Cevimeline

Pharmaceutical drug

Routes of
administrationBy mouth (capsules)ATC code

N07AX03 (WHO)

Legal statusLegal status

In general: ℞ (Prescription only)

Pharmacokinetic dataProtein binding<20%Identifiers

IUPAC name

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

CAS Number

107233-08-9^Y

PubChem CID

83898

DrugBank

DB00185^Y

ChemSpider

75707^Y

UNII

K9V0CDQ56E

KEGG

D07667^Y

ChEBI

CHEBI:3568^N

ChEMBL

ChEMBL1201267^N

CompTox Dashboard (EPA)

DTXSID801342027 DTXSID40274384, DTXSID801342027

Chemical and physical dataFormulaC₁₀H₁₇NOSMolar mass199.31 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O1[C@H](SC[C@@]12CN3CCC2CC3)C

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^Y
Key:WUTYZMFRCNBCHQ-PSASIEDQSA-N^Y

^NY (what is this?) (verify)

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)^[1]^[2] and Sjögren's syndrome.^[1] It increases the production of saliva.^[2]

Side effects

Known side effects include nausea, vomiting, diarrhea, excessive sweating, rash, headache, runny nose, cough, drowsiness, hot flashes, blurred vision, and difficulty sleeping.^[3]

Contraindications include asthma and angle closure glaucoma.^{[citation needed]}

Mechanism of action

Cevimeline is a cholinergic agonist.^[2] It has a particular effect on M₁ and M₃ receptors.^[2] By activating the M₃ receptors of the parasympathetic nervous system, cevimeline stimulates secretion by the salivary glands, thereby alleviating dry mouth.

References

^ ^a ^b Ono M, Takamura E, Shinozaki K, Tsumura T, Hamano T, Yagi Y, Tsubota K (July 2004). "Therapeutic effect of cevimeline on dry eye in patients with Sjögren's syndrome: a randomized, double-blind clinical study". American Journal of Ophthalmology. 138 (1): 6–17. doi:10.1016/j.ajo.2004.02.010. PMID 15234277.
^ ^a ^b ^c ^d Fox RI, Fox CM (2019). "Management of Sjögren's". Dubois' Lupus Erythematosus and Related Syndromes (9th ed.). Elsevier. pp. 745–758. doi:10.1016/B978-0-323-47927-1.00060-8. ISBN 978-0-323-47927-1.
^ "Cevimeline". MedicineNet. Retrieved 12 October 2007.

External links

Evoxac (cevimeline HCl hydrate capsules) Full Prescribing Information

Muscarinic acetylcholine receptor modulators

mAChRsTooltip Muscarinic acetylcholine receptors

Agonists	77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B Alvameline AQRA-741 Arecoline Bethanechol Bevonium Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Clozapine Desmethylclozapine (norclozapine) Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796
Antagonists	3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol) Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine, buclizine, captodiame, chlorphenamine (chlorpheniramine), cinnarizine, clemastine, cyproheptadine, dimenhydrinate, dimetindene, diphenhydramine, doxylamine, meclizine, mequitazine, perlapine, phenindamine, pheniramine, phenyltoloxamine, promethazine, propiomazine, triprolidine) AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g., clozapine, fluperlapine, olanzapine (+fluoxetine), rilapine, quetiapine, tenilapine, zotepine) Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol, +indacaterol, +neostigmine) Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol) Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., femoxetine, paroxetine) Telenzepine Terodiline Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g., amitriptyline (+perphenazine), amitriptylinoxide, butriptyline, cidoxepin, clomipramine, desipramine, desmethyldesipramine, dibenzepin, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nitroxazepine, northiaden (desmethyldosulepin), nortriptyline, protriptyline, quinupramine, trimipramine) Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Trospium chloride Typical antipsychotics (e.g., chlorpromazine, chlorprothixene, cyamemazine (cyamepromazine), loxapine, mesoridazine, thioridazine) Umeclidinium bromide (+vilanterol) WIN-2299 Xanomeline Zamifenacin

Agonists