Licofelone
기본 정보
- CAS
156897-06-2- 표준 SMILES
CC1(C)Cc2c(-c3ccccc3)c(-c3ccc(Cl)cc3)c(CC(=O)O)n2C1- InChIKey
UAWXGRJVZSAUSZ-UHFFFAOYSA-N- 분자식
- C23H22ClNO2
- 평균 분자량
- 379.9 g/mol
- 단동위원소 질량
- 379.13390662
개요
Licofelone is a member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine substituted by methyl, methyl, carboxymethyl, 4-chlorophenyl, and phenyl groups at positions 2, 2, 5, 6, and 7, respectively. It is a dual inhibitor of cyclooxygenase isoforms and 5-lipoxygenase and is under development for treatment of osteoarthritis. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antineoplastic agent, an anticonvulsant, a neuroprotective agent and an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor. It is a monocarboxylic acid, a member of pyrrolizines and a member of monochlorobenzenes.
이름 및 식별자
- 우선 이름
- Licofelone
- IUPAC
- 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid
- 영어명
- Licofelone
- 분자식
- C23H22ClNO2
- 분자량
- 379.88
이름 및 동의어
Licofelone156897-06-2ML 3000licofelona6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acidlicofelonumP5T6BYS22Y2,3-Dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acid2,2-Dimethyl-6-(4-chlorophenyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acidDTXSID40166154(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)-acetic acid(2-(4-Chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)-acetic acid
이름 더 보기
icofeLLicofelone, >=99%Licofelone, ML-3000Licofelone USP/EP/BP16-dihydrotanshinone ILicofelone, 10 mM in DMSO1H-Pyrrolizine-5-aceticacid, 6-(4-chlorophenyl)-2,3-dihydro-2,2-diMethyl-7-phenyl-
[2-(4-Chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetic acid(2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acidRefChem:153386DTXCID3088645ML-3000Licofelone [INN]2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid[6-(4-CHLOROPHENYL)-2,2-DIMETHYL-7-PHENYL-2,3-DIHYDRO-1H-PYRROLIZIN-5-YL]ACETIC ACID
물성
구조 계산 물성
- XLogP
- 5.2
- 극성 표면적
- 42.2 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 27
- 형식 전하
- 0
- 복잡도
- 536
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
물리화학적 성질
- 녹는점
- 162 · 162-163°C
- 끓는 점
- 539.7 · 539.7±50.0 °C(Predicted)
- 밀도
- 1.23 · 1.23
- 저장 조건
- -20 °C · -20°C Freezer
- 용해도
- 클로로포름, 메탄올에 용해됨
- 산도 계수 (pKa)
- 4.47 · 4.47±0.10(Predicted)
- 물리적 상태
- 고체
- 색상
- 황백색에서 밝은 노란색까지
화학적 성질
Yellowish Solid
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
안전 데이터
- 신호 어
- Warning
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302
화학 및 산업
약리 정보
PharmacodynamicsLicofelone belongs to a novel class of dual-acting anti-inflammatory drugs called COX/LO inhibitors. This group of drugs simultaneously inhibits the enzymes cyclooxygenase (COX) and 5-lipoxygenase (LO).
Mechanism of ActionLicofelone, through combined 5-LOX/COX-inhibition, reduces levels of inflammatory prostaglandins and leukotrienes.
Metabolism/MetabolitesLicofelone has known human metabolites that include (2S,3S,4S,5R)-6-[2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, Licofelone M2, and Licofelone M4.
MeSH Pharmacological Classification
Compounds capable of relieving pain without the loss of CONSCIOUSNESS.
Substances that reduce or suppress INFLAMMATION.
Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
응용 분야
개요Cross-talk between lipoxygenase (LO) and cyclooxygenase (COX) pathways has been observed in human osteoarthritic synovial explants which creates an arachidonic acid shunting phenomenon, stimulating interleukin-1β (IL-1β) synthesis. Licofelone is a dual inhibitor of cyclooxygenase (COX) and lipoxygenase (LO) pathways, that decreases levels of prostaglandin E2, leukotriene B4, and lipoxins and prevents lipopolysaccharide-stimulated IL-1β expression. The IC50 values for inhibition of human thrombocyte COX and human 5-LO are 0.16 μM and 0.23 μM, respectively. Unlike other non-steroidal anti-inflammatory drugs, licofelone causes little or no damage to the gastric mucosa in rabbit parietal cells. This is presumably the result of licofelone’s affects on acid-secretory mechanisms, mediated by the inhibition of 5-LO activity.
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