Encyclopedia / Pharmaceutical Intermediates / Organic Intermediate / Custom Manufacturing

Mirabegron

CAS：223673-61-8
MW:396.5059
MF：C21H24N4O2S

Mirabegron, with the chemical formula C21H24N4O2S and CAS registry number 223673-61-8, is a compound known for its use as a selective β3-adrenergic receptor agonist. This medication is primarily used to treat overactive bladder (OAB) symptoms such as urinary frequency, urgency, and incontinence. Mirabegron works by relaxing the smooth muscle of the bladder, increasing the bladder's storage capacity and reducing the urge to urinate. It is available in oral tablet form and is typically taken once daily. Common side effects may include increased blood pressure, headache, and urinary tract infections. Mirabegron has been shown to be effective in improving OAB symptoms and is considered a safe and well-tolerated treatment option for individuals with this condition.

View more+

Email Tweet Share

Names and ldentifier
Properties
Use and Manufacturing
Msds
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Mirabegron

1.2 Synonyms: (2R)-2-(2-AMinothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)aMino]ethyl]acetic Acid Anilide; 2-(2-aMino-1,3-thiazol-4-yl)-N-(4-{2-[(2-hydroxy-2-phenylethyl)aMino]ethyl}phenyl)acetaMide; 2-(2-Amino-1,3-thiazol-4-yl)-N-[4-(2-{[(2R)-2-hydroxy-2-phenylethyl]amino}ethyl)phenyl]acetamide; 2-AMino-N-[4-[2-[[(2R)-2-hydroxy-2-phenyl-ethyl]aMino]-ethyl]phenyl]-4-thiazoleacetaMide; 4-Thiazoleacetamide, 2-amino-N-(4-(2-(((2R)-2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)-; 4-Thiazoleacetamide, 2-amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-; Betanis; Betmiga; Mirabegron(YM 178); MIRABEQRON; Myrbetriq; N-(4-(2-(2-hydroxy-2-phenylethylamino)ethyl)phenyl)-2-(2-aminothiazol-4-yl)acetamide; YM 178; YM-178;

View all

1.3 CAS No.: 223673-61-8

1.4 CID: 9865528

1.5 EINECS: 800-126-3

1.6 Molecular Formula: C21H24N4O2S

1.7 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

1.8 InChkey: PBAPPPCECJKMCM-IBGZPJMESA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)C(CNCCC2=CC=C(C=C2)NC(=O)CC3=CSC(=N3)N)O

1.10 Isomers Smiles: C1=CC=C(C=C1)[C@H](CNCCC2=CC=C(C=C2)NC(=O)CC3=CSC(=N3)N)O

2. Properties

2.1 Chemical Properties: White to Off-White Solid

2.2 pKa: 13.51±0.70(Predicted)

2.3 Water Solubility: Insoluble

2.4 StorageTemp: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

3. Use and Manufacturing

3.1 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.

3.2 Description

Mirabegron, with the chemical formula C21H24N4O2S, has the CAS number 223673-61-8. It is a medication used to treat overactive bladder. Mirabegron appears as a white to pale yellow powder. It does not have a distinct odor. Its basic structure consists of a benzene ring attached to a sulfonamide group and an amine group. This compound is slightly soluble in water. Mirabegron is considered safe for use when taken as directed by a healthcare professional. However, like any medication, it may cause side effects in some individuals. It is important to follow the prescribed dosage and consult a doctor if any adverse reactions occur. Mirabegron should be stored in a cool and dry place, away from direct sunlight.

Applicable Fields

Overactive Bladder Treatment: Mirabegron is primarily used for the treatment of overactive bladder. It works by relaxing the muscles of the bladder, which helps to reduce the frequent urge to urinate, urgency, and incontinence associated with this condition. The mechanism of action involves stimulating beta-3 adrenergic receptors in the bladder, leading to relaxation of the detrusor muscle.

Storage Conditions: Cool and dry place.

View all

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Eye irritation, Category 2

Reproductive toxicity, Category 2

Specific target organ toxicity – repeated exposure, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H319 Causes serious eye irritation H361 Suspected of damaging fertility or the unborn child H373 May cause damage to organs through prolonged or repeated exposure H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention. P314 Get medical advice/attention if you feel unwell. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

5. Computed Properties

Molecular Weight：396.5059g/mol
Molecular Formula：C₂₁H₂₄N₄O₂S
Compound Is Canonicalized：True
Exact Mass：2.1
XLogP3-AA：396.16199719
Monoisotopic Mass：396.16199719
Complexity：467
Rotatable Bond Count：9
Hydrogen Bond Donor Count：4
Hydrogen Bond Acceptor Count：6
Topological Polar Surface Area：129
Heavy Atom Count：：28
Defined Atom Stereocenter Count：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceB7sABAAAAAAAAAAAAAAAAAAWAAAAAwYAAAAAAAAAAB0AAAHgQQCAAADBzl3gax0ZLIEgisAyVydACC8KlhCjkIiJU4bIiKNjrg1ZGEcAhk1APY2CeQwKAOCAAAAAAAAAAQAAAAAAAAAAAAAAAAAA==

6.Other Information

Target: Value

β3-adrenoceptor: 22.4 nM(EC50)

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.

View all

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.

View all

Chemical 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).

View all

7. Toltal 127 Suppliers View more

Hebei Saisier Technology Co., LTD

^1YR

Tel: Update Time:2024/11/15

inquire

Weifang Xingbei International Trade Co., Ltd

^1YR

Tel: Update Time:2024/11/15

inquire

Baoji Guokang Healthchem co.,ltd

^1YR

Tel: Update Time:2024/11/15

inquire

Top quality Mirabegron CAS 223673-61-8 with best price

Wuhan Fortuna Chemical Co., Ltd.

^1YR

Tel: Update Time:2024/08/08

inquire

CANGZHOU ENKE PHARMA-TECH CO.,LTD

^1YR

Tel: Update Time:2024/11/12

inquire

8. Related Questions

: Is Mirabegron the New Solution for Overactive Bladder?Overactive bladder (OAB) is a common condition that significantly affects the quality of life for patients. The International Continence Society defines OAB as a syndrome characterized by urgency, wit..; Want to know more about Mirabegron? Discover its benefits and usage!Minai.com data shows that in 2020, the total market size of chemical drugs and urinary system drugs at the terminals of China's urban public hospitals, county-level public hospitals, urban community c..; What is the significance of Mirabegron in the treatment of Overactive Bladder (OAB)?Mirabegron (mirabegron, 1) is a β-3 adrenergic receptor agonist that relaxes the detrusor smooth muscle by stimulating the β-3 adrenergic receptors, thereby increasing bladder capacity. It is used t..; What are the instructions for using Mirabegron?Background and Overview Mirabegron (mirabegron) tablets were developed by the Japanese pharmaceutical company Astellas and were launched in Japan on September 16, 2011. They were approved by the U.S. ..

9. Realated Product Infomation