Glycopyrrolate Chemical Properties

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)

Safety Information

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)

MSDS

• Language:English Provider:(1,1-Dimethyl-2,3,4,5-tetrahydropyrrol-3-yl) 2-cyclopentyl-2-hydroxy-2-phenyl-acetate bromide

Glycopyrrolate Usage And Synthesis

Description

Glycopyrrolate is an antagonist of muscarinic acetylcholine receptors (mAChRs; K_is = 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.

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