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    Codeine Sulfate

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    2D Structure
    Also known as: Codeine sulfate, 3-methylmorphine sulfate salt, Schembl24864, Chembl284671
    Molecular Formula
    C18H23NO7S
    Molecular Weight
    397.4  g/mol
    InChI Key
    REJWPZYIFAQSIK-FFHNEAJVSA-N
    Codeine Sulfate is the sulfate salt form of codeine, a naturally occurring phenanthrene alkaloid and opioid agonist with analgesic, antidiarrheal and antitussive activity. Codeine sulfate mimics the actions of opioids by binding to the opioid receptors at many sites within the central nervous system (CNS). Stimulation of the mu-subtype opioid receptor stimulates the exchange of GTP for GDP on the G-protein complex and subsequently inhibits adenylate cyclase. This results in a decrease in intracellular cAMP and leads to a reduction in the release of neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline. The analgesic effect of codeine sulfate is likely due to its metabolite morphine, which induces opening of G-protein-coupled inwardly rectifying potassium (GIRK) channels and blocks the opening of N-type voltage-gated calcium channels, thereby resulting in hyperpolarization and reduced neuronal excitability.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol;sulfuric acid
    2.1.2 InChI
    InChI=1S/C18H21NO3.H2O4S/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;1-5(2,3)4/h3-6,11-13,17,20H,7-9H2,1-2H3;(H2,1,2,3,4)/t11-,12+,13-,17-,18-;/m0./s1
    2.1.3 InChI Key
    REJWPZYIFAQSIK-FFHNEAJVSA-N
    2.1.4 Canonical SMILES
    CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O.OS(=O)(=O)O
    2.1.5 Isomeric SMILES
    CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O.OS(=O)(=O)O
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. Codeine Sulfate

    2. 3-methylmorphine Sulfate Salt

    3. Schembl24864

    4. Chembl284671

    2.3 Create Date
    2006-03-21
    3 Chemical and Physical Properties
    Molecular Weight 397.4 g/mol
    Molecular Formula C18H23NO7S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count1
    Exact Mass397.11952325 g/mol
    Monoisotopic Mass397.11952325 g/mol
    Topological Polar Surface Area125 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity590
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameCodeine sulfate
    Active IngredientCodeine sulfate
    Dosage FormTablet; Solution
    RouteOral
    Strength30mg/5ml; 60mg; 30mg; 15mg
    Market StatusPrescription
    CompanyLannett Holdings; Roxane

    2 of 2  
    Drug NameCodeine sulfate
    Active IngredientCodeine sulfate
    Dosage FormTablet; Solution
    RouteOral
    Strength30mg/5ml; 60mg; 30mg; 15mg
    Market StatusPrescription
    CompanyLannett Holdings; Roxane

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Pharmacological Classes
    Opioid Agonist [EPC]; Full Opioid Agonists [MoA]