U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula 2C10H17NOS.2ClH.H2O
Molecular Weight 489.563
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEVIMELINE HYDROCHLORIDE

SMILES

O.Cl.Cl.C[C@H]1O[C@]2(CS1)CN3CC[C@H]2CC3.C[C@H]4O[C@]5(CS4)CN6CC[C@H]5CC6

InChI

InChIKey=ZSTLCHCDLIUXJE-ZGBAEQJLSA-N
InChI=1S/2C10H17NOS.2ClH.H2O/c2*1-8-12-10(7-13-8)6-11-4-2-9(10)3-5-11;;;/h2*8-9H,2-7H2,1H3;2*1H;1H2/t2*8-,10-;;;/m00.../s1

HIDE SMILES / InChI

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

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 H2O
Molecular Weight 18.0153
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
AF102B, a muscarinic M1 receptor agonist, mimics some effects of acetylcholine on neurons of rat hippocampus slices.
1992 Sep 10
A new medication for treatment of dry mouth in Sjögren's syndrome.
2001 Apr
M1 muscarinic agonists can modulate some of the hallmarks in Alzheimer's disease: implications in future therapy.
2003
Gateways to clinical trials.
2003 Sep
[The effectiveness of cevimeline hydrochloride on dry cough in Sjögren's syndrome].
2004 Apr
[Clinical significance of cevimeline hydrochloride in the treatment of dry mouth in patients with Sjögren's syndrome].
2004 Oct
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Cevimeline hydrochloride improved cholinergic dysfunction in a patient with pure autonomic failure.
2006 Jan
Degradation of submandibular gland AQP5 by parasympathetic denervation of chorda tympani and its recovery by cevimeline, an M3 muscarinic receptor agonist.
2008 Jul
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 Wed Jul 05 23:10:41 UTC 2023
Edited
by admin
on Wed Jul 05 23:10:41 UTC 2023
Record UNII
P81Q6V85NP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEVIMELINE HYDROCHLORIDE
MART.   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
Cevimeline hydrochloride [WHO-DD]
Common Name English
CEVIMELINE HYDROCHLORIDE [USAN]
Common Name English
SALIGREN
Brand Name English
SND-5008
Code English
CEVIMELINE HYDROCHLORIDE [MART.]
Common Name English
CEVIMELINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
EVOXAC
Brand Name English
CEVIMELINE HYDROCHLORIDE HEMIHYDRATE
MI  
Common Name English
CEVIMELINE HYDROCHLORIDE HEMIHYDRATE [MI]
Common Name English
SNK-508
Code English
CEVIMELINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
AF102B
Code English
SPIRO(1-AZABICYCLO(2.2.2)OCTANE-3,5'-(1,3)OXATHIOLANE), 2'-METHYL-, HYDROCHLORIDE, HYDRATE (2:1), CIS-
Common Name English
(±)-CIS-2-METHYLSPIRO(1,3-OXATHIOLANE-5,3'-QUINUCLIDINE)HYDROCHLORIDE, HEMIHYDRATE
Common Name English
CEVIMELINE HCL
Common Name English
FKS-508
Code English
SNI-2011
Code English
AF-102B
Code English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1104210
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
USAN
HH-59
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
FDA UNII
P81Q6V85NP
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
CAS
153504-70-2
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL168815
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
DRUG BANK
DBSALT000805
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
DAILYMED
P81Q6V85NP
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
NCI_THESAURUS
C1337
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
RXCUI
260036
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
Cevimeline hydrochloride
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
MERCK INDEX
M3303
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID9022788
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
EVMPD
SUB128462
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
PUBCHEM
73416227
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
SMS_ID
100000153922
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
EVMPD
SUB01186MIG
Created by admin on Wed Jul 05 23:10:41 UTC 2023 , Edited by admin on Wed Jul 05 23:10:41 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY