41340-25-4
Etodolac
CAS: 41340-25-4
Molecular Formula: C17H21NO3
41340-25-4 - Names and Identifiers
| Name | Etodolac |
| Synonyms | Etodolac Etodolac Imp.(EP) Etodolac impurity 22α-Hydroxyerythrodiol Solution, 100ppm 4-b)indole-1-aceticacid,1,3,4,9-tetrahydro-1,8-diethyl-pyrano( 1,3,4,9-tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-aceticacid 4-b]indole-1-aceticacid,1,8-diethyl-1,3,4,9-tetrahydro-pyrano[ 1,8-DIETHYL-1,3,4,9-TETRAHYDROPYRANO[3,4-B]INDOLE-1-ACETIC ACID 1,8-DIETHYL-1,3,4,9-TETRAHYDRO-PYRANO[3,4-B]INDOLE-1-ACETIC ACID (R)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid |
| CAS | 41340-25-4 |
| EINECS | 629-689-1 |
| InChI | InChI=1/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20) |
| InChIKey | NNYBQONXHNTVIJ-QGZVFWFLSA-N |
41340-25-4 - Physico-chemical Properties
| Molecular Formula | C17H21NO3 |
| Molar Mass | 287.35 |
| Density | 1.193±0.06 g/cm3(Predicted) |
| Melting Point | 145-1480C |
| Boling Point | 507.9±45.0 °C(Predicted) |
| Water Solubility | 40mg/L(37 ºC) |
| Solubility | Soluble in DMSO (100 mM), and ethanol (100 mM). |
| Appearance | neat |
| Color | White to Orange to Green |
| Merck | 14,3874 |
| pKa | 4.65(at 25℃) |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to heat and light |
| MDL | MFCD00133313 |
| Physical and Chemical Properties | Crystals were obtained from hexane-chloroform, melting point 145-148 °c. |
| Use | Used as an anti-inflammatory analgesic |
41340-25-4 - Risk and Safety
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R40 - Limited evidence of a carcinogenic effect R36 - Irritating to the eyes R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | UQ0360000 |
| HS Code | 29349990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
41340-25-4 - Nature
Open Data Verified Data
crystals were obtained from hexane-chloroform with a melting point of 145 to 148 °c.
Last Update：2024-01-02 23:10:35
41340-25-4 - Preparation Method
Open Data Verified Data
O-ethylaniline reacts with trichloroacetaldehyde hydrate and hydroxylamine to form oxime at the same time of acylation, cyclization catalyzed by sulfuric acid, reduction with lithium aluminum hydride to form indole derivatives, and reaction with oxalyl chloride and ethanol, it is condensed with ethyl propionyl acetate and finally hydrolyzed to form etodolac.
Last Update：2025-06-10 22:55:16
41340-25-4 - Standard
Authoritative Data Verified Data
This product is (± )1, 8-diethyl-1, 3,4, 9-tetrahydropyrano [3,4-6] Indole -1-acetic acid. Calculated as dried product, the content of C17H21N03 shall not be less than 98.5%.
Last Update：2024-01-02 23:10:35
41340-25-4 - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder.
- This product is soluble in ethanol, almost insoluble in water.
melting point
The melting point of this product (General 0612) is 144~150 ℃.
Last Update：2022-01-01 13:36:18
41340-25-4 - Application
Open Data Verified Data
The United States AHP's subsidiary, Ayerst, was first listed in the UK in 1985. Etodolac is a non-steroidal anti-inflammatory drug with anti-inflammatory, analgesic and antipyretic effects. It can selectively inhibit prostaglandin synthesis at the site of inflammation and anti-inflammatory. Its mechanism of action is the same as that of other NSAIDs. Absorption was rapid and there was no sign of accidental accumulation of the drug. For the treatment of rheumatoid arthritis, rheumatoid arthritis, osteoarthritis and postoperative pain. It is a drug suitable for the treatment of elderly patients.
Last Update：2025-08-19 16:24:40
41340-25-4 - Differential diagnosis
Authoritative Data Verified Data
- appropriate amounts of this product and the etodolac reference product were dissolved and diluted with acetone to prepare a solution containing about 1 mg per 1 ml as the test solution and the reference solution. According to the thin layer chromatography (General 0502) test, absorb the above two solutions each 5 u1, respectively point on the same silica gel GF254 thin layer plate, with toluene-anhydrous ethanol-glacial acetic acid (70:30:0.5) for the development of the agent, expand, take out, dry, set the UV lamp (254nm) under the inspection, the position and color of the main spot displayed by the test solution should be consistent with the main spot of the control solution.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
Last Update：2022-01-01 13:36:19
41340-25-4 - Exam
Authoritative Data Verified Data
color of solution
take this product O.lg, Add 10ml of mixed solution of methanol-water (4: 6), shake to dissolve, the solution should be colorless, such as color, with yellow No. 2 Standard Colorimetric solution (General rule 0901 first method) comparison, not deeper.
Related substances
- take an appropriate amount of this product, weigh it accurately, dissolve it with acetonitrile and dilute it to make a solution containing about 0.5mg per 1 ml, which is used as a test solution, A solution containing about 1 ug per 1ml was prepared as a control solution by quantitative dilution with acetonitrile. Separately take appropriate amounts of etodolac reference product and 1-methyletodolac (impurity I) reference product, add acetonitrile to dissolve and dilute to prepare a mixed solution containing about 0.5mg of etodolac and about 10ug of impurity I per 1 ml, as a system suitability solution. According to high performance liquid chromatography (General 0512) determination. The mobile phase A was phosphoric acid solution, and the mobile phase B was 0.6%(ml/ml) phosphoric acid acetonitrile solution. The flow rate was 1ml per minute, and the gradient elution was carried out according to the following table; the detection wavelength was 225nm.
- 20ul of the applicable solution of the system is injected into the human liquid chromatograph, and the chromatogram is recorded. The separation degree between impurity I and the peak of Etodolac should be greater than 6.0. 20 u1 of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatograms were recorded. If there are impurity peaks in the chromatogram of the test solution, impurity I and 8-methyl etodolac (impurity II) (impurity I and impurity II have the same retention time) the sum of peak areas shall not be greater than 2.5 times (0.5%) of the main peak area of the control solution, and the peak area of other individual impurities shall not be greater than the main peak area of the control solution (0.2%), the sum of each impurity peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution.
residual solvent
take about 0.lg of this product, precision weighing, in the top empty bottle, precision plus N,N-dimethylformamide 2mU seal, as a test solution; Take the appropriate amount of methanol and toluene, precision weighing, quantitative dilution with N,N-dimethylformamide is made into a mixed solution containing 0.15mg of methanol and 0.0445mg of toluene per 1 ml. Take 2ml for precision measurement, place it in a top empty bottle, and seal it, as a control solution. According to the determination method of residual solvent (General Principle 0861 second method), the capillary column with 6% cyanopropyl phenyl-94% dimethyl polysiloxane (or similar polar) as stationary liquid is used as the column, and the initial temperature is 40°C, hold for 5 minutes, then raise the temperature to 220°C at a rate of 35°C per minute for 2 minutes; The inlet temperature is 200°C, the detector temperature is 260°C; The equilibrium temperature of the headspace bottle is 80°C, the equilibration time was 30 minutes. Take the reference solution into the headspace, record the chromatogram, and the separation degree between the methanol peak and the toluene peak should meet the requirements. The test solution and the reference solution are respectively injected in the headspace, and the chromatogram is recorded. The residual amount of methanol and toluene shall be calculated by the peak area according to the external standard method.
chloride
take 0.2g of this product, add methanol 34ml, shake to dissolve, add water 6ml, check according to law (General rule 0801), and standard sodium chloride solution 6.0, the control solution prepared by adding 34ml of methanol should not be more concentrated (0.03%).
loss on drying
take this product, with phosphorus pentoxide as desiccant, at 60°C under reduced pressure drying to constant weight, weight loss should 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 item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 13:36:20
41340-25-4 - Content determination
Authoritative Data Verified Data
take this product about 0.5g, precision weighing, add neutral ethanol (phenolphthalein indicator liquid neutral) 30ml, dissolved, add phenolphthalein indicator liquid drops, with sodium hydroxide titration solution (O.lmol/L) titration. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 28.74mg of C17H21NO3.
Last Update：2022-01-01 13:36:20
41340-25-4 - Category
Authoritative Data Verified Data
antipyretic analgesic, non-steroidal anti-inflammatory drugs.
Last Update：2022-01-01 13:36:21
41340-25-4 - Storage
Authoritative Data Verified Data
sealed and stored in a dry place.
Last Update：2022-01-01 13:36:21
41340-25-4 - Etodolac Tablets
Authoritative Data Verified Data
This product contains etodolac (C17H21N03) should be the label amount of 95.0% ~ 105.0%.
trait
This product is a film-coated tablet, white or off-white after removal of the coating.
identification
- take an appropriate amount of fine powder of this product, add ethanol to dissolve and dilute to make a solution containing etodolac 5ug per lml, filter, and continue the filtrate to be determined by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at wavelengths of 226nm and 280nm, and a minimum absorption at a wavelength of 247nm.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- Related Substances: take an appropriate amount of fine powder of this product, weigh it precisely, dissolve it with acetonitrile and dilute it to make a solution containing 0.5mg of etodolac per lml, filter it, and continue the filtrate as the test solution; an appropriate amount was taken in a precise amount and quantitatively diluted with acetonitrile to prepare a solution containing about 1 μg per 1 ml as a control solution. The appropriate amounts of etodolac reference substance and impurity I reference substance were separately taken, and acetonitrile was added to dissolve and dilute to prepare a mixed solution containing about 0.5mg of etodolac and about 10ug of impurity I per 1 ml, which was used as a system applicable solution. The determination was carried out according to the method for related substances of etodolac. If there are impurity peaks in the chromatogram of the test solution, the sum of the peak areas of impurity I and impurity II (both have the same retention time) shall not be greater than 2.5 times (0.5%) of the main peak area of the control solution, other single impurity peak area shall not be greater than the main peak area of the control solution (0.2% ) , and the sum of each impurity peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution.
- dissolution: take 0931 mol/L potassium dihydrogen phosphate in phosphate buffer solution (pH 6.8) according to the dissolution and release determination method (General rule 0.2, first method), add 0.2mol/L sodium hydroxide solution 100 ml, add water to ML) as the dissolution medium, the rotation speed is rpm, operate according to law, after 30 minutes, take appropriate amount of solution and filter, accurately take appropriate amount of continued filtrate, quantitatively dilute with dissolution medium to prepare 12ug solution per lml, according to UV-Vis spectrophotometry (General rule 0401), determine the absorbance at the wavelength of 278nm; Take an appropriate amount of etodolac reference substance, precisely weigh it, add dissolution medium to dissolve and quantitatively dilute it into a solution containing 12ug per lml, and determine it by the same method, the dissolution amount of each tablet was calculated. The limit is 80% 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
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using octyl silane bonded silica gel as filler; Acetonitrile-water-phosphoric acid (500:500:0.25) as mobile phase; Flow rate of 1.5 per minute; the detection wavelength was 274NM. Take appropriate amounts of etodolac reference substance and impurity I reference substance, add mobile phase to dissolve and dilute to make a mixed solution containing etodolac about 0.2mg and impurity I about 10ug per 1 ml, and inject 20u1 into human liquid chromatograph, record the chromatogram, the separation between impurity I and the peak of etodolac shall be in accordance with the requirements.
- determination of 20 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (equivalent to etodolac 50mg ), put in 250ml measuring flask, add appropriate amount of mobile phase, shake to dissolve etodolac, dilute to the scale with mobile phase, shake well, filter, take the filtrate as the test solution, and inject 10ul into human liquid chromatograph accurately, record the chromatogram; an appropriate amount of etodolac reference substance was carefully weighed, dissolved and quantitatively diluted with mobile phase to make a solution containing 0.2mg per 1 ml. The same method was used to determine 6 according to the external standard method and the peak area was calculated.
category
with etodolac.
specification
(1)0.2g (2)0.4g
storage
shading, sealed preservation,
Last Update：2022-01-01 13:36:22
41340-25-4 - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Non-steroidal anti-inflammatory drugs | Etodolac (Etodolac), also known as Etodolac, indole pyranic acid, rodin, etc., the trade name is Lodine is a new generation of COX-2 highly selective non-steroidal anti-inflammatory drugs. This product is a weakly acidic drug, which is a molecular form at a lower pH value, which is beneficial to the absorption of the drug. This product is widely used in the clinical treatment of postoperative pain. It has analgesic and anti-inflammatory effects, which can relieve the symptoms of rheumatoid arthritis and osteoarthritis, delay the bone pathological changes caused by arthritis, and can selectively inhibit prostaglandin synthesis and anti-inflammatory at the inflammatory site. It is especially suitable for elderly patients. This product is white crystalline powder with melting point of 145~148 ℃. Etodolac was first developed by a subsidiary of AHP in the United States. It was successfully listed in the United Kingdom in 1985, and then listed in France, the United States, Germany, Japan and other countries. |
| mechanism of action | this product is a non-steroidal anti-inflammatory drug. Its effect is similar to that of aspirin. It selectively inhibits the biosynthesis of prostaglandins by blocking the activity of cyclooxygenase at the inflammatory site. The inhibition of gastric PGE2 is slight and transient, so the adverse reactions of gastrointestinal tract are small. Oral absorption is rapid, a single dose of 200 mg, Tmax is 1 h,Cmax is about 18.6 μg/ml. T1/2 is 7.4 h. PPB is 95%. The drug does not accumulate in the body. After being metabolized by tissue cells, the 60% of the dose is excreted within 24 hours. 74% is excreted through the kidneys with urine and 19% with feces., This product can reduce the incidence and severity of bone and joint damage, and can reverse the progression of the disease. Current research shows that this product has no teratogenic effect in animal tests, and has little effect on fertility and general reproductive function. |
| pharmacokinetics | at present, according to foreign studies, the drug is well absorbed when taken orally, there is no obvious first-pass effect, and the systemic bioavailability reaches 80% or more. When the drug is administered within 600mg every 12 hours, the area under the blood concentration-time curve is proportional to the dose. More than 99% of etodonac is bound to plasma protein, and the free part is less than 1%. A single dose of 200-600mg was administered, and its average peak plasma concentration (Cmax) was in the range of 14±4-37±9 μg/ml within 80±30 minutes. The mean plasma clearance was 47(± 16)ml/hr/kg and the clearance half-life was 7.3(± 4.0) hours. Etodonac is metabolized by the liver, and the 16% dose is excreted in feces. For this product, the dosage is usually not determined according to body weight, but when recommending the dosage, a certain reference is made according to body weight. |
| Synthetic route | Etodonate ester is first prepared, then hydrolyzed, acidified, organic phase crystallized, and toluene (or benzene)-petroleum ether refined. Therefore, it can be used as raw materials for industrial 7-ethylchromoammonia alcohol and ethyl propionyl acetate, first synthesize ethyl etodulic acid, and directly prepare crude etodulic acid through hydrolysis and aqueous acidification, and then use isopropanol-water Recrystallization to obtain the fine products of etodulic acid. Fig. 1 shows the synthetic route of etodac |
| usage and dosage | this product has different dosage for different purposes, as follows: 1. for pain relief: the recommended dosage for acute pain is 0.2-0.4g, once every 8 hours, and the maximum daily dosage is not more than 1.2g. For those weighing less than 60kg, the maximum daily dose should not exceed 20mg/kg body weight. Etodonac still has analgesic effects in some patients. 2. For chronic diseases: such as osteoarthritis and rheumatoid arthritis: the recommended dose is 0.4-1.2g per day, taken orally in divided doses, the maximum daily dose should not exceed 1.2g, and the maximum daily dose should not exceed 20mg/kg body weight for those weighing more than 60kg. The dose of etodonac is less than 0.4g per day, taken orally in divided doses, or 0.4g or 0.6g per night, which has certain curative effect in some patients. |
| adverse reactions | allergic symptoms such as rash, eczema, pruritus, erythema, etc. are occasionally seen; nausea, diarrhea, upper abdominal pain, heartburn, dyspepsia, abdominal distension, abdominal pain, gastrointestinal cramps, constipation and vomiting are seen in gastrointestinal tract; headache, dizziness, drowsiness, insomnia, nervousness, anxiety, depression, general malaise, fatigue, weakness, frequent urination, palpitations, edema or tinnitus can be seen in the central nervous system and other systems. Rare ALT, AST, BUN rise, hemoglobin, white blood cells, red blood cells, thrombocytopenia. (2016-01-24) |
| precautions | the safety of medication for pregnant and lactating women has not yet been determined and should be used with caution. It is not suitable for women with the first 3 months of pregnancy. People who are allergic to this product, patients who are allergic to aspirin and other NSAIDs, and patients with active peptic ulcer are contraindicated. People with a history of digestive tract including peptic ulcer should be closely monitored, and the drug should be stopped immediately when peptic ulcer occurs. Although this product has no direct effect on platelets, it inhibits prostaglandin biosynthesis to some extent and interferes with platelet function. Platelet function should be carefully observed. Patients with liver and kidney insufficiency can interfere with the elimination of drugs, so possible side effects should be observed and the drug dose should be adjusted as needed. |
| use | indole acetic acid non-steroidal anti-inflammatory drugs have analgesic and anti-inflammatory effects. It can selectively inhibit prostaglandin synthesis and anti-inflammatory at the inflammatory site. Absorption is rapid and there is no sign of accidental accumulation of drugs. It is used to treat rheumatoid arthritis, rheumatoid arthritis, osteoarthritis and postoperative pain relief. It is a drug suitable for the treatment of elderly patients. used as anti-inflammatory analgesic |
| Production method | o-ethylaniline reacts with trichloroacetaldehyde hydrate and hydroxylamine to form oxime at the same time of acylation, and then cyclize under sulfuric acid catalysis, and reduce with lithium aluminum hydride to generate indole derivatives, react with oxalyl chloride and ethanol to introduce 1, 2-dicarbonyl side chains at the 3 position, lithium aluminum hydride is reduced to hydroxyethyl, and ethyl propionyl acetate is condensed and cyclized, and finally hydrolyzed. |
Last Update：2024-04-09 02:00:08
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View History
41340-25-4
C.I. 14010
Sephadex LH-20
NAPTHOL RED FGR
C.I. Disperse Red 135
capreomycin
DISODIUM METHYL ARSONATE HYDRATE
usafth-3
CS-2314
COUMARINOL
C.I. 14010
Sephadex LH-20
NAPTHOL RED FGR
C.I. Disperse Red 135
capreomycin
DISODIUM METHYL ARSONATE HYDRATE
usafth-3
CS-2314
COUMARINOL