FLURBI프로FEN
FLURBI프로FEN · 바이프로펜 · 플루르비프로펜 · 2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoic acid · ANSAID · Zepolas · rac-Flurbiprofen · 2-(2-fluorobiphenyl-4-yl)propanoic acid
식별자 및 물리적 특성
| CAS No. | 5104-49-4 |
|---|---|
| 분자식 | C15H13FO2 |
| 평균 분자량 | 244.26 g/mol |
| 단동위원소 질량 | 244.08995788 g/mol |
| SMILES | CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1 |
| InChIKey | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
| PubChem CID | 3394 |
| ChEMBL | CHEMBL563 |
| ChEBI | CHEBI:5130 |
| EC No. | 225-827-6 |
| DTXSID | DTXSID0037231 |
| 현지명 | FLURBI프로FEN |
화학 및 물리적 성질
| XLogP | 4.2 |
|---|---|
| 극성 표면적 | 37.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 18 |
| 형식 전하 | 0 |
| 복잡도 | 286 |
| 의약품 | Pharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic productsPharmaceuticals -> Analgesics and anti-inflammatories |
| LogP(분배 계수) | 3.8 |
| 용해도 | 2.49e-02 g/L메탄올: 용해성50mg/mL |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalFDA approved drugs -> Active ingredientPharmaceuticals |
| 녹는점 | 110-111 °C110 - 111 °C110-112 °C(lit.) |
| Physical Description | Solid |
| Dissociation Constants | 4.034.224.3 |
| Collision Cross Section | 155.9 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 끓는 점 | 376.2±30.0 °C(Predicted) |
| 밀도 | 1.1795 (estimate) |
| 저장 조건 | Sealed in dry,Room Temperature |
| pKa(산도 계수) | pKa 3.80(H2O) (Uncertain) |
| 물리적 상태 | 흰색 고체 |
| 색상 | 흰색에서 황백색까지 |
| 생물학적 소스 | synthetic |
| 용해도 | 8mg/L(상온) |
| Merck | 14,4199 |
| InChI | InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18) |
| InChIKey | SYTBZMRGLBWNTM-UHFFFAOYSA-N |
| SMILES | FC1C=C(C=CC=1C1C=CC=CC=1)C(C)C(=O)O |
| EPA | [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-?-methyl- (5104-49-4) |
화학적 성질
White to Off-White Crystalline Solid
안전 및 규제
| GHS 분류 | DangerH301 (98.2%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 114 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Hazard Traits - Developmental ToxicityReproductive Toxicity |
| 기타 안전 정보 | IMAP assessments - [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-.alpha.-methyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (98.2%) |
| Treatment | Patients should be managed by symptomatic and supportive care following overdose with a nonsteroidal anti-inflammatory drug. There are no specific antidotes. Emesis and/or activated charcoal (60 to 100 g in adults, 1 to 2 g/kg in children) and/or osmotic cathartic may be indicated in patients seen within 4 hours of ingestion with symptoms, or following a large overdose (5 to 10 times the usual dose). Forced diuresis, alkalization of urine, hemodialysis, or hemoperfusion may not be useful due to high protein binding. (L1712) |
| Hepatotoxicity | Prospective studies show that mild elevations in serum aminotransferase levels can occur in up to 15% of patients taking NSAIDs such as flurbiprofen, but the abnormalities are generally transient, mild and asymptomatic, often resolving even with drug continuation. Marked aminotransferase elevations above 3 times the upper limit of normal (ULN) occur in less than 1% of patients. Clinically apparent liver injury with jaundice from flurbiprofen is rare and only individual case descriptions have been published. The latency to onset is within 1 to 4 weeks of starting. The pattern of enzyme elevations is typically cholestatic, but hepatocellular cases have been described. Immunoallergic features are present in some cases (low grade fever, rash), but are generally not prominent, and autoantibody formation is rare. Most cases resolve promptly on stopping therapy. Flurbiprofen is not mentioned in large case series on drug induced liver injury or acute liver failure from the United States, but was listed as the second most common agent implicated in drug-induced liver injury in a case series from Turkey, one of which was fatal. |
용도
개요
Flurbiprofen synthesis was originally reported in 1974. During a study of the pharmacological properties of a large number of substituted phenylalkanoic acids, including ibuprofen and ibufenac, the most potent were found to be substituted 2-(4-biphenyl)propionic acids. Further toxicological and pharmacological studies indicated that flurbiprofen possessed the most favorable therapeutic profile, so it was selected for further clinical development. It was not marketed until 1987, when it was introduced as the sodium salt as Ocufen, the first topical NSAID indicated for ophthalmic use in the United States. The indication for Ocufen is the same as that for Profenal—that is, to inhibit intraoperative miosis induced by prostaglandins in cataract surgery.
용도
An anti-inflammatory used as an analgesic.
일반 설명
Flurbiprofen (Ansaid, Ocufen, Froben), is another drug inthis class indicated for both acute and long-term managementof RA and OA but with a more complex mechanism ofaction. Unlike the other drugs in this class, it does not undergochiral inversion (i.e., the conversion of the “inactive”[R]-enantiomer to the active, [S]-enantiomer). Similar to aspirinand other salicylates, both flurbiprofen enantiomersblock COX-2 induction as well as inhibiting the nuclearfactor-κB-mediated polymorphonuclear leukocyte apoptosissignaling; therefore, both enantiomers are believed to contributeequally to its overall anti-inflammatory action.(R)-flurbiprofen is actually a strong clinical candidate forthe treatment of Alzheimer disease, because it has beenshown to reduce Aβ42 production by human cells.