기본 정보
- CAS
149709-62-6- 표준 SMILES
CCOC(=O)[C@H](C)C[C@@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)CCC(=O)O- InChIKey
PYNXFZCZUAOOQC-UTKZUKDTSA-N- 분자식
- C24H29NO5
- 평균 분자량
- 411.5 g/mol
- 단동위원소 질량
- 411.20457303
이름 및 식별자
- 우선 이름
- Sacubitril
- IUPAC
- 4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acid
- 영어명
- AHU-377
- 분자식
- C24H29NO5
- 분자량
- 411.49
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
149709-62-6- PubChem CID
- 9811834
- DTXSID
DTXSID20164370- ChEMBL
CHEMBL3137301- ChEBI
CHEBI:134714- UNII
- 17ERJ0MKGI
- EC Number
- 810-278-2
- Nikkaji
- J3.050.252C
물성
구조 계산 물성
- XLogP
- 3.7
- 극성 표면적
- 92.7 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 12
- 무거운 원자 수
- 30
- 형식 전하
- 0
- 복잡도
- 550
물리화학적 성질
- 끓는 점
- 656.9 · 656.9±55.0 °C(Predicted)
- 밀도
- 1.151 · 1.151±0.06 g/cm3(Predicted)
- 저장 조건
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 용해도
- 41.1 mg/mL · ≥41.1 mg/mL in DMSO; ≥21.45 mg/mL in H2O with ultrasonic; ≥26.85 mg/mL in EtOH with ultrasonic
- 물리적 상태
- 기름
- 산도 계수 (pKa)
- 4.72 · 4.72±0.10(Predicted)
- 색상
- 무색의
- InChIKey
- PYNXFZCZUAOOQC-VNLCLAKNNA-N
- SMILES
- C(O)(=O)CCC(N[C@@H](C[C@@H](C)C(OCC)=O)CC1=CC=C(C2=CC=CC=C2)C=C1)=O |&1:7,9,r|
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Warning
H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin];H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies.;There is 1 notification provided by 1 of 2 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
독성 정보
Hepatotoxicity
The large prospective, placebo-controlled trials of sacubitril-valsartan in patients with heart failure usually did not mention or list ALT elevations or severe hepatic adverse events or deaths. In the FDA clinical review of data from these trials, elevations in ALT or AST were said to arise in 1.3% of patients on sacubitril-valsartan but a similar portion of those on enalapril [1.0%], and all elevations were judged to be unrelated to therapy and likely due to congestive liver disease due to heart failure. A single case of jaundice with aminotransferase elevations occurred, but in a patient who had stopped combination therapy because of worsening renal dysfunction and who was experiencing acute decompensated heart failure. Since approval and more widespread use of sacubitril-valsartan there have been at least two reports of acute liver injury attributed to its use. Both cases were relatively mild and resolved rapidly once the drug was stopped. Whether the injury was due to sacubitril or valsartan (or an interaction of both) was not clear. Valsartan, like other commonly used angiotensin receptor blockers, is known to be a rare cause of acute liver injury. The contribution of the underlying heart failure and possible congestive hepatopathy is also an issue. The reported cases did not have a liver biopsy and were not rechallenged with the drug which might have clarified the causality.;Likelihood score: D (possible rare cause of clinically apparent liver injury, which may be due to valsartan rather than sacubitril).
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Sacubitril is available in the United States only in combination with valsartan. Milk levels after the lowest dose of the combination are very low. If sacubitril milk levels of the highest dosage (4 times greater) are proportional to maternal dosage, they would still be quite low. Valsartan was undetectable at this dosage, so the combination product appears unlikely to affect the nursing infant.;◉ Effects in Breastfed Infants;Two women taking sacubitril 24 mg and valsartan 26 mg (Entresto) did not observe any symptoms in their breastfed infants. Their extent of breastfeeding was not reported.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
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
Pharmacodynamics
n a 7-day valsartan-controlled study in patients with reduced ejection fraction (HFrEF), administration of sacubitril + valsartan (Entresto) resulted in a significant non-sustained increase in natriuresis, increased urine cGMP, and decreased plasma MR-proANP and NT-proBNP compared to valsartan. In a 21-day study in HFrEF patients, it significantly increased urine ANP and cGMP and plasma cGMP, and decreased plasma NT-proBNP, aldosterone and endothelin-1. In clinical studies, this combination had no effect on QTc interval.
Mechanism of Action
Sacubitril's active metabolite, LBQ657 inhibits neprilysin, a neutral endopeptidase that would typically cleave natiuretic peptides, which includes: atrial natriuretic peptide (ANP), brain natriuretic peptide (BNP), and c-type natriuretic peptide (CNP). ANP and BNP are released under atrial and ventricle stress, which activate downstream receptors leading to vasodilation, natriuresis and diuresis. Under normal conditions, neprilysin breaks down other vasodilating peptides and also vasoconstrictors such as angiotensin I and II, endothelin-1 and peptide amyloid beta-protein. Therefore, the inhibition of neprilysin leads to reduced breakdown and increased concentration of endogenous natriuretic peptides in addition to increased levels of vasoconstricting hormones such as angiotensin II. (However, when combined with valsartan, would result in blocking of angiotensin II to its receptor, preventing the vasoconstrictive effects and resulting in a decrease in vascular resistance and blood pressure.) Cardiovascular and renal effects of sacubitril is a result of the increased levels of peptides that are normally degraded by neprilysin.
Absorption, Distribution and Excretion
Peak plasma concentrations of sacubitril and it's metabolite, LBQ657 are reached in 0.5 hours and 2 hours respectively. Food does not clinically affect the systemic exposure of sacubitril or LBQ657. The oral bioavailability of sacubitril is >60%. It should be noted that the valsartan found in this combination is more bioavailable than other market available valsartan.
52% to 68% of sacubitril (primarily as the active metabolite LBQ657) is excreted in urine. 37% to 48% of sacubitril (primarily as LBQ657) is excreted in feces
103 L
상·하류 제품 정보
상류 원료
하류 제품
공급사100 곳
관련 반응
화합물 노트
불러오는 중…