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 |
---|---|---|---|---|
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: 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) Sources: Page: SB96US03Rash (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: 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 |
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 |
---|---|---|
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 |
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AF102B, a muscarinic M1 receptor agonist, mimics some effects of acetylcholine on neurons of rat hippocampus slices. | 1992 Sep 10 |
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A new medication for treatment of dry mouth in Sjögren's syndrome. | 2001 Apr |
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M1 muscarinic agonists can modulate some of the hallmarks in Alzheimer's disease: implications in future therapy. | 2003 |
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Gateways to clinical trials. | 2003 Sep |
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Transplantation of cultured salivary gland cells into an atrophic salivary gland. | 2004 |
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[The effectiveness of cevimeline hydrochloride on dry cough in Sjögren's syndrome]. | 2004 Apr |
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[Clinical significance of cevimeline hydrochloride in the treatment of dry mouth in patients with Sjögren's syndrome]. | 2004 Oct |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Cevimeline hydrochloride improved cholinergic dysfunction in a patient with pure autonomic failure. | 2006 Jan |
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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on
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Record UNII |
K9V0CDQ56E
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C47796
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WHO-ATC |
N07AX03
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NDF-RT |
N0000000104
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NDF-RT |
N0000000104
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NDF-RT |
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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107233-08-9
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K9V0CDQ56E
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C66873
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3568
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44281
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CHEMBL168815
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DB00185
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m3303
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CEVIMELINE
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K9V0CDQ56E
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100000081517
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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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