Umeclidinium bromide
- Iupac Name：diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide
- CAS No.: 869113-09-7
- Molecular Weight：508.48976
- Modify Date.: 2023-02-17 07:02
- Introduction: Umeclidinium bromide is a long-acting muscarinic acetylcholineantagonist developed by GlaxoSmithKline and approvedby the US FDA at the end of 2013 for use in combination withvilanterol, a b2 agonist, for the treatment of chronic obstructivepulmonary disease. Due to umeclidinium’s poor oral bioavailability,the drug is administrated by inhalation as dry powder.
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1. Names and Identifiers
- 1.1 Name
- Umeclidinium bromide
- 1.2 Synonyms
1-(2-(benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)quinuclidin-1-ium bromide 1-[2-(Benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-quinuclidinium Bromide 1-[2-(Benzyloxy)ethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide 1-Azoniabicyclo[2.2.2]octane, 1-(hydroxydiphenylmethyl)-4-[2-(phenylmethoxy)ethyl]-, bromide (1:1) 1-Azoniabicyclo[2.2.2]octane, 4-(hydroxydiphenylmethyl)-1-[2-(phenylmethoxy)ethyl]-, bromide (1:1) 4-[2-(Benzyloxy)ethyl]-1-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide CS-1562 DIPHENYL-[1-(2-PHENYLMETHOXYETHYL)-1-AZONIABICYCLO[2.2.2]OCTAN-4-YL]METHANOL diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol,bromide GSK 573719A GSK573719A GSK-573719A MFCD18782614 Umeclidinium (bromide) Umeclidinium bromide (JAN/USAN) Umeclidinium bromide [USAN] Umeclidinium bromide(GSK573719A) umeclidinium(gsk573719a) Umeclinidium bromide UNII-7AN603V4JV
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- 1.3 CAS No.
- 869113-09-7
- 1.4 CID
- 11519069
- 1.5 EINECS(EC#)
- 638-761-1
- 1.6 Molecular Formula
- C29H34BrNO2 (isomer)
- 1.7 Inchi
- InChI=1S/C29H34NO2.BrH/c31-29(26-12-6-2-7-13-26,27-14-8-3-9-15-27)28-16-19-30(20-17-28,21-18-28)22-23-32-24-25-10-4-1-5-11-25;/h1-15,31H,16-24H2;1H/q+1;/p-1
- 1.8 InChIkey
- PEJHHXHHNGORMP-UHFFFAOYSA-M
- 1.9 Canonical Smiles
- C1C[N+]2(CCC1(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)CCOCC5=CC=CC=C5.[Br-]
- 1.10 Isomers Smiles
- C1C[N+]2(CCC1(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)CCOCC5=CC=CC=C5.[Br-]
2. Properties
- 2.1 Precise Quality
- 507.17700
- 2.1 PSA
- 29.46000
- 2.1 logP
- 2.10280
- 2.1 StorageTemp
- under inert gas (nitrogen or Argon) at 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A quaternary ammonium salt that is the bromide salt of umeclidinium. Used in combination with vilanterol for long-term maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease.
4. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Acute toxicity - Inhalation, Category 4
Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H332 Harmful if inhaled H400 Very toxic to aquatic life H411 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. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P391 Collect spillage. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
5. Other Information
- 5.0 Description
- Umeclidinium bromide is a long-acting muscarinic acetylcholine antagonist developed by GlaxoSmithKline and approved by the US FDA at the end of 2013 for use in combination with vilanterol, a b2 agonist, for the treatment of chronic obstructive pulmonary disease. Due to umeclidinium’s poor oral bioavailability, the drug is administrated by inhalation as dry powder.
- 5.1 Uses
- Umeclidinium Bromide is considered as a potentially long-acting antimuscarinic agent.
- 5.2 Definition
- ChEBI: A quaternary ammonium salt that is the bromide salt of umeclidinium. Used in combination with vilanterol for long-term maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease.
- 5.3 Chemical Synthesis
- Commercially available ethyl isonipecotate (278) was alkylated with 1-bromo-2-chloroethane in the presence of K2CO3 in acetone to give ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (279). This material was then treated with lithium diisopropylamine (LDA) in THF to affect a transannular substitution reaction resulting in the cyclized quinuclidine 280 in 96% yield. Excess of phenyllithium was added to ester 280 in THF starting at low temperature then gradually warming to room temperature to give tertiary alcohol 281 in 61% yield. Amine 281 was finally alkylated with benzyl 2- bromoethyl ether (282) in MeCN/CHCl3 at elevated temperatures to afford umeclidinium bromide (XXXV) in 69% yield.
6. Computational chemical data
- Molecular Weight: 508.48976g/mol
- Molecular Formula: C29H34BrNO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 507.17729
- Monoisotopic Mass: 507.17729
- Complexity: 543
- Rotatable Bond Count: 8
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 29.5
- Heavy Atom Count: 33
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 2
- CACTVS Substructure Key Fingerprint: AAADcfB6MAAAEAAAAAAAAAAAAAAAAAAAAAA8ePECAAAAAAABUAAAHgAACAAADkThmAYwAIMABgCAAiBCAAACAAAgAAAIiAAICIgKJiKAsRiHcAAkwAGYuAewwOAPgAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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8. Realated Product Infomation
skype
1YR
