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SML0281

Sigma-Aldrich

Ivabradine hydrochloride

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C27H36N2O5 · HCl
Numéro CAS:
148849-67-6
Poids moléculaire :
505.05
Numéro MDL:
MFCD00929899
Code UNSPSC :
12352200
ID de substance PubChem :
329825289
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

[α]/D +5 to +9°, c = 1 in DMSO

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: ≥5 mg/mL (warmed)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

HLUKNZUABFFNQS-ZMBIFBSDSA-N

Informations sur le gène

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).

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H400

Conseils de prudence

P273 - P391 - P501

Classification des risques

Aquatic Acute 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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