| Version |
1.0 |
| Creation Date |
2009-07-21 20:26:51 |
| Update Date |
2010-03-18 21:58:11 |
| Accession Number |
T3D2784 |
| Name |
Secobarbital |
| Compound Type |
- Adjuvant
- Adjuvant, Anesthesia
- Barbiturate
- Drug
- GABA Modulator
- Hypnotic and Sedative
|
| Description |
Secobarbital (marketed by Eli Lilly and Company under the brand names Seconal and Tuinal) is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.[PubChem] (V940) |
| Synonyms |
- (+/-)-Secobarbital
- Secobarbital Sodium
- Secobarbitale [DCIT]
- Secobarbitalum [INN-Latin]
- Sodium quinalbarbitone
- Sodium Secobarbital
|
| Chemical IUPAC Name |
5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione |
| Chemical Formula |
C12H18N2O3 |
| Chemical Structure |
 |
| CAS Registry Number |
76-73-3 |
| InChI Identifier |
InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17) |
| InChI Key |
InChIKey=KQPKPCNLIDLUMF-UHFFFAOYSA-N |
| PubChem Compound ID |
31143  |
| KEGG ID |
Not Available |
| UniProt ID |
Not Available |
| OMIM ID |
Not Available |
| ChEBI ID |
9073 |
| BioCyc ID |
Not Available |
| SuperToxic ID |
Not Available |
| CTD ID |
Not Available |
| Stitch ID |
Secobarbital |
| DrugBank ID |
DB00418 |
| PDB ID |
Not Available |
| ACToR ID |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Secobarbital |
| Monoisotopic Mass |
238.131742 |
| MOL File |
Show |
| PDB File |
Show |
| SDF File |
Show |
| SMILES |
CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O |
| Appearance |
Not Available |
| Melting Point |
100 oC |
| Solubility |
550 mg/L |
| Predicted LogP |
2.0338 |
| Route of Exposure |
Oral (T742); Parenteral (T742); Rectal (T742). |
| Mechanism of Action |
Secobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. |
| Metabolism |
Not Available |
| Toxicity Values |
Not Available |
| Lethal Dose |
Not Available |
| Carcinogenicity (IARC Classification) |
Not Available |
| Uses/Sources |
Not Available |
| Minimum Risk Level |
Not Available |
| Health Effects |
Secobarbital causes slurred speech, disorientation and "drunken" behavior. It is physically and psychologically addictive. |
| Symptoms |
Symptoms of Secorbital overdose include confusion (severe); decrease in or loss of reflexes; drowsiness (severe); fever; irritability (continuing); low body temperature; poor judgment; shortness of breath or slow or troubled breathing; slow heartbeat; slurred speech; staggering; trouble in sleeping; unusual movements of the eyes; weakness (severe). (T742) |
| Treatment |
Not Available |
| General References |
- V940 - Wikipedia. Secobarbital. Last Updated 3 October 2009.
- T742 - Drugs.com
|
| Targets |
- Gamma-aminobutyric acid receptor subunit alpha-1
|
|
Target 1
[top]
|
| Target 1 ID |
36 |
| Target 1 Name |
Gamma-aminobutyric acid receptor subunit alpha-1 |
| Target 1 Mechanism of Action |
Secobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. |
| Target 1 Description |
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel |
| Target 1 Synonyms |
- GABA(A) receptor subunit alpha-1
|
| Target 1 Gene Name |
GABRA1 |
| Target 1 Protein Sequence |
>Gamma-aminobutyric acid receptor subunit alpha-1
MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLLDGYDNRLRPG
LGERVTEVKTDIFVTSFGPVSDHDMEYTIDVFFRQSWKDERLKFKGPMTVLRLNNLMASK
IWTPDTFFHNGKKSVAHNMTMPNKLLRITEDGTLLYTMRLTVRAECPMHLEDFPMDAHAC
PLKFGSYAYTRAEVVYEWTREPARSVVVAEDGSRLNQYDLLGQTVDSGIVQSSTGEYVVM
TTHFHLKRKIGYFVIQTYLPCIMTVILSQVSFWLNRESVPARTVFGVTTVLTMTTLSISA
RNSLPKVAYATAMDWFIAVCYAFVFSALIEFATVNYFTKRGYAWDGKSVVPEKPKKVKDP
LIKKNNTYAPTATSYTPNLARGDPGLATIAKSATIEPKEVKPETKPPEPKKTFNSVSKID
RLSRIAFPLLFGIFNLVYWATYLNREPQLKAPTPHQ
|
| Target 1 Number of Residues |
456 |
| Target 1 Molecular Weight |
51801.4 |
| Target 1 Theoretical pI |
9.61 |
| Target 1 GO Classification |
|
Function
|
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity |
|
Process
|
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
gamma-aminobutyric acid signaling pathway
anion transport
inorganic anion transport
chloride transport
physiological process
cellular physiological process
transport
ion transport |
|
Component
|
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane |
|
| Target 1 General Function |
Involved in chloride channel activity |
| Target 1 Pathways |
Not Available |
| Target 1 Reactions |
Not Available |
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 252-273
- 279-300
- 313-334
- 422-443
|
| Target 1 Essentiality |
Non Essential |
| Target 1 Domain Function |
PF02931:Neur_chan_LBD
PF02932:Neur_chan_memb |
| Target 1 GenBank ID Protein |
Not Available |
| Target 1 UniProtKB ID |
P14867 |
| Target 1 Cellular Location |
Cell junction, synapse, postsynaptic cell membrane |
| Target 1 Gene Sequence |
Not Available |
| Target 1 GenBank Gene ID |
Not Available |
| Target 1 GeneCard ID |
GABRA1 |
| Target 1 GenAtlas ID |
GABRA1 |
| Target 1 HGNC ID |
HGNC:4075 |
| Target 1 Chromosome Location |
Not Available |
| Target 1 Locus |
5q34-q35 |
| Target 1 SNPs |
SNPJam Report |
| Target 1 Toxin References |
- S912 - Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed ]
- S911 - Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed ]
|
| Target 1 General References |
2465923; 15489334; 2847710; 11992121; 16718694 |
