Details of the Drug

General Information of Drug (ID: DM2M3ZA)

Drug Name
Glycopyrrolate
Synonyms
GLYCOPYRROLATE; 596-51-0; Glycopyrrolate bromide; Robinul; Gastrodyn; Tarodyl; Nodapton; Tarodyn; Asecryl; Copyrrolate; Cuvposa; Glycopyrronii bromidum; AHR-504; ROBINUL FORTE; Robinal; Robanul; Bromuro de glicopirronio; Bromure de glycopyrronium; NVA-237; AHR 504; Glycopyrronii bromidum [INN-Latin]; EINECS 209-887-0; Bromure de glycopyrronium [INN-French]; Bromuro de glicopirronio [INN-Spanish]; 3-Hydroxy-1,1-dimethylpyrrolidinium bromide
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1], [2]
Chronic obstructive pulmonary disease CA22 Approved [3], [4]
Therapeutic Class
Anticholinergic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
0		 Molecular Weight 398.3
Topological Polar Surface Area Not Available
Rotatable Bond Count 5
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 4
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 16.8 mL/min/kg [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.65 hours [5]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.37 L/kg [5]
Chemical Identifiers
Formula
C19H28BrNO3
IUPAC Name
(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide
Canonical SMILES
C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
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
Cross-matching ID
PubChem CID
11693
ChEBI ID
CHEBI:90972
CAS Number
596-51-0
TTD ID
D0M0AM
VARIDT ID
DR01412
ACDINA ID
D00305

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Muscarinic acetylcholine receptor M1 (CHRM1) TTZ9SOR ACM1_HUMAN Antagonist [6], [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Anaesthesia
ICD Disease Classification 9A78.6
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Muscarinic acetylcholine receptor M1 (CHRM1) DTT CHRM1 4.61E-07 -0.59 -0.73
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 8.54E-01 1.24E-02 7.20E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite E00392 104805 Diluent
Calcium hydrogenphosphate E00294 24441 Diluent
Calcium pyrophosphate E00307 24632 Acidulant; Diluent
Calcium stearate E00244 15324 lubricant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Glycopyrrolate 1.5 mg tablet 1.5 mg Oral Tablet Oral
Glycopyrrolate 0.0156 mg powder 0.0156 mg Inhalant Powder Oral
Glycopyrrolate 1 mg tablet 1 mg Oral Tablet Oral
Glycopyrrolate 2 mg tablet 2 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040568.
3 Clinical pipeline report, company report or official report of Novartis.
4 ClinicalTrials.gov (NCT02181023) Acute Effect of Aclidinium on Hyperinflation and Ventilation Inhomogeneity in Severe COPD Patients. U.S. National Institutes of Health.
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Autonomic cardiovascular control during a novel pharmacologic alternative to ganglionic blockade. Clin Pharmacol Ther. 2008 May;83(5):692-701.
7 A pharmacological profile of glycopyrrolate: interactions at the muscarinic acetylcholine receptor. Gen Pharmacol. 1992 Nov;23(6):1165-70.
8 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
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10 Cisplatin and oxaliplatin, but not carboplatin and nedaplatin, are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family). J Pharmacol Exp Ther. 2006 Nov;319(2):879-86.
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15 Upregulation of histone acetylation reverses organic anion transporter 2 repression and enhances 5-fluorouracil sensitivity in hepatocellular carcinoma
16 Comparison of type I and type II organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5.
17 Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
18 Influx Transport of Cationic Drug at the Blood-Retinal Barrier: Impact on the Retinal Delivery of Neuroprotectants. Biol Pharm Bull. 2017;40(8):1139-1145.
19 Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4- oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists. J Med Chem. 1993 Apr 2;36(7):842-7.
20 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
21 Demonstration of bladder selective muscarinic receptor binding by intravesical oxybutynin to treat overactive bladder. J Urol. 2004 Nov;172(5 Pt 1):2059-64.
22 Accidental acute clidinium toxicity. Emerg Med J. 2009 Jun;26(6):460.
23 The role of M1 muscarinic cholinergic receptors in the discriminative stimulus properties of N-desmethylclozapine and the atypical antipsychotic dr... Psychopharmacology (Berl). 2009 Apr;203(2):295-301.
24 Ultraviolet spectroscopic estimation of microenvironments and bitter tastes of oxyphenonium bromide in cyclodextrin solutions. J Pharm Sci. 1999 Aug;88(8):759-62.
25 Formulation and biopharmaceutical evaluation of transdermal patch containing benztropine. Int J Pharm. 2008 Jun 5;357(1-2):55-60.
26 Negative crosstalk between M1 and M2 muscarinic autoreceptors involves endogenous adenosine activating A1 receptors at the rat motor endplate. Neurosci Lett. 2009 Aug 14;459(3):127-31.
27 Capillary gas chromatography of trihexyphenidyl, procyclidine and cycrimine in biological fluids. J Chromatogr. 1989 Sep 29;494:135-42.
28 [Characterization of muscarinic receptors in undifferentiated thyroid cells in Fisher rats]. Endocrinol Nutr. 2009 Mar;56(3):106-11.