Details
Stereochemistry | RACEMIC |
Molecular Formula | C10H17NOS |
Molecular Weight | 199.313 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1O[C@]2(CS1)CN3CC[C@H]2CC3
InChI
InChIKey=WUTYZMFRCNBCHQ-WPRPVWTQSA-N
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-/m0/s1
Molecular Formula | C10H17NOS |
Molecular Weight | 199.313 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/cevimeline.html | http://www.rxlist.com/evoxac-drug.htm
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 |
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Target ID: CHEMBL245 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | EVOXAC Approved UseCevimeline is indicated for the treatment of symptoms of dry mouth in patients with Sjögren’s Syndrome. Launch Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.09 mg/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642962 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.52 mg × h/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642962 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.09 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642962 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
CEVIMELINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
Disc. AE: Abdominal pain, Rash... AEs leading to discontinuation/dose reduction: Abdominal pain (grade 3-4) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
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: |
unhealthy, 54.2 Health Status: unhealthy Age Group: 54.2 Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Central muscarinic activities of an M1-selective agonist: preferential effect on reversal of amnesia. | 1990 Jan 15 |
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[The effectiveness of cevimeline hydrochloride on dry cough in Sjögren's syndrome]. | 2004 Apr |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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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 |
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Effects of cevimeline on the immunolocalization of aquaporin-5 and the ultrastructure of salivary glands in Sjögren's syndrome model mice. | 2009 |
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[Analysis of epitopes and function of anti-M3 muscarinic acetylcholine receptor antibodies in patients with Sjögren's syndrome]. | 2010 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20224229
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
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Record UNII |
K9V0CDQ56E
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NCI_THESAURUS |
C47796
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N07AX03
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N0000000104
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N0000000104
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N0000000104
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WHO-VATC |
QN07AX03
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LIVERTOX |
NBK548833
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NDF-RT |
N0000175884
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DB00185
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CEVIMELINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST |
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
These oxidations (in vitro) required NADPH, and were markedly
inhibited by SKF-525A, indicating that cytochrome P450 (CYP) was involved
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METABOLITE -> PARENT |
mainly catalyzed (in vitro) to sulfoxides by CYP2D6/3A4
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
mainly catalyzed (In vitro) to sulfoxides and N-oxide by CYP2D6/3A4 in liver and FMO1 in kidney
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METABOLITE -> PARENT |
MINOR
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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