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Ipratropium

HCID 657309
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Basic information

CAS
148841-40-1
Standard SMILES
CC(C)[N+]1(C)[C@@H]2CC[C@H]1CC(OC(=O)C(CO)c1ccccc1)C2
InChIKey
OEXHQOGQTVQTAT-BZQJJPTISA-N
Molecular formula
C20H30NO3+
Average molar mass
332.5 g/mol
Monoisotopic mass
332.22256882

Overview

Ipratropium is a quaternary ammonium ion, a propanoate ester and a tropane alkaloid.

Names & identifiers

Preferred name
Ipratropium
IUPAC
[(1R,5S)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

Names & synonyms

ipratropiumipratropium bromideIpratropium ionIpratropium cation60205-81-4N-Isopropylatropine[(1S,5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate(3-endo,8-syn)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octaneGR88G0I6ULIpatropium BromideIpratropium, exo-Ipratropium, anti-
Show more names
Ipratropium, exo,anti-ZEN3TX7PXMIPRATROPIUM [VANDF]SCHEMBL3125HGQ623MT4HIPRATROPIUM [WHO-DD]9TY76QB93QCHEBI:5956

Database identifiers

CAS
148841-40-1、148906-07-4、60205-81-4
PubChem CID
657309
DTXSID
DTXSID9048437
ChEMBL
CHEMBL1740585
ChEBI
CHEBI:5956
UNII
9TY76QB93Q、GR88G0I6UL、HGQ623MT4H、ZEN3TX7PXM
Nikkaji
J281.651B

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
24
Formal charge
1
Complexity
430

Experimental & physicochemical properties

Solubility · 2 items

Freely soluble

7.01e-04 g/L

Human DrugsPharmaceuticals
Boiling PointDecomposes at 230 ºC
Melting Point230 - 232 °C
Physical DescriptionSolid
Collision Cross Section178.51 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Chemistry & industry

Pharmacology

Protein BindingThe protein binding of ipratropium is very low as the level of circulating ipratropium is very minimal. The bound state represents only from 0-9% of the administered dose.
Pharmacodynamics · 1 item

Ipratropium is a short-acting agent that inhibits the parasympathetic nervous system at the level of the airway which then produces bronchodilatation. The effect of this agent starts after 1-2 hours and it is known to last only from 4 to 6 hours. As part of the effect, ipratropium relaxes the bronchial airways which reverse the narrowing that accounts for wheezy breathing, chest tightness, cough and abnormal gas exchange. In clinical trials where ipratropium was used in the initial management of status asthmaticus, it was demonstrated a clear benefit in pulmonary function in children and adults. However, the continuous use of ipratropium after an acute asthmatic attack is not proven to be significantly advantageous nor the prophylactic administration of this agent.

Mechanism of Action · 1 item

Ipratropium acts as an antagonist of the muscarinic acetylcholine receptor. This effect produces the inhibition of the parasympathetic nervous system in the airways and hence, inhibit their function. The function of the parasympathetic system in the airway is to generate bronchial secretions and constriction and hence, the inhibition of this action can lead to bronchodilation and fewer secretions. At the cellular level, the diameter of the airways is controlled by the release of acetylcholine into the muscle cells causing them to contract and producing a narrow airway. Thus administration of ipratropium stops the activity of acetylcholine in the smooth muscle preventing the contraction and producing relaxed airways.

Biological Half-LifeIpratropium presents a short half-life of about 1.6 hours.
Metabolism/Metabolites · 1 item

Ipratropium is metabolized in the gastrointestinal tract by the activity of the cytochrome P-450 isoenzymes. From the orally administered dose, about 90% of the dose is excreted unchanged. The absorbed portion is partially metabolized by ester hydrolysis to inactive metabolites, tropic acid and tropane.

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Compound notes

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Absorption, Distribution and Excretion · 4 items

Ipratropium is a topically active but poorly absorbed agent. The lack of absorption potential in the mucosal surfaces is associated with the presence of a charge in the 5-valent nitrogen. The molecule itself presents very large topic effectiveness however, it does not produce detectable blood levels nor systemic effects. Serum levels of ipratropium after oral or inhaled administration are very low, corresponding to only 1-2% of the administered dose. These low levels peak after 1-2 hours and it presents a low bioavailability of 2%.

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. From the urine eliminated portion, almost all the drug is found unchanged. However, when ipratropium is orally administered, due to its low absorption, most of the dose is recovered in the feces with a very minimal amount found in the urine.

Ipratropium has a volume of distributions of 4.6 L/kg and hence, it is known to be highly distributed in the tissues.

The average clearance rate of ipratropium is of 2.3 L/min with a renal clearance of 0.9 L/min.

Cellular LocationsMembrane

Uses & manufacturing

Use ClassificationPharmaceuticals