Tiaprofenic acid

Base Information

• Chemical Name: Tiaprofenic acid
• CAS No.: 33005-95-7
• Molecular Formula: C14H12O3S
• Molecular Weight: 260.313
• European Community (EC) Number: 251-329-3
• UNII: 1LS1T6R34C
• DSSTox Substance ID: DTXSID5023665
• Nikkaji Number: J3.176C
• Wikipedia: Tiaprofenic_acid
• Wikidata: Q419926
• NCI Thesaurus Code: C90908
• Pharos Ligand ID: PQWYB81F651D
• Metabolomics Workbench ID: 43587
• ChEMBL ID: CHEMBL365795
• Mol file: 33005-95-7.mol

Synonyms:Apo-Tiaprofenic;FC 3001;Flanid;Novo-Tiaprofenic;Nu-Tiaprofenic;PMS-Tiaprofenic;RU 15060;Surgam;Surgam SA;tiaprofenic acid;tiaprofenic acid, calcium salt

Chemical Property of Tiaprofenic acid

Chemical Property:

• Vapor Pressure: 6.8E-09mmHg at 25°C
• Melting Point: 96° (isopropyl ether)
• Refractive Index: 1.612
• Boiling Point: 450.251 °C at 760 mmHg
• PKA: 4.05±0.10(Predicted)
• Flash Point: 226.104 °C
• PSA: 82.61000
• Density: 1.29 g/cm³
• LogP: 3.16720
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Practically insoluble in water, freely soluble in acetone, in ethanol (96 per cent) and in methylene chloride.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 260.05071541
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

99% ^*data from raw suppliers

Tiaprofenic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(S1)C(=O)C2=CC=CC=C2)C(=O)O
• Uses: Antiinflammatory;Cyclooxygenase inhibitor
• Therapeutic Function: Antiinflammatory
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: 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 heparins, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: 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 bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Tiaprofenic acid

There total 12 articles about Tiaprofenic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-thiophen-2-yl-propionic acid (54955-39-4) + benzoyl chloride (98-88-4) → tiaprofenic acid (33005-95-7)

Guidance literature:

With aluminum (III) chloride; In ethyl acetate; at 20 ℃; for 5h; Cooling with ice;

Reference yield: 68.0%

methyl α-methylthio-α-(5-benzoyl-thien-2-yl)-propionate (67355-14-0) + sodium thiomethoxide (5188-07-8) → tiaprofenic acid (33005-95-7)

Guidance literature:

In methanol; dichloromethane; water;

Reference yield:

2-chloro-2-(2-thienyl)ethane (28612-98-8) → tiaprofenic acid (33005-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere

2: sulfuric acid; acetic acid / 6 h / 125 °C

3: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice

With aluminum (III) chloride; sulfuric acid; potassium carbonate; acetic acid; In ethyl acetate; acetonitrile;

upstream raw materials:

methyl α-methylthio-α-(5-benzoyl-thien-2-yl)-propionate

sodium thiomethoxide

2-thiophen-2-yl-propionic acid

benzoyl chloride

Downstream raw materials:

(5-ethyl-2-thienyl)phenylmethanone

2-benzoyl-5-acetylthiophene

2-Benzoyl-5-(1-hydroxyethyl)thiophene

[5-(1-Methoxy-ethyl)-thiophen-2-yl]-phenyl-methanone

Refernces

• 1、 -. "Preparation method for tiaprofenic acid". Paragraph 0042; 0052-0053. . Retrieved 2018/04/02.
• 2、 -. "Synthetic process for non-steroidal anti-inflammatory drug tiaprofenic acid". Paragraph 0051; 0052; 0064; 0065. . Retrieved 2018/01/11.