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22254-24-6

Basic Information
CAS No.: 22254-24-6
Name: Ipratropium bromide
Molecular Structure:
Molecular Structure of 22254-24-6 (Ipratropium bromide)
Formula: C20H30NO3.Br
Molecular Weight: 412.42
Synonyms: 8-Azoniabicyclo[3.2.1]octane,3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide,(3-endo,8-syn)- (9CI);8-Isopropylatropinium bromide (6CI,7CI);8-Azoniabicyclo[3.2.1]octane,3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide,(endo,syn)-;Atrovent;N-Isopropylatropinium bromide;N-Isopropylnoratropinium bromomethylate;Sch100;Sch 1000;
EINECS: 244-873-8
Density:
Melting Point: 230-232 °C
Boiling Point:
Flash Point:
Solubility: Freely soluble in water
Appearance: white powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/22-36
Safety: 26
Transport Information:
PSA: 46.53000
LogP: -0.18310
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Chemistry

Product Name: Ipratropium bromide (CAS NO.22254-24-6)

Molecular Formula: C20H30BrNO3
Molecular Weight: 412.37g/mol
Mol File: 22254-24-6.mol
EINECS: 244-873-8
Melting Point: 230-232°C
H-Bond Donor: 1
H-Bond Acceptor: 4
Structure Descriptors of Ipratropium bromide (CAS NO.22254-24-6):
  IUPAC Name: (8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate bromide
  Canonical SMILES: CC(C)[N+]1(C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C.[Br-]
  InChI: InChI=1S/C20H30NO3.BrH/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;1H/q+1;/p-1 
  InChIKey: LHLMOSXCXGLMMN-UHFFFAOYSA-M
Classification Code: Drug / Therapeutic Agent; Human Data; Reproductive Effect; Skin / Eye Irritant

Uses

 Ipratropium bromide (CAS NO.22254-24-6) is administered by inhalation for the treatment of obstructive lung diseases.
It is also combined with albuterol (salbutamol) (trade names Combivent and Duoneb, in Italy known as Breva) for the management of chronic obstructive pulmonary disease (COPD) and asthma. It is also combined with fenoterol (trade names Duovent and Berodual N) for the management of asthma.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 1300mg/kg (1300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 985, 1976.
dog LDLo intravenous 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 985, 1976.
mammal (species unspecified) LD50 intravenous 10mg/kg (10mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Postgraduate Medical Journal, Supplement. Vol. 51(Suppl,
man TCLo inhalation 1ug/kg (0.001mg/kg) GASTROINTESTINAL: OTHER CHANGES British Medical Journal. Vol. 292, Pg. 380, 1986.
mouse LD50 intraperitoneal 72mg/kg (72mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 417, 1978.
mouse LD50 intravenous 12290ug/kg (12.29mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 985, 1976.
mouse LD50 oral 1001mg/kg (1001mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 985, 1976.
mouse LD50 subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 985, 1976.
rabbit LD50 oral 1557mg/kg (1557mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 417, 1978.
rat LD50 intraperitoneal 113mg/kg (113mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: TETANY
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 176, 1979.
rat LD50 intravenous 15700ug/kg (15.7mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 489, 1979.
rat LD50 oral 1663mg/kg (1663mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 985, 1976.
rat LD50 subcutaneous 635mg/kg (635mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: TETANY

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 176, 1979.

Safety Profile

A poison by intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by ingestion. Human systemic effects by inhalation of very small amounts: gastrointestinal changes. An experimental teratogen. Experimental reproductive effects. An eye irritant. Used as a bronchodilator. When heated to decomposition it emits toxic fumes of NOx and Br. See also BROMIDES.

Specification

 Ipratropium bromide , its CAS NO. is 22254-24-6, the synonyms are [(1R,5S)-8-Methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate bromide ; 8-Isopropylnoratropine methobromide ; 3-alpha-Hydroxy-8-isopropyl-1-alpha-H,5-alpha-H-tropanium bromide (+-)-tropate ; N-Isopropylnoratropinium bromomethylate .