Co-crystallization of anti-inflammatory pharmaceutical contaminants and rare carboxylic acid–pyridine supramolecular synthon breakdown

CrystEngComm ◽  
2018 ◽  
Vol 20 (41) ◽  
pp. 6377-6381 ◽  
Author(s):  
Qixuan Zheng ◽  
Samantha L. Rood ◽  
Daniel K. Unruh ◽  
Kristin M. Hutchins
Keyword(s):  
Carboxylic Acid ◽  
Mefenamic Acid ◽  
Supramolecular Synthon ◽  
Pharmaceutical Contaminants ◽  
Anti Inflammatory

Co-crystallization of the pharmaceutical contaminants mefenamic acid and naproxen is reported; one co-crystal exhibits a rare carboxylic acid–pyridine synthon breakdown.

Design and Synthesis of Novel Ibuprofen Derivatives as Selective COX-2 inhibitors and potential anti-inflammatory agents: Evaluation of PGE2, TNF-α, IL-6 and histopathological study

2021 ◽  
Vol 17 ◽  
Author(s):  
Peter Amir Halim ◽  
Hala Bakr El-Nassan ◽  
Yara Sayed El-Dash
Keyword(s):  
Carboxylic Acid ◽  
Gastric Mucosa ◽  
Docking Simulation ◽  
Histopathological Study ◽  
Acid Moiety ◽  
Rat Serum ◽  
Tnf Α ◽  
Cox 2 ◽  
Anti Inflammatory

Background: The reported binding mode of ibuprofen in the COX-2 binding site indicated that the carboxylic group binds with Arg-120 and Tyr-355 at the entrance of the cyclooxygenase channel and does not extend into the pocket. This accounted for the non-selectivity of ibuprofen. Based on this fact, we assumed that extending the length of the carboxylic acid moiety in ibuprofen and adding more bulky rigid groups as well as bulky groups carrying H-bonding functions might increase the selectivity and reduce the side effects of ibuprofen while maintaining its analgesic and anti-inflammatory activities. Objective: In this work, four series of ibuprofen derivatives were designed and prepared. The compounds were designed by increasing the length of the carboxylate group along with the incorporation of large hydrophobic groups. Method: Four series of ibuprofen derivatives were synthesized starting from ibuprofen. Their chemical structure was confirmed by spectral data. All the compounds were tested for their COX inhibitory activity. Results : The best COX-2 activity and selectivity were obtained with compounds 5c and 5d, which were subjected to further in vivo testing (carrageenan-induced paw edema, rat serum PGE2, TNF- α and IL-6, hot plate latency test) to investigate their anti-inflammatory and analgesic activities as well as their effects on the gastric mucosa. The anti-inflammatory activity of both compounds was comparable to that of ibuprofen, diclofenac, and indomethacin. Both compounds suppressed the production of PGE2 as well as the rat serum concentrations of both TNF-α and IL-6. This potent anti-inflammatory and analgesic behavior was not accompanied by any effect on the gastric mucosa. Docking simulation studies of the two compounds explained the higher selectivity for the COX-2 enzyme. Conclusion: Potent and selective ibuprofen derivatives can be successively obtained by extending the length of the carboxylic acid moiety in ibuprofen and adding more bulky rigid groups as well as bulky groups with H-bonding functions.

scholarly journals Synthesis, Characterization and Acute Anti-inflammatory Evaluation of New Mefenamic Acid Derivatives Having 4-Thiazolidinone Nucleus

2019 ◽  
Vol 28 (1) ◽  
pp. 138-146
Author(s):  
Mustafa H. Ali Alsafi ◽  
Muthanna S. Farhan
Keyword(s):  
Side Effects ◽  
Mefenamic Acid ◽  
Paw Edema ◽  
Compound I ◽  
Reference Drug ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Derivatives Of ◽  
Cox 1 ◽  
Inflammatory Effect

Mefenamic acid (MA) is one of the non-steroidal anti-inflammatory drugs, it is widely used probably due to having both anti-inflammatory and analgesic activity, the main side effects of mefenamic acid include gastrointestinal tract (GIT) disturbance mainly diarrhea, peptic ulceration, and gastric bleeding. The analgesic effects of NSAIDs are probably linked to COX-2 inhibition, while COX-1 inhibition is the major cause of this classic adverse effects. Introduction of thiazolidinone may lead to the increase in the bulkiness leads to the preferential inhibition of COX-2 rather than COX-1 enzyme. The study aimed to synthesize derivatives of mefenamic acid with more potency and to decrease the drug's potential side effects, new series of 4-thiazolidinone derivatives of mefenamic acid were synthesized IVa-g. The synthetic procedures for target compounds and their intermediates are designed to be as follows: acylation of secondary amine of mefenamic acid by chloroacetylchloride to produce compound (I), then reaction between compound (I) and hydrazine hydrate to form hydrazine derivative of mefenamic acid (compound II). After that, Schiff base formation by addition of seven benzaldehyde derivatives and finally, cyclization in presence of thioglycolic acid to form 4-thiazolidinone heterocyclic ring. The characterization of the titled compounds has been established on the basis of their spectral FTIR, 1HNMR data, and by measurements of their physical properties. In vivo acute anti-inflammatory effect of the synthesized compounds was evaluated in rats using egg-white induced edema model of inflammation. The tested compounds and the reference drug produced significant reduction of paw edema with respect to the effect of dimethyl sulfoxide 10%v/v (control group). Compound IVe showed more potent effect than mefenamic acid at 240-300 min, while at time 300 min, compounds IVa and IVd exhibit more potent anti-inflammatory effect than mefenamic acid (50mg/kg, i.p.) as they reduced paw edema significantly more than mefenamic acid at mentioned intervals (p<0.05) . On the other hand compound IVc exhibited lower anti-inflammatory effect.

scholarly journals Effectiveness of Pugun Tanoh Leaves Ethanol Extract (Curanga fel-terrae (Lour.) Merr) as an Anti-inflammation in Patients after Tooth Extraction at Dental and Mouth Hospital of Dentistry Faculty, Universitas Sumatera Utara

2020 ◽  
Vol 8 (D) ◽  
pp. 209-212
Author(s):  
Hendry Rusdy ◽  
Marianne Marianne ◽  
Baginda Mangatur Gurning
Keyword(s):  
Treatment Group ◽  
Mefenamic Acid ◽  
Tooth Extraction ◽  
Ethanol Extract ◽  
Control Group ◽  
Analog Scale ◽  
Chi Square ◽  
Chi Square Test ◽  
Anti Inflammatory ◽  
Anti Inflammation

BACKGROUND: Pugun Tanoh (Curanga fel-terrae (Lour.) Merr) is one of the medicinal plants. C. fel-terrae often used by the Karo tribe of Tiga Lingga Village, Kabupaten Dairi, Provinsi Sumatera Utara to treat diarrhea, asthma, cough, scabies, inflammation, bruising, and abdominal pain. Hence, it is necessary to examine the anti-inflammatory effects of Pugun Tanoh leaf extract. AIM: The present study aimed to determine the effectiveness of Pugun Tanoh leaves ethanol extract as an anti-inflammatory in patients after tooth extraction at Dental and Mouth Hospital of Dentistry Faculty, Universitas Sumatera Utara. METHODS: There were two research groups, namely the treatment group, which was given the extract plus amoxicillin 500 mg and mefenamic acid 500 mg as well as the control group who were only given amoxicillin 500 mg and mefenamic acid 500 mg without the extract. However, the instructions given to the patient are only required to take 500 mg of amoxicillin as an antibiotic, but for the 500 mg mefenamic acid drug, it is only instructed to drink it if there is pain that is felt by the patient. After the extracted teeth, the treatment group was given C. fel-terrae leaves ethanol extract 1.1 mg/kg on the tooth extraction socket using a 3 ml syringe then measurements were made on day 1 and day 2 after the extract was given using a visual analog scale (VAS) and through direct observation. Statistical analysis using the t-test independent and Chi-square test (significant p < 0.05). RESULTS: The treatment group did not have signs of inflammation both on the 1st and 2nd days after tooth extraction, while the control group had signs of inflammation both on the 1st day and the 2nd day after tooth extraction. In the treatment group, there were no patients who took the mefenamic acid drug while in the control group, it was found that all patients took mefenamic acid because they felt post-extraction pain. Statistical result are obtained with p = 0.00 (p < 0.05). CONCLUSION: C. fel-terrae leaves ethanol extract is effective to be used as an anti-inflammatory in patients after tooth extraction combined with amoxicillin 500 mg and mefenamic acid 500 mg.

Molecular docking, synthesis and biological screening of mefenamic acid derivatives as anti-inflammatory agents

2017 ◽  
Vol 801 ◽  
pp. 28-34 ◽  
Author(s):  
Jignasa K. Savjani ◽  
Suja Mulamkattil ◽  
Bhavesh Variya ◽  
Snehal Patel
Keyword(s):  
Molecular Docking ◽  
Mefenamic Acid ◽  
Biological Screening ◽  
Anti Inflammatory

scholarly journals Synthesis and Biological Evaluation of New Heteroaryl Carboxylic Acid Derivatives as Anti-inflammatory-Analgesic Agents

2013 ◽  
Vol 61 (2) ◽  
pp. 222-228 ◽  
Author(s):  
Khaled Abouzid Mohamed Abouzid ◽  
Nadia Abdalla Khalil ◽  
Eman Mohamed Ahmed ◽  
Sawsan Abo-Bakr Zaitone
Keyword(s):  
Carboxylic Acid ◽  
Biological Evaluation ◽  
Analgesic Agents ◽  
Anti Inflammatory ◽  
Synthesis And Biological Evaluation

Multidrug salt forms of norfloxacin with non-steroidal anti-inflammatory drugs: solubility and membrane permeability studies

CrystEngComm ◽  
2018 ◽  
Vol 20 (41) ◽  
pp. 6420-6429 ◽  
Author(s):  
Biswajit Bhattacharya ◽  
Amit Mondal ◽  
Saundray Raj Soni ◽  
Susobhan Das ◽  
Surojit Bhunia ◽  
...  
Keyword(s):  
Membrane Permeability ◽  
Mefenamic Acid ◽  
Dissolution Properties ◽  
Inflammatory Drugs ◽  
Anti Inflammatory ◽  
Permeability Studies ◽  
Salt Forms

Dissolution properties and membrane permeability studies were conducted for four newly prepared multidrug salts of norfloxacin with four NSAIDs, diclofenac, diflunisal, mefenamic acid and indomethacin.

A New Supramolecular Synthon Using N-Methylaniline. The Crystal Structure of the 1 : 1 Adduct of N-Methylaniline with 5-Nitrofuran-2-carboxylic Acid

1998 ◽  
Vol 51 (9) ◽  
pp. 867 ◽  
Author(s):  
Daniel E. Lynch ◽  
Lisa C. Thomas ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Proton Transfer ◽  
Single Crystal ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Supramolecular Synthon ◽  
X Ray ◽  
C 23 ◽  
A Cell

The crystal structure of the 1 : 1 adduct of N-methylaniline with 5-nitrofuran-2-carboxylic acid has been determined by single-crystal X-ray diffraction. Crystals are monoclinic, space group P21/c with Z 4 in a cell of dimensions a 8·467(5), b 6·106(2), c 23·95(1) Å, β 94·48(3)°. The molecules associate in a tetrameric, proton-transfer formation which has potential as a new supramolecular synthon.

scholarly journals A New Bithiophene from the Root of Echinops grijsii

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Fang-Pin Chang ◽  
Chien-Chih Chen ◽  
Hui-Chi Huang ◽  
Sheng-Yang Wang ◽  
Jih-Jung Chen ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Cell Line ◽  
Natural Source ◽  
Inflammatory Activity ◽  
Raw 264.7 ◽  
Raw 264.7 Cell ◽  
Anti Inflammatory ◽  
First Time ◽  
Raw 264.7 Cell Line

A new bithiophene, 5-(4-hydroxy-3-methoxy-1-butyny)-2,2′-bithiophene (1), and sixteen known thiophenes: 2-(3,4-dihydroxybut-1-ynyl)-5-(penta-1,3-diynyl)thiophene (2), α-terthienyl (3), 5-(3,4-dihydroxybut-1-ynyl)-2,2′-bithiophene (4), 5-acetyl-2,2′-bithiophene (5), 5-formyl-2,2′-bithiophene (6), methyl 2,2′-bithiophene-5-carboxylate (7), 5-(but-3-en-1-ynyl)-2,2′-bithiophene (8), 5-(4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene (9), cardopatine (10), isocardopatine (11), 5-(3-hydroxy-4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene (12), 5-(3-hydroxymethyl-3-isovaleroyloxyprop-1-ynyl)-2,2′-bithiophene (13), 5-(4-hydroxy-1-butynyl)-2,2′-bithiophene (14), 5-(4-acetoxy-1-butynl)-2,2′-bithiophene (15), 2,2′-bithiophene-5-carboxylic acid (16) and 2-(4-hydroxybut-1-ynyl)-5-(penta-1,3-diynyl)thiophene (17) were isolated from the roots of Echinops grijisii Hance. Among them, compounds 6, 7 and 16 were isolated from a natural source for the first time. Compounds 2, 4 and 14 exhibited significant anti-inflammatory activity against nitrite of LPS-stimulated production in the RAW 264.7 cell line.

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