IPRATROPIUM

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H30NO3
Molecular Weight	332.4571
Optical Activity	( + / - )
Defined Stereocenters	4 / 5
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

SMILES

CC(C)[N@+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@@H](CO)C3=CC=CC=C3

InChI

InChIKey=OEXHQOGQTVQTAT-VQCHGODESA-N

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?/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H29NO3
Molecular Weight	331.4492
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	4 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Ipratropium (ipratropium bromide, ATROVENT® HFA) is a muscarinic antagonist structurally related to atropine but often considered safer and more effective for inhalation use. It is indicated for the maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. Ipratropium (ipratropium bromide, ATROVENT® HFA) is an anticholinergic (parasympatholytic) agent which, based on animal studies, appears to inhibit vagally-mediated reflexes by antagonizing the action of acetylcholine, the transmitter agent released at the neuromuscular junctions in the lung. Anticholinergics prevent the increases in intracellular concentration of Ca2+ which is caused by interaction of acetylcholine with the muscarinic receptors on bronchial smooth muscle.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 169	Antagonist 2,778	0.49 nM [Ki]
Muscarinic acetylcholine receptor M2 121	Antagonist 2,778	1.5 nM [Ki]
Muscarinic acetylcholine receptor M3 159	Antagonist 2,778	0.51 nM [Ki]
Muscarinic acetylcholine receptor M4 86	Antagonist 2,778	0.66 nM [Ki]
Muscarinic acetylcholine receptor M5 62	Antagonist 2,778	1.7 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174	Primary		Approved 8,429	ATROVENT HFA

C_max

Value	Dose	Co-administered	Analyte	Population
33.5 pg/mL	20 μg 4 times / day multiple, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens
35.4 pg/mL	20 μg 4 times / day steady-state, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens
31.7 pg/mL	20 μg 4 times / day steady-state, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1.04 pg × h/mL	20 μg 4 times / day multiple, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens
131 pg × h/mL	20 μg 4 times / day steady-state, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens
123 pg × h/mL	20 μg 4 times / day steady-state, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h	20 μg 4 times / day multiple, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
95.5%	20 μg 4 times / day multiple, respiratory	ALBUTEROL	IPRATROPIUM plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
168 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 18 - 75 years	Disc. AE: Nasal disorder NOS, Nasal dryness...
168 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 2 - 5 years	Disc. AE: Epistaxis...
84 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 2 - 5 years	Disc. AE: Epistaxis, Upper respiratory tract infection...
200 ug single, respiratory Highest studied dose	unhealthy, mean 40.7 years	Disc. AE: Nausea and vomiting...
42 ug 1 times / day steady, respiratory Recommended	unhealthy, mean 42.6 years	Other AEs: Nasal disorder NOS...

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AEs

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AE	Significance	Dose	Population
Nasal disorder NOS	17% Disc. AE	168 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 18 - 75 years
Epistaxis	2% Disc. AE	168 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 18 - 75 years
Nasal dryness	2% Disc. AE	168 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 18 - 75 years
Epistaxis	1 patient Disc. AE	168 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 2 - 5 years
Ear infection	1 patient Disc. AE	84 ug 3 times / day steady, respiratory Highest studied dose	unhealthy, 2 - 5 years

Showing 1 to 5 of 10 entries

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 OCT2 647 OCT3 150 MATE1 306 MATE2 263	OCTN1 47 OCTN2 50 OCT1 327 OCT2 355 OCT3 80 MATE1 135 MATE2 96

Drug as perpetrator

Show entries

Target	Modality	Activity
OCT1 543	inhibitor 3,277	yes [IC50 17.4 uM]
OCT3 150	inhibitor 3,277	yes [IC50 2.5 uM]
OCT2 648	inhibitor 3,277	yes [IC50 3.6 uM]
MATE1 308	inhibitor 3,277	yes [IC50 30.5 uM]
MATE2 263	inhibitor 3,277	yes [IC50 62.8 uM]

Showing 1 to 5 of 5 entries

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Drug as victim

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Target	Modality	Activity
MATE1 135	substrate 3,367	strong
MATE2 96	substrate 3,367	strong
OCT1 327	substrate 3,367	strong
OCT2 355	substrate 3,367	strong
OCT3 80	substrate 3,367	strong

Showing 1 to 5 of 7 entries

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
KeyOrganics	KS-5051
Pharmeks	PHAR218016
ZINC	ZINC000013782937	http://zinc15.docking.org/substances/ZINC000013782937

Showing 1 to 3 of 3 entries

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PubMed

Show entries

Title	Date	PubMed
Styrofoam cup, ipratropium bromide, and anisocoria.	1999 May	10349535
Blurred vision from ipratropium bromide inhalation.	1999 May 1	10344619
Blurred vision from ipratropium bromide inhalation.	2000 May 15	10832501
Unilateral fixed dilated pupil in a ventilated child with asthma.	2000 Sep	11142280
Bronchodilators for the prevention and treatment of chronic lung disease in preterm infants.	2001	11687053

Showing 1 to 5 of 40 entries

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Patents

Sample Use Guides

In Vivo Use Guide

The usual starting dose of ATROVENT® HFA is two inhalations four times a day. Patients may take additional inhalations as required; however, the total number of inhalations should not exceed 12 in 24 hours.

Route of Administration: Oral

In Vitro Use Guide

Ba 679 BR, atropine, and ipratropium bromide inhibited electrical field stimulation (EFS)-induced contraction with IC50 values of 0.17, 0.74, and 0.58 nM, respectively, in guinea pig trachea. Ba 679 BR had a slower onset and longer duration of action than atropine or ipratropium bromide (the times required to attain 50% of the maximum response were 34.8, 3.8, and 7.6 min, respectively, and the times required for 50% recovery of the response were 540, 31.6, and 81.2 min, respectively).