Ipratropium bromide

Structural formula
	Structural formula with incomplete stereochemistry
General
Non-proprietary name	Ipratropium bromide
other names	[8-Methyl-8- (1-methylethyl) -8-azoniabicyclo [3.2.1] oct-3-yl] -3-hydroxy-2-phenyl-propanoatium bromide ( IUPAC ) ; N - (2-propyl) atropinium bromide;
Molecular formula	C 20 H 30 BrNO 3
External identifiers / databases
EC number	244-873-8
ECHA InfoCard	100.040.779
PubChem	657308
DrugBank	DB00332
Wikidata	Q424294
Drug information
ATC code	R03 BB01 ; R01 AX03 ;
Drug class	Antiarrhythmics; Anticholinergics;
properties
Molar mass	412.37 g · mol -1
Physical state	firmly
Melting point	230-232 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-332-319
	P: 305 + 351 + 338
Toxicological data	1663 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ipratropium bromide is a drug that is used to treat chronic obstructive pulmonary disease and cardiac arrhythmias . Like other muscarinic receptor antagonists, it is rarely used in the therapy of bronchial asthma . Ipratropium bromide is a quaternary ammonium compound and a derivative of atropine , which can be produced semi-synthetically or fully synthetically by N -alkylation. The only active ingredient used is the salt with bromide as the counterion.

Clinical information

As an anticholinergic , it blocks the conduction of excitation at the muscarinic acetylcholine receptor through competitive antagonism . When inhaled, for example as a metered dose aerosol, it has a local effect and prevents constriction of the bronchial muscles. As a quaternary compound, ipratropium bromide is more poorly absorbed than tertiary ammonium compounds . However, this is desirable in therapy in order to circumvent central effects of parasympatholytics , such as inhibition of bronchial secretion or paralysis of the ciliated epithelium .

Side effects

Rarely, urinary retention , increased intraocular pressure in narrow-angle glaucoma and cardiac arrhythmias can occur. In 2008 , an analysis was carried out on the basis of observations that suggested that the use of drugs containing ipratropium bromide could promote the development of heart attacks and strokes . This resulted in a 50% increase in the relative risk for such side effects. The starting level of the absolute number of cases and thus the absolute number of new cases was low. Nevertheless, until the safety of the active ingredient has been finally clarified, it was recommended that patients with corresponding risks be monitored regularly.

Interactions

The effect of ipratropium bromide can be increased with simultaneous use of β- sympathomimetics and xanthine derivatives such as theophylline .

Contraindication

It should be avoided in the following diseases:

mechanical stenoses (narrowing in the gastrointestinal tract)
Megacolon (an enlarged colon)
acute pulmonary edema (excessive water retention in the lungs)
Cerebral sclerosis (acute diseases of the brain tissue)
Tachyarrhythmias (irregular heartbeat with a greatly increased heart rate)
Angle-closure glaucoma (glaucoma)

The active ingredient must not be taken during breastfeeding or during the last three months of pregnancy.

Pharmacological information

When used by inhalation, the onset of action occurs after around five minutes and the duration of action is around four to six hours. Ipratropium bromide also has a wide therapeutic range. No severe anticholinergic symptoms due to an overdose are to be expected after inhalation. However, when used systemically, an overdose can cause symptoms that require treatment, such as tachycardia , micturition inhibition or intestinal paralysis. Cholinergics such as pyridostigmine or neostigmine are then used as antidotes .

Trade names

Monopreparations

Atropair (CH), Atrovent (D, A, CH), IPRAXA (D), Itrop (D), Nebu-Iprasal (D), Rhinovent (CH), IpraBronch (D)

Combination preparations

Berodual (D, A), Berodualin (A), Combivent (A), Otrivin Duo (A)

literature

Ernst Mutschler among other things: drug effects. Textbook of pharmacology and toxicology . 8th edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 2001, ISBN 3-8047-1763-2 .

Individual evidence

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 882-883, ISBN 978-0-911910-00-1 .
↑ ^a ^b Entry on ipratropium bromide in the GESTIS substance database of the IFA , accessed on February 21, 2017(JavaScript required) .
↑ Entry on ipratropium bromide in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ C. Vogelmeier, R. Buhl u. a .: Guideline of the German Respiratory League and the German Society for Pneumology and Respiratory Medicine for the diagnosis and treatment of patients with chronic obstructive bronchitis and emphysema (COPD). In: Pneumology. 61, 2007, p. E1, doi : 10.1055 / s-2007-959200 . ( PDF )
↑ nzz.ch: Good for the lungs, bad for the heart , October 1, 2008.
↑ Contraindications. Retrieved August 28, 2017 .

[MERCK_Index-1] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 882-883, ISBN 978-0-911910-00-1 .

[GESTIS-2] Entry on ipratropium bromide in the GESTIS substance database of the IFA , accessed on February 21, 2017(JavaScript required) .

[ChemIDplus-3] Entry on ipratropium bromide in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] C. Vogelmeier, R. Buhl u. a .: Guideline of the German Respiratory League and the German Society for Pneumology and Respiratory Medicine for the diagnosis and treatment of patients with chronic obstructive bronchitis and emphysema (COPD). In: Pneumology. 61, 2007, p. E1, doi : 10.1055 / s-2007-959200 . ( PDF )

[5] zz.ch: Good for the lungs, bad for the heart , October 1, 2008.

[6] Contraindications. Retrieved August 28, 2017 .