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    Chemistry

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    Also known as: Homatropine methylbromide, Homatropine methobromide, Omatropina metilbromuro, Methylhomatropine bromide, 80-49-9, 8-methylhomatropinium bromide
    Molecular Formula
    C17H24BrNO3
    Molecular Weight
    370.3  g/mol
    InChI Key
    FUFVKLQESJNNAN-UHFFFAOYSA-M
    Homatropine Methylbromide
    Homatropine Methylbromide is the methylbromide salt of homatropine, a synthetic tertiary amine alkaloid with antimuscarinic properties. Homatropine methylbromide, a competitive inhibitor of acetylcholine at the muscarinic receptor, blocks parasympathetic nerve stimulation, thereby inhibiting pepsin and gastrin secretion. When administered in high doses, this drug produces inhibitory effects on acetylcholine activity, specifically on smooth muscle located in the gastrointestinal, biliary, and genitourinary tracts, resulting in an anti-spasmodic effect.
    1 2D Structure

    Homatropine Methylbromide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl) 2-hydroxy-2-phenylacetate;bromide
    2.1.2 InChI
    InChI=1S/C17H24NO3.BrH/c1-18(2)13-8-9-14(18)11-15(10-13)21-17(20)16(19)12-6-4-3-5-7-12;/h3-7,13-16,19H,8-11H2,1-2H3;1H/q+1;/p-1
    2.1.3 InChI Key
    FUFVKLQESJNNAN-UHFFFAOYSA-M
    2.1.4 Canonical SMILES
    C[N+]1(C2CCC1CC(C2)OC(=O)C(C3=CC=CC=C3)O)C.[Br-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Hmbromide

    2. Homatropine Methylbromide

    3. Homatropine Methylbromide Iodide, (3(r)-endo)-isomer

    4. Homatropine Methylbromide Iodide, (3(s)-endo)-isomer

    5. Homatropine Methylbromide, (3(r)-endo)-isomer

    6. Homatropine Methylbromide, (3(s)-endo)-isomer

    7. Homatropine Methylbromide, Endo-(+-)-isomer

    2.2.2 Depositor-Supplied Synonyms

    1. Homatropine Methylbromide

    2. Homatropine Methobromide

    3. Omatropina Metilbromuro

    4. Methylhomatropine Bromide

    5. 80-49-9

    6. 8-methylhomatropinium Bromide

    7. Tropinium Methobromide Mandelate

    8. Homatropine Methyl Bromide

    9. Methylhomatropinum Bromatum

    10. Methylbromure D'homatropine

    11. 3-alpha-hydroxy-8-methyl-1-alpha-h,5-alpha-h-tropanium Bromide Mandelate

    12. Nsc34399

    13. Schembl77827

    14. Chebi:50373

    15. Akos015896228

    16. Db00725

    17. 3-[2-hydroxy(phenyl)acetoxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane Bromide

    18. Ncgc00094694-01

    19. Ncgc00094694-02

    20. Db-056442

    21. D90875

    22. H-2560

    2.3 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 370.3 g/mol
    Molecular Formula C17H24BrNO3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass369.09396 g/mol
    Monoisotopic Mass369.09396 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity374
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count3
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Used in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcers, gastric ulcers and duodenal ulcers, to reduce further gastric acid secretion and delay gastric emptying.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Homatropine methylbromide belongs to the group of medicines called anti-muscarinics. Homatropine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.

    5.2 ATC Code

    A - Alimentary tract and metabolism

    A03 - Drugs for functional gastrointestinal disorders

    A03B - Belladonna and derivatives, plain

    A03BB - Belladonna alkaloids, semisynthetic, quaternary ammonium compounds

    A03BB06 - Homatropine methylbromide

    5.3 Mechanism of Action

    Homatropine is a quaternary ammonium muscarinic acetylcholine receptor antagonist. The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Homatropine methylbromide inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. Depending on the dose, anticholinergics may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder.

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    12-Jan-2021
    12-Aug-2024
    KGS
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