Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H12N2O3.C4H11N |
| Molecular Weight | 305.3721 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCNCC.CCC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2
InChI
InChIKey=HRIVMPCILUGJNH-UHFFFAOYSA-N
InChI=1S/C12H12N2O3.C4H11N/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16;1-3-5-4-2/h3-7H,2H2,1H3,(H2,13,14,15,16,17);5H,3-4H2,1-2H3
| Molecular Formula | C12H12N2O3 |
| Molecular Weight | 232.2353 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C4H11N |
| Molecular Weight | 73.1368 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01174
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01174
Phenobarbital is a barbiturate derivative used to treat insomnia and anxiety, seizures, hyperbilirubinemia in neonates and cholestasis. Phenobarbital promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | LUMINAL Approved UseShort-term treatment of insomnia. However, generally not used orally as a hypnotic because several hours are required to achieve maximal effectsa and barbiturates have decreased effectiveness for sleep induction and maintenance after 2 weeks. |
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| Primary | LUMINAL Approved UseRelief of anxiety, tension, and apprehension. However, barbiturates used infrequently for routine sedation, since there are few clinical situations in which oral barbiturates provide a safety or efficacy advantage over nonbarbiturate sedatives/hypnotics. |
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| Primary | LUMINAL Approved UseManagement of tonic-clonic seizures and partial seizures; used alone (particularly in infants and young children) or, more commonly, in combination with phenytoin or other anticonvulsants. |
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| Preventing | LUMINAL Approved UsePrevention of febrile seizures in infants and young children. |
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| Primary | LUMINAL Approved UseSecond-line agent in the termination of status epilepticus; may be useful to prevent seizure recurrence after seizures are initially terminated with other anticonvulsants (e.g., diazepam, phenytoin) or for termination of status epilepticus that does not respond to initial therapy with other anticonvulsants. Usefulness of parenteral phenobarbital in terminating acute seizure episodes is limited by its slow onset of action |
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| Preventing | LUMINAL Approved UseProphylactic management of epilepsy. |
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| Primary | LUMINAL Approved UsePrevention and treatment of hyperbilirubinemia in neonates |
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| Primary | LUMINAL Approved UseHas been used to reduce bilirubin concentrations in patients with congenital nonhemolytic unconjugated hyperbilirubinemia or chronic intrahepatic cholestasis. Has been used in the management of hyperlipemia associated with intrahepatic and extrahepatic cholestasis |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Enhancement of GABAergic inhibition: a mechanism of action of benzodiazepines, phenobarbital, valproate and L-cycloserine in the cat spinal cord. | 1982 |
|
| General anaesthetic actions on ligand-gated ion channels. | 1999 Aug 15 |
|
| On the mechanism of alleviation by phenobarbital of the malfunction of an epilepsy-linked GABA(A) receptor. | 2006 Sep 26 |
Patents
Sample Use Guides
Phenobarbital is administered orally or by IM or slow IV injection. For treatment of anxiety, phenobarbital is administered orally 6 mg/kg daily or 180 mg/m2 daily, in 3 equally divided doses. For treatment of seizure disorders, the drug is administered orally 15–50 mg 2 or 3 times daily. Alternatively, 3–5 mg/kg or 125 mg/m2 daily; IV or IM 4–6 mg/kg daily for 7–10 days to reach therapeutic blood concentrations; alternatively, 10–15 mg/kg daily.
Route of Administration:
Other
Potentiation of the GABAA by phenobarbital was evaluated in HEK293 cells expressing recombinant rat GABAA receptors. Currents were recorded using the cell-flow technique and corrected for receptor desensitization. Co-application of phenobarbital with 300uM GABA lead to 20-30 amplification of chloride currents with EC50 of 100-200 uM
| Substance Class |
Chemical
Created
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Edited
Sat Dec 16 08:29:54 GMT 2023
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| Record UNII |
RB423CG92E
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| Record Status |
Validated (UNII)
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