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

• ChemBase ID: 70
• Molecular Formular: C10H17NOS
• Molecular Mass: 199.31308
• Monoisotopic Mass: 199.10308517
• SMILES: S1C[C@@]2(O[C@H]1C)C1CCN(C2)CC1
• Canonical SMILES: C[C@H]1SC[C@]2(O1)CN1CCC2CC1
• InChI: InChI=1S/C10H17NOS/c1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11/h8-9H,2-7H2,1H3/t8-,10-/m1/s1
• InChIKey: WUTYZMFRCNBCHQ-PSASIEDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5'R)-5'-methyl-4-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolane]
• IUPAC Traditional name: cevimeline
• Brand Name: Evoxac; Saligren
• Synonyms: Cevimeline hydrochloride; Cevimeline hydrochloride hemihydrate; Cevimeline hydrochloride hydrate; Cevimeline

Database IDs

• CAS Number: 107233-08-9
• PubChem SID: 160963533
• PubChem CID: 83898

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.954783
• LogD (pH = 7.4): -0.22276455
• Log P: 0.9964063
• Molar Refractivity: 55.9221 cm^3
• Polarizability: 22.251616 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.46
• LOG S: -1.92
• Solubility (Water): 2.41e+00 g/l

PROPERTIES

Physical Property

• Solubility: Very soluble
• Hydrophobicity(logP): 1.3

DETAILS

DrugBank - DB00185

• Drug Groups: approved
• Description: Cevimeline is a parasympathomimetic and muscarinic agonist, with particular effect on M3 receptors. It is indicated by the Food and Drug Administration for the treatment of dry mouth associated with Sj?gren's syndrome. [Wikipedia]
• Indication: For the treatment of symptoms of dry mouth in patients with Sjögren's Syndrome.
• Pharmacology: Cevimeline is a cholinergic agonist which binds to muscarinic receptors. Muscarinic agonists in sufficient dosage can increase secretion of exocrine glands, such as salivary and sweat glands and increase tone of the smooth muscle in the gastrointestinal and urinary tracts.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, isozymes CYP2D6 and CYP3A4 are responsible for the metabolism of cevimeline. Approximately 44.5% of the drug is converted to cis and trans-sulfoxide, 22.3% to glucuronic acid conjugate, and 4% to N-oxide of cevimeline. Approximately 8% of the trans-sulfoxide metabolite is then converted into the corresponding glucuronic acid conjugate.
• Absorption: Rapidly absorbed with peak concentration after 1.5 to 2 hours
• Half Life: 5 ± 1 hours
• Protein Binding: < 20%
• Elimination: After 24 hours, 84% of a 30 mg dose of cevimeline was excreted in urine.
• Distribution: * 6 L/kg
• External Links: Wikipedia; RxList; Drugs.com