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B2185

Sigma-Aldrich

Bisoprolol hemifumarate salt

≥98% (HPLC), solid

Synonym(s):

1-[4-[[2-(1-Methylethoxy)ethoxy]methyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanol hemifumarate salt

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About This Item

Empirical Formula (Hill Notation):
C18H31NO4 · .5C4H4O4
CAS Number:
104344-23-2
Molecular Weight:
383.48
MDL number:
MFCD00792743
UNSPSC Code:
12352200
PubChem Substance ID:
24724414
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >20 mg/mL

originator

Teva

SMILES string

OC(=O)\C=C\C(O)=O.CC(C)NCC(O)COc1ccc(COCCOC(C)C)cc1.CC(C)NCC(O)COc2ccc(COCCOC(C)C)cc2

InChI

1S/2C18H31NO4.C4H4O4/c2*1-14(2)19-11-17(20)13-23-18-7-5-16(6-8-18)12-21-9-10-22-15(3)4;5-3(6)1-2-4(7)8/h2*5-8,14-15,17,19-20H,9-13H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+

InChI key

VMDFASMUILANOL-WXXKFALUSA-N

Gene Information

human ... ADRB1(153)

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Application

Bisoprolol hemifumarate salt has been used as a β-adrenergic receptor (β-AR) antagonist in cardiac fibrosis mice model.

Biochem/physiol Actions

Bisoprolol hemifumarate is useful in oral formulations due to its high bioavailability. It also shows long elimination half-life.
Cardioselective β1-adrenoceptor antagonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Teva. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H361fd,H373

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2 - STOT RE 2

Target Organs

Heart

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Pharmacokinetics and metabolism of bisoprolol enantiomers in humans
Horikiri Y, et al.
Journal of Pharmaceutical Sciences, 87(3), 289-294 (1998)
A E Tattersfield et al.
British journal of clinical pharmacology, 18(3), 343-347 (1984-09-01)
Bisoprolol is a new beta-adrenoceptor antagonist which has shown beta-adrenoceptor selectivity in studies in isolated tissues. Bronchial and cardiac beta-adrenoceptor blockade were assessed in eight normal subjects before and after oral ingestion of placebo, bisoprolol 20 and 40 mg, metoprolol
Astrid Kassner et al.
The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation, 31(10), 1127-1135 (2012-09-15)
Response to catecholamines is blunted in terminal heart failure due to β-receptor downregulation and uncoupling from adenylyl cyclase (AC). Improved myocardial responsiveness to catecholamines after ventricular assist device (VAD) support is associated with upregulation of β1-adrenergic receptors (β1-ARs). Little is
Akira Sezai et al.
The Journal of thoracic and cardiovascular surgery, 144(5), 1241-1248 (2012-08-04)
We previously performed a trial of intravenous landiolol hydrochloride during and after cardiac surgery (the PASCAL trial) and demonstrated a preventive effect on postoperative atrial fibrillation (AF). In the present study, we investigated the efficacy of increasing the dose and
János Tomcsányi et al.
Orvosi hetilap, 154(7), 267-271 (2013-02-12)
The authors describe two cases of takotsubo cardiomyopathy developing after an abrupt withdrawal of carvedilol and bisoprolol. Takotsubo or stress cardiomyopathy is characterized by acute and reversible cardiac dysfunction without coronary artery disease. It is triggered by acute emotional or
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