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Identification
Name Butethal
Accession Number DB01353
Type small molecule
Groups illicit, approved
Description

Butethal is a sedative and a hypnotic drug.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Butyl-5-ethylbarbituric acid
5-Ethyl-5-butylbarbituric acid
5-Ethyl-5-N-butylbarbituric acid
Butabarbitol
Butobarbital
Butobarbitalum
Butobarbitone
Butobarbitural
Butyl,5-ethylbarbituric acid
Salts Not Available
Brand names
Name Company
Budorm
Etoval
Hyperbutal
Longanoct
Meonal
Monodorm
Neonal
Sonerile
Soneryl
Brand mixtures Not Available
Categories
  • Anti-anxiety Agents
  • Hypnotics and Sedatives
  • Barbiturates
CAS number 77-28-1
Weight Average: 212.2456
Monoisotopic: 212.116092388
Chemical Formula C10H16N2O3
InChI Key InChIKey=STDBAQMTJLUMFW-UHFFFAOYSA-N
InChI
InChI=1S/C10H16N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3-6H2,1-2H3,(H2,11,12,13,14,15)
Plain Text
IUPAC Name
5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione
SMILES
CCCCC1(CC)C(=O)NC(=O)NC1=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Barbiturates
Substructures
  • Barbiturates
  • Carbonyl Compounds
  • Carboxylic Acids and Derivatives
  • Amino Ketones
  • Ureas and Derivatives
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Carboxamides and Derivatives
Pharmacology
Indication For the treatment of insomnia.
Pharmacodynamics Butethal (also known as butobarbitone and butobarbital) belongs to a group of medicines called the barbiturates. It is thought to act on receptors in the brain (GABA receptors) causing the release of the chemical GABA. This chemical inhibits certain areas of the brain resulting in sleepiness.
Mechanism of action Butethal 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. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Absorption Rapidly absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hepatic.
Route of elimination Not Available
Half life 37 hours
Clearance Not Available
Toxicity Signs of 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).
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 128.5 °C PhysProp
water solubility 4880 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 1.73 HANSCH,C ET AL. (1995)
logS -1.64 ADME Research, USCD
pKa 7.86 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 1.27e+00 g/l ALOGPS
logP 1.65 ALOGPS
logP 1.61 ChemAxon
logS -2.2 ALOGPS
pKa (strongest acidic) 8.48 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 75.27 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 53.45 ChemAxon
polarizability 21.62 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02618 Link_out
PubChem Compound 6473 Link_out
PubChem Substance 46508397 Link_out
ChemSpider 6229 Link_out
Therapeutic Targets Database DAP000687 Link_out
PharmGKB PA164748035 Link_out
Wikipedia http://en.wikipedia.org/wiki/Butobarbital Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Aminophylline The barbiturate, butethal, decreases the effect of aminophylline.
Betamethasone The barbiturate, butethal, may decrease the effect of the corticosteroid, betamethasone.
Clomifene The enzyme inducer, butethal, decreases the effect of the hormone agent, clomifene.
Conjugated Estrogens The enzyme inducer, butethal, decreases the effect of the hormone agent, conjugated estrogens.
Cyclosporine The barbiturate, butethal, increases the effect of cyclosporine.
Dexamethasone The barbiturate, butethal, may decrease the effect of the corticosteroid, dexamethasone.
Diethylstilbestrol The enzyme inducer, butethal, decreases the effect of the hormone agent, diethylstilbestrol.
Doxycycline The anticonvulsant, butethal, decreases the effect of doxycycline.
Estradiol The enzyme inducer, butethal, decreases the effect of the hormone agent, estradiol.
Ethinyl Estradiol This product may cause a slight decrease of contraceptive effect
Felodipine The barbiturate, butethal, decreases the effect of felodipine.
Fludrocortisone The barbiturate, butethal, may decrease the effect of the corticosteroid, fludrocortisone.
Folic Acid Folic acid decreases the effect of anticonvulsant, butethal.
Gefitinib The CYP3A4 inducer, butethal, may decrease the serum concentration and therapeutic effects of gefitinib.
Griseofulvin The barbiturate, butethal, decreases the effect of griseofulvin.
Hydrocortisone The barbiturate, butethal, may decrease the effect of the corticosteroid, hydrocortisone.
Levonorgestrel Phenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone The enzyme inducer, butethal, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol The enzyme inducer, butethal, decreases the effect of the hormone agent, megestrol.
Methadone The barbiturate, butethal, decreases the effect of methadone.
Metronidazole The barbiturate, butethal, decreases the effect of metronidazole.
Nifedipine The barbiturate, butethal, decreases the effect of the calcium channel blocker, nifedipine.
Norethindrone This product may cause a slight decrease of contraceptive effect
Oxtriphylline The barbiturate, butethal, decreases the effect of oxtriphylline.
Prednisolone The barbiturate, butethal, may decrease the effect of the corticosteroid, prednisolone.
Prednisone The barbiturate, butethal, may decrease the effect of the corticosteroid, prednisone.
Quinidine The anticonvulsant, butethal, decreases the effect of quinidine.
Theophylline The barbiturate, butethal, decreases the effect of theophylline.
Triamcinolone The barbiturate, butethal, may decrease the effect of the corticosteroid, triamcinolone.
Food Interactions Not Available
Targets

1. Gamma-aminobutyric-acid receptor subunit alpha-1

Pharmacological action: yes
Actions: potentiator

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

Organism class: human
UniProt ID: P14867 Link_out
Gene: GABRA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. Pubmed
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
  3. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  4. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed
  5. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  6. 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
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Gamma-aminobutyric-acid receptor subunit alpha-2

Pharmacological action: yes
Actions: potentiator

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

Organism class: human
UniProt ID: P47869 Link_out
Gene: GABRA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed

3. Gamma-aminobutyric-acid receptor subunit alpha-3

Pharmacological action: yes
Actions: potentiator

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

Organism class: human
UniProt ID: P34903 Link_out
Gene: GABRA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed

4. Gamma-aminobutyric-acid receptor subunit alpha-4

Pharmacological action: yes
Actions: potentiator

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

Organism class: human
UniProt ID: P48169 Link_out
Gene: GABRA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed

5. Gamma-aminobutyric-acid receptor subunit alpha-5

Pharmacological action: yes
Actions: potentiator

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

Organism class: human
UniProt ID: P31644 Link_out
Gene: GABRA5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed

6. Gamma-aminobutyric-acid receptor subunit alpha-6

Pharmacological action: yes
Actions: potentiator

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

Organism class: human
UniProt ID: Q16445 Link_out
Gene: GABRA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. Pubmed
  2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed

7. Neuronal acetylcholine receptor subunit alpha-4

Pharmacological action: unknown
Actions: antagonist

After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane

Organism class: human
UniProt ID: P43681 Link_out
Gene: CHRNA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. Pubmed
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

8. Neuronal acetylcholine receptor subunit alpha-7

Pharmacological action: unknown
Actions: antagonist

After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane

Organism class: human
UniProt ID: P36544 Link_out
Gene: CHRNA7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. Pubmed
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

9. Glutamate receptor 2

Pharmacological action: unknown
Actions: antagonist

Receptor for glutamate. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists. This receptor binds AMPA(quisqualate) > glutamate > kainate

Organism class: human
UniProt ID: P42262 Link_out
Gene: GRIA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed

10. Glutamate receptor, ionotropic kainate 2

Pharmacological action: unknown
Actions: antagonist

L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. The postsynaptic actions of Glu are mediated by a variety of receptors that are named according to their selective agonists. May be involved in the transmission of light information from the retina to the hypothalamus. This receptor binds domoate > kainate > quisqualate > 6-cyano-7-nitroquinoxaline-2,3-dione > L-glutamate = 6,7- dinitroquinoxaline-2,3-dione > dihydrokainate

Organism class: human
UniProt ID: Q13002 Link_out
Gene: GRIK2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. Pubmed
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed
Comments
Drug created on July 06, 2007 13:49 / Updated on February 08, 2013 16:20