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Merck

SML0281

Sigma-Aldrich

Ivabradine hydrochloride

≥98% (HPLC)

Synonym(e):

3-[3-[[[(7S)-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-one hydrochloride

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About This Item

Empirische Formel (Hill-System):
C27H36N2O5 · HCl
CAS-Nummer:
Molekulargewicht:
505.05
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Optische Aktivität

[α]/D +5 to +9°, c = 1 in DMSO

Lagerbedingungen

desiccated

Farbe

white to beige

Löslichkeit

H2O: ≥5 mg/mL (warmed)

Lagertemp.

2-8°C

SMILES String

Cl.COc1cc2CCN(CCCN(C)C[C@H]3Cc4cc(OC)c(OC)cc34)C(=O)Cc2cc1OC

InChI

1S/C27H36N2O5.ClH/c1-28(17-21-11-20-14-25(33-4)26(34-5)16-22(20)21)8-6-9-29-10-7-18-12-23(31-2)24(32-3)13-19(18)15-27(29)30;/h12-14,16,21H,6-11,15,17H2,1-5H3;1H/t21-;/m1./s1

InChIKey

HLUKNZUABFFNQS-ZMBIFBSDSA-N

Angaben zum Gen

human ... HCN4(10021)

Anwendung

Ivabradine hydrochloride has been used as a potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel (HCN)2 blocker in embryoid body (EB) and rat engineered heart tissue (EHT).
Ivabradine hydrochloride has been used to investigate the effects of ivabradine on human primary chondrocytes (HPCs) to explore its potential in the treatment of osteoarthritis (OA).

Biochem./physiol. Wirkung

Ivabradine hydrochloride is an open channel blocker of neuronal I(h) and related cardiac I(f) channels, which are comprised of subunits of the hyperpolarisation-activated cyclic nucleotide-gated (HCN) channels, in particular HCN4. Ivabradine has antianginal activity. It lowers heart rate and reduces myocardial oxygen demand.
Ivabradine is used to treat chronic heart failure.

Leistungsmerkmale und Vorteile

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Cyclic Nucleotide-Gated (CNG) and Hyperpolarization Activated Cyclic Nucleotide-Gated (HCN) Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Piktogramme

Environment

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Aquatic Acute 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Die Dokumentenbibliothek aufrufen

Ivabradine as adjuvant treatment for chronic heart failure
Stoppe C, et al.
Cochrane database of systematic reviews (Online), 2018(4) (2018)
Julius Niehoff et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 38(2), 646-658 (2016-02-06)
Heart rate variability (HRV) refers to the fluctuation of the time interval between consecutive heartbeats in humans. It has recently been discovered that cardiomyocytes derived from human embryonic and induced pluripotent stem cells show beat rate variability (BRV) that is
Dissecting hiPSC-CM pacemaker function in a cardiac organoid model
Schulze ML, et al.
Biomaterials (2019)
Xianxiang Xiang et al.
International immunopharmacology, 66, 347-353 (2018-12-07)
Ivabradine is most commonly used for the treatment of worsening cardiac failure in patients who cannot tolerate the maximum dose of β-blockers or in whom treatment with β-blockers is contraindicated. While ivabradine is regarded as a highly selective "funny current"
Ivabradine abrogates TNF-alpha-induced degradation of articular cartilage matrix
Xiang X, et al.
International Immunopharmacology, 66, 347-353 (2019)

Verwandter Inhalt

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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