Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H29NO3.ClH |
Molecular Weight | 415.953 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=CC2=C(C=C1OC)C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)C2
InChI
InChIKey=XWAIAVWHZJNZQQ-UHFFFAOYSA-N
InChI=1S/C24H29NO3.ClH/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18;/h3-7,14-15,17,20H,8-13,16H2,1-2H3;1H
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 | C24H29NO3 |
Molecular Weight | 379.492 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Donepezil, marketed under the trade name Aricept, is a medication used in the palliative treatment of Alzheimer's disease. Aricept is indicated for the treatment of dementia of the Alzheimer’s type. Efficacy
has been demonstrated in patients with mild to moderate Alzheimer’s Disease, as well
as in patients with severe Alzheimer’s Disease. Donepezil is postulated to exert its therapeutic effect by enhancing
cholinergic function. This is accomplished by increasing the concentration of
acetylcholine through reversible inhibition of its hydrolysis by acetylcholinesterase. Donepezil has been tested in other cognitive disorders including Lewy body dementia and Vascular dementia, but it is not currently approved for these indications. Donepezil has also been studied in patients with Mild Cognitive Impairment, schizophrenia, attention deficit disorder, post-coronary bypass cognitive impairment, cognitive impairment associated with multiple sclerosis, and Down syndrome.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
6.7 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ARICEPT Approved UseDonepezil hydrochloride orally disintegrating tablets, USP are an acetylcholinesterase inhibitor indicated for the treatment of dementia of the Alzheimer's type. Efficacy has been demonstrated in patients with mild, moderate, and severe Alzheimer's Disease (1). Donepezil hydrochloride orally disintegrating tablets, USP are indicated for the treatment of dementia of the Alzheimer's type. Efficacy has been demonstrated in patients with mild, moderate, and severe Alzheimer's disease. Launch Date8.4888001E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
34.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
60.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2889.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5051.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
72.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
73.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760 |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DONEPEZIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
175 mg single, transdermal Dose: 175 mg Route: transdermal Route: single Dose: 175 mg Sources: |
healthy, 24.9±3.3 years n = 9 Health Status: healthy Age Group: 24.9±3.3 years Sex: M Population Size: 9 Sources: |
|
175 mg 1 times / 3 days steady, transdermal Dose: 175 mg, 1 times / 3 days Route: transdermal Route: steady Dose: 175 mg, 1 times / 3 days Sources: |
healthy, 24.9±3.3 years n = 9 Health Status: healthy Age Group: 24.9±3.3 years Sex: M Population Size: 9 Sources: |
|
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Disc. AE: Bradycardia, Diarrhea... AEs leading to discontinuation/dose reduction: Bradycardia (0.7%) Sources: Page: p. 50Diarrhea (1.7%) Nausea (1.9%) Vomiting (2.9%) QT interval prolonged (0.4%) Anorexia (0.3%) Dizziness (1.1%) Headache (0.4%) Somnolence (0.6%) Syncope (0.2%) Aggression (0.5%) Agitation (0.8%) Confusional state (0.7%) |
50 mg single, oral Overdose |
unhealthy, 79 years n = 1 Health Status: unhealthy Condition: Alzheimer disease Age Group: 79 years Sex: F Population Size: 1 Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Sources: Vomiting (1 patient) Bradycardia (1 patient) |
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, 80 years n = 1 Health Status: unhealthy Condition: Alzheimer disease Age Group: 80 years Sex: F Population Size: 1 Sources: |
Disc. AE: Myoclonus... AEs leading to discontinuation/dose reduction: Myoclonus (1 patient) Sources: |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult n = 315 Health Status: unhealthy Age Group: adult Population Size: 315 Sources: |
Other AEs: Diarrhea, Nausea... Other AEs: Diarrhea (3%) Sources: Nausea (3%) Vomiting (2%) |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: |
unhealthy, adult n = 350 Health Status: unhealthy Age Group: adult Population Size: 350 Sources: |
Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (<1%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Syncope | 0.2% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Anorexia | 0.3% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Headache | 0.4% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
QT interval prolonged | 0.4% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Aggression | 0.5% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Somnolence | 0.6% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Bradycardia | 0.7% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Confusional state | 0.7% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Agitation | 0.8% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Dizziness | 1.1% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Diarrhea | 1.7% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Nausea | 1.9% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Vomiting | 2.9% Disc. AE |
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: Page: p. 50 |
unhealthy, 73.9 years n = 967 Health Status: unhealthy Condition: Alzheimer disease Age Group: 73.9 years Sex: M+F Population Size: 967 Sources: Page: p. 50 |
Bradycardia | 1 patient | 50 mg single, oral Overdose |
unhealthy, 79 years n = 1 Health Status: unhealthy Condition: Alzheimer disease Age Group: 79 years Sex: F Population Size: 1 Sources: |
Nausea | 1 patient | 50 mg single, oral Overdose |
unhealthy, 79 years n = 1 Health Status: unhealthy Condition: Alzheimer disease Age Group: 79 years Sex: F Population Size: 1 Sources: |
Vomiting | 1 patient | 50 mg single, oral Overdose |
unhealthy, 79 years n = 1 Health Status: unhealthy Condition: Alzheimer disease Age Group: 79 years Sex: F Population Size: 1 Sources: |
Myoclonus | 1 patient Disc. AE |
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, 80 years n = 1 Health Status: unhealthy Condition: Alzheimer disease Age Group: 80 years Sex: F Population Size: 1 Sources: |
Vomiting | 2% | 10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult n = 315 Health Status: unhealthy Age Group: adult Population Size: 315 Sources: |
Diarrhea | 3% | 10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult n = 315 Health Status: unhealthy Age Group: adult Population Size: 315 Sources: |
Nausea | 3% | 10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult n = 315 Health Status: unhealthy Age Group: adult Population Size: 315 Sources: |
Diarrhea | <1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: |
unhealthy, adult n = 350 Health Status: unhealthy Age Group: adult Population Size: 350 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? | 2001 |
|
EEG changes during long-term treatment with donepezil in Alzheimer's disease patients. | 2001 |
|
Pharmacokinetic rationale for switching from donepezil to galantamine. | 2001 |
|
Switching previous therapies for Alzheimer's disease to galantamine. | 2001 |
|
A double-blind placebo-controlled case study of the use of donepezil to improve cognition in a schizoaffective disorder patient: functional MRI correlates. | 2001 |
|
Clinical and cost-effectiveness of donepezil, rivastigmine and galantamine for Alzheimer's disease: a rapid and systematic review. | 2001 |
|
Cerebral blood flow and metabolic abnormalities in Alzheimer's disease. | 2001 Apr |
|
Muscarinic agonists and antagonists in the treatment of Alzheimer's disease. | 2001 Apr |
|
Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder. | 2001 Apr |
|
Determination of inhibitors' potency (IC50) by a direct high-performance liquid chromatographic method on an immobilised acetylcholinesterase column. | 2001 Apr 5 |
|
Maintaining functional and behavioral abilities in Alzheimer disease. | 2001 Aug |
|
Maintaining cognitive function in Alzheimer disease: how effective are current treatments? | 2001 Aug |
|
Motor cortex disinhibition in Alzheimer's disease. | 2001 Aug |
|
A 1-year, placebo-controlled preservation of function survival study of donepezil in AD patients. | 2001 Aug 14 |
|
Randomized placebo-controlled trial of donepezil in patients with progressive supranuclear palsy. | 2001 Aug 14 |
|
Donepezil in schizophrenia--is it helpful? An experimental design case study. | 2001 Dec |
|
[Alzheimer dementia. Comparison of the effectiveness of cholinesterase inhibitors and gingko]. | 2001 Dec 13 |
|
Donepezil-induced REM sleep augmentation enhances memory performance in elderly, healthy persons. | 2001 Feb |
|
[Early recognition not hopeless. Alzheimer disease can be delayed]. | 2001 Feb 8 |
|
Donepezil for Down's syndrome. | 2001 Jan |
|
Use of cholinesterase inhibitors for treatment of Alzheimer disease. | 2001 Jul |
|
Open-label study of donepezil in traumatic brain injury. | 2001 Jul |
|
An open-label, 24-week pilot study of the methyl donor betaine in Alzheimer disease patients. | 2001 Jul-Sep |
|
Huperzine A and donepezil protect rat pheochromocytoma cells against oxygen-glucose deprivation. | 2001 Jun 22 |
|
Amyloid precursor protein in platelets of patients with Alzheimer disease: effect of acetylcholinesterase inhibitor treatment. | 2001 Mar |
|
Open-label, multicenter, phase 3 extension study of the safety and efficacy of donepezil in patients with Alzheimer disease. | 2001 Mar |
|
Analysis and enantioresolution of donepezil by capillary electrophoresis. | 2001 Mar |
|
Platelet amyloid precursor protein forms in AD: a peripheral diagnostic tool and a pharmacological target. | 2001 Nov |
|
SCH 57790, a selective muscarinic M(2) receptor antagonist, releases acetylcholine and produces cognitive enhancement in laboratory animals. | 2001 Nov 16 |
|
[A comparison of cholinesterase inhibitors and ginkgo extract in treatment of Alzheimer dementia]. | 2001 Nov 29 |
|
Synthesis and screening for antiacetylcholinesterase activity of (1-benzyl-4-oxopiperidin-3-ylidene)methylindoles and -pyrroles related to donepezil. | 2001 Nov 8 |
|
Treatment of tardive dyskinesia with donepezil: a pilot study. | 2001 Oct |
|
Donepezil for Alzheimer's disease: pharmacodynamic, pharmacokinetic, and clinical profiles. | 2001 Winter |
|
Economic evaluation of donepezil treatment for Alzheimer's disease in Japan. | 2002 |
|
Feasibility of vascular dementia treatment with cholinesterase inhibitors. | 2002 Feb |
|
[Pharmacotherapy for the treatment of Alzheimer's disease--the present state and the development in the future]. | 2002 Jan |
|
A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Down syndrome and Alzheimer's disease--pilot study. | 2002 Mar |
|
A 1-year, randomized, placebo-controlled study of donepezil in patients with mild to moderate AD. | 2002 Mar 12 |
|
Determination of donepezil, an acetylcholinesterase inhibitor, in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection. | 2002 Mar 5 |
Sample Use Guides
Mild to Moderate Alzheimer’s Disease - 5 mg or 10 mg
administered once daily
Moderate to Severe Alzheim er’s Disease - 10 mg or 23 mg
administered once daily
A dose of 10 mg once daily can be administered once patients have been
on a daily dose of 5 mg for 4 to 6 weeks. A dose of 23 mg once daily can
be administered once patien ts have been on a dose of 10 mg once daily
for at least 3 months
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16570913
Donepezil inhibited freshly prepared human erythrocyte AChE with IC50 22 nM
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:00:59 UTC 2023
by
admin
on
Wed Jul 05 23:00:59 UTC 2023
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Record UNII |
3O2T2PJ89D
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
BALAXUR (REFUSED: ALZHEIMER DISEASE)
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EMA ASSESSMENT REPORTS |
ACRESCENT (REFUSED: ALZHEIMER DISEASE)
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NCI_THESAURUS |
C47792
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737535
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3O2T2PJ89D
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3O2T2PJ89D
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4696
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CHEMBL502
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5741
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100000091200
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M4738
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DBSALT000938
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758882
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1224981
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C2603
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120011-70-3
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236559
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DTXSID0046698
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Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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