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Revision as of 02:32, 15 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot← Previous edit Latest revision as of 06:39, 25 October 2024 edit undo76.174.0.57 (talk) Cats. 
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{{Short description|Pharmaceutical drug}}
{{drugbox
{{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400287226 | verifiedrevid = 460027190
| IUPAC_name = 2-methyspiro (1,3- oxathiolane- 5,3) quinuclidine
| IUPAC_name = (2''R'',2''R'')-2'-Methylspirooctane-2,5'-oxathiolane]
| image = Cevimeline.svg | image = Cevimeline.svg
| width = 175
| image2 = Cevimeline 3D.png | image2 = Cevimeline 3D.png

<!--Clinical data-->
| tradename = Evoxac
| Drugs.com = {{drugs.com|monograph|cevimeline-hydrochloride}}
| MedlinePlus = a608025
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category = C
⚫ | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
⚫ | legal_UK = <!-- GSL / P / POM / CD -->
⚫ | legal_US = <!-- OTC / Rx-only -->
⚫ | legal_status = Rx-only
| routes_of_administration = ] (])

<!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | protein_bound = <20%
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =

<!--Identifiers-->
⚫ | 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_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 75707 | ChemSpiderID = 75707
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K9V0CDQ56E | UNII = K9V0CDQ56E
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/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
⚫ | KEGG = D07667
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201267
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 3568

<!--Chemical data-->
⚫ | C=10 | H=17 | N=1 | O=1 | S=1
| smiles = O1(SC12CN3CCC2CC3)C | smiles = O1(SC12CN3CCC2CC3)C
| InChIKey = WUTYZMFRCNBCHQ-PSASIEDQBZ
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WUTYZMFRCNBCHQ-PSASIEDQSA-N | StdInChIKey = WUTYZMFRCNBCHQ-PSASIEDQSA-N
⚫ | CAS_number = 107233-08-9
⚫ | ATC_prefix = N07
⚫ | ATC_suffix = AX03
⚫ | ATC_supplemental =
⚫ | PubChem = 83898
⚫ | DrugBank = APRD00224
⚫ | KEGG_Ref = {{keggcite|changed|kegg}}
⚫ | KEGG = D07667
⚫ | C=10 | H=17 | N=1 | O=1 | S=1
| molecular_weight = 489.565 g/mol
⚫ | bioavailability =
⚫ | protein_bound = < 20%
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category = C
⚫ | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
⚫ | legal_UK = <!-- GSL / P / POM / CD -->
⚫ | legal_US = <!-- OTC / Rx-only -->
⚫ | legal_status = Rx only
| routes_of_administration = Oral
}} }}


'''Cevimeline''' ('''Evoxac''') is a ] and ],<ref name="pmid15234277">{{cite journal |author=Ono M, Takamura E, Shinozaki K, ''et al.'' |title=Therapeutic effect of cevimeline on dry eye in patients with Sjögren's syndrome: a randomized, double-blind clinical study |journal=Am. J. Ophthalmol. |volume=138 |issue=1 |pages=6–17 |year=2004 |month=July |pmid=15234277 |doi=10.1016/j.ajo.2004.02.010 |url=http://linkinghub.elsevier.com/retrieve/pii/S0002939404001369}}</ref> with particular effect on ]s. It is used in the treatment of ] associated with ]. '''Cevimeline''' (trade name '''Evoxac''') is a synthetic analog of the natural alkaloid ] with a particular agonistic effect on ] and ]s. It is used in the treatment of ] and ].


== Mechanism of action == == Medical uses ==
Cevimeline is used in the treatment of ] (dry mouth)<ref name="Ono_2004">{{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 }}</ref><ref name="Fox_2019">{{cite book | vauthors = Fox RI, Fox CM | chapter = Management of Sjögren's |title=Dubois' Lupus Erythematosus and Related Syndromes|publisher=] |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}}</ref> and ].<ref name="Ono_2004" /> It increases the production of saliva.<ref name="Fox_2019" />

⚫ By activating the M<sub>3</sub> receptors of the ], cevimeline stimulates secretion by the ]s, thereby alleviating dry mouth.


== Side effects == == Side effects ==
⚫ Known side effects include ], ], ], excessive ], ], ], ], ], ], ]es, ], and ].<ref>{{cite web | url = http://www.medicinenet.com/cevimeline-oral/article.htm] | work = MedicineNet | title = Cevimeline | access-date = 12 October 2007 }}</ref>

⚫ Known side effects include ], ], ], excessive ], ], ], ], ], ], ]es, ], and ].<ref> MedicineNet: Cevimeline. Accessed 10/12/2007</ref>


Contraindications include ] and ].{{citation needed|date=December 2010}} Contraindications include ] and ].{{citation needed|date=December 2010}}

== Mechanism of action ==
⚫ Cevimeline is a cholinergic agonist.<ref name="Fox_2019" /> It has a particular effect on ] and ]s.<ref name="Fox_2019" /> By activating the M<sub>3</sub> receptors of the ], cevimeline stimulates secretion by the ]s, thereby alleviating dry mouth.

== See also ==
* ] — a similar parasympathomimetic medication for dry mouth (])
* ] — a similar muscarinic parasympathomimetic with longer-lasting effect


== References == == References ==
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== External links == == External links ==
* *


{{Muscarinic acetylcholine receptor modulators}}
{{Cholinergics}}


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