Glycopyrrolate
- CAS No.
- 596-51-0
- Chemical Name:
- Glycopyrrolate
- Synonyms
- GLYCOPYRRONIUM;GLYCOPYROLATE;robinul;Glycopyrronium impurity N;Glycopyrronium for peak identification CRS;ahr504;NVA237;tarodyn;tarodyl;robanul
- CBNumber:
- CB7299542
- Molecular Formula:
- C19H28BrNO3-
- Molecular Weight:
- 398.33
- MDL Number:
- MFCD00072137
- MOL File:
- 596-51-0.mol
- MSDS File:
- SDS
Melting point | 192-195°C |
---|---|
Density | 1.3222 (rough estimate) |
refractive index | 1.6200 (estimate) |
storage temp. | 2-8°C |
solubility | H2O: ≥24mg/mL |
form | powder |
color | white to tan |
Merck | 14,4501 |
Stability | Hygroscopic |
InChI | InChI=1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1 |
InChIKey | VPNYRYCIDCJBOM-UHFFFAOYSA-M |
SMILES | C(O)(C(=O)OC1CC[N+](C)(C)C1)(C1=CC=CC=C1)C1CCCC1.[Br-] |
CAS DataBase Reference | 596-51-0(CAS DataBase Reference) |
FDA UNII | V92SO9WP2I |
ATC code | A03AB02,D11AA01,R03BB06 |
NCI Drug Dictionary | glycopyrrolate |
SAFETY
Risk and Safety Statements
Symbol(GHS) | GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H302-H315-H319-H335 | |||||||||
Precautionary statements | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 | |||||||||
Hazard Codes | Xi | |||||||||
Risk Statements | 36/37/38 | |||||||||
Safety Statements | 26 | |||||||||
WGK Germany | 3 | |||||||||
RTECS | UY4337630 | |||||||||
HS Code | 29339900 | |||||||||
Toxicity | LD50 (72 hr.) in female mice, female rats (mg/kg): 107, 196 i.p.; in male rats (mg/kg): 1150 orally (Franko) | |||||||||
NFPA 704 |
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Glycopyrrolate price More Price(38)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | SML0029 | Glycopyrrolate ≥98% (HPLC) | 596-51-0 | 5mg | $97.2 | 2024-03-01 | Buy |
Sigma-Aldrich | BP1110 | Glycopyrronium bromide British Pharmacopoeia (BP) Reference Standard | 596-51-0 | 100mg | $269 | 2024-03-01 | Buy |
Sigma-Aldrich | 1296009 | Glycopyrrolate United States Pharmacopeia (USP) Reference Standard | 596-51-0 | 200mg | $436 | 2024-03-01 | Buy |
TCI Chemical | G0392 | Glycopyrrolate >98.0%(HPLC)(T) | 596-51-0 | 100mg | $180 | 2024-03-01 | Buy |
Cayman Chemical | 16498 | Glycopyrrolate ≥95% | 596-51-0 | 5mg | $57 | 2024-03-01 | Buy |
Glycopyrrolate Chemical Properties,Uses,Production
Description
Glycopyrrolate is an antagonist of muscarinic acetylcholine receptors (mAChRs; Kis = 0.42, 1.77, 0.52, 0.78, and 1.29 nM for the M1-M5 receptors, respectively). It induces relaxation of precontracted isolated human bronchi when used at concentrations of 0.01, 0.1, or 1 μM. Glycopyrrolate reduces post-prandial gastric antral motility in dogs when administered at a dose of 0.01 mg/kg. It inhibits salivation in a rat model of sialorrhea induced by pilocarpine with an ED50 value of 0.74 μg/kg. Formulations containing glycopyrrolate have been used in the treatment of sialorrhea, peptic ulcers, and chronic obstructive pulmonary disease (COPD).
Chemical Properties
White Solid
Originator
Robinul,Robins,US,1961
Uses
For use as a preoperative antimuscarinic to reduce salivary, tracheobronchial, and pharyngeal secretions, to reduce the volume and free acidity of gastric secretions and to block cardiac vagal inhibitory reflexes during induction of anesthesia and intubat
Uses
sunscreen
Uses
Inhaled glycopyrrolate of is used to treat air flow blockage and prevent worsening of chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. COPD is a long-term lung disease that causes bronchospasm (difficulty with breathing).
Uses
Glycopyrrolate inhibits secretion of digestive juices and restores normal stomach function. It is used for treating stomach ulcers, inflamed intestine, and also as a pre-operational drug for inhibiting excess stomach secretion.
Uses
A synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.
Definition
ChEBI: A quaternary ammonium salt composed of 3-{[cyclopentyl(hydroxy)phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium and bromide ions in a 1:1 ratio.
Manufacturing Process
A mixture of 42.5 grams (0.17 mol) of methyl α-cyclopentyl mandelate and 18
grams (0.175 mol) of 1-methyl-3-pyrrolidinol in 500 ml of heptane was
refluxed under a Dean and Stark moisture trap, with the addition of four 0.1
gram pieces of sodium at 1-hour intervals. After 5 hours' refluxing the
solution was concentrated to one-half volume, and extracted with cold 3N HCl.
The acid extract was made alkaline with aqueous sodium hydroxide and
extracted with ether which was washed, dried over sodium sulfate, filtered
and concentrated. The residue was fractionated at reduced pressure. Yield 33
grams (64%); BP 151° to 154°C/0.2 mm, nD23= 1.5265.
The hydrochloride salt was precipitated as an oil from an ethereal solution of
the base with ethereal hydrogen chloride. It was crystallized from butanone;
MP 170° to 171.5°C.
The methyl bromide quaternary was prepared by saturating a solution of the
base in dry ethyl acetate with methyl bromide. After standing for 9 days the resulting crystalline solid was filtered and recrystallized from butanone and
from ethyl acetate; MP 193° to 194.5°C.
brand name
Robinul (Baxter Healthcare); Robinul (Sciele).
Therapeutic Function
Spasmolytic
General Description
Glycopyrrolate, 3-hydroxy-1,1-dimethylpyrrolidinium bromide -cyclopentylmandelate(Robinul), occurs as a white, crystalline powder that is solublein water or alcohol but practically insoluble in chloroformor ether.
Glycopyrrolate is a typical anticholinergic and possesses,at adequate dosage levels, the atropine-like effectscharacteristic of this class of drugs. It has a spasmolyticeffect on the musculature of the GI tract as well as the genitourinarytract. It diminishes gastric and pancreatic secretionsand the quantity of perspiration and saliva. Its sideeffects are also typically atropine-like (i.e., dryness of themouth, urinary retention, blurred vision, constipation).Glycopyrrolate is a more potent antagonist on M1 than onM2 and M3 receptors. The low affinity of M2 receptorsmay, in part, explain the low incidence of tachycardiaduring use of this drug as an antispasmodic.77 Because ofits quaternary ammonium character, glycopyrrolate rarelycauses CNS disturbances, although in sufficiently highdosage, it can bring about ganglionic and myoneural junctionblock.
Biochem/physiol Actions
Glycopyrrolate is long-acting muscarinic antagonist (LAMA). It is kinetically selective muscarinic M3 receptor antagonist.
Mechanism of action
Glycopyrrolate exhibits onset of action within 1 minute when given intravenously and an elimination half-life of approximately 50 minutes. Glycopyrrolate undergoes urinary excretion and elimination.
Clinical Use
Glycopyrrolate is used as an adjunct in the management of pepticulcer and other GI ailments associated with hyperacidity,hypermotility, and spasm. In common with other anticholinergics,its use does not preclude dietary restrictions or use ofantacids and sedatives if these are indicated.
Side effects
- dry mouth
- blurred vision
- vision problems
- loss of taste
- headache
- nervousness
- confusion
- drowsiness
Safety Profile
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and Br-. See also BROMIDES.
Synthesis
Glycopyrrolate, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide (14.1.22), is synthesized from the methyl ester of |á-cyclopentylmandelic acid (14.1.20) by transesterification using 3-hydroxy-1-methylpyrrolidine as an alcohol component, which forms the ester (14.1.21), which is further transformed into a quaternary salt upon reaction with methylbromide, giving glycopyrrolate (14.1.22). The starting methyl ester of |á-cyclopentylmandelic acid (14.1.20) is synthesized by reacting cyclopentylmagnesiumbromide with the methyl ester of phenylglyoxylic acid [17,18].
Veterinary Drugs and Treatments
Glycopyrrolate injection is approved for use in dogs and cats. The FDA approved indication for these species is as a preanesthetic anticholinergic agent. The drug is also used to treat sinus bradycardia, sinoatrial arrest, and incomplete AV block, where anticholinergic therapy may be beneficial. When cholinergic agents such as neostigmine or pyridostigmine are used to reverse neuromuscular blockade due to non-depolarizing muscle relaxants, glycopyrrolate may be administered simultaneously to prevent the peripheral muscarinic effects of the cholinergic agent.
Glycopyrrolate Preparation Products And Raw materials
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
BIONNA MEDICINE CO.,LTD | 01056380788-8515; +8618518759099 | 790226113@qq.com | China | 52 | 58 |
HAINAN POLY PHARMCEUTICAL CO. LTD | +86-0571-89385087 +8613616530509 | ff@hnpoly.com | China | 118 | 58 |
Anhui Dexinjia Biopharm Co., Ltd | +86-531-82375818 +8615064153060 | sales01@jndxj.com | China | 291 | 58 |
Shaanxi Dideu Medichem Co. Ltd | +86-29-81148696 +86-15536356810 | 1022@dideu.com | China | 3878 | 58 |
Hebei Kingfiner Technology Development Co.Ltd | +86-15532196582 +86-15373005021 | lisa@kingfinertech.com | China | 2990 | 58 |
Anhui Ruihan Technology Co., Ltd | +8617756083858 | daisy@anhuiruihan.com | China | 994 | 58 |
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. | +86-18600796368 +86-18600796368 | sales@sjar-tech.com | China | 260 | 58 |
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD | +8615383190639 | admin@86-ss.com | China | 1000 | 58 |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 18628 | 58 |
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View Lastest Price from Glycopyrrolate manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2024-09-23 | Glycopyrrolate
596-51-0
|
US $990.00-800.00 / kg | 1kg | 99% | 5000 | HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD | ||
2024-09-20 | Glycopyrrolate
596-51-0
|
US $0.00 / g | 1g | More Than 99% | 100kg/Month | BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. | ||
2024-09-18 | Glycopyrrolate
596-51-0
|
US $0.00-0.00 / KG | 1g | 99%min | 100g | WUHAN FORTUNA CHEMICAL CO., LTD |
- Glycopyrrolate
596-51-0
- US $990.00-800.00 / kg
- 99%
- HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
- Glycopyrrolate
596-51-0
- US $0.00 / g
- More Than 99%
- BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
- Glycopyrrolate
596-51-0
- US $0.00-0.00 / KG
- 99%min
- WUHAN FORTUNA CHEMICAL CO., LTD