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    Anticholinergic Drugs

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    Kiran
    The document summarizes the structure-activity relationships of anticholinergic drugs. It notes that potent anticholinergics typically have different carbocyclic or heterocyclic rings substituted at R1 and R2, with one ring usually aromatic. The R3 substituent is often a hydroxyl or hydroxymethyl group, which increases binding strength. The X substituent is commonly an ester but is not required. The N substituent is usually a quaternary ammonium salt. Therapeutic uses of anticholinergics include treating smooth muscle spasms and reducing secretions. Common examples are atropine, hyoscyamine, propantheline, and oxybutynin

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    Anticholinergic Drugs

    Uploaded by

    Kiran
    223 views14 pages
    The document summarizes the structure-activity relationships of anticholinergic drugs. It notes that potent anticholinergics typically have different carbocyclic or heterocyclic rings substituted at R1 and R2, with one ring usually aromatic. The R3 substituent is often a hydroxyl or hydroxymethyl group, which increases binding strength. The X substituent is commonly an ester but is not required. The N substituent is usually a quaternary ammonium salt. Therapeutic uses of anticholinergics include treating smooth muscle spasms and reducing secretions. Common examples are atropine, hyoscyamine, propantheline, and oxybutynin

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    Medicinal Chemistry

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    The document summarizes the structure-activity relationships of anticholinergic drugs. It notes that potent anticholinergics typically have different carbocyclic or heterocyclic rings substituted at R1 and R2, with one ring usually aromatic. The R3 substituent is often a hydroxyl or hydroxymethyl group, which increases binding strength. The X substituent is commonly an ester but is not required. The N substituent is usually a quaternary ammonium salt. Therapeutic uses of anticholinergics include treating smooth muscle spasms and reducing secretions. Common examples are atropine, hyoscyamine, propantheline, and oxybutynin

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    223 views14 pages

    Anticholinergic Drugs

    Uploaded by

    Kiran
    The document summarizes the structure-activity relationships of anticholinergic drugs. It notes that potent anticholinergics typically have different carbocyclic or heterocyclic rings substituted at R1 and R2, with one ring usually aromatic. The R3 substituent is often a hydroxyl or hydroxymethyl group, which increases binding strength. The X substituent is commonly an ester but is not required. The N substituent is usually a quaternary ammonium salt. Therapeutic uses of anticholinergics include treating smooth muscle spasms and reducing secretions. Common examples are atropine, hyoscyamine, propantheline, and oxybutynin

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 14

    Antcholinergic Drugs

    Presented By:
    Mr. Kiran D. Baviskar,
    Assist. Professor
    Dept. of Pharmaceutics,

    Smt. Sharadchandrika Suresh Patil College of Pharmacy, Chopda.


    SAR of Anticholinergics:

    R1
    R2---------X –(CH2)n-N
    R3
    1.Substituents R1, & R2 should be carbocyclic or heterocyclic
    rings for maximal potency.
    The rings can be identical but the more potent compounds
    have different rings.
    Generally, one ring is aromatic & other saturated or possessing
    only one olefinic bond.

    Substituents Rl ,& R2 can be combined into a fused aromatic


    tricyclic ring system such as that found in propantheline.
    The size of these substituents is limited e.g. Substitution of
    naphthalene rings for Rl & R2 affords compounds that are
    inactive, because of steric hindrance of the binding of these
    compounds to muscarinic receptor.
    2. The R3 substituent can be a hydrogen atom, a
    hydroxyl group, a hydroxymethyl group, a
    carboxamide or it can be a component of one of the
    R1, & R2 ring system.

    When this substituent is either a hydroxyl or a


    hydroxymethyl group, the antagonist is usually more
    potent than the same compound without this group.

    The hydroxyl group increases binding strength by


    participating in a hydrogen bond interaction at the
    receptor.
    3. The X- substituent is an ester in most potent
    anticholinergics but it is not an absolute necessity for
    muscarinic antagonist activity. This substituent can be
    ether oxygen or it can be absent completely.

    4. The N substituent is a quaternary ammonium salt in


    potent anticholinergic drugs but tertiary amine also
    possesses antagonist activity by binding to receptor in
    the cationic site. The alkyl substitutes are usually
    methyl, ethyl, propyl or isopropyl.
    5.The distance between the ring substituted carbon &
    the amine nitrogen is not critical, the length of the
    alkyl chain connecting these may be from 2 to 4
    carbons.
    Most potent anticholinergic agents have 2 methylene
    units in this chain.
    THERAPEUTIC APPLICATIONS
    1. Muscarinic antagonists are employed as both prescription
    drugs & OTC medications.
    Because they act as competitive (reversible) antagonist of
    Acetylcholine. These compounds have pharmacological
    effects opposite to that of muscarinic agonist.
    Responses of Muscarinic antagonist include decreased
    contractions of smooth muscle of the GI tract & urinary tract,
    dilation of pupils & decreased gastric, mucociliary & salivary
    secretions.
    So anticholinergic compounds have therapeutic value in
    treating smooth muscle spasm associated with increased
    tone of the GIT or with overactive bladder, in
    ophthalmologic examinations & in treatment of gastric
    ulcers.
    2. Compounds possessing muscarinic antagonist activity are
    the common components of cold & flu remedies that act to
    reduce nasal & upper respiratory tract secretions.

    3. Anticholinergic agent decrease gastric acids secretion &


    were widely used to manage peptic ulcers. When used
    systemically, they produce side effects such as blurred vision,
    photophobia, dry mouth and difficulty in urination. These side
    effects reduce patient compliance.
    4. Anticholinergic agent exhibit mydriatic action and can be
    used with caution because of their effect on intraocular
    pressure. Drainage of canal of schlemm is restricted by the iris
    when pupil is dilated and this cause an increase in intraocular
    pressure. Hence these are contraindicated in patients with
    glaucoma.

    5. Atropine is used in treatment of central & peripheral


    symptoms associated with poisoning by organophosphorous
    anticholinesterase agents.
    1. Solanaceous alkaloids and its synthetic analogues
    e.g. Atropine, Hyoscyamine, Hyoscine (scopolamine),
    Homatropine, Tiotropium, Ipratropium.

    2. Amino alcohol esters


    e.g. Propantheline, Methantheline, Oxybutynin, Dicyclomine,
    Cyclopentolate, Clidinium, Eucatropine, Glycopyrrolate.

    3. Amino alcohol ethers


    e.g.Benztropine,Orphenadrine.
    4. Amino alcohols
    e. g. Biperiden, Procyclidine, Tridihexethyl chloride,
    trihexphenidyl, Tolterodine.

    5. Amino amides
    e.g. Tropicamide, Isopropamide, Darifenacin.

    6. Miscellaneous ions
    e.g. Diphemanil, Ethopropazine, Papaverine.

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