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SML0281

Sigma-Aldrich

Ivabradine hydrochloride

≥98% (HPLC)

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

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About This Item

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

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

signalword

Warning

hcodes

H400

Hazard Classifications

Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Saki Miyake et al.
PloS one, 14(5), e0217209-e0217209 (2019-05-28)
Recently, attention has been focused on the role of hyperpolarization-activated cyclic nucleotide-gated (HCN) channels in the mechanism of and as a treatment target for neuropathic and inflammatory pain. Ivabradine, a blocker of HCN channels, was demonstrated to have an effect
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
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