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Mirabegron

Product Name
Mirabegron
CAS No.
223673-61-8
Chemical Name
Mirabegron
Synonyms
Mirabelon;YM 178;CS-732;Betmiga;Mirabello;Mirabegron;MIRABEQRON;Mira veron;Mirabregon;Mirabellon
CBNumber
CB22493967
Molecular Formula
C21H24N4O2S
Formula Weight
396.51
MOL File
223673-61-8.mol
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Mirabegron Property

Melting point:
138-140°C
Boiling point:
690.0±55.0 °C(Predicted)
Density 
1.313
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
Chloroform (Slightly, Heated), Methanol (Slightly)
form 
Solid
pka
13.51±0.70(Predicted)
color 
White to Pale Yellow
InChI
InChI=1S/C21H24N4O2S/c22-21-25-18(14-28-21)12-20(27)24-17-8-6-15(7-9-17)10-11-23-13-19(26)16-4-2-1-3-5-16/h1-9,14,19,23,26H,10-13H2,(H2,22,25)(H,24,27)/t19-/m0/s1
InChIKey
PBAPPPCECJKMCM-IBGZPJMESA-N
SMILES
S1C=C(CC(NC2=CC=C(CCNC[C@H](O)C3=CC=CC=C3)C=C2)=O)N=C1N
CAS DataBase Reference
223673-61-8
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML2480
Product name
Mirabegron
Purity
≥98% (HPLC)
Packaging
5MG
Price
$115
Updated
2024/03/01
Sigma-Aldrich
Product number
SML2480
Product name
Mirabegron
Purity
≥98% (HPLC)
Packaging
25MG
Price
$277.2
Updated
2024/03/01
Cayman Chemical
Product number
17319
Product name
Mirabegron
Purity
≥98%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
17319
Product name
Mirabegron
Purity
≥98%
Packaging
5mg
Price
$108
Updated
2024/03/01
Cayman Chemical
Product number
17319
Product name
Mirabegron
Purity
≥98%
Packaging
10mg
Price
$195
Updated
2024/03/01
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Mirabegron Chemical Properties,Usage,Production

Description

Betanis (Mirabegron) was approved in July 2011 by the Japanese Ministry of Health, Labour, and Welfare for the treatment of urgency, urinary frequency, and urinary urge urinary incontinence associated with overactive bladder (OAB). Mirabegron is synthesized by coupling 4-nitrophenethyl amine to (R)-2-hydroxy-2-phenylacetic acid. The resulting amide is reduced to an amine. The nitro group is then reduced and the resulting aniline is coupled to 2-(2-aminothiazol-4-yl) acetic acid to give mirabegron. Mirabegron has an EC50 of 22 nM (intrinsic activity=0.8) for β3-AR with no detectable activity for β1- andβ2-AR (EC50>10,000 nM). In an anesthetized rat rhythmic bladder contraction model in which bladder contractions are induced by saline, mirabegron at 3 mg/kg iv decreased the frequency of rhythmic bladder contraction without suppressing contraction amplitude. These data suggest that the activation of β3-AR increases bladder capacity without influencing the frequency of bladder contraction.

Chemical Properties

White to Off-White Solid

Originator

Astellas Pharma Inc. (Japan)

Uses

Mirabegron is a selective β3-adrenoceptor agonist with EC50 of 22.4 nM.

Uses

A potent bladder relaxant compound

Uses

Potent bladder relaxant and reagent for diabetes remedy.;Labeled Mirabegron, intended for use as an internal standard for the quantification of Mirabegron by GC- or LC-mass spectrometry.

Definition

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2-amino-1,3-thiazol-4-ylacetic acid with the anilino group of (1R)-2-{[2-(4-aminophenyl)ethyl]amino}-1-phenylethanol. Used for the treatment of overactive ladder syndrome.

brand name

Betanis

Clinical Use

Mirabegron is an orally active β3-adrenoceptor agonist currently in development by Astellas Pharma for the treatment of overactive bladder (OAB). The drug is a nanomolar EC50 antagonist against human β3-AR biochemical assays with good selectivity over b1- and β2-ARs. Mirabegron demonstrates a novel mechanism by targeting the β3-AR for bladder relaxation to help manage OAB symptoms such as increased urinary urgency and frequency and urgency incontinence. However, mirabegron is a cytochrome P450 2D6 inhibitor, and it raises a concern for drug–drug interaction with concomitant administration of other cytochrome P450 2D6 substrates.

Synthesis

The synthesis of mirabegron began with a condensation reaction between (R)-styrene oxide (182) and 4-nitrophenylethylamine (183) in refluxing isopropanol to yield corresponding aminoalcohol 184 in 22% yield. Aminoalcohol 184 was protected as its N-Boc derivative with t-butyl dicarbonate in THF in 96% yield, and this was followed by nitro group hydrogenative reduction with 10% Pd/C to give free amine 185 in 96% yield. Aniline 185 was coupled with 2-amino-4-thiazolyl acetic acid 186 in the presence of EDCI and HOBt to give amide 187 in 85% yield. Removal of the Boc group was affected with 4 N HCl solution in a 2:1 volume ratio in ethyl acetate to obtain mirabegron HCl in 52% yield. The HCl salt was neutralized with 1 N NaOH to deliver mirabegron (XVII).

Drug interactions

Potentially hazardous
interactions with other drugs None known

Metabolism

Metabolised via multiple pathways involving dealkylation, oxidation, (direct) glucuronidation, and amide hydrolysis. Renal elimination of mirabegron is primarily through active tubular secretion along with glomerular filtration.

storage

Store at -20°C

Mirabegron Preparation Products And Raw materials

Raw materials

Preparation Products

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Mirabegron Suppliers

Canada 2 China 416 Germany 1 India 61 The Netherlands 1 United Kingdom 2 United States 16 Global 499
MedChemexpress LLC
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Eastar Chemical Corp
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View Lastest Price from Mirabegron manufacturers

HangZhou RunYan Pharma Technology Co.,LTD.
Product
Mirabegron 223673-61-8
Price
US $0.00-0.00/g
Min. Order
10g
Purity
99% HPLC
Supply Ability
10000
Release date
2024-09-10
Anhui Dexinjia Biopharm Co., Ltd
Product
Mirabegron 223673-61-8
Price
US $1000.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500kg per month
Release date
2020-03-13
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Mirabegron 223673-61-8
Price
US $0.00/g
Min. Order
1g
Purity
99%min
Supply Ability
1000g
Release date
2021-10-18

223673-61-8, MirabegronRelated Search:

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