ChemicalBook > CAS DataBase List > Ivabradine

Ivabradine

Product Name: Ivabradine
CAS No.: 155974-00-8
Chemical Name: Ivabradine
Synonyms: Ivabradine sulfate;Ivabradine;Ivabridine –;Ivabradine API;Ivabradine USP/EP/BP;Ivabradine HCl Premix;N-desmethyl ivabridine-d6;Ivabradine(Hydrochloride form);3-[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-one;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
CBNumber: CB41178988
Molecular Formula: C27H36N2O5
Formula Weight: 468.59
MOL File: 155974-00-8.mol

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Ivabradine Property

Boiling point:: 626.9±55.0 °C(Predicted)
Density: 1.146±0.06 g/cm3(Predicted)
pka: 8.77±0.50(Predicted)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

AvaChem

Product number: 2176B
Product name: Ivabradine
Packaging: 10mg
Price: $39
Updated: 2021/12/16

AvaChem

Product number: 2176B
Product name: Ivabradine
Packaging: 100mg
Price: $59
Updated: 2021/12/16

AvaChem

Product number: 2176B
Product name: Ivabradine
Packaging: 1g
Price: $249
Updated: 2021/12/16

AvaChem

Product number: 2176B
Product name: Ivabradine
Packaging: 10g
Price: $1190
Updated: 2021/12/16

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Ivabradine Chemical Properties,Usage,Production

Description

Ivabradine is a first selective and specific If inhibitor that was approved by EMEA in November for symptomatic treatment of chronic stable angina pectoris in patients with normal sinus rhythm. This is the first agent to lower heart rate by inhibiting the cardiac pacemaker If current. The compound was discovered and developed by Servier and is currently being marketed in Ireland.

Uses

Ivabradine is a potent and orally active HCN (hyperpolarization-activated cyclic nucleotide-gated) channel blocker that inhibits the cardiac pacemaker current (If). Ivabradine reduces dose-dependently heart rate without modification of blood pressure. Ivabradine shows anticonvulsant, anti-ischaemic and anti-anginal activity[1][2][3][4].

Definition

ChEBI: 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. Use (as its hydrochloride salt) to treat patients with angina who have intolerance to beta blockers and/or heart failure.

Synthesis

The convergent synthesis of ivabradine was accomplished by coupling the key benzocylclobutanyl amine 73 with oxadioxalane 76 in an in situ deprotection and amination as shown in Scheme 13. For the synthesis of the key amine 73, cyano group of compound 69 is reduced with borane-THF to give amine 70 in 90% yield, which was reacted with ethyl chloroformate to give carbamate 71 in 80% yield. Complete reduction of the carbamate was accomplished by refluxing with LAH in THF to give racemic methyl amine 72 in 92% yield, which was then resolved by crystallizing with N-acetyl ¨CL-glutamic acid to give chiral salt 73. Prior to the next step, the amine is converted to the hydrochloride salt.
The coupling partner 76 to make ivabradine was prepared from the azepinone 74 by first reacting with bromoethyldioxalane to give 75. The olefin in 75 was reduced by hydrogenating with palladium/carbon catalyst at 55??C to give 76. To the same pot, the amine 73 was added and hydrogenated to give reductive amination product ivabradine hydrochloride (X) in very good yields.

in vivo

Ivabradine (1, 10, 20 mg/kg; i.p.) shows anticonvulsant and neuroprotective action in mice^[3].
Ivabradine (5, 10, 20 mg/kg;p.o.; daily for 1 weeks) lowers heart rate in mice with enhanced sympathoadrenergic activities^[4].

Animal Model:	25-30 g, 6 weeks male Swiss mice^[3]
Dosage:	1, 10, 20 mg/kg
Administration:	I.p.; for 3 days
Result:	Attenuated PTZ- and PICRO-induced seizures while presented an antioxidant effect in all brain areas studied, and reduced cleaved caspase-3 expression in the CA1 and DG region of PICRO- and PTZ-treated mice, respectively.

Animal Model:	3-4 months transgenic (TG) mice with cardiac-restricted overexpression of b2AR^[4]
Dosage:	5, 10, 20 mg/kg
Administration:	P.o; daily for 1 weeks
Result:	Reduced the maximal HR increase in response to the b-agonist isoproterenol, without modifying the response of contractile parameters at 10 mg/kg.

References

[1] Tardif JC, et al. Efficacy of ivabradine, a new selective I(f) inhibitor, compared with atenolol in patients with chronic stable angina. Eur Heart J. 2005 Dec;26(23):2529-36. DOI:10.1093/eurheartj/ehi586
[2] Mulder P, et al. Heart rate slowing for myocardial dysfunction/heart failure. Adv Cardiol. 2006;43:97-105. DOI:10.1159/000095431
[3] Cavalcante TMB, et al. Ivabradine possesses anticonvulsant and neuroprotective action in mice. Biomed Pharmacother. 2019 Jan;109:2499-2512. DOI:10.1016/j.biopha.2018.11.096
[4] Du XJ, et al. I(f) channel inhibitor ivabradine lowers heart rate in mice with enhanced sympathoadrenergic activities. Br J Pharmacol. 2004 May;142(1):107-12. DOI:10.1038/sj.bjp.0705696

Ivabradine Preparation Products And Raw materials

Raw materials

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View Lastest Price from Ivabradine manufacturers

Hebei Mingeng Biotechnology Co., Ltd

Product: Ivabradine 155974-00-8
Price: US $200.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000kg/Month
Release date: 2022-11-27

Shijiazhuang Gantuo Biotechnology Co., Ltd

Product: Ivabradine 155974-00-8
Price: US $100.00/mg
Min. Order: 10mg
Purity: 99%
Supply Ability: 1000g
Release date: 2023-03-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: ivabradine 155974-00-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-26

155974-00-8, IvabradineRelated Search:

Ivabradine IMpurity Ivabradine Impurity 15 Dehydro Ivabradine Oxalate Ivabradine Impurity 1 Hydrochloride 3-[3-[[[(7S)-3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]Methyl]MethylaMino]propyl]-1,3-dihydro-7,8-diMethoxy-H-3-benzazepin-2-one (Z)-3-(3-chloropropyl)-7,8-diethyl-1H-benzo[d] azepin-2 (3H)-one 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one edoxaban Ivabradine Impurity 1 Hydrochloride 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 3-(3-Chloropropyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one 7-DeMethyl Ivabradine Hydroxy Ivabradine N-Desmethyl Ivabradine D6 HCl (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Ivabradine hydrochloride N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide Ivabradine Impurity 21 HCl

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

3-[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-one

Ivabradine

Ivabridine –

7-(3-((((R)-4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)Methyl)(Methyl)aMino)propyl)-2,3-diMethoxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-one

Ivabradine sulfate

Ivabradine(Hydrochloride form)

2H-3-Benzazepin-2-one, 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-

Ivabradine HCl Premix

Ivabradine USP/EP/BP

IvabradineQ: What is Ivabradine Q: What is the CAS Number of Ivabradine Q: What is the storage condition of Ivabradine Q: What are the applications of Ivabradine

Ivabradine API

N-desmethyl ivabridine-d6

155974-00-8

API