홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /화합물

Difelikefalin

HCID 24794466
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1024828-77-0
표준 SMILES
CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](N)Cc1ccccc1)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(C(=O)O)CC1
InChIKey
FWMNVWWHGCHHJJ-SKKKGAJSSA-N
분자식
C36H53N7O6
평균 분자량
679.8 g/mol
단동위원소 질량
679.40573244

개요

Difelikefalin (CR845) is an agonist of kappa opioid receptors (KORs) useful in the treatment of pruritus secondary to chronic kidney disease. KORs were first associated with itching in 1984. Further investigations revealed that dynorphins, endogenous agonists of KORs, work to inhibit the itching sensation at the spinal cord level, and scratching could be elicited in mouse models with the administration of KOR antagonists. These revelations led to the study of KOR agonists as a potential treatment option in patients suffering from pruritic conditions. Pruritus associated with chronic kidney disease (also called uremic pruritus) affects 50-60% of all patients on dialysis and 25% of non-dialysis patients with chronic kidney disease. The clinical burden of uremic pruritus in this patient population is being increasingly recognized as contributing to a significant reduction in patient quality of life, poor outcomes, and even mortality. Options for therapy are limited - with no FDA-approved treatments, off-label [gabapentin] was the most evidence-based and widely available treatment. Difelikefalin received FDA approval in August 2021 (under the brand name Korsuva), becoming the first FDA-approved therapy for patients with chronic kidney disease suffering from uremic pruritus. Difelikefalin was later approved by the EMA in April 2022 for the same indication.

이름 및 식별자

우선 이름
Difelikefalin
IUPAC
4-amino-1-[(2R)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid
영어명
Difelikefalin
분자식
C36H53N7O6
분자량
679.85

이름 및 동의어

Difelikefalin1024828-77-0KorsuvaCR845CR-845MR13A9difelicefalinadifelikefalineFE202845NA1U919MROFE-202845MR-13A9
이름 더 보기
CR 845Difelikefalin (CR845)CKD-943FE 202845DifeilikefalinD5-Difelikefalin TriHCl
4-amino-1-[(2R)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acidDTXSID4010328964-Piperidinecarboxylic acid, N1-(D-phenylalanyl-D-phenylalanyl-D-leucyl-D-lysyl)-4-amino-4-Piperidinecarboxylic acid, 4-amino-1-((2R)-6-amino-2-(((2R)-2-(((2R)-2-(((2R)-2-amino-1-oxo-3-phenylpropyl)amino)-1-oxo-3-phenylpropyl)amino)-4-methyl-1-oxopentyl)amino)-1-oxohexyl)-4-amino-1-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-amino-3-phenylpropanamido]-3-phenylpropanamido]-4-methylpentanamido]hexanoyl]piperidine-4-carboxylic aciddifelikefalinum4-amino-1-((2R)-6-amino-2-(((2R)-2-(((2R)-2-(((2R)-2-amino-3-phenylpropanoyl)amino)-3-phenylpropanoyl)amino)-4-methylpentanoyl)amino)hexanoyl)piperidine-4-carboxylic acid4-amino-1-((2R)-6-amino-2-((2R)-2-((2R)-2-((2R)-2-amino-3-phenylpropanamido)-3-phenylpropanamido)-4-methylpentanamido)hexanoyl)piperidine-4-carboxylic acid

데이터베이스 식별자

CAS
1024828-77-0

물성

구조 계산 물성

XLogP
-0.6
극성 표면적
223 Ų
수소 결합 공여자 수
7
수소 결합 수용자 수
9
회전 가능 결합 수
18
무거운 원자 수
49
형식 전하
0
복잡도
1,080

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
SolubilitySoluble
Human DrugsEMA approved medicines: Human medicine

물리화학적 성질

끓는 점
1005.5 · 1005.5±65.0 °C(Predicted)
밀도
1.214 · 1.214±0.06 g/cm3(Predicted)
산도 계수 (pKa)
2.05 · 2.05±0.20(Predicted)
물리적 상태
Solid
색상
White to off-white
InChIKey
FWMNVWWHGCHHJJ-SKKKGAJSSA-N
SMILES
N1(C(=O)[C@@H](CCCCN)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CC2=CC=CC=C2)N)CCC(N)(C(O)=O)CC1

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Hepatotoxicity · 1건

In registration trials of difelikefalin, elevations in serum liver-associated enzyme levels were uncommon and no more frequent than in controls. Serum alkaline phosphatase elevations occurred in 12.7% vs 12.0% of participants, and there were no ALT elevations above 3 times the upper limit of normal (ULN). Since approval and more widespread use of difelikefalin, there have been no published reports of hepatotoxicity attributed to its use.

Adverse Effects · 1건

Phase 3 clinical trials involving patients with end-stage renal disease requiring dialysis suffering from uremic pruritus involved a study design. Patients received IV difelikefalin at weight-based doses of 1.0 mcg per kg 3 times a week in the venous circuit of their dialysis machine for 12 weeks. This study demonstrated the following most common adverse effects:

Toxicity Summary · 1건

At supratherapeutic levels (15 mcg per mL), concern for respiratory depression or euphoric effects has not been demonstrated. Difelikefalin has been studied in rats and determined to cause diuresis by activating central kappa opioid receptors. Mild to moderate hypernatremia has been reported at supratherapeutic doses of 1.0, 2.0, and 5.0 mcg per kg. Any induced electrolyte imbalance observed during treatment should be managed per the standard of care in conjunction with the termination of medication administration and identification of any additional etiologies for the electrolyte disturbance. The adverse effects mentioned previously, including hypoesthesia, paresthesia, and somnolence, are self-limiting at supratherapeutic doses.

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 Code · 2건

V - Various

QV - Various

Protein BindingDifelikefalin is approximately 23-28% protein-bound in plasma, although the specific proteins to which it binds are unclear.
Pharmacodynamics · 1건

Difelikefalin is administered to patients undergoing hemodialysis for chronic kidney disease (CKD) to prevent and treat the pruritus often associated with CKD. It is administered via bolus intravenous injection at the end of each hemodialysis treatment. As it works on opioid receptors, difelikefalin can cause dizziness, somnolence, and other CNS depressant effects that may impair mental or physical abilities - as such, patients should be advised to avoid operating dangerous machinery until the effect of difelikefalin on that patient is known.

Mechanism of Action · 1건

Difelikefalin is a synthetic peptide and agonist of kappa opioid receptors (KORs), which have long been known to be involved with the itching sensation (in addition to playing some role in addiction). Endogenous KOR agonists - called dynorphins - have a neuroinhibitory effect on the itching sensation at the spinal cord level and mouse models have shown KOR agonist antipruritic activity when used to treat itching induced by different pruritogens. Although the specifics of the mechanism have yet to be elucidated, the administration of KOR agonists, like difelikefalin, in patients with uremic pruritus has proven an effective means to suppress scratching and improve their quality of life.

Biological Half-LifeThe half-life of difelikefalin in hemodialysis patients prior to dialysis ranges between 23 and 31 hours.
Metabolism/MetabolitesDifelikefalin is not metabolized to any appreciable extent and is not a substrate for cytochrome P450 enzymes.
FDA Pharmacological Classification · 6건

NA1U919MRO

DIFELIKEFALIN

Established Pharmacologic Class [EPC] - Kappa Opioid Receptor Agonist

관련 반응

0건
반응 기록 만들기

현재 필터 조건에 해당하는 반응 기록이 없습니다.

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
PubChem CID
24794466
DTXSID
DTXSID401032896
ChEMBL
CHEMBL3989915
UNII
NA1U919MRO
Nikkaji
J3.804.659D

Mechanisms of Action [MoA] - Opioid kappa Receptor Agonists

Difelikefalin is a Kappa Opioid Receptor Agonist. The mechanism of action of difelikefalin is as an Opioid kappa Receptor Agonist.

DIFELIKEFALIN

Absorption, Distribution and Excretion · 4건

Difelikefalin is administered via bolus intravenous injection with each hemodialysis treatment - for this reason, each dose is effectively 100% bioavailable.

Following intravenous difelikefalin administration to hemodialysis patients, approximately 11% of the dose was excreted in the urine, 59% in the feces, and 20% in the dialysate.

The mean volume of distribution of difelikefalin is approximately 238 mL/kg.

One cycle of hemodialysis reduces difelikefalin plasma concentrations by 70-80% and no detectable drug remains after two cycles.

응용 분야

용도Difelikefalin is used in the formation of oral formulations of kappa opioid receptor agonists for the treatment of variety of kappa opioid receptor-assocd. diseases and conditions such as pain, pruritus and inflammation.