Welcome to LookChem.com Sign In|Join Free

CAS

  • or

41340-25-4

Post Buying Request

41340-25-4 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

41340-25-4 Usage

Non-steroidal anti-inflammatory drugs

Etodolac (trade name: Lodine), also known as ethoxycolic acid, indoleacetic acid, and rhododine, is a new generation of non-steroidal anti-inflammatory drug highly selective to COX-2. This product is a weak acidic drug, existing in a molecular form under the condition of lower pH value which is conducive to drug absorption. This product is widely used in the clinical treatment of postoperative pain. It has analgesic and anti-inflammatory effects, being able to relieve the symptoms of rheumatoid arthritis and osteoarthritis, delaying the pathological changes caused by arthritis. In inflammatory site, it can selectivity inhibit the prostaglandin synthesis to exert its anti-inflammatory effect. It is especially applicable to the elderly patients. This product appears as white crystalline powder with the melting point of 145~148 ℃. Etodolac was first developed by a subsidiary of AHP in the United States. It had been successfully listed in the UK in 1985, followed by being listed in France, the United States, Germany, Japan and other countries.

NSAID

Etodolac (Etodolac), also known as indole acetic acid, indole acetic acid pyran and rodin etc, and the tradename is Lodine, a new generation of non-steroidal anti-inflammatory drugs which has a high selective of COX-2. This product is a kind of weak acid drug and has the form of molecular at lower pH values which is conducive to drug absorption. This product is widely used in the clinical treatment of pain after surgery, has a good effect of analgesic and anti-inflammatory that can relieve symptoms of rheumatoid arthritis and osteoarthritis, delay the bone pathology caused by arthritis and synthesis the prostaglandin at the sites of inflammation selectively. The product apply to the elderly patients. The etodolac is white crystalline powder, has the melting point of 145~148 ℃. Etodolac was first developed by the subsidiary of AHP and successfully listed in the UK in 1985. The product have been listed in many countries like France, the United States, Germany and Japan etc.

Chemical properties

It is crystallized by the hexane-chloroform, with the melting point of 145~148 ℃.

Mechanism

This product is non-steroidal anti-inflammatory drugs. Its effects is similar to aspirin. It can inactivated the cyclooxygenase at the sites of inflammation thereby inhibit the biosynthesis of prostaglandins selectively.The product has little side effect for the gastrointestinal since its inhibition of PGE2 is mild and transient. It can be quickly absorbed by oral with a single dose of 200mg.It has the Tmax of 1 h, Cmax of 18.6 μg/ml, T1/2 of 7.4 h and PPB of 95%. The product do not accumulate in the body and 60% of the dose can be excreted after 24hr by the cellular metabolism, among the them, 74% is excreted in urine by the kidneys and 19% in feces. The product can reduce the incidence and damage of bone and joint and improce the condition of patients. The current study shows that the product has no teratogenic effect in? animal experiments and has little impact on fertility and reproductive function.

Pharmacokinetics

Different sources of media describe the Pharmacokinetics of 41340-25-4 differently. You can refer to the following data:
1. According to the current study abroad, the drug is well absorbed orally and has the the systemic bioavailability of 80% or more. The dosage should be within 600mg every 12 hours, the area under the curve of plasma concentration-time is in direct proportion to the dosage. More than 99% of etodolac can combine with the plasma protein, the free fraction is less than 1%. The single dose is at the range of 200-600mg and the the average peak plasma concentration (Cmax) within 80 ± 30 the minute is in the scope of 14 ± 4-37 ± 9μg/ml range. The average plasma clearance rate is 47 (± 16) ml/hr/kg and the elimination half-life is 7.3 (± 4.0) hours. Etodolac can be metabolized by the liver and 16% of the dose excreted by the faeces. The dose of the product is not determined by the weight, but the recommended dosage can use the body weight as reference.
2. Etodolac is rapidly absorbed following oral administration, with maximum serum levels being achieved within 1 to 2 hours, and it is highly bound to plasma proteins (99%) with pKa 4.7. The penetration of etodolac into synovial fluid is greater than or equal to that of tolmetin, piroxicam, or ibuprofen. Only diclofenac appears to provide greater penetration.

Uses

Different sources of media describe the Uses of 41340-25-4 differently. You can refer to the following data:
1. (1) The non-steroidal anti-inflammatory drugs of Indole acetic acid class has the analgesic and anti-inflammatory effect. It can inhibit prostaglandin synthesis at the site of inflammation selectively. The product can be absorbed rapidly and has no signs of drug savings. It can be used for the treatment of rheumatoid arthritis, rheumatoid arthritis, osteoarthritis and postoperative pain relief etc. It is a medicament that suitable for elderly patients. (2) Using as anti-inflammatory drugs.
2. betaadrenergic agonist
3. Etodolac is a non-steroidal anti-inflammatory drug (NSAID) that selectively inhibits cyclooxygenase-2 (COX-2). Etodolac displays anti-inflammatory effects in both adjuvant arthritic and normal rats. E todolac is an anti-inflammatory; analgesic.
4. For acute and long-term management of signs and symptoms of osteoarthritis and rheumatoid arthritis, as well as for the management of pain.
5. Etodolac is a non-steroidal anti-inflammatory drug (NSAID). Product Data Sheet

Used in Particular Diseases

Acute Gouty Arthritis: Dosage and Frequency: 300 mg twice daily

Production method

The acylation reaction of o-ethyl aniline, chloral hydrate and hydroxylamine can form the oxime, after the cyclization by using the sulfuric as the catalyst and the reduction by lithium aluminium hydride , oxime can turn into the indole derivatives. The reaction with the oxalyl chloride and ethanol can bring 1,2-carbonyl side chain in 3 bit and then be restored to hydroxyethyl by lithium aluminium hydride, after the condensation , cyclization with? ethyl propionylacetate and hydrolyzation. The final product-etodolac can be obtained.

Synthetic routes

The etodolac ester should be prepared at first, and the final product can be obtained after the hydrolyzation, acidification, crystallization of the organic phase and rectification by the toluene (or benzene)-refined petroleum ether. Using the industrial 7-Ethyl tryptophol and? ethyl propionylacetateas as the raw material to synthesis the etodolac ethyl, and get the crude etodolac by hydrolyzation and acidification. The refined etodolac can be obtained by recrystallization with isopropanol-water. Figure 1 shows the synthetic route of etodolac

Usage and dosage

The usage are various with the different applications, as follows: 1. For pain: The recommended dose is 0.2-0.4g every 8 hours for acute pain , the maximum daily dose should not exceed 1.2g. The maximum daily dose for the patients who weight under 60kg should not exceed 20mg per kilogram of body weight. The etodolac still has analgesic effect on some patients. 2. For chronic diseases such as osteoarthritis and rheumatoid arthritis: The recommended dose of daily is 0.4-1.2g in divided doses orally, the maximum daily dose should not exceed 1.2g. The maximum daily dose for the patients who weight over 60kg should not exceed 20mg per kilogram of body weight. The daily dose for etodolac is 0.4g or less in divided doses.It has a certain effect for some patients.

Adverse drug reaction

The product may cause some side effect like the allergic symptoms include the rash, eczema, itching and redness etc; nausea, diarrhea, abdominal pain, heartburn, indigestion, bloating, abdominal pain, stomach cramps, constipation and vomiting for the gastrointestinal system; headache , dizziness, drowsiness, insomnia, nervousness, anxiety, depression, general malaise, fatigue, weakness, frequent urination, palpitations, edema and tinnitus for the central nervous system. The side effect like the increasing of the ALT, AST and BUN , the decline of the hemoglobin, white blood cells, red blood cells and thrombocytopenia are rarely. The mechanism of action of Etodolac, the route of synthesis, adverse reactions, etc., were edited by Baoquan, lookchem. (2016-11-18)

Attention

The drug security of pregnant and lactating women has not been established and should be used with caution. The first three months of pregnancy should not use this drug. The patients who allergic to aspirin and other NSAIDs or have the active peptic ulcer can not use this product disabled. The patients with the history of gastrointestinal disease include peptic ulcer should be closely monitored and be discontinued immediately when the peptic ulcer come. Even it has no direct effect on platelets, but the inhibition of prostaglandin biosynthesis can interfere the platelet function in some ways. The patients who has liver and kidney dysfunction sjpi;d adjust the dose according to need.

Description

Etodolac (etodolic acid) is a non-steroidal antiinflammatory/analgesic agent useful in the treatment of various inflammatory conditions, including rheumatoid and osteoarthritis.

Chemical Properties

Crystalline Solid

Originator

Ayerst (USA)

Definition

ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active.

Indications

Etodolac (Lodine) is indicated for the treatment of osteoarthritis, rheumatoid arthritis, and acute pain. It inhibits COX-2 with slightly more selectivity than COX-1 and therefore produces less GI toxicity than many other NSAIDs. Common adverse effects include skin rashes and CNS effects.

Brand name

Lodine(Wyeth).

General Description

Etodolac (Lodine, Ultradol), a chiral, COX-2 selectiveNSAID drug that is marketed as a racemate, possesses an indolering as the aryl portion of this group of NSAID drugs.It shares many similar properties of this group and is indicatedfor short- and long-term management of pain and OA.Similar to ketorolac, etodolac exhibits several uniqueenantioselective pharmacokinetic properties. For example,the “inactive” (R)-enantiomer has approximately a 10-foldhigher plasma concentration than the active (S)-enantiomer.Furthermore, the active (S)-enantiomer is less protein boundthan its (R)-enantiomer and therefore has a very large volumeof distribution. It is well absorbed with an elimination halflifeof 6 to 8 hours. Etodolac is extensively metabolized intothree major inactive metabolites, 6-hydroxy etodolac (via aromatichydroxylation), 7-hydroxy-etodolac (via aromatic hydroxylation),and 8-(1'-hydroxylethyl) etodolac (via benzylichydroxylation), which are eliminated as the correspondingether glucuronides. Its unstable, acyl glucuronide, however,is subject to enterohepatic circulation and reactivation tothe parent drug, similar to other NSAIDS in this class.

Biological Activity

Non-steroidal anti-inflammatory drug (NSAID) that selectively inhibits cyclooxygenase-2 (COX-2) (IC 50 values are 53 and >100 μ M for COX-2 and COX-1 respectively). Displays anti-inflammatory effects in both adjuvant arthritic and normal rats.

Biochem/physiol Actions

Non-steroidal anti-inflammatory compound that is a non-selective inhibitor of COX-1 and COX-2.

Mechanism of action

The primary mechanism of action appears to be inhibition of the biosynthesis of prostaglandins at the cyclooxygenase step, with no inhibition of the lipoxygenase system. Etodolac, however, possesses a more favorable ratio of inhibition of prostaglandin biosynthesis in human rheumatoid synoviocytes and chondrocytes than by cultured human gastric mucosal cells compared to ibuprofen, indomethacin, naproxen, diclofenac, and piroxicam.

Clinical Use

Etodolac is promoted as the first of a new chemical class of anti-inflammatory drugs, the pyranocarboxylic acids. Although not strictly an arylacetic acid derivative (because there is a two-carbon atom separation between the carboxylic acid function and the hetero-aromatic ring), it still possesses structural characteristics similar to those of the heteroarylacetic acids and is classified here. It was introduced in the United States in 1991 for acute and long-term use in the management of osteoarthritis and as an analgetic. It also possesses antipyretic activity. Etodolac is marketed as a racemic mixture, although only the S-(+)-enantiomer possesses anti-inflammatory activity in animal models. Etodolac also displays a high degree of enantioselectivity in its inhibitory effects on the arachidonic acid cyclooxygenase system.

Veterinary Drugs and Treatments

Etodolac is labeled for the management of pain and inflammation associated with osteoarthritis in dogs. It may find uses, however, for a variety of conditions where pain and/or inflammation should be treated.

Drug interactions

Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect, increased risk of nephrotoxicity and hyperkalaemiaAnalgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac, increased risk of side effects and haemorrhage.Antibacterials: possibly increased risk of convulsions with quinolones.Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparin, dabigatran and edoxaban - avoid long term use with edoxaban.Antidepressants: increased risk of bleeding with SSRIs and venlafaxine.Antidiabetic agents: effects of sulphonylureas enhanced.Antiepileptics: possibly increased phenytoin concentration.Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavirCiclosporin: may potentiate nephrotoxicityCytotoxic agents: reduced excretion of methotrexate; increased risk of bleeding with erlotinib.Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics.Lithium: excretion decreased.Pentoxifylline: increased risk of bleedingTacrolimus: increased risk of nephrotoxicity.

Metabolism

Etodolac is metabolized to three hydroxylated metabolites and to glucuronide conjugates, none of which possesses important pharmacological activity. Metabolism appears to be the same in the elderly as in the general population, so no dosage adjustment appears necessary. Etodolac is indicated for the management of the signs and symptoms of osteoarthritis and for the management of pain.

references

[1] kumagai k1, kubo m, imai s, toyoda f, maeda t, okumura n, matsuura h, matsusue y.the cox-2 selective blocker etodolac inhibits tnfα-induced apoptosis in isolated rabbit articular chondrocytes. int j mol sci. 2013 sep 30;14(10):19705-15. [2] hakozaki m1, hojo h, kikuchi s, abe m. etodolac, a selective cyclooxygenase-2 inhibitor, induces apoptosis by activating caspases in human malignant rhabdoid tumor cells (frtk-1). oncol rep. 2007 jan;17(1):169-73.

Check Digit Verification of cas no

The CAS Registry Mumber 41340-25-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,3,4 and 0 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 41340-25:
(7*4)+(6*1)+(5*3)+(4*4)+(3*0)+(2*2)+(1*5)=74
74 % 10 = 4
So 41340-25-4 is a valid CAS Registry Number.
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)

41340-25-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (E0858)  Etodolac  >98.0%(HPLC)(T)

  • 41340-25-4

  • 5g

  • 550.00CNY

  • Detail
  • TCI America

  • (E0858)  Etodolac  >98.0%(HPLC)(T)

  • 41340-25-4

  • 25g

  • 1,790.00CNY

  • Detail
  • Sigma-Aldrich

  • (E2470000)  Etodolac  European Pharmacopoeia (EP) Reference Standard

  • 41340-25-4

  • E2470000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000768)  Etodolac for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 41340-25-4

  • Y0000768

  • 1,880.19CNY

  • Detail
  • USP

  • (1268706)  Etodolac  United States Pharmacopeia (USP) Reference Standard

  • 41340-25-4

  • 1268706-400MG

  • 4,326.66CNY

  • Detail
  • Sigma

  • (E0516)  Etodolac  

  • 41340-25-4

  • E0516-10MG

  • 912.60CNY

  • Detail
  • Sigma

  • (E0516)  Etodolac  

  • 41340-25-4

  • E0516-50MG

  • 3,361.41CNY

  • Detail

41340-25-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name etodolac

1.2 Other means of identification

Product number -
Other names Hypen

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:41340-25-4 SDS

41340-25-4Synthetic route

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol
41340-36-7

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol

ethyl propanoylacetate
4949-44-4

ethyl propanoylacetate

etodolac
41340-25-4

etodolac

Conditions
ConditionsYield
(i) TsOH, benzene, (ii) aq. NaOH, EtOH; Multistep reaction;
2,2-Dimethyl-propionic acid 2-(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetoxymethyl ester

2,2-Dimethyl-propionic acid 2-(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetoxymethyl ester

A

2,2-Dimethyl-propionic acid 2-((S)-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetoxymethyl ester

2,2-Dimethyl-propionic acid 2-((S)-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetoxymethyl ester

B

etodolac
41340-25-4

etodolac

Conditions
ConditionsYield
With Lipase QL In di-isopropyl ether; water for 192h; Product distribution; Ambient temperature; various lipase enzymes;
(R)-etodolac
87226-41-3

(R)-etodolac

etodolac
41340-25-4

etodolac

Conditions
ConditionsYield
With tin(IV) chloride In tetrahydrofuran; dichloromethane for 4h; Heating / reflux;
sulfuric acid In isopropyl alcohol at 20℃; for 23h; Product distribution / selectivity;
(R)-etodolac
87226-41-3

(R)-etodolac

(S)-etodolac
87249-11-4

(S)-etodolac

etodolac
41340-25-4

etodolac

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 20℃; for 2h;
Stage #1: (R)-etodolac; (S)-etodolac In dichloromethane at 20℃; for 2h;
Stage #2: With sodium hydroxide; formic acid at 0℃; for 1h; pH=5;
(S)-etodolac
87249-11-4

(S)-etodolac

etodolac
41340-25-4

etodolac

Conditions
ConditionsYield
sulfuric acid In isopropyl alcohol at 20℃; for 4 - 18h; Product distribution / selectivity;
boron trifluoride diethyl etherate In isopropyl alcohol at 20℃; for 15h; Product distribution / selectivity;
7-ethyl-2-(1H-indol-3-yl)ethan-1-ol
41340-36-7

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol

methyl propanoyl acetate
30414-53-0

methyl propanoyl acetate

etodolac
41340-25-4

etodolac

Conditions
ConditionsYield
With sulfuric acid In methanol Pictet-Spengler Synthesis;
etodolac
41340-25-4

etodolac

(+/-)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)ethanol
200880-25-7

(+/-)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)ethanol

Conditions
ConditionsYield
With LiAlH4 In tetrahydrofuran; hexane; ethyl acetate98%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h;92%
N-tert-butoxycarbonyl-3-aminopropanol
58885-58-8

N-tert-butoxycarbonyl-3-aminopropanol

etodolac
41340-25-4

etodolac

Boc-aminopropanol-etodolac

Boc-aminopropanol-etodolac

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;96%
Magnolol
528-43-8

Magnolol

etodolac
41340-25-4

etodolac

5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

5,5'-diallyl-2'-hydroxy-[1,1'-biphenyl]-2-yl-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;90%
With dmap In dichloromethane at 25 - 30℃;90%
acetic acid
64-19-7

acetic acid

etodolac
41340-25-4

etodolac

2-(dimethylamino)ethyl 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetamide acetate

2-(dimethylamino)ethyl 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetamide acetate

Conditions
ConditionsYield
Stage #1: N,N-dimethylethylenediamine; etodolac With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In acetonitrile at 20℃; for 3h;
Stage #2: acetic acid In ethyl acetate
89.4%
2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

etodolac
41340-25-4

etodolac

2,2,2-trichloroethyl ((1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)methyl)carbamate

2,2,2-trichloroethyl ((1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)methyl)carbamate

Conditions
ConditionsYield
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Schlenk technique; Sealed tube;86%
methanol
67-56-1

methanol

etodolac
41340-25-4

etodolac

methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)-indole-1-acetate

methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)-indole-1-acetate

Conditions
ConditionsYield
With sulfuric acid for 8h; Reflux;85%
With sulfuric acid for 3h; Reflux;66%
With sulfuric acid
With sulfuric acid for 3h; Reflux;
3-hydroxypropyl selenocyanate
115423-27-3

3-hydroxypropyl selenocyanate

etodolac
41340-25-4

etodolac

3-selenocyanatopropyl 2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

3-selenocyanatopropyl 2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Conditions
ConditionsYield
Stage #1: etodolac In N,N-dimethyl-formamide at 25℃; for 0.5h;
Stage #2: 3-hydroxypropyl selenocyanate In N,N-dimethyl-formamide at 25℃; for 16h;
85%
thymol
89-83-8

thymol

etodolac
41340-25-4

etodolac

2-isopropyl-5-methylphenyl 2-(1,8‑diethyl-4,9-dihydro-3Hpyrano[3,4-b]indol-1-yl)acetate

2-isopropyl-5-methylphenyl 2-(1,8‑diethyl-4,9-dihydro-3Hpyrano[3,4-b]indol-1-yl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 72h; Steglich Esterification;83.5%
etodolac
41340-25-4

etodolac

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetamide
591752-31-7

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetamide

Conditions
ConditionsYield
Stage #1: etodolac With oxalyl dichloride at 20℃;
Stage #2: With ammonium hydroxide
82.5%
curcumin
458-37-7

curcumin

etodolac
41340-25-4

etodolac

((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) bis(2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate)

((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) bis(2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate)

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;80%
curcumin
458-37-7

curcumin

etodolac
41340-25-4

etodolac

A

C36H35NO8

C36H35NO8

B

C51H50N2O10

C51H50N2O10

Conditions
ConditionsYield
With dmap In dichloromethane at 25 - 30℃;A 56%
B 80%
Magnolol
528-43-8

Magnolol

etodolac
41340-25-4

etodolac

5,5'-diallyl-[1,1'-biphenyl]-2,2'-diyl-bis(2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate)

5,5'-diallyl-[1,1'-biphenyl]-2,2'-diyl-bis(2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate)

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;78%
With dmap In dichloromethane at 25 - 30℃;78%
benzyl bromide
100-39-0

benzyl bromide

etodolac
41340-25-4

etodolac

2-(9-benzyl-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid

2-(9-benzyl-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 50℃; for 2h;73%
1-selenocyano-2-ethylamine hydrobromide

1-selenocyano-2-ethylamine hydrobromide

etodolac
41340-25-4

etodolac

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-N-(2-selenocyanatoethyl)acetamide

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-N-(2-selenocyanatoethyl)acetamide

Conditions
ConditionsYield
Stage #1: etodolac With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 25℃; for 0.5h;
Stage #2: 1-selenocyano-2-ethylamine hydrobromide In dichloromethane; N,N-dimethyl-formamide at 25℃; for 16h;
72%
2-azido-1-phenylethan-1-one
1816-88-2

2-azido-1-phenylethan-1-one

etodolac
41340-25-4

etodolac

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-N-(2-oxo-2-phenylethyl)acetamide

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-N-(2-oxo-2-phenylethyl)acetamide

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 110℃; for 10h; Sealed tube;72%
2-selenocyanatopropanamine hydrobromide

2-selenocyanatopropanamine hydrobromide

etodolac
41340-25-4

etodolac

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-N-(3-selenocyanatopropyl)acetamide

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-N-(3-selenocyanatopropyl)acetamide

Conditions
ConditionsYield
Stage #1: etodolac With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere;
Stage #2: 2-selenocyanatopropanamine hydrobromide In dichloromethane; N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;
65%
Stage #1: etodolac With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 25℃; for 0.5h;
Stage #2: 2-selenocyanatopropanamine hydrobromide In dichloromethane; N,N-dimethyl-formamide at 25℃; for 16h;
60%
etodolac
41340-25-4

etodolac

C17H23NO2

C17H23NO2

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere;59%
{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)
38780-40-4, 52691-24-4, 61848-70-2, 61848-66-6, 61848-62-2

{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)

etodolac
41340-25-4

etodolac

C23H34ClN3O3Pt

C23H34ClN3O3Pt

Conditions
ConditionsYield
With sodium carbonate; silver nitrate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;52%
dihydrocapsaicin
19408-84-5

dihydrocapsaicin

etodolac
41340-25-4

etodolac

(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 2-methoxy-4-[(8-methyl-nonanoylamino)-methyl]-phenyl ester
1224429-03-1

(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 2-methoxy-4-[(8-methyl-nonanoylamino)-methyl]-phenyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30 - 35℃;49.6%
Propargylamine
2450-71-7

Propargylamine

etodolac
41340-25-4

etodolac

C20H24N2O2

C20H24N2O2

Conditions
ConditionsYield
Stage #1: etodolac With triethylamine In tetrahydrofuran at -50℃; for 1h; Inert atmosphere;
Stage #2: Propargylamine With isobutyl chloroformate In tetrahydrofuran at -50 - 20℃; for 13h; Inert atmosphere;
46.8%
ammonium hydroxide
1336-21-6

ammonium hydroxide

oxalyl dichloride
79-37-8

oxalyl dichloride

etodolac
41340-25-4

etodolac

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetamide
591752-31-7

2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetamide

Conditions
ConditionsYield
N,N-dimethyl-formamide In tetrahydrofuran; hexane; dichloromethane; ethyl acetate35%
potassium ethyl methylmalonate
103362-70-5

potassium ethyl methylmalonate

etodolac
41340-25-4

etodolac

C19H23NO4

C19H23NO4

Conditions
ConditionsYield
Stage #1: etodolac With 1,1'-carbonyldiimidazole Inert atmosphere;
Stage #2: potassium ethyl methylmalonate With magnesium chloride Inert atmosphere;
35%
capsaicin
404-86-4

capsaicin

etodolac
41340-25-4

etodolac

(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 2-methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenyl ester
1224429-01-9

(1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 2-methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30 - 35℃;30.2%
etodolac
41340-25-4

etodolac

A

1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid
111478-86-5

1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid

B

1,8-diethyl-4-hydroxy-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid

1,8-diethyl-4-hydroxy-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid

Conditions
ConditionsYield
With iodosylbenzene; Cl8TTPFe(III)Cl In dichloromethane at 20℃; for 2h;A 20%
B 25%
etodolac
41340-25-4

etodolac

methyl iodide
74-88-4

methyl iodide

A

3a,10-diethyl-5,6,6a,11-tetrahydro-6a-methylfuro<3',2'2,3>pyrano<3,4-b>indol-2(3H)-one
114737-77-8

3a,10-diethyl-5,6,6a,11-tetrahydro-6a-methylfuro<3',2'2,3>pyrano<3,4-b>indol-2(3H)-one

B

2-(1,8-diethyl-9-methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)acetic acid
114720-05-7

2-(1,8-diethyl-9-methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)acetic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 50℃; for 2h;A 20%
B 16%
etodolac
41340-25-4

etodolac

7-ethyl-2-(1-methylenepropyl)-1H-indole-3-ethanol

7-ethyl-2-(1-methylenepropyl)-1H-indole-3-ethanol

Conditions
ConditionsYield
In methanol for 72h; Heating; pH 6.0;20%
(OC-6-33)-(diammine)dichloridodihydroxidoplatinum(IV)
125074-46-6, 31246-62-5, 31246-63-6, 31246-66-9, 53261-25-9

(OC-6-33)-(diammine)dichloridodihydroxidoplatinum(IV)

etodolac
41340-25-4

etodolac

C34H46Cl2N4O6Pt

C34H46Cl2N4O6Pt

Conditions
ConditionsYield
With triethylamine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;19.5%
etodolac
41340-25-4

etodolac

A

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol
41340-36-7

7-ethyl-2-(1H-indol-3-yl)ethan-1-ol

B

7-ethyl-2-(1-methyl-1-propenyl)-1H-indole-3-ethanol

7-ethyl-2-(1-methyl-1-propenyl)-1H-indole-3-ethanol

C

7-ethyl-2-(1-methylenepropyl)-1H-indole-3-ethanol

7-ethyl-2-(1-methylenepropyl)-1H-indole-3-ethanol

D

1,8-diethyl-1-methyl-1,3,4,9-tetrahydropyrano-<3,4-b>indole

1,8-diethyl-1-methyl-1,3,4,9-tetrahydropyrano-<3,4-b>indole

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 85℃; for 18h; Product distribution; Rate constant; Thermodynamic data; Ea, ΔS<*>, mechanism of etodolac degradation in aqueous solutionsat various temperatures (75-905 deg C), time and pH, effect of pH and temperature, catalytic effect of buffer system;
etodolac
41340-25-4

etodolac

(+)-etodolac
87249-11-4

(+)-etodolac

41340-25-4Relevant articles and documents

HPLC monitoring of acid catalyzed conversion of 7-ethyltryptophol to methyl ester of etodolac

Habinovec, Iva,Car, Zeljka,Ribic, Rosana,Galic, Nives,Novak, Predrag,Mestrovic, Ernest,Tomic, Srdanka

, (2017/05/29)

Small scale experimental model for the preparation of methyl ester of etodolac, the key intermediate in the synthesis of nonsteroidal drug etodolac, is thoroughly investigated in order to define the key parameters needed for its large scale production. Ox

Method for the racemization of etodolic acid

-

Page 2, (2008/06/13)

A method for the resolution of etodolic acid by crystallization of its salt with optically active 1-phenylethylamine and subsequent recovery of the (R,S) etodolic acid from the mother liquors of crystallization by racemization and crystallization is described.

Enzymatic resolution of new anti-inflammatory drug etodolac

Mizuguchi, Eisaku,Itanami, Makiko,Achiwa, Kazuo

, p. 149 - 152 (2007/10/03)

Optically active etodolac (1) was easily prepared by lipase-catalyzed kinetic resolution. The unnecessary enantiomer as a by-product of the resolution could be racemized and was converted to a repeated substrate for the enzymatic reaction.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 41340-25-4