Vis spectrophotometry (General rule 0401), dissolved and quantitatively diluted with methanol to prepare a solution containing about 5ug per 1 ml, which was determined and calculated by the same method.
category
with Tranilast.
specification
O.lg
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:44:50
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID - Reference Information
| biological activity | Tranilast (SB 252218, MK-341, Rizaben, MK 341, Tranpro) is an anti-allergic compound. |
| uses | anti-allergic drug, which is an allergic reaction mediator and has the function of stabilizing mast cells and basophilic granulocyte cell membrane. Suitable for the treatment of bronchial asthma, allergic rhinitis, atopic dermatitis, etc. for the treatment of bronchial asthma and allergic rhinitis. |
| production method | anthranilic acid (I) and compound (II) are condensed to obtain the product. |
Last Update：2024-04-09 19:05:12
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Supplier List
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Product Name: Tranilast Visit Supplier Webpage Request for quotationCAS: 53902-12-8
Tel: 18301782025
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Mobile: 18021002903
QQ: 3008007409
Multiple SpecificationsSpot supply
Product Name: Tranilast Visit Supplier Webpage Request for quotationCAS: 53902-12-8
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Spot supply
Product Name: Tranilast Visit Supplier Webpage Request for quotationCAS: 53902-12-8
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Spot supply
Product Name: TRANILAST Visit Supplier Webpage Request for quotationCAS: 53902-12-8
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328
WhatsApp: +86-18821248368
Multiple SpecificationsSpot supply
Product Name: Tranilast Visit Supplier Webpage Request for quotationCAS: 53902-12-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
View History
2-[[3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]AMINO] BENZOIC ACID
IRINOTECAN HYDROCHLORIDE TRIHYDRATE
1H-indazole-5-carbaldehyd...
Pyrimidine, 2-(4-methyl-1-piperazinyl)-4,6-di-2-thienyl-, hydrobromide (1:1)
methyl 3-bromo-4-oxocyclopentanecarboxylate
3-Pyridinemethanamine, N-(2,2,6,6-tetramethyl-4-piperidinyl)-
cobaltous oxygen(-2) anion
4,5,6,7-四氢-5-甲基-噻唑并[5,4-c]吡啶-2-羧酸 盐酸盐
(3aR,4R,6S,6aS)-4-[叔丁氧羰基氨基]-3-(1-乙基丙基)-3a,5,6,6a-四氢-4H-环戊并[d]异恶唑-6-羧酸甲酯
Thiocarbonic acid, anhydrosulphide with methyl thiohypochlorite
IRINOTECAN HYDROCHLORIDE TRIHYDRATE
1H-indazole-5-carbaldehyd...
Pyrimidine, 2-(4-methyl-1-piperazinyl)-4,6-di-2-thienyl-, hydrobromide (1:1)
methyl 3-bromo-4-oxocyclopentanecarboxylate
3-Pyridinemethanamine, N-(2,2,6,6-tetramethyl-4-piperidinyl)-
cobaltous oxygen(-2) anion
4,5,6,7-四氢-5-甲基-噻唑并[5,4-c]吡啶-2-羧酸 盐酸盐
(3aR,4R,6S,6aS)-4-[叔丁氧羰基氨基]-3-(1-乙基丙基)-3a,5,6,6a-四氢-4H-环戊并[d]异恶唑-6-羧酸甲酯
Thiocarbonic acid, anhydrosulphide with methyl thiohypochlorite