ChemicalBook > CAS DataBase List > Glycopyrrolate

Glycopyrrolate

Product Name
Glycopyrrolate
CAS No.
596-51-0
Chemical Name
Glycopyrrolate
Synonyms
GLYCOPYRRONIUM;GLYCOPYROLATE;robinul;Glycopyrronium impurity N;Glycopyrronium for peak identification CRS;ahr504;NVA237;tarodyl;asecryl;robanul
CBNumber
CB7299542
Molecular Formula
C19H28BrNO3-
Formula Weight
398.33
MOL File
596-51-0.mol
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Glycopyrrolate Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0029
Product name
Glycopyrrolate
Purity
≥98% (HPLC)
Packaging
5mg
Price
$97.2
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1110
Product name
Glycopyrronium bromide
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100mg
Price
$269
Updated
2024/03/01
Sigma-Aldrich
Product number
1296009
Product name
Glycopyrrolate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
G0392
Product name
Glycopyrrolate
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$180
Updated
2024/03/01
Cayman Chemical
Product number
16498
Product name
Glycopyrrolate
Purity
≥95%
Packaging
5mg
Price
$57
Updated
2024/03/01
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Glycopyrrolate Chemical Properties,Usage,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

sunscreen

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

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

Raw materials

Preparation Products

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View Lastest Price from Glycopyrrolate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Glycopyrrolate 596-51-0
Price
US $0.00-0.00/KG
Min. Order
1g
Purity
99%min
Supply Ability
100g
Release date
2021-06-02
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Glycopyrrolate 596-51-0
Price
US $990.00-800.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-19
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Glycopyrrolate 596-51-0
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-09-13

596-51-0, GlycopyrrolateRelated Search:

Dimethyl carbonate Ipratropium bromide monohydrate Benzyldodecyldimethylammonium bromide Dimethyl sebacate Dimethyl sulfide Dimethyl sulfoxide Dimethyl ether Pinaverium bromide Tiotropium bromide Dimethyl sulfate N,N-Dimethylformamide Ethidium bromide Dimethyl fumarate ETHANE Sodium bromate Rocuronium bromide Allyl bromide Methyl 2-hydroxyisobutyrate

  • 1,1-dimethyl-3-hydroxypyrrolidiniumbromidealpha-cyclopentylmandelate
  • 1-methyl-3-pyrrolidylalpha-phenylcyclopentaneglycolatemethobromide
  • ahr504
  • asecryl
  • gastrodyn
  • glycopyrrolatebromide
  • nodapton
  • pyrrolidinium,1,1-dimethyl-3-hydroxy-,bromide,alpha-cyclopentylmandelate
  • robanul
  • robinul
  • tarodyl
  • tarodyn
  • 3-([Cyclopentylhydroxyphenylacetyl] oxy)-1,1-dimethylpyrrolidinium bromide
  • Glycopyrrone bromide
  • Pyrrolidinium, 3-(cyclopentylhydroxyphenylacetyl)oxy-1,1-dimethyl-, bromide
  • 1,1-Dimethyl-3-hydroxypyrrolidinium bromide α-cyclopentylmandelate
  • 3-Hydroxy-1,1-dimethylpyrrolidinium bromide α-cyclopentylmandelate (6CI, 7CI)
  • Copyrrolate
  • NSC 250836
  • NSC 251251
  • NSC 251252
  • Pyrrolidinium, 3-hydroxy-1,1-dimethyl-, bromide, α-cyclopentylmandelate (8CI)
  • β-1-Methyl-3-pyrrolidyl-α-cyclopentylmandelate methobromide
  • GLYCOPYROLATE
  • 1,1-Dimethyl-3-hydroxypyrrolidinium bromide a-cyclopentylmandelate
  • 3-Hydroxy-1,1-dimethylpyrrolidinium bromide a-cyclopentylmandelate
  • b-1-Methyl-3-pyrrolidyl-a-cyclopentylmandelate methobromide
  • 1,1-Dimethyl-3-[(2-cyclopentyl-2-phenyl-2-hydroxyacetyl)oxy]pyrrolidine-1-ium
  • 3-(Hydroxycyclopentylphenylacetoxy)-1,1-dimethylpyrrolidinium
  • 3-(Phenylcyclopentylhydroxyacetoxy)-1,1-dimethylpyrrolidinium
  • Robinul【parasympathetic drug】
  • (1,1-dimethyl-2,3,4,5-tetrahydropyrrol-3-yl) 2-cyclopentyl-2-hydroxy-2-phenyl-acetate bromide
  • GLYCOPYRROLATE
  • GLYCOPYRRONIUM
  • 3-(alpha-cyclopentylmandeloyloxy)-1,1-dimethylpyrrolidinium bromide
  • Glycopyrronium impurity
  • GLYCOPYRROLATE BROMIDE; GLYCOPYRRONIUM BROMIDE
  • 3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-diMethylpyrrolidiniuM broMide
  • Glycopyrrolate (200 mg)
  • 3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-diMethylpyrrolidin-1-iuM broMide
  • Glycopyrrolate IMpurity (Dehydro Glycopyrrole)
  • 1-methyl-3-pyrrolidyl α-phenyl-α-cyclopentylglycolate methobromide
  • 3-(2-phenyl-2-cyclopentylglycoloyloxy)-1,1-dimethylpyrrolidinium bromide
  • 3-hydroxy-1,1-dimethylpyrrolidinium bromide α-cyclopentylmandelate
  • NSC 2512
  • α-cyclopentylmandelic acid ester with 3-hydroxy-1,1-dimethylpyrrolidinium bromide
  • Glycopyrronium for peak identification
  • Glycopyrronium impurity N
  • Glycopyrrolate(596-51-0)
  • BULK DRUGS GLYCOPYRROLATE
  • Glycopyrrolate&gt
  • Glycopyrrolate Bromide EP impurity N
  • Glycopyrrolate Glycopyrrolate
  • Glycopyrronium impurity N CRS
  • Glycopyrronium for peak identification CRS
  • Glycopyrrolate (Glycopyrrone Bromide)
  • Glycopyrronium bromide CRS
  • Glycopyrrolate USP/EP/BP