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Details

Stereochemistry RACEMIC
Molecular Formula C10H17NOS.ClH
Molecular Weight 235.774
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEVIMELINE HYDROCHLORIDE ANHYDROUS

SMILES

Cl.C[C@H]1O[C@]2(CS1)CN3CC[C@H]2CC3

InChI

InChIKey=SURWTGAXEIEOGY-GNAZCLTHSA-N
InChI=1S/C10H17NOS.ClH/c1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11;/h8-9H,2-7H2,1H3;1H/t8-,10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C10H17NOS
Molecular Weight 199.313
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/cevimeline.html | http://www.rxlist.com/evoxac-drug.htm

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. Cevimeline is indicated for the treatment of symptoms of dry mouth in patients with Sjögren’s Syndrome. Known side effects include nausea, vomiting, diarrhea, excessive sweating, rash, headache, runny nose, cough, drowsiness, hot flashes, blurred vision, and difficulty sleeping. Cevimeline should be administered with caution to patients taking beta adrenergic antagonists, because of the possibility of conduction disturbances. Drugs with para-sympathomimetic effects administered concurrently with cevimeline can be expected to have additive effects. Cevimeline might interfere with desirable antimuscarinic effects of drugs used concomitantly.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
EVOXAC

Approved Use

Cevimeline is indicated for the treatment of symptoms of dry mouth in patients with Sjögren’s Syndrome.

Launch Date

9.4754878E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.09 mg/g
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEVIMELINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.52 mg × h/g
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEVIMELINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.09 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEVIMELINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
CEVIMELINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Disc. AE: Abdominal pain, Rash...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (grade 3-4)
Rash (grade 3-4)
Depression (grade 3-4)
Joint dislocation (grade 3-4)
Granulocytopenia (grade 3-4)
Vertigo (grade 3-4)
LE syndrome (grade 3-4)
Sweating increased (grade 3-4)
Sources: Page: SB96US03
AEs

AEs

AESignificanceDosePopulation
Abdominal pain grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Depression grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Granulocytopenia grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Joint dislocation grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
LE syndrome grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Rash grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Sweating increased grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
Vertigo grade 3-4
Disc. AE
60 mg 3 times / day multiple, oral
MTD
Dose: 60 mg, 3 times / day
Route: oral
Route: multiple
Dose: 60 mg, 3 times / day
Sources: Page: SB96US03
unhealthy, 54.2
n = 362
Health Status: unhealthy
Condition: Sjogren's syndrome
Age Group: 54.2
Sex: M+F
Population Size: 362
Sources: Page: SB96US03
PubMed

PubMed

TitleDatePubMed
Amelioration of experimental amnesia (passive avoidance failure) in rodents by the selective M1 agonist AF102B.
1988 Dec
Central muscarinic activities of an M1-selective agonist: preferential effect on reversal of amnesia.
1990 Jan 15
Gateways to clinical trials.
2003 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Effect of a muscarinic M3 receptor agonist on gastric motility.
2007 Nov
The efficacy of cevimeline hydrochloride in the treatment of xerostomia in Sjögren's syndrome in southern Chinese patients: a randomised double-blind, placebo-controlled crossover study.
2008 Apr
Effects of cevimeline on the immunolocalization of aquaporin-5 and the ultrastructure of salivary glands in Sjögren's syndrome model mice.
2009
[Analysis of epitopes and function of anti-M3 muscarinic acetylcholine receptor antibodies in patients with Sjögren's syndrome].
2010
New epitopes and function of anti-M3 muscarinic acetylcholine receptor antibodies in patients with Sjögren's syndrome.
2010 Oct
Patents

Sample Use Guides

The recommended dose of cevimeline hydrochloride is 30 mg taken three times a day.
Route of Administration: Oral
Cevimeline increased the intracellular Ca2+ concentration of parotid gland acinar and duct cells over 1 uM in a dose-dependent manner.
Substance Class Chemical
Created
by admin
on Sat Dec 16 03:08:07 UTC 2023
Edited
by admin
on Sat Dec 16 03:08:07 UTC 2023
Record UNII
H0913EZ23C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEVIMELINE HYDROCHLORIDE ANHYDROUS
Common Name English
CEVIMELINE HYDROCHLORIDE ANHYDROUS [MI]
Common Name English
(±)-CIS-2-METHYLSPIRO(1,3-OXATHIOLANE-5,3'-QUINUCLIDINE)HYDROCHLORIDE
Common Name English
SPIRO(1-AZABICYCLO(2.2.2)OCTANE-3,5'-(1,3)OXATHIOLANE), 2'-METHYL-, HYDROCHLORIDE, CIS-
Common Name English
Code System Code Type Description
PUBCHEM
22083401
Created by admin on Sat Dec 16 03:08:07 UTC 2023 , Edited by admin on Sat Dec 16 03:08:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID10891421
Created by admin on Sat Dec 16 03:08:07 UTC 2023 , Edited by admin on Sat Dec 16 03:08:07 UTC 2023
PRIMARY
CAS
107220-28-0
Created by admin on Sat Dec 16 03:08:07 UTC 2023 , Edited by admin on Sat Dec 16 03:08:07 UTC 2023
PRIMARY
SMS_ID
100000088039
Created by admin on Sat Dec 16 03:08:07 UTC 2023 , Edited by admin on Sat Dec 16 03:08:07 UTC 2023
PRIMARY
FDA UNII
H0913EZ23C
Created by admin on Sat Dec 16 03:08:07 UTC 2023 , Edited by admin on Sat Dec 16 03:08:07 UTC 2023
PRIMARY
MERCK INDEX
m3303
Created by admin on Sat Dec 16 03:08:07 UTC 2023 , Edited by admin on Sat Dec 16 03:08:07 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY