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SML0281

Sigma-Aldrich

Ivabradine hydrochloride

≥98% (HPLC)

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Synonym(s):
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
Empirical Formula (Hill Notation):
C27H36N2O5 · HCl
CAS Number:
148849-67-6
Molecular Weight:
505.05
MDL number:
MFCD00929899
UNSPSC Code:
12352200
PubChem Substance ID:
329825289
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +5 to +9°, c = 1 in DMSO

storage condition

desiccated

color

white to beige

solubility

H2O: ≥5 mg/mL (warmed)

storage temp.

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

InChI key

HLUKNZUABFFNQS-ZMBIFBSDSA-N

Gene Information

human ... HCN4(10021)

Application

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 Actions

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.

Features and Benefits

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.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Ivabradine abrogates TNF-alpha-induced degradation of articular cartilage matrix
Xiang X, et al.
International Immunopharmacology, 66, 347-353 (2019)
Ivabradine as adjuvant treatment for chronic heart failure
Stoppe C, et al.
Cochrane database of systematic reviews (Online), 2018(4) (2018)
Hao Zhang et al.
The Journal of pharmacology and experimental therapeutics, 368(1), 50-58 (2018-11-10)
An injury of the somatosensory system causes neuropathic pain, which is usually refractory to conventional analgesics, thus warranting the development of novel drugs against this kind of pain. The mechanism of neuropathic pain in rats that had undergone left L5
Elka Popova et al.
Acta neurobiologiae experimentalis, 80(2), 192-204 (2020-07-01)
Hyperpolarization‑activated and cyclic nucleotide‑gated (HCN) channels are well expressed in the vertebrate retina. Their role in formation of electroretinographic (ERG) responses to stimulus onset (b‑wave) and stimulus offset (d‑wave) are largely unknown. In this study we investigated the effects of
Hanna Bueno-Levy et al.
Frontiers in pharmacology, 10, 1566-1566 (2020-02-06)
Catecholaminergic polymorphic ventricular tachycardia (CPVT) is an inherited, stressed-provoked ventricular arrhythmia. CPVT is treated by β-adrenergic receptor blockers, Na+ channel inhibitors, sympathetic denervation, or by implanting a defibrillator. We showed recently that blockers of SK4 Ca2+-activated K+ channels depolarize the
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