Ipratropium bromide

• Catalog No.: DB00332
• CAS Number: 60205-81-4
• M. F.: C20H30BrNO3
• M. W.: 412.3611

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)

• 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 (t_{1/2 α}) and terminal elimination-phase half-life (t_{1/2 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: Wikipedia; RxList; Drugs.com

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.