Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H10N2O2 |
| Molecular Weight | 142.1558 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)CN1CCCC1=O
InChI
InChIKey=GMZVRMREEHBGGF-UHFFFAOYSA-N
InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
| Molecular Formula | C6H10N2O2 |
| Molecular Weight | 142.1558 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB09210Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20163115 | https://www.ncbi.nlm.nih.gov/pubmed/16459490 | https://www.ncbi.nlm.nih.gov/pubmed/10210031 | https://www.drugs.com/uk/piracetam-800mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/16007238 | https://www.ncbi.nlm.nih.gov/pubmed/17284293
Sources: https://www.drugbank.ca/drugs/DB09210
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20163115 | https://www.ncbi.nlm.nih.gov/pubmed/16459490 | https://www.ncbi.nlm.nih.gov/pubmed/10210031 | https://www.drugs.com/uk/piracetam-800mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/16007238 | https://www.ncbi.nlm.nih.gov/pubmed/17284293
Piracetam (sold under many brand names) is a nootropic drug in the racetams group, with chemical name 2-oxo-1-pyrrolidine acetamide. It shares the same 2-oxo-pyrrolidone base structure with pyroglutamic acid. Piracetam is a cyclic derivative of the neurotransmitter gamma-aminobutyric acid (GABA), originally marketed in 1971 by UCB Pharma. Presently piracetam is used in many European countries, Asia and South America. In the United States, it is not approved by the US Food and Drug Administration for any medical use and it is not permitted to be sold as a dietary supplement. In the UK, piracetam is prescribed mainly for myoclonus but is used off-label for other conditions. Evidence to support its use for many conditions is unclear. Piracetam's mechanism of action, as with racetams in general, is not fully understood. The drug influences neuronal and vascular functions and influences cognitive function without acting as a sedative or stimulant. It is hypothesized to act on ion channels or ion carriers, thus leading to increased neuron excitability. GABA brain metabolism and GABA receptors are not affected by piracetam. It has been found to increase blood flow and oxygen consumption in parts of the brain, but this may be a side effect of increased brain activity rather than a primary effector mechanism of action for the drug.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20163115 |
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Target ID: CHEMBL3503 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20163115 |
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Target ID: CHEMBL3504 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20163115 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Nootropil Approved UseUnknown |
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| Primary | Nootropil Approved UseUnknown |
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| Preventing | Nootropil Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
85.3 μg/mL |
3200 mg single, oral dose: 3200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
173.7 μg/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
177 μg/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
211.2 μg/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
173.7 μg/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
136.5 μg/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
521.7 μg × h/mL |
3200 mg single, oral dose: 3200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1192.5 μg × h/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1590.1 μg × h/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1661.7 μg × h/mL |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1192.5 μg × h/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1199.3 μg × h/mL |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.6 h |
3200 mg single, oral dose: 3200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.6 h |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5 h |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5 h |
6400 mg 3 times / day steady-state, oral dose: 6400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.6 h |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.2 h |
6400 mg single, oral dose: 6400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRACETAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
99% |
PIRACETAM serum | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12 g 2 times / day multiple, oral Highest studied dose Dose: 12 g, 2 times / day Route: oral Route: multiple Dose: 12 g, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Stomach upset, Ulcer... AEs leading to discontinuation/dose reduction: Stomach upset (6.6%) Sources: Ulcer (0.4%) Eczema (0.4%) Allergy (0.4%) Cerebral seizures (0.4%) Depression (0.4%) Heartburn (0.4%) Gastritis (0.4%) Weight increase (0.4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Allergy | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Cerebral seizures | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Depression | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Eczema | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Gastritis | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Heartburn | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Ulcer | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Weight increase | 0.4% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Stomach upset | 6.6% Disc. AE |
1.6 g 3 times / day multiple, oral Recommended Dose: 1.6 g, 3 times / day Route: oral Route: multiple Dose: 1.6 g, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Effect of the novel dipeptide nootropic agent noopept and its metabolite cyclo-L-prolylglycine on the transcallosal evoked potential in the rat brain]. | 2002-07-12 |
|
| [Experimental and clinical rationale for complex treatment of mental disorders in clean-up workers of the Chernobyl nuclear plant accident]. | 2002-07-12 |
|
| Aggravation of partial seizures by antiepileptic drugs: is there evidence from clinical trials? | 2002-07-09 |
|
| Levetiracetam does not alter the pharmacokinetics of an oral contraceptive in healthy women. | 2002-07 |
|
| The anti-epileptic drug levetiracetam reverses the inhibition by negative allosteric modulators of neuronal GABA- and glycine-gated currents. | 2002-07 |
|
| [Levetiracetam: an anti-epileptic drug with interesting pharmacokinetic properties]. | 2002-06-29 |
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| DM235 (sunifiram): a novel nootropic with potential as a cognitive enhancer. | 2002-06 |
|
| [Anti-arrhythmic properties of GABA and GABA-ergic system activators]. | 2002-05-25 |
|
| [Levetiracetam: a molecule with a novel mechanism of action in the pharmaceutical treatment of epilepsy]. | 2002-05-20 |
|
| [Effects of piracetam on the cognitive functions verified by electrophysiologic methods]. | 2002-05-19 |
|
| Piracetam and vinpocetine exert cytoprotective activity and prevent apoptosis of astrocytes in vitro in hypoxia and reoxygenation. | 2002-05 |
|
| Brain neurotransmitter receptor binding and nootropic studies on Indian Hypericum perforatum Linn. | 2002-05 |
|
| Levetiracetam in the treatment of paroxysmal kinesiogenic choreoathetosis. | 2002-05 |
|
| Efficacy and safety of levetiracetam in children with partial seizures: an open-label trial. | 2002-05 |
|
| Antidepressant activity of memory-enhancing drugs in the reduction of submissive behavior model. | 2002-04-05 |
|
| Levetiracetam--a new drug for epilepsy. | 2002-04 |
|
| Effects of the novel antiepileptic drug levetiracetam on spontaneous recurrent seizures in the rat pilocarpine model of temporal lobe epilepsy. | 2002-04 |
|
| A new antiepileptic drug. | 2002-04 |
|
| The new antiepileptic drug levetiracetam normalises chlordiazepoxide withdrawal-induced anxiety in mice. | 2002-03-29 |
|
| [Effect of piracetam on the conditional reflex memory under probable reinforcement conditions]. | 2002-03-02 |
|
| Suppression of cortical myoclonus by levetiracetam. | 2002-03 |
|
| A comparison of the efficacy of carbamazepine and the novel anti-epileptic drug levetiracetam in the tetanus toxin model of focal complex partial epilepsy. | 2002-03 |
|
| Levetiracetam opposes the action of GABAA antagonists in hypothalamic neurones. | 2002-03 |
|
| In vitro antioxidant properties of pentoxifylline, piracetam, and vinpocetine. | 2002-02-20 |
|
| Neuroprotective agents in acute ischemic stroke. | 2002-02 |
|
| Breath holding spells in a 3-day-old neonate: an unusual early presentation in a family with a history of breath holding spells. | 2002-02 |
|
| Carbamazepine toxicity during combination therapy with levetiracetam: a pharmacodynamic interaction. | 2002-02 |
|
| Levetiracetam: a different approach to the pharmacotherapy of epilepsy. | 2002-02 |
|
| Controlled pilot study of piracetam for pediatric opsoclonus-myoclonus. | 2002-01-22 |
|
| [Scavenger effect of various cerebrovascular drugs]. | 2002-01-06 |
|
| Using the new antiepilepsy drugs in children. | 2002-01 |
|
| Three new drugs for epilepsy: levetiracetam, oxcarbazepine, and zonisamide. | 2002-01 |
|
| Selective blockade of N-type calcium channels by levetiracetam. | 2002-01 |
|
| Dose-response effect of levetiracetam 1000 and 2000 mg/day in partial epilepsy. | 2002-01 |
|
| Newer therapies in the drug treatment of epilepsy. | 2002-01 |
|
| Levetiracetam for acute mania. | 2002-01 |
|
| Clinical efficacy of piracetam in cognitive impairment: a meta-analysis. | 2002 |
|
| The clinical challenge of posthypoxic myoclonus. | 2002 |
|
| Piracetam for fetal distress in labour. | 2002 |
|
| [Piracetam in combined pathogenetic therapy of recurrent duodenal ulcer]. | 2002 |
|
| Design and study of piracetam-like nootropics, controversial members of the problematic class of cognition-enhancing drugs. | 2002 |
|
| Pyrrolidone derivatives. | 2001-12-01 |
|
| Levetiracetam psychosis in children with epilepsy. | 2001-12 |
|
| Pharmacokinetic study of levetiracetam in children. | 2001-12 |
|
| Effect of levetiracetam in patients with epilepsy and interictal epileptiform discharges. | 2001-12 |
|
| Improving effects of SSF on memory deficits and pathological changes of neural and immunological systems in senescent mice. | 2001-12 |
|
| Piracetam in post-hypoxic action myoclonus. | 2001-11 |
|
| [Levetiracetam]. | 2001-11 |
|
| Levetiracetam: a novel antiepileptic drug. | 2001-11 |
|
| Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug. | 2001 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16007238
The dosing of piracetam varies according to indication. For cognitive disorders and vertigo it is 2.4–4.8 g daily p.o., for dyslexia it is 3.2 g daily p.o., for cortical myoclonus it is 7.2–24.0 g daily p.o., for prophylaxis of vaso-occlusive crises in sickle cell anemia it is 160 mg/kg/day p.o., and for remission of vaso-occlusive crises it is 300 mg/kg/day i.v. in four divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17284293
Primary cultures of mice cortical neurons were washed twice in glucose-free Earle’s solution (143 mM NaCl, 5.4 mM KCl, 1.8 mM CaCl2, 1.0 mM MgSO4, 1.0 mM NaH2PO4, 2.4 mM HEPES, and pH 7.4) at 37 OC and placed in an incubator containing 95 % N2 and 5 % CO2 for 4 h. The neurons were then fed with high glucose DMEM (Earle’s solution), and returned to the normal incubator for a 4 h recovery. Those neurons for control underwent the same procedure except the oxygen/glucose deprivation treatment. For the drug treatment groups, piracetam (PIR, 500 or 1,000 mkM/l) or nimodipine (NIMO, 10 mkM/l) was given 12 h before OGD or during OGD and for the following 4 h. The OGD control group was treated with vehicle (PBS).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:45:54 GMT 2025
by
admin
on
Mon Mar 31 18:45:54 GMT 2025
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| Record UNII |
ZH516LNZ10
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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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WHO-VATC |
QN06BX03
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DSLD |
4054 (Number of products:5)
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WHO-ATC |
N06BX03
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FDA ORPHAN DRUG |
20987
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NCI_THESAURUS |
C1509
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7529
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C66410
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7491-74-9
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100000091987
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231-312-7
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D010889
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8351
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4843
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758191
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DTXSID5044491
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ZH516LNZ10
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2687
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DB09210
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CHEMBL36715
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2197
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PIRACETAM
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SUB09892MIG
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m8870
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
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TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM) |
This action is very weak and its clinical effects may not necessarily be mediated by this action.
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ACTIVE MOIETY |
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