Details of the Drug

General Information of Drug (ID: DMFQ320)

Drug Name

Ipratropium

Synonyms

Aerodose; Atrovent; Atrovent Hfa; Ipatropium Bromide; Ipratropium bromide; X8M; Apo-Ipravent; Apovent (TN); Atrovent (TN); Kendral-Ipratropium; [(5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; [(1R,5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; [(1R,5S)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate; [(1R,5S)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate; (3-endo,8-syn)-3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane; (3-endo,8-syn)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane; (8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate; 3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azoniabicyclo[3.2.1]octane

Indication

Disease Entry	ICD 11	Status	REF
Obstructive lung disease	CA22.Z	Approved	[1]
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Therapeutic Class

Bronchodilator Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

332.5

Logarithm of the Partition Coefficient (xlogp)

2.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 8.3 mcg/L [2]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.9 h [2]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: The bioavailability of drug is 93% [2]
Clearance: The renal clearance of drug is 0.9 L/min [4]
Elimination: About 80-100% of the administered dose of ipratropium is excreted in the urine leaving less than 20% of the dose to be eliminated through the feces [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.6 hours [5]
Metabolism: The drug is metabolized via the cytochrome P450 isoenzymes [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.0088 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.95% [7]
Vd: The volume of distribution (Vd) of drug is 4.6 L/kg [4]

Chemical Identifiers

Formula: C20H30NO3+
IUPAC Name: [(1S,5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate
Canonical SMILES: CC(C)[N+]1([C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C
InChI: InChI=1S/C20H30NO3/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15/h4-8,14,16-19,22H,9-13H2,1-3H3/q+1/t16-,17+,18?,19?,21?
InChIKey: OEXHQOGQTVQTAT-BZQJJPTISA-N

Cross-matching ID

PubChem CID: 657309
ChEBI ID: CHEBI:5956
CAS Number: 60205-81-4
DrugBank ID: DB00332
TTD ID: D0S0AS
VARIDT ID: DR00277

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Muscarinic acetylcholine receptor M3 (CHRM3)	TTQ13Z5	ACM3_HUMAN	Modulator	[8]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation/carnitine transporter 1 (SLC22A4)	DT2EG60	S22A4_HUMAN	Substrate	[9]
Organic cation/carnitine transporter 2 (SLC22A5)	DT3HUVD	S22A5_HUMAN	Substrate	[9]
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Obstructive lung disease

ICD Disease Classification

CA22.Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Muscarinic acetylcholine receptor M3 (CHRM3)	DTT	CHRM3	4.61E-07	-0.59	-0.73
Organic cation transporter 1 (SLC22A1)	DTP	SLC22A1	8.54E-01	1.24E-02	7.20E-02
Organic cation/carnitine transporter 2 (SLC22A5)	DTP	OCTN2	3.49E-09	1.50E-01	6.50E-01
Organic cation/carnitine transporter 1 (SLC22A4)	DTP	OCTN1	2.26E-01	5.94E-02	1.21E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Ipratropium

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Umeclidinium	DM4E8O9	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Umeclidinium.	Chronic obstructive pulmonary disease [CA22]	[11]
Tiotropium	DMFDC0Q	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Tiotropium.	Chronic obstructive pulmonary disease [CA22]	[11]
Revefenacin	DMMP5SI	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[11]
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Coadministration of a Drug Treating the Disease Different from Ipratropium (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Bethanechol	DMCLHO0	Moderate	Antagonize the effect of Ipratropium when combined with Bethanechol.	Abnormal micturition [MF50]	[12]
Scopolamine	DMOM8AL	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Scopolamine.	Addictive disorder [6C50-6C5Z]	[11]
Mepyramine	DMB4SFH	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Mepyramine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[13]
Phenyltoloxamine	DMKAEQW	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Phenyltoloxamine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[13]
Tripelennamine	DMZBU15	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Tripelennamine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[11]
Hydroxyzine	DMF8Y74	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Hydroxyzine.	Anxiety disorder [6B00-6B0Z]	[11]
Promazine	DMZAL7W	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Promazine.	Appearance/behaviour symptom [MB23]	[11]
Desipramine	DMT2FDC	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[11]
Acetylcholine	DMDF79Z	Moderate	Antagonize the effect of Ipratropium when combined with Acetylcholine.	Cataract [9B10]	[14]
Trimipramine	DM1SC8M	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Trimipramine.	Depression [6A70-6A7Z]	[11]
Cyclobenzaprine	DM1YBRM	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Cyclobenzaprine.	Depression [6A70-6A7Z]	[11]
Imipramine	DM2NUH3	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Imipramine.	Depression [6A70-6A7Z]	[11]
Nortriptyline	DM4KDYJ	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Nortriptyline.	Depression [6A70-6A7Z]	[11]
Clomipramine	DMINRKW	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Clomipramine.	Depression [6A70-6A7Z]	[11]
Amoxapine	DMKITQE	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Amoxapine.	Depression [6A70-6A7Z]	[11]
Protriptyline	DMNHTZI	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Protriptyline.	Depression [6A70-6A7Z]	[11]
Doxepin	DMPI98T	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Doxepin.	Depression [6A70-6A7Z]	[11]
Maprotiline	DMPWB7T	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Maprotiline.	Depression [6A70-6A7Z]	[11]
Hyoscyamine	DM804UR	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Hyoscyamine.	Digestive system disease [DE2Z]	[11]
Mepenzolate	DM8YU2F	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Mepenzolate.	Digestive system disease [DE2Z]	[11]
Oxybutynine	DMJPBAX	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Oxybutynine.	Discovery agent [N.A.]	[11]
Meclizine	DMS7T13	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Meclizine.	Dizziness and giddiness [MB48]	[11]
Trihexyphenidyl	DMB19L8	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Trihexyphenidyl.	Dystonic disorder [8A02]	[11]
Diphenhydramine	DMKQTBA	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Diphenhydramine.	Episodic vestibular syndrome [AB31]	[11]
Solifenacin	DMG592Q	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Solifenacin.	Functional bladder disorder [GC50]	[11]
Tolterodine	DMSHPW8	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Tolterodine.	Functional bladder disorder [GC50]	[11]
Darifenacin	DMWXLYZ	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Darifenacin.	Functional bladder disorder [GC50]	[11]
Propantheline	DM2EN6G	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Propantheline.	Gastric ulcer [DA60]	[11]
Isoflurophate	DMBSK7X	Moderate	Antagonize the effect of Ipratropium when combined with Isoflurophate.	Glaucoma [9C61]	[14]
Pilocarpine	DMV9ADG	Moderate	Antagonize the effect of Ipratropium when combined with Pilocarpine.	Glaucoma [9C61]	[12]
Belladonna	DM2RBWK	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Belladonna.	Infectious gastroenteritis/colitis [1A40]	[11]
Propiomazine	DMKY8V1	Minor	Additive anticholinergic effects by the combination of Ipratropium and Propiomazine.	Insomnia [7A00-7A0Z]	[15]
R0-93877	DMM4U9G	Moderate	Antagonize the effect of Ipratropium when combined with R0-93877.	Irritable bowel syndrome [DD91]	[16]
Clidinium	DMUMQZ0	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Clidinium.	Irritable bowel syndrome [DD91]	[11]
Dicyclomine	DMZSDGX	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Dicyclomine.	Irritable bowel syndrome [DD91]	[11]
Physostigmine	DM2N0TO	Moderate	Antagonize the effect of Ipratropium when combined with Physostigmine.	Lips/oral mucosa miscellaneous disorder [DA02]	[14]
Doxylamine	DMKOXFE	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Doxylamine.	Morning sickness disorder [SC00]	[11]
Phenindamine	DMDTC7R	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Phenindamine.	Nasopharyngitis [CA00]	[11]
Dimenhydrinate	DM264B3	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Dimenhydrinate.	Nausea/vomiting [MD90]	[11]
Prochlorperazine	DM53SRA	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Prochlorperazine.	Nausea/vomiting [MD90]	[11]
Promethazine	DM6I5GR	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Promethazine.	Nausea/vomiting [MD90]	[11]
Cyclizine	DM9G7BS	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Cyclizine.	Nausea/vomiting [MD90]	[11]
Thiethylperazine	DMU3IET	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Thiethylperazine.	Nausea/vomiting [MD90]	[11]
Flavoxate	DMKV4NL	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Flavoxate.	Pain [MG30-MG3Z]	[11]
Biperiden	DME78OA	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Biperiden.	Parkinsonism [8A00]	[11]
Procyclidine	DMHFJDT	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Procyclidine.	Parkinsonism [8A00]	[11]
Orphenadrine	DMW542E	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Orphenadrine.	Parkinsonism [8A00]	[11]
Methylscopolamine	DM5VWOB	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Methylscopolamine.	Peptic ulcer [DA61]	[11]
Levomepromazine	DMIKFEL	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Levomepromazine.	Psychotic disorder [6A20-6A25]	[11]
Fluphenazine	DMIT8LX	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Fluphenazine.	Psychotic disorder [6A20-6A25]	[11]
Triflupromazine	DMKFQJP	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Triflupromazine.	Psychotic disorder [6A20-6A25]	[11]
Cyproheptadine	DM92AH3	Minor	Additive anticholinergic effects by the combination of Ipratropium and Cyproheptadine.	Rheumatoid arthritis [FA20]	[15]
Mesoridazine	DM2ZGAN	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Mesoridazine.	Schizophrenia [6A20]	[11]
Thioridazine	DM35M8J	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Thioridazine.	Schizophrenia [6A20]	[11]
Aripiprazole	DM3NUMH	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Aripiprazole.	Schizophrenia [6A20]	[11]
Loxapine	DM8AI9U	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Loxapine.	Schizophrenia [6A20]	[11]
Haloperidol	DM96SE0	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Haloperidol.	Schizophrenia [6A20]	[11]
Perphenazine	DMA4MRX	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Perphenazine.	Schizophrenia [6A20]	[11]
Molindone	DMAH70G	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Molindone.	Schizophrenia [6A20]	[11]
Chlorpromazine	DMBGZI3	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Chlorpromazine.	Schizophrenia [6A20]	[11]
Thiothixene	DMDINC4	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Thiothixene.	Schizophrenia [6A20]	[11]
Clozapine	DMFC71L	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Clozapine.	Schizophrenia [6A20]	[11]
Trifluoperazine	DMKBYWI	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Trifluoperazine.	Schizophrenia [6A20]	[11]
Risperidone	DMN6DXL	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Risperidone.	Schizophrenia [6A20]	[11]
Olanzapine	DMPFN6Y	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Olanzapine.	Schizophrenia [6A20]	[11]
Pimozide	DMW83TP	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Pimozide.	Schizophrenia [6A20]	[11]
Atropine	DMEN6X7	Minor	Additive anticholinergic effects by the combination of Ipratropium and Atropine.	Unspecific substance harmful effect [NE6Z]	[15]
Chlorpheniramine	DM5URA2	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Chlorpheniramine.	Vasomotor/allergic rhinitis [CA08]	[11]
Triprolidine	DM7SWIA	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Triprolidine.	Vasomotor/allergic rhinitis [CA08]	[11]
Methdilazine	DMAUHQX	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[11]
Carbinoxamine	DMCT31R	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Carbinoxamine.	Vasomotor/allergic rhinitis [CA08]	[11]
Trimeprazine	DMEMV9D	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[13]
Brompheniramine	DMFOVSD	Minor	Additive anticholinergic effects by the combination of Ipratropium and Brompheniramine.	Vasomotor/allergic rhinitis [CA08]	[15]
Dexbrompheniramine	DMKVWGE	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Dexbrompheniramine.	Vasomotor/allergic rhinitis [CA08]	[11]
Acrivastine	DMTIGA0	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Acrivastine.	Vasomotor/allergic rhinitis [CA08]	[11]
Azatadine	DMZ80SB	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Azatadine.	Vasomotor/allergic rhinitis [CA08]	[11]
Procainamide	DMNMXR8	Moderate	Additive anticholinergic effects by the combination of Ipratropium and Procainamide.	Ventricular tachyarrhythmia [BC71]	[11]
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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 325).
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8	Role of parasympathetic nerves and muscarinic receptors in allergy and asthma.Chem Immunol Allergy.2012;98:48-69.
9	Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95.
10	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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12	Benjamin KW "Toxicity of ocular medications." Int Ophthalmol Clin 19 (1979): 199-255. [PMID: 376469]
13	Product Information. Anoro Ellipta (umeclidinium-vilanterol). GlaxoSmithKline, Research Triangle Park, NC.
14	Multum Information Services, Inc. Expert Review Panel.
15	Gilman AG, Rall TW, Nies AS, Taylor P, eds. "Goodman and Gilman's the Pharmacological Basis of Therapeutics. 8th ed." New York, NY: Pergamon Press Inc. (1990):.
16	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".