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    Chemistry

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    Also known as: 173553-37-2, 107220-28-0, Cevimeline hydrochloride, 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hydrochloride), Cevimeline hcl, 2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride
    Molecular Formula
    C10H18ClNOS
    Molecular Weight
    235.77  g/mol
    InChI Key
    SURWTGAXEIEOGY-UHFFFAOYSA-N
    Cevimeline Hydrochloride
    Cevimeline Hydrochloride is a cholinergic analogue with glandular secretion stimulatory activity. Cevimeline binds to and activates muscarinic receptors, thereby increasing the secretions in exocrine salivary and sweat glands. This cholinergic agonist also increases the tone of smooth muscle in the gastrointestinal and urinary tracts. Cevimeline is being studied as a treatment for dry mouth caused by radiation therapy to the head and neck.
    1 2D Structure

    Cevimeline Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride
    2.1.2 InChI
    InChI=1S/C10H17NOS.ClH/c1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11;/h8-9H,2-7H2,1H3;1H
    2.1.3 InChI Key
    SURWTGAXEIEOGY-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1OC2(CN3CCC2CC3)CS1.Cl
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 2-methyspiro(1,3-oxathiolane-5,3)quinuclidine

    2. Af 102b

    3. Af 102b, (cis-(+))-isomer

    4. Af 102b, (trans)-isomer

    5. Af-102b

    6. Af102b

    7. Cevimeline

    8. Cevimeline Hydrochloride

    9. Evoxac

    10. Fks 508

    11. Fks-508

    12. Sni 2011

    13. Sni-2011

    2.2.2 Depositor-Supplied Synonyms

    1. 173553-37-2

    2. 107220-28-0

    3. Cevimeline Hydrochloride

    4. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hydrochloride)

    5. Cevimeline Hcl

    6. 2-methylspiro[1,3-oxathiolane-5,3'-1-azabicyclo[2.2.2]octane];hydrochloride

    7. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] Hydrochloride

    8. Spiro[1-azabicyclo[2.2.2]octane-3,5'-[1,3]oxathiolane], 2'-methyl-,hydrochloride

    9. Af-102b

    10. Schembl861315

    11. Dtxsid701338114

    12. Bcp12519

    13. Cs-b1634

    14. Yga55337

    15. Akos037650732

    16. Cs-15234

    17. Ft-0664491

    18. A925456

    19. J-001739

    20. (+/-)-cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine]

    21. Cis-2-methylspiro[1,3-oxathiolane-5,3'-quinuclidine]hydrochloride

    22. 2-methyl-1'-azaspiro[[1,3]oxathiolane-5,3'-bicyclo[2.2.2]octane] (hcl)

    23. 5'-methyl-4-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolane] Hydrochloride

    2.3 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 235.77 g/mol
    Molecular Formula C10H18ClNOS
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass235.0797631 g/mol
    Monoisotopic Mass235.0797631 g/mol
    Topological Polar Surface Area37.8 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity215
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Muscarinic Agonists

    Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)

    Parasympathomimetics

    Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

    4.2 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Cholinergic Receptor Agonist [EPC]; Cholinergic Muscarinic Agonists [MoA]

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    05-May-2021
    30-Apr-2024
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