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CAS No.: 53164-05-9

Acemetacin is a non-steroidal anti-inflammatory drug and a glycolic acid ester of indometacin that is a cyclooxygenase inhibitor.

Synonyms: TVX 1322

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Quality Control of [ 53164-05-9 ] Purity: 98% SDS Specification

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Product Details of [ 53164-05-9 ]

CAS No. :	53164-05-9
Formula :	C₂₁H₁₈ClNO₆
M.W :	415.82
Synonyms :	TVX 1322
MDL No. :	MFCD00151473
InChI Key :	FSQKKOOTNAMONP-UHFFFAOYSA-N
Pubchem ID :	1981

Safety of [ 53164-05-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H300-H310-H330
Precautionary Statements:	P260-P264-P280-P284-P301+P310-P302+P350
Class:	6.1
UN#:	2811
Packing Group:	Ⅱ

Calculated chemistry of [ 53164-05-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	29
Num. arom. heavy atoms	15
Fraction Csp3	0.19
Num. rotatable bonds	8
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	107.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	94.83 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.88
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.47
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.86
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.8
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.44

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.91
Solubility	0.00509 mg/ml ; 0.0000122 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.89
Solubility	0.000535 mg/ml ; 0.00000129 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.83
Solubility	0.000608 mg/ml ; 0.00000146 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.86 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<3.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.89

Application In Synthesis [ 53164-05-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 53164-05-9 ]

[ 53164-05-9 ] Synthesis Path-Downstream 1~24

1
[ 53164-05-9 ]
2-(4-Chlorphenyl)-6-methoxy-4H-3.1-benzoxazinon-4 [ No CAS ]
N-(4-Chlor-benzoyl)-5-methoxy-anthranilsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-essigsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-acetoxy-essigsaeure [ No CAS ]

Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 127 - 134

2
[ 53164-05-9 ]
2-Acetyl-N-(4-chlor-benzoyl)-4-methoxy-anilin [ No CAS ]
N-(4-Chlor-benzoyl)-5-methoxy-anthranilsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-essigsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-acetoxy-essigsaeure [ No CAS ]

Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 127 - 134

3
[ 53164-04-8 ]
[ 53164-05-9 ]

Yield	Reaction Conditions	Operation in experiment
97.8%	With aluminum (III) chloride; In dichloromethane; N,N-dimethyl-formamide; at 80℃; for 24.0h;	a synthetic method of acemetacin, the steps of which areA. 100 g (0.198 mol) of acesulfame benzyl ester was dissolved in 400 mL of dichloromethane, and then 250 mL of N,N-dimethylaniline was added to obtain a solution A.B. 100 mL of dichloromethane was added to 79.2 g (0.594 mol of 1) of A1C13, and solution A was slowly added at zero.C. After the addition is completed, the reaction is raised to room temperature for 55 or 58 or 60 or 63 or 65 minutes. After the reaction is completed, the reaction mixture is poured into ice water, stirred for 28 or 29 or 30 or 31 or 32 minutes, and then filtered to obtain a crude product. acematecinD. The crude acemetacin obtained in the step C is recrystallized from acetone and water (volume ratio of 2:1), decolorized by adding activated carbon, and the crystals are dried at 80 C for 24 hours to obtain 80.4 g of pure Asi. Mesin, the yield is 97.8%. The purity was determined by HPLC to be greater than 99.8%.The other steps are the same as in the first embodiment.

Reference： [1]Patent: CN108440374,2018,A .Location in patent: Paragraph 0023-0028; 0030-0035; 0037-0042; 0044-0049; 0051-0
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 3348 - 3353
[3]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 1314 - 1325

Yield	Reaction Conditions	Operation in experiment
97.1%		EXAMPLE 5 The t-butyl ester of acemetacin (201 mg) was dissolved in 3.5 ml of formic acid and the resultant solution was stirred at room temperature for 3 hours. Formic acid was caused to evaporate under reduced pressure. The residue was taken up in 400 ml of a 1:5 liquid mixture of acetone and benzene and insoluble material was removed by filtration. The solvent was then driven off from the filtrate. The residue was recrystallized from benzene to obtain 172 mg of acemetacin as pale yellowish crystals (yield: 97.1%).
86-91%		EXAMPLE 4 Acemetacin 0.003 mole of tetrakis-triphenylphosphine-palladium-(O) is added to 0.03 mole of acemetacin allyl ester in 50 ml of tetrahydrofuran, under nitrogen. 0.3 mole of piperidine is added dropwise at 20-25 C., with stirring, and stirring is then continued for 2 hours at room temperature (check by thin layer chromatography). 200 ml of half-concentrated hydrochloric acid are added dropwise with cooling, the phases are separated off, the aqueous phase is extracted twice with methylene chloride and the combined organic phases are evaporated in vacuo. The residue is recrystallized from toluene. Yield: 86-91% of theory; melting point: 150 C.
		EXAMPLE 5 (ACEMETACIN) 0.4 g of p-toluenesulphonic acid is added to 9.6 g of tert.-butyl ester of acemetacin according to example 1 in 30 ml of acetic acid, and the mixture is stirred at 100 C. for 4 to 5 hours. After the mixture has cooled down to room temperature, 50 ml of water are added. Acemetacin precipitates, is filtered off with suction and is recrystallized from acetone/water. Yield: 8.0 g=90.6% of theory of pure product.

		EXAMPLE 14 (solution) Polyisobutylene of molecular weight 400,000: 40.00 g Thinly liquid paraffin: 50.00 g Polyterpene resin from alpha-pinene: 10.00 g Acemetacin: 17.65 g Release: about 12% after 6 hours.
		Preparation of acemetacin Splitting of the protective group of acemetacin derivative according to the invention The 4-methoxybenzyl ester (5.35 g=0.01 mol) prepared as described above is dissolved in 5.4 g (0.05 mol) of anisole, and 0.73 g (0.02 mol) of glacial acetic acid/HCl (75.9 mg of HCl/ml) is added while stirring and in the absence of moisture. After a reaction time of 5 hours, the conversion is quantitative. 1.8 g (0.023 mol) of ammonium acetate are added to the reaction mixture, the mixture is stirred for 10 minutes, 20 ml of water are added, and stirring is continued for a further 10 minutes. Thereafter, the mixture is extracted with 40 ml of toluene, the organic phase is washed neutral and dried over Na2 SO4, and the solvent is distilled off. The residue is stirred throughly with 200 ml of petroleum ether. Crystals are formed, and are filtered off under suction, washed with petroleum ether and dried. The substance is purified by dissolving it in methylene chloride, adding 80 ml of carbon tetrachloride and distilling off the methylene chloride at 70 C. Acemetacin crystallises at room temperature. Recrystallisation from toluene gave the pure substance in a yield of 2.8 g=67.3% of theory, with a melting point of 150-151 C.
		EXAMPLE 7 Acemetacin 31.9 g of acemetacin allyl ester, 100 ml of toluene, 2.3 g of triphenylphosphine and 0.75 g of palladium on charcoal (5% strength) are taken as an initial charge, under nitrogen. 11.9 g of piperidine are added dropwise, with stirring, and the mixture is then stirred for a further 3 hours at 90 C. It is filtered hot and the catalyst is rinsed with hot toluene. The filtrate is evaporated, the residue is taken up in methylene chloride (about 300 ml) and this solution is washed with half-concentrated hydrochloric acid (100 ml) and then with water. After removal of the solvent in vacuo, the residue is recrystallized from toluene. Yield: 27.3 g=94% of theory; melting point: 150

6
[ 53164-05-9 ]
5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester [ No CAS ]
[ 74-11-3 ]

Reference： [1]Journal of Pharmaceutical Sciences,2001,vol. 90,p. 298 - 309
[2]Journal of Pharmaceutical Sciences,2001,vol. 90,p. 298 - 309
[3]Journal of Organic Chemistry,2006,vol. 71,p. 3718 - 3726

7
[ 53164-05-9 ]
[ 2882-15-7 ]
[ 53-86-1 ]
5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester [ No CAS ]
[ 74-11-3 ]

Reference： [1]Carbohydrate research,2002,vol. 337,p. 1387 - 1395

8
[ 53164-05-9 ]
[ 1613-88-3 ]