Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H29NO3.ClH.H2O |
Molecular Weight | 433.968 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.COC1=CC2=C(C=C1OC)C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)C2
InChI
InChIKey=HLJIZAKUNCTCQX-UHFFFAOYSA-N
InChI=1S/C24H29NO3.ClH.H2O/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;1H2
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 | ( + / - ) |
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 |
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 Date1996 |
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 |
|
The beneficial effect of cholinesterase inhibitors on patients suffering from Parkinson's disease and dementia. | 2001 |
|
Galantamine for Alzheimer's disease. | 2001 |
|
Pharmacokinetic rationale for switching from donepezil to galantamine. | 2001 |
|
Pharmacokinetic profiles of current therapies for Alzheimer's disease: implications for switching to galantamine. | 2001 |
|
Cerebral blood flow and metabolic abnormalities in 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 |
|
Prevalence, costs, and treatment of Alzheimer's disease and related dementia: a managed care perspective. | 2001 Aug |
|
Motor cortex disinhibition in Alzheimer's disease. | 2001 Aug |
|
A 1-year, randomized, placebo-controlled study of donepezil in patients with mild to moderate AD. | 2001 Aug 14 |
|
A 1-year, placebo-controlled preservation of function survival study of donepezil in AD patients. | 2001 Aug 14 |
|
A randomized, double-blind, placebo-controlled study of the efficacy and safety of donepezil in patients with Alzheimer's disease in the nursing home setting. | 2001 Dec |
|
Galantamine: new preparation. The fourth cholinesterase inhibitor for Alzheimer's disease. | 2001 Dec |
|
Unsafe prescription medication switching recommendations. | 2001 Dec |
|
[Alzheimer dementia. Comparison of the effectiveness of cholinesterase inhibitors and gingko]. | 2001 Dec 13 |
|
Donepezil, rivastigmine, and vitamin E in Alzheimer disease: a combined P300 event-related potentials/neuropsychologic evaluation over 6 months. | 2001 Jan-Feb |
|
[A patient with probable dementia with Lewy bodies, who showed improvement of dementia and parkinsonism by the administratim of donepezil]. | 2001 Jul |
|
Featured CME topic: dementia. Medication update. | 2001 Jul |
|
Use of cholinesterase inhibitors for treatment of Alzheimer disease. | 2001 Jul |
|
Open-label study of donepezil in traumatic brain injury. | 2001 Jul |
|
Equity in the new NHS: hard lessons from implementing a local healthcare policy on donepezil. | 2001 Jul 28 |
|
Newest developments in dementia treatment and prevention. | 2001 Jul-Aug |
|
Cholinergic modulation of speed of early information processing: the effect of donepezil on inspection time. | 2001 Jun |
|
Huperzine A and donepezil protect rat pheochromocytoma cells against oxygen-glucose deprivation. | 2001 Jun 22 |
|
[Recent development of anti-dementia drugs]. | 2001 Mar |
|
Alzheimer's disease and related disorders. | 2001 May |
|
Ameliorative effects of azaindolizinone derivative ZSET845 on scopolamine-induced deficits in passive avoidance and radial-arm maze learning in the rat. | 2001 Nov |
|
[Malignant syndrome caused by a combination of bromperidol and donepezil hydrochloride in a patient with probable dementia with Lewy bodies]. | 2001 Nov |
|
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 |
|
[Anticholinesterase agents in Alzheimer's disease]. | 2001 Sep |
|
Donepezil for Alzheimer's disease: pharmacodynamic, pharmacokinetic, and clinical profiles. | 2001 Winter |
|
Economic evaluation of donepezil treatment for Alzheimer's disease in Japan. | 2002 |
|
Donepezil management of schizophrenia with associated dementia. | 2002 Apr |
|
Donepezil in the treatment of Alzheimer's disease: long-term efficacy and safety. | 2002 Feb |
|
Feasibility of vascular dementia treatment with cholinesterase inhibitors. | 2002 Feb |
|
Atrophy of the substantia innominata on magnetic resonance imaging and response to donepezil treatment in Alzheimer's disease. | 2002 Feb 8 |
|
[Pharmacotherapy for the treatment of Alzheimer's disease--the present state and the development in the future]. | 2002 Jan |
|
A new HPLC method to determine Donepezil hydrochloride in tablets. | 2002 Jan 1 |
|
[Alzheimer dementia. Intervening as early as possible]. | 2002 Jan 17 |
|
Therapeutic effects of an acetylcholinesterase inhibitor (donepezil) on memory in Wernicke-Korsakoff's disease. | 2002 Jan-Feb |
|
Lewy body dementia: case report and discussion. | 2002 Jan-Feb |
|
How many patients complete an adequate trial of donepezil? | 2002 Jan-Mar |
|
A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Down syndrome and Alzheimer's disease--pilot study. | 2002 Mar |
|
Comparison of citalopram, perphenazine, and placebo for the acute treatment of psychosis and behavioral disturbances in hospitalized, demented patients. | 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 |
|
In vitro toxicity of rivastigmine and donepezil in cells of epithelial origin. | 2002 Mar-Apr |
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
Sat Dec 16 08:45:37 GMT 2023
by
admin
on
Sat Dec 16 08:45:37 GMT 2023
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Record UNII |
7KZL5YRL6W
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Record Status |
Validated (UNII)
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Record Version |
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