Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H9NO2 |
| Molecular Weight | 103.1198 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC(O)=O
InChI
InChIKey=BTCSSZJGUNDROE-UHFFFAOYSA-N
InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
2,5-Dimethyl-N-Phenyl-3H-diazaphophol-4-imine is a quinonoid tautomer of GABAA and GABAB agonist progabide. According to quantum mechanical calculations, a quinonoid form is predominant in polar solvents, while aromatic tautomer is prevalent in apolar solvents. Progabide is a prodrug of gamma-aminobutyric acid and was investigated for the treatment of epilepsy, Parkinson's disease, schizophrenia, clinical depression, anxiety disorder, and other diseases. Progabide was marketed in France by Sanofi Aventis under tradename Gabrene for use in monotherapy and also as adjunctive therapy for generalized tonic-clonic, myoclonic, partial seizures, and for Lennox‐Gastaut syndrome, in both children and adults.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 |
200.0 nM [Ki] | ||
Target ID: CHEMBL2093872 |
40.0 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | THERAPENTIN-90 Approved UseGabapentin Capsules is indicated as adjunctive therapy in the treatment of partial seizures with and without secondary generalization in patients over 12 years of age with epilepsy. Gabapentin Capsules is also indicated as adjunctive therapy in the treatment of partial seizures in pediatric patients age 3 – 12 years. Launch Date2011 |
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| Primary | Gammalon Approved UseGamma-aminobutyric acid helps to restore the metabolism of the brain: activates energy processes, improves glucose utilization and blood supply, increases the respiratory activity of tissues. GABA has a mild psychostimulant effect, has anticonvulsant activity, stabilizes high blood pressure, improves memory, increases the productivity of thinking, helps restore speech and movements after disorders of cerebral circulation.
Given these properties of the active substance, Gammalon is prescribed for adult patients with:
Vascular diseases of the brain (damage of cerebral vessels, atherosclerosis, caused by hypertension), especially in cases when they are accompanied by sleep disorders, headache, dizziness;
Atherosclerosis of cerebral arteries with concomitant phenomena of softening of the brain;
Conditions after cerebrovascular accident, stroke, traumatic brain injury;
Chronic cerebrovascular insufficiency, dyscirculatory encephalopathy, characterized by impaired attention, memory and speech, headaches and dizziness;
Symptom complex of motion sickness (sea, air sickness);
Alcohol encephalopathy;
Alcoholic polyneuritis.
In pediatrics, Gammalon, according to the instructions, is used for:
Cerebral palsy;
Lag of mental development, accompanied by reduced mental activity;
Consequences of birth and / or craniocerebral trauma;
Symptom complex of motion sickness. |
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| Primary | Gammalon Approved UseGamma-aminobutyric acid helps to restore the metabolism of the brain: activates energy processes, improves glucose utilization and blood supply, increases the respiratory activity of tissues. GABA has a mild psychostimulant effect, has anticonvulsant activity, stabilizes high blood pressure, improves memory, increases the productivity of thinking, helps restore speech and movements after disorders of cerebral circulation.
Given these properties of the active substance, Gammalon is prescribed for adult patients with:
Vascular diseases of the brain (damage of cerebral vessels, atherosclerosis, caused by hypertension), especially in cases when they are accompanied by sleep disorders, headache, dizziness;
Atherosclerosis of cerebral arteries with concomitant phenomena of softening of the brain;
Conditions after cerebrovascular accident, stroke, traumatic brain injury;
Chronic cerebrovascular insufficiency, dyscirculatory encephalopathy, characterized by impaired attention, memory and speech, headaches and dizziness;
Symptom complex of motion sickness (sea, air sickness);
Alcohol encephalopathy;
Alcoholic polyneuritis.
In pediatrics, Gammalon, according to the instructions, is used for:
Cerebral palsy;
Lag of mental development, accompanied by reduced mental activity;
Consequences of birth and / or craniocerebral trauma;
Symptom complex of motion sickness. |
|||
| Primary | Gammalon Approved UseGamma-aminobutyric acid helps to restore the metabolism of the brain: activates energy processes, improves glucose utilization and blood supply, increases the respiratory activity of tissues. GABA has a mild psychostimulant effect, has anticonvulsant activity, stabilizes high blood pressure, improves memory, increases the productivity of thinking, helps restore speech and movements after disorders of cerebral circulation.
Given these properties of the active substance, Gammalon is prescribed for adult patients with:
Vascular diseases of the brain (damage of cerebral vessels, atherosclerosis, caused by hypertension), especially in cases when they are accompanied by sleep disorders, headache, dizziness;
Atherosclerosis of cerebral arteries with concomitant phenomena of softening of the brain;
Conditions after cerebrovascular accident, stroke, traumatic brain injury;
Chronic cerebrovascular insufficiency, dyscirculatory encephalopathy, characterized by impaired attention, memory and speech, headaches and dizziness;
Symptom complex of motion sickness (sea, air sickness);
Alcohol encephalopathy;
Alcoholic polyneuritis.
In pediatrics, Gammalon, according to the instructions, is used for:
Cerebral palsy;
Lag of mental development, accompanied by reduced mental activity;
Consequences of birth and / or craniocerebral trauma;
Symptom complex of motion sickness. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
688.53 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26617516/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
.GAMMA.-AMINOBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
767.77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26617516/ |
2 g 3 times / day steady-state, oral dose: 2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
.GAMMA.-AMINOBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
932.91 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26617516/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
.GAMMA.-AMINOBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1078.11 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26617516/ |
2 g 3 times / day steady-state, oral dose: 2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
.GAMMA.-AMINOBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26617516/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
.GAMMA.-AMINOBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26617516/ |
2 g 3 times / day steady-state, oral dose: 2 g route of administration: Oral experiment type: STEADY-STATE co-administered: |
.GAMMA.-AMINOBUTYRIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| GABAergic system in the endocrine pancreas: a new target for diabetes treatment. | 2015 |
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| Neurotransmitters as food supplements: the effects of GABA on brain and behavior. | 2015 |
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| Gamma-aminobutyric acid (GABA) stimulates pancreatic cancer growth through overexpressing GABAA receptor pi subunit. | 2007-10-15 |
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| Glutamate- and GABA-based CNS therapeutics. | 2006-02 |
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| Mechanisms of action of antiepileptic drugs. | 2005 |
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| Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures. | 1999-09 |
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| Co-administration of progabide inhibits haloperidol-induced oral dyskinesias in rats. | 1992-02-25 |
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| GABAergic modulation of lindane (gamma-hexachlorocyclohexane)-induced seizures. | 1989-08 |
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| Therapeutic response to progabide in neuroleptic- and L-dopa-induced dyskinesias. | 1987-06 |
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| GABA receptor agonists and extrapyramidal motor function: therapeutic implications for Parkinson's disease. | 1987 |
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| Anticonvulsant profile of drugs which facilitate GABAergic transmission on convulsions mediated by a GABAergic mechanism. | 1986-02 |
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| Clinical activity of GABA agonists in neuroleptic- and L-dopa-induced dyskinesia. | 1985 |
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| Pharmacology of the GABAergic system: effects of progabide, a GABA receptor agonist. | 1984 |
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| Biphasic effects of direct, but not indirect, GABA mimetics and antagonists on haloperidol-induced catalepsy. | 1980-03 |
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| Effect of the new gamma-aminobutyric acid agonist SL 76 002 on striatal acetylcholine: relation to neuroleptic-induced extrapyramidal alterations. | 1980 |
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| Biphasic effect of direct GABA mimetic drugs on haloperidol-induced catalepsy [proceedings]. | 1979-11 |
|
| [Potential therapeutic activity of GABA-mimetic drugs in neuropsychiatry]. | 1979 |
|
| gamma-Aminobutyric acid in brain: its formation from glutamic acid. | 1950-11 |
Patents
Sample Use Guides
Patients will receive the Active GABA (Gamma-Amino Butyric Acid) capsules. Each capsule 250mg. Dosage will be calculated according to body surface area of the child and divided between 2 meals/day. Larger dose taken with larger meal.
Route of Administration:
Oral
The HEK293 cells constitutively expressing exogenous GABA receptor π subunit (GABRP) revealed the growth-promoting effect of GABA treatment (serial concentrations: 0, 1, 10, 100 μmol/L);for 6 d). GABA treatment stimulated GABRP-positive pancreatic ductal adenocarcinoma (PDAC) cell proliferatio and activated the mitogen-activated protein kinase/extracellular signal–regulated kinase (MAPK/Erk) cascade. These findings imply that GABA and GABRP could play important roles in PDAC development and progression, and that this pathway can be a promising molecular target for the development of new therapeutic strategies for PDAC.
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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DSLD |
443 (Number of products:610)
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WHO-VATC |
QN03AG03
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WHO-ATC |
N03AG03
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EPA PESTICIDE CODE |
30802
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JECFA EVALUATION |
4-AMINOBUTYRIC ACID
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NCI_THESAURUS |
C687
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| Code System | Code | Type | Description | ||
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257
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PRIMARY | |||
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GAMMA-AMINOBUTYRIC ACID
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200-258-6
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100000078174
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595
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D005680
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1020023
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618771
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ALTERNATIVE | |||
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70582
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DTXSID6035106
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4617
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C80523
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2ACZ6IPC6I
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27418
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618257
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16865
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2ACZ6IPC6I
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1749
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m1695
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PRIMARY | Merck Index | ||
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1262
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SUB127282
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CHEMBL96
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DB02530
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119
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56-12-2
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SUB13946MIG
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
