기본 정보
- CAS
155974-00-8- 표준 SMILES
COc1cc2c(cc1OC)CC(=O)N(CCCN(C)C[C@H]1Cc3cc(OC)c(OC)cc31)CC2- InChIKey
ACRHBAYQBXXRTO-OAQYLSRUSA-N- 분자식
- C27H36N2O5
- 평균 분자량
- 468.6 g/mol
- 단동위원소 질량
- 468.26242225
개요
Ivabradine is a member of the class of benzazepines that is 7,8-dimethoxy-1,3,4,5-tetrahydro-3-benzazepin-2-one in which the amide hydrogen is replaced by a [{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]propyl} group. Used (as its hydrochloride salt) to treat patients with angina who have intolerance to beta blockers and/or heart failure. It has a role as a cardiotonic drug. It is an aromatic ether, a benzazepine, a carbobicyclic compound and a tertiary amino compound. It is a conjugate base of an ivabradine(1+).
이름 및 식별자
- 우선 이름
- Ivabradine
- IUPAC
- 3-[3-[[(7S)-3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]methyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one
- 현지명
- 이바브라딘
- 영어명
- Ivabradine
- 분자식
- C27H36N2O5
- 분자량
- 468.59
이름 및 동의어
Ivabradine155974-00-8S-16257IvabradinaS 162573H48L0LPZQDTXSID20482403-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-oneCHEBI:85966s16257(S)-3-(3-(((3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one2H-3-Benzazepin-2-one, 3-(3-(((3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, (S)-
이름 더 보기
이바브라딘Ivabradine sulfateIvabridine –Ivabradine APIIvabradine USP/EP/BPIvabradine HCl PremixN-desmethyl ivabridine-d6Ivabradine(Hydrochloride form)3-[3-[[(8S)-3,4-dimethoxy-8-bicyclo[4.2.0]octa-1,3,5-trienyl]methyl-methyl-amino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one
Ivabradinum3-(3-((((7S)-3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)(methyl)amino)propyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one3-(3-(((8S)-3,4-dimethoxy-8-bicyclo(4.2.0)octa-1,3,5-trienyl)methyl-methylamino)propyl)-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one3-[3-[[(8S)-3,4-dimethoxy-8-bicyclo[4.2.0]octa-1,3,5-trienyl]methyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-oneRefChem:56735S162572S162602S 162572
물성
구조 계산 물성
- XLogP
- 2.4
- 극성 표면적
- 60.5 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 10
- 무거운 원자 수
- 34
- 형식 전하
- 0
- 복잡도
- 663
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Cardiovascular Agents
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
Endocrine DisruptorsPotential endocrine disrupting compound
물리화학적 성질
- 끓는 점
- 626.9 · 626.9±55.0 °C(Predicted)
- 밀도
- 1.146 · 1.146±0.06 g/cm3(Predicted)
- 산도 계수 (pKa)
- 8.77 · 8.77±0.50(Predicted)
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
독성 정보
HepatotoxicityIn large preregistration clinical trials, similar proportions of patients taking ivabradine as taking placebo developed ALT elevations [15% vs 17%] while ALT elevations above 5 times the upper limit of normal were uncommon [
Adverse EffectsThe most common adverse effects associated with ivabradine administration, according to the product label, include bradycardia, atrial fibrillation, hypertension, and phosphenes.
Toxicity SummarySigns and Symptoms of Overdose
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
화학 및 산업
약리 정보
ATC Code
C01EB17
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding70% bound to plasma proteins.
Pharmacodynamics
The funny channels (If) open during repolarization and close during depolarization, making ivabradine's activity dependent on heart rate or the closing and opening of the channels. Therefore ivabradine exhibits use-dependence and is more pharmacologically active at higher heart rates. Ivabradine exhibits a linear dose-dependent heart-rate lowering activity (bradycardic effect) until a maximum dose of 30-40mg. At higher doses, the concentration of ivabradine tends to plateau, reducing risk of serious sinus bradycardia. It has been shown that the metabolite of ivabradine lowers heart rate as well, contributing to ivabradine's overall effect.
Mechanism of Action
Ivabradine lowers heart rate by selectively inhibiting If channels ("funny channels") in the heart in a concentration-dependent manner without affecting any other cardiac ionic channels (including calcium or potassium). Ivabradine binds by entering and attaching to a site on the channel pore from the intracellular side and disrupts If ion current flow, which prolongs diastolic depolarization, lowering heart rate. The If currents are located in the sinoatrial node and are the home of all cardiac pacemaker activity. Ivabradine therefore lowers the pacemaker firing rate, consequently lowering heart rate and reducing myocardial oxygen demand. This allows for an improved oxygen supply and therefore mitigation of ischemia, allowing for a higher exercise capacity and reduction in angina episodes.
Biological Half-Life2 hours.
Metabolism/Metabolites
Ivabradine is extensively metabolized by oxidation in the gut and liver by cytochrome P450 3A4 enzyme. Its active metabolite, N-desmethylated derivative, is also metabolized by CYP 3A4. Ivabradine's affinity for CYP 3A4 is low, making it unlikely to affect the metabolism of other drugs; however potent inhibitors or inducers of CYP 3A4 may affect ivabradine's plasma concentration and pharmacodynamic effects and should not be co-administered.
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19건
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