Odanacatib
기본 정보
- CAS
603139-19-1- 표준 SMILES
CC(C)(F)C[C@H](N[C@@H](c1ccc(-c2ccc(S(C)(=O)=O)cc2)cc1)C(F)(F)F)C(=O)NC1(C#N)CC1- InChIKey
FWIVDMJALNEADT-SFTDATJTSA-N- 분자식
- C25H27F4N3O3S
- 평균 분자량
- 525.6 g/mol
- 단동위원소 질량
- 525.17092555
개요
Odanacatib is an inhibiter of cathepsin K which was originally developed be Merck & Co as a new treatment for osteoporosis. The drug made it to phase III trials before abandoned due to increased stroke.
이름 및 식별자
- 우선 이름
- Odanacatib
- IUPAC
- (2S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-[4-(4-methylsulfonylphenyl)phenyl]ethyl]amino]pentanamide
- 영어명
- Odanacatib
- 분자식
- C25H27F4N3O3S
- 분자량
- 525.56
이름 및 동의어
Odanacatib603139-19-1MK-0822MK0822N673F6W2VH(2S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-[4-(4-methylsulfonylphenyl)phenyl]ethyl]amino]pentanamideL-1037536DTXSID40209075L-001037536(2S)-N-(1-Cyanocyclopropyl)-4-fluoro-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)pentanamideodanacatibum(2S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4-(4-methylsulfonylphenyl)phenyl)ethyl)amino)pentanamide
이름 더 보기
CS-700OdacatibUnii-N673F6W2vhOdanacatib, >=98%Odanacatib(Mk0822)(MK0822,Odanacatib)Odanacatib,MK-0822,MK0822
RefChem:856152A10BH01DTXCID60131566(2S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((1S)-2,2,2-trifluoro-1-(4'-methanesulfonyl-(1,1'-biphenyl)-4-yl)ethyl)amino)pentanamideOdanacatib (MK-0822)MK 0822Odanacatib [USAN]Odanacatib (MK0822)
물성
구조 계산 물성
- XLogP
- 4.1
- 극성 표면적
- 107 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 9
- 무거운 원자 수
- 36
- 형식 전하
- 0
- 복잡도
- 934
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.64
물리화학적 성질
- 녹는점
- 223 · 223-224 °C
- 끓는 점
- 681.6 · 681.6±55.0 °C(Predicted)
- 밀도
- 1.35 · 1.35
- 저장 조건
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 용해도
- 클로로포름(약간 용해됨, 가열, 초음파 처리), 메탄올(약간 용해됨, 초음파 처리)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 12.06 · 12.06±0.20(Predicted)
- 색상
- 흰색에서 황백색까지
- 안정성
- 흡습성
- InChIKey
- FWIVDMJALNEADT-SFTDATJTSA-N
- SMILES
- C(NC1(C#N)CC1)(=O)[C@@H](N[C@@H](C1=CC=C(C2=CC=C(S(C)(=O)=O)C=C2)C=C1)C(F)(F)F)CC(F)(C)C
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H372 (100%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
P260, P264, P270, P319, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 35 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 CategoriesSTOT RE 1 (100%)
안전 데이터
- 신호 어
- Danger
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H373
화학 및 산업
약리 정보
Protein Binding97.5% bound to plasma proteins.
PharmacodynamicsIncreases bone mineral density and reduces risk of fractures in osteoporosis.
Mechanism of Action
Odanacatib inhibits cathepsin K, likely by binding to its active site. Cathepsin K is a cysteine protease enzyme which is secreted by osteoclasts. Cathepsin K is responsible for the breakdown of collagen in the bone matrix as part of bone resorption. The inhibition of this enzyme results in decreased bone resorption without affecting bone deposition resulting in increased bone mineral density. This increased bone mineral density strengthens the bone which leads to fewer fractures in osteoporosis.
Biological Half-LifeApparent half life observed to be 87.3-94.7h.
Metabolism/Metabolites
The major metabolite is the product of hydroxylation by CYP3A4 and CYP2C8. This metabolite is active but is 25 times less effective at inhibiting cathepsin K than odanacatib. The other metabolites are produced through glutathione conjugation, hydrolysis, dealkylation, glucuronidation, oxidation, and cyclization.
Absorption, Distribution and Excretion
Tmax of 2-6h. The absolute bioavailabilities observed with 30mg and 50 mg doses are 70% and 30% respectively. When taken with high fat meals the 50mg dose's bioavailability increases to 49% and tmax increases to 10.5h.
16.9% excreted in urine. 74.5% excreted in feces.
100L
Total clearance of 0.8L/h.
응용 분야
용도MK-0822 is a newly developed bone-targeting dual action pro-drug for osteoporosis and bone metastasis. It is also an inhibitor of cathepsin K, an enzyme involved in bone resorption.
관련 반응
3건
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