Tiaprofenic Acid
(Synonyms: 噻洛芬酸) 目录号 : GC45579A COX inhibitor and NSAID
Cas No.:33005-95-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tiaprofenic acid is a COX inhibitor and a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory and analgesic activities.1 It inhibits synthesis of prostaglandin E2 and PGF2α from arachidonic acid in bovine seminal vesicle microsomes and inhibits thromboxane B2 formation in human umbilical cord arteries bathed in clotting human blood (IC50 = 0.71 μM).2,1 Tiaprofenic acid has anti-inflammatory activity in rat models of carrageenan-induced edema and adjuvant-induced arthritis and has analgesic activity in acetic acid- or phenylquinone-induced writhing tests in rodents.1
References
1. Sorkin, E.M., and Brogden, R.N. Tiaprofenic acid. A review of its pharmacological properties and therapeutic efficacy in rheumatic diseases and pain states. Drugs 29(3), 208-235 (1985).
2. Schr•r, K., and Seidel, H. Blood-vessel wall arachidonate metabolism and its pharmacological modification in a new in vitro assay system. Naunyn Schmiedebergs Arch. Pharmacol. 337(2), 177-182 (1988).
| Cas No. | 33005-95-7 | SDF | |
| 别名 | 噻洛芬酸 | ||
| Canonical SMILES | O=C(C1=CC=C(C(C)C(O)=O)S1)C2=CC=CC=C2 | ||
| 分子式 | C14H12O3S | 分子量 | 260.3 |
| 溶解度 | DMF: 15mg/mL,DMSO: 20mg/mL,Ethanol: 20mg/mL,Ethanol:PBS (pH 7.2) (1:10): 0.09mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.8417 mL | 19.2086 mL | 38.4172 mL |
| 5 mM | 0.7683 mL | 3.8417 mL | 7.6834 mL |
| 10 mM | 0.3842 mL | 1.9209 mL | 3.8417 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Tiaprofenic Acid. A reappraisal of its pharmacological properties and use in the management of rheumatic diseases
Drugs 1995 Dec;50(6):1050-75.PMID:8612471DOI:10.2165/00003495-199550060-00010.
Tiaprofenic Acid is a nonsteroidal anti-inflammatory drug (NSAID) used in the treatment of patients with rheumatic diseases and other clinical conditions of pain and inflammation. Like other propionic acid derivatives, Tiaprofenic Acid is effective and generally well tolerated. Comparative studies in patients with rheumatoid arthritis or osteoarthritis receiving Tiaprofenic Acid 600 mg/day demonstrated improvements in pain intensity, duration of morning stiffness, articular index and other clinical variables which were similar to those achieved with alternative NSAIDs. Tolerability was also comparable between Tiaprofenic Acid and other NSAIDs in most trials; the most frequently reported adverse events involved the gastrointestinal tract. Some studies showed a trend towards fewer patient withdrawals because of adverse events with Tiaprofenic Acid than with NSAIDs such as indomethacin. Current evidence suggests that nonbacterial cystitis is more likely to be associated with Tiaprofenic Acid than with other NSAIDs. This reaction should, however, be considered in the perspective of its infrequent occurrence and its typical reversibility, and against the wider background of the established usage of Tiaprofenic Acid and its overall tolerability profile which is similar to that of other NSAIDs. Unlike indomethacin, Tiaprofenic Acid was not associated with increased cartilage degradation in a recently completed large clinical trial known as LINK, which evaluated the effects of long term administration in patients with osteoarthritis of the knee. Thus, Tiaprofenic Acid is an established option among the range of NSAIDs used in the treatment of patients with rheumatic diseases, with efficacy and tolerability profiles that are relatively well characterised. The availability of a sustained release dosage form of Tiaprofenic Acid, which has a similar efficacy and tolerability profile to the standard formulation, provides a convenient once daily dosage regimen.
Clinical pharmacokinetics of Tiaprofenic Acid and its enantiomers
Clin Pharmacokinet 1996 Nov;31(5):331-47.PMID:9118583DOI:10.2165/00003088-199631050-00002.
Tiaprofenic Acid is a chiral nonsteroidal anti-inflammatory drug (NSAID) of the 2-arylpropionic acid (2-APA) class. A common structural feature of 2-APA NSAIDs is a sp3-hybridised tetrahedral chiral carbon heteroatom within the propionic acid side chain moiety, with the S-enantiomer possessing most of the beneficial anti-inflammatory activity. However, all Tiaprofenic Acid preparations to date are marketed as the racemate. Tiaprofenic Acid has been suggested to exhibit limited pharmacokinetic stereoselectivity. The synovium is the proposed site of action of NSAIDs when used for musculoskeletal disorders, and substantial concentrations of Tiaprofenic Acid are attained in synovial fluid. Recent data suggested that possibility of stereoselective distribution of Tiaprofenic Acid into synovium and cartilage. Hence, data generated using non-stereospecific assays may not always be extrapolated to explain the disposition of the individual enantiomers. Tiaprofenic Acid is rapidly and almost completely absorbed when given orally. The area under the plasma concentration-time curve (AUC) of Tiaprofenic Acid is proportional to the oral dose administered. A sustained release dosage form is available, which may be beneficial due to the short terminal phase half-life of Tiaprofenic Acid (3 to 6 hours). The bioavailability is the same as that with conventional rapid release preparations, although the peak plasma drug concentration is reduced and time peak is prolonged. Tiaprofenic Acid binds extensively to plasma albumin. These is negligible R to S inversion upon oral administration. Tiaprofenic Acid is eliminated following extensive biotransformation to glucuronide-conjugated metabolites. Approximately 60% is eliminated as conjugates excreted in urine, and little drug is eliminated unchanged. The rate of excretion of Tiaprofenic Acid and its conjugates may be related to renal function; accumulation of conjugates occurs in end-stage renal disease, but not in young individuals or elderly patients. Potentially clinically important drug interactions with Tiaprofenic Acid have been demonstrated for some anticoagulants and probenecid. Relationships between Tiaprofenic Acid concentrations in biological matrices and therapeutic or toxic effects have not yet been elucidated for this drug.
Tiaprofenic Acid. A review of its pharmacological properties and therapeutic efficacy in rheumatic diseases and pain states
Drugs 1985 Mar;29(3):208-35.PMID:3886353DOI:10.2165/00003495-198529030-00002.
Tiaprofenic Acid is a new non-steroidal anti-inflammatory agent advocated for use in rheumatoid arthritis, osteoarthritis, musculoskeletal disorders, soft-tissue injuries and inflammatory conditions and acute pain of varying origin. Published data suggest that Tiaprofenic Acid 600 mg daily in 2 or 3 divided doses is comparable in effectiveness with aspirin, diclofenac, ibuprofen, indomethacin, naproxen, piroxicam and sulindac in the treatment of rheumatoid arthritis and osteoarthritis. More controlled clinical trials are necessary to evaluate its potential in rheumatic conditions other than rheumatoid arthritis and osteoarthritis. In controlled studies in patients with acute pain following surgery or trauma, Tiaprofenic Acid was more effective than placebo and as effective as aspirin and indomethacin. While Tiaprofenic Acid produced fewer side effects than aspirin in rheumatoid arthritis treatment, and indomethacin in the treatment of osteoarthritis, results have generally shown the short term tolerability of Tiaprofenic Acid to be similar to that of other non-steroidal anti-inflammatory drugs. As no one of the non-steroidal anti-inflammatory agents is the most suitable drug for all patients requiring such therapy, Tiaprofenic Acid should be considered along with other drugs of this type in the therapy of arthritic conditions and of acute postoperative or posttraumatic pain.
Single dose oral Tiaprofenic Acid for acute postoperative pain in adults
Cochrane Database Syst Rev 2009 Oct 7;2009(4):CD007542.PMID:19821426DOI:10.1002/14651858.CD007542.pub2.
Background: Tiaprofenic Acid is a a non-steroidal anti-inflammatory drug (NSAID). It is widely available around the world, with indications for osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, periarticular disorders, and strains and sprains. This review sought to evaluate the efficacy and safety of oral Tiaprofenic Acid in acute postoperative pain, using clinical studies of patients with established pain, and with outcomes measured primarily over 6 hours using standard methods. This type of study has been used for many decades to establish that drugs have analgesic properties. Objectives: To assess the efficacy of single dose oral Tiaprofenic Acid in acute postoperative pain, and any associated adverse events. Search strategy: We searched Cochrane CENTRAL, MEDLINE, EMBASE and the Oxford Pain Relief Database for studies to June 2009. Selection criteria: Randomised, double blind, placebo-controlled trials of single dose orally administered Tiaprofenic Acid in adults with moderate to severe acute postoperative pain. Data collection and analysis: Two review authors independently assessed trial quality and extracted data. We planned to use area under the "pain relief versus time" curve to derive the proportion of participants with Tiaprofenic Acid experiencing at least 50% pain relief over 4 to 6 hours, using validated equations; to use number needed to treat to benefit (NNT); the proportion of participants using rescue analgesia over a specified time period; time to use of rescue analgesia; information on adverse events and withdrawals. Main results: Not one of eleven studies identified by the searches and examined in detail studied oral Tiaprofenic Acid against placebo in patients with established postoperative pain and therefore no results are available. Authors' conclusions: In the absence of evidence of efficacy for oral Tiaprofenic Acid in acute postoperative pain, its use in this indication is not justified at present. Because trials clearly demonstrating analgesic efficacy in the most basic of acute pain studies is lacking, use in other indications should be evaluated carefully. Given the large number of available drugs of this and similar classes which are effective, there is no urgent research agenda for this particular drug.
Synthesis and evaluation of tiaprofenic acid-derived UCHL5 deubiquitinase inhibitors
Bioorg Med Chem 2021 Jan 15;30:115931.PMID:33341501DOI:10.1016/j.bmc.2020.115931.
The ubiquitin-proteasome system (UPS) plays an important role in maintaining protein homeostasis by degrading intracellular proteins. In the proteasome, poly-ubiquitinated proteins are deubiquitinated by three deubiquitinases (DUBs) associated with 19S regulatory particle before degradation via 20S core particle. Ubiquitin carboxyl-terminal hydrolase L5 (UCHL5) is one of three proteasome-associated DUBs that control the fate of ubiquitinated substrates implicated in cancer survival and progression. In this study, we have performed virtual screening of an FDA approved drug library with UCHL5 and discovered Tiaprofenic Acid (TA) as a potential binder. With molecular docking analysis and in-vitro DUB assay, we have designed, synthesized, and evaluated a series of TA derivatives for inhibition of UCHL5 activity. We demonstrate that one TA derivative, TAB2, acts as an inhibitor of UCHL5.