Loxoprofen
데이터를 보충하는 중입니다. 잠시 후 페이지를 새로 고치면 최신 내용을 볼 수 있습니다
기본 정보
- CAS
68767-14-6- 표준 SMILES
CC(C(=O)O)c1ccc(CC2CCCC2=O)cc1- InChIKey
YMBXTVYHTMGZDW-UHFFFAOYSA-N- 분자식
- C15H18O3
- 평균 분자량
- 246.3 g/mol
- 단동위원소 질량
- 246.12559444
개요
Loxoprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-oxocyclopentyl)methyl]phenyl group. A prodrug that is rapidly converted into its active trans-alcohol metabolite following oral administration. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a prodrug. It is a monocarboxylic acid and a member of cyclopentanones. It is functionally related to a propionic acid. It is a conjugate acid of a loxoprofen(1-).
이름 및 식별자
- 우선 이름
- Loxoprofen
- IUPAC
- 2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoic acid
- 영어명
- Loxoprofen
- 분자식
- C15H18O3
- 분자량
- 246.31
이름 및 동의어
Loxoprofen68767-14-62-(4-((2-Oxocyclopentyl)methyl)phenyl)propanoic acidLoxoprofeneLoxoprofenoLoxoprofen acidLoxoprofenum2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoic acid3583H0GZAPDTXSID1045164CS-600
이름 더 보기
IOXOPROFEN2-[4-(2-OXO-CYCLOPENTYLMETHYL)-PHENYL]-PROPIONIC ACIDA-METHYL-4-[(2-OXOCYCLOPENTYL)METHYL]BENZENEACETIC ACIDLoxoprofen-d6Loxoprofen RS
DTXCID9025164CHEBI:761722-(4-((2-oxocyclopentyl)methyl)phenyl)propionic acid2-OCPPP2-[4-[(2-Oxocyclopentyl)methyl]phenyl]propionic Acidalpha-Methyl-4-((2-oxocyclopentyl)methyl)benzeneacetate sodium salt dihydrateRefChem:924941Koloxo
데이터베이스 식별자
- CAS
68767-14-6、80382-23-6- PubChem CID
- 3965
- DTXSID
DTXSID1045164
물성
구조 계산 물성보충 중
- XLogP
- 2.4
- 극성 표면적
- 54.4 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 18
- 형식 전하
- 0
- 복잡도
- 316
실험 및 물리화학적 성질
DrugsPharmaceutical
물리화학적 성질
- 녹는점
- 108.5 · 108.5-111°
- 끓는 점
- 0.3 · bp0.3 190-195°
- 밀도
- 1.182 · 1.182±0.06 g/cm3(Predicted)
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 4.39 · 4.39±0.10(Predicted)
- 색상
- 흰색에서 황백색까지
- Merck
- 14 · 14,5589
- InChI
- InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)
- InChIKey
- YMBXTVYHTMGZDW-UHFFFAOYSA-N
- SMILES
- C(C1CCCC1=O)C1C=CC(C(C)C(=O)O)=CC=1
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS ClassificationNot Classified
유해성 정보
Hazard Classes and CategoriesNot Classified
독성 정보
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Loxoprofen
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
안전 데이터
- wgk
- 3
- HS 번호
- 2918.99.3000
- safety_code
- 22-24/25
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein Binding99% albumin-bound. At doses of loxoprofen greater than 500 mg/day, clearance of the drug increases as saturation of plasma protein binding occurs at higher doses.
Pharmacodynamics
Loxoprofen is a non-selective inhibitor of cyclooxygenase enzymes, which are responsible for the formation of various biologically active pain, fever, and inflammatory mediators. These include prostaglandins, prostacyclin, thromboxane, and arachidonic acid.
Mechanism of Action
Loxoprofen itself is a prodrug and carries little-to-no pharmacological activity - it is rapidly metabolized to its trans-alcohol form, which is a potent and non-selective inhibitor of cyclooxygenase. Cyclooxygenase (COX) is present in 2 forms, COX-1 and COX-2, with each serving different functions. COX-1 is present in human cells and is constitutively released, performing cellular housekeeping functions such as mucus production and platelet aggregation. COX-2 is induced in human cells post-injury or due to other stimuli, is triggered to appear in large quantities at the sites of injury/stimuli, and is ultimately responsible for the mediation of inflammation and pain. Loxoprofen's active metabolite inhibits both COX isoforms, resulting in reduced expression of several mediators of pain, inflammation, and fever (e.g. prostaglandins, prostacyclin, thromboxane, etc).
Biological Half-LifeThe elimination half-life of Loxoprofen is approximately 15 hours. Steady concentration is achieved after 2-3 doses.
Metabolism/Metabolites
Loxoprofen is a prodrug that is rapidly converted to its active trans-alcohol metabolite by carbonyl reductase in the liver. This same process also results in a cis-alcohol metabolite, though this isomer carries little pharmacological activity. The parent drug has also been observed to undergo oxidation via CYP3A4/5 to two hydroxylated metabolites (M3 and M4) and glucuronidation by UGT2B7 to two glucuronide metabolites (M5 and M6). The alcohol metabolites of loxoprofen also undergo glucuronide conjugation via UGT2B7 to two glucuronide metabolites (M7 and M8) prior to excretion. When applied in topical formulations, loxoprofen is metabolized to its active trans-alcohol form by carbonyl reductase in the skin.
관련 반응
643건
화합물 노트
불러오는 중…