cevimeline

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460027190

| IUPAC_name = (2R,2R)-2'-Methylspiro[4-azabicyclo[2.2.2]octane-2,5'-[1,3]oxathiolane]

| image = Cevimeline.svg

| width = 175

| image2 = Cevimeline 3D.png

| tradename = Evoxac

| Drugs.com = {{drugs.com|monograph|cevimeline-hydrochloride}}

| MedlinePlus = a608025

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category = C

| legal_AU =

| legal_UK =

| legal_US =

| legal_status = Rx-only

| routes_of_administration = By mouth (capsules)

| bioavailability =

| protein_bound = <20%

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 107233-08-9

| ATC_prefix = N07

| ATC_suffix = AX03

| ATC_supplemental =

| PubChem = 83898

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00185

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 75707

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = K9V0CDQ56E

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07667

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201267

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 3568

| C=10 | H=17 | N=1 | O=1 | S=1

| smiles = O1[C@H](SC[C@@]12CN3CCC2CC3)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WUTYZMFRCNBCHQ-PSASIEDQSA-N

}}

Cevimeline (trade name Evoxac) is a synthetic analog of the natural alkaloid muscarine with a particular agonistic effect on M₁ and M₃ receptors. It is used in the treatment of dry mouth and Sjögren's syndrome.

Medical uses

Cevimeline is used in the treatment of xerostomia (dry mouth){{cite journal | vauthors = Ono M, Takamura E, Shinozaki K, Tsumura T, Hamano T, Yagi Y, Tsubota K | title = Therapeutic effect of cevimeline on dry eye in patients with Sjögren's syndrome: a randomized, double-blind clinical study | journal = American Journal of Ophthalmology | volume = 138 | issue = 1 | pages = 6–17 | date = July 2004 | pmid = 15234277 | doi = 10.1016/j.ajo.2004.02.010 }}{{cite book | vauthors = Fox RI, Fox CM | chapter = Management of Sjögren's |title=Dubois' Lupus Erythematosus and Related Syndromes|publisher=Elsevier |year=2019 |isbn=978-0-323-47927-1|edition=9th|pages=745-758|language=en |doi=10.1016/B978-0-323-47927-1.00060-8}} and Sjögren's syndrome. It increases the production of saliva.

Side effects

Known side effects include nausea, vomiting, diarrhea, excessive sweating, rash, headache, runny nose, cough, drowsiness, hot flashes, blurred vision, and difficulty sleeping.{{cite web | url = http://www.medicinenet.com/cevimeline-oral/article.htm] | work = MedicineNet | title = Cevimeline | access-date = 12 October 2007 }}

Contraindications include asthma and angle closure glaucoma.{{citation needed|date=December 2010}}

Mechanism of action

Cevimeline is a cholinergic agonist. It has a particular effect on M₁ and M₃ receptors. By activating the M₃ receptors of the parasympathetic nervous system, cevimeline stimulates secretion by the salivary glands, thereby alleviating dry mouth.