Sacubitril

HCID 9811834

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

Sacubitril149709-62-6AHU-377AHU377sucabitrilAHU 377Sacubitrilo17ERJ0MKGI4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acidDTXSID20164370ENTRESTO COMPONENT SACUBITRIL(2R,4S)-5-(biphenyl-4-yl)-4-((3-carboxypropionyl)amino)-2-methylpentanoic acid ethyl ester
이름 더 보기
Sacubitril(AHU-377)(2R,4S)-5-([1,1'-Biphenyl]-4-yl)-4-(3-carboxypropanamido)-2-methylpentanoic acidSacubitril APISacubitril, 10 mM in DMSOvalsartan/sacubitril Impurity 1AHU-37AHU-77LCZ697SACUBRITIL
3-{[(2S,4R)-1-{[1,1'-biphenyl]-4-yl}-5-ethoxy-4-methyl-5-oxopentan-2-yl]carbamoyl}propanoic acidsacubitrilum3-(((2S,4R)-1-((1,1'-biphenyl)-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)carbamoyl)propanoic acid4-(((2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl)amino)-4-oxobutanoic acidRefChem:884341DTXCID3086861810-278-24-(((2S,4R)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid

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

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)

안전 및 규제

GHS 분류

GHS Classification · 6건

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

Hazard Classes and CategoriesSkin Sens. 1 (50%);Eye Irrit. 2 (50%)

독성 정보

Hepatotoxicity · 1건

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 · 1건

◉ 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

ATC CodeC09DX04
Protein BindingSacubitril and it's metabolite, LBQ657 are highly bound to plasma protein (94-97%).
Pharmacodynamics · 1건

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 · 1건

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.

Biological Half-LifeThe half life of sacubitril is 1.1 to 3.6 hours, and the half life of it's metabolite LBQ657 is 9.9 to 11.1 hours.
Metabolism/MetabolitesSacubitril is metabolized to LBQ657 by esterases. A low concentration (<10%) of a hydroxyl metabolite has been identified in plasma.

공급사100 곳

天津始加生物医药科技有限公司15022261580 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]

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