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Ipratropium bromide_Molecular_structure_CAS_60205-81-4)
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Ipratropium bromide

Catalog No. DB00332 Name DrugBank
CAS Number 60205-81-4 Website http://www.ualberta.ca/
M. F. C20H30BrNO3 Telephone (780) 492-3111
M. W. 412.3611 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 216

SYNONYMS

IUPAC name
(1R,5R)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide
IUPAC Traditional name
atrovent bromide
Brand Name
Atrovent Aerosol
Apo-Ipravent
Narilet
Apovent
Atronase
Atrovent
Atrovent Nasal
Bitrop
Rhinotrop
Rhinovent
Rinovagos
Aerodose
Aerovent
Atrovent HFA
Disne-Asmol
Ipravent
Ipvent
Kendral-Ipratropium
Rinatec
Rinoberen
Vagos
Synonyms
Ipratropium Bromide
N-Isopropylatropine
Ipatropium Bromide
ipratropium

DATABASE IDS

CAS Number 60205-81-4

PROPERTIES

Solubility Freely soluble

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A muscarinic antagonist structurally related to atropine but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic. [PubChem]
Indication For maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease, including chronic bronchitis and emphysema.
Pharmacology Ipratropium bromide, a synthetic ammonium compound structurally similar to atropine, is used as a bronchodilator in the management of cholinergic-mediated bronchospasm associated with chronic obstructive pulmonary disease and in the treatment of rhinorrhea associated with the common cold or with allergic or nonallergic seasonal rhinitis.
Toxicity LD50=1001mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Partially metabolized to at least 8 metabolites formed primarily via hydrolysis and conjugation. The main metabolites are N-isopropylnortropium methobromide, which is formed by enzymatic hydrolysis of the ester; α-phenylacrylic acid-N-isopropylnortropine-ester methobromide, which is formed by enzymatic loss of a water; and phenylacetic acid-N-isopropylnortropine-ester methobromide, which is formed by enzymatic loss of a CH3OH-group. These metabolites appear to be inactive.
Absorption Inhalation (local)-minimal; Nasal-rapid and minimal
Half Life 2-4 hours after administration orally, IV or by oral inhalation (radiolabeled ipratropium bromide assay measures parent drug and its metabolites). Using a radioreceptor assay that measures only unchanged ipratropium bromide, the initial distribution-phase half-life (t1/2 α) and terminal elimination-phase half-life (t1/2 β) were 0.07 and 1.6 hours, respectively, following a single 2 mg IV dose of the drug in healthy adults.
Protein Binding Minimally (0 to 9% in vitro) bound to plasma albumin and α1-acid glycoproteins
Elimination Primarily eliminated renally via active secretion.
Distribution * 4.6 L/kg
Clearance * 2.3 L/min (total clearance of active ingredient)
References
Yamatake Y, Sasagawa S, Yanaura S, Okamiya Y: [Antiallergic asthma effect of ipatropium bromide (Sch 1000) in dogs (author's transl)] Nippon Yakurigaku Zasshi. 1977 Oct;73(7):785-91. [Pubmed]
Abdine HH, Belala F, and Al-Badra AA. (2003). Ipratropium bromide: Methods of chemical and biochemical synthesis. In H.G. Brittain (Ed.). _Profiles of drug substances, excipients and related methodology_ (pp. 85-99). Amsterdam, Netherlands: Elsevier Academic Press.
External Links
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REFERENCES

  • Yamatake Y, Sasagawa S, Yanaura S, Okamiya Y: [Antiallergic asthma effect of ipatropium bromide (Sch 1000) in dogs (author's transl)] Nippon Yakurigaku Zasshi. 1977 Oct;73(7):785-91. PubmedAbdine HH, Belala F, and Al-Badra AA. (2003). Ipratropium bromide: Methods of chemical and biochemical synthesis. In H.G. Brittain (Ed.). _Profiles of drug substances, excipients and related methodology_ (pp. 85-99). Amsterdam, Netherlands: Elsevier Academic Press.