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Identification
NameTalbutal
Accession NumberDB00306  (APRD01333)
TypeSmall Molecule
GroupsApproved, Illicit
Description

Talbutal, also called 5-allyl-5-sec-butylbarbituric acid, is a barbiturate with a short to intermediate duration of action. Talbutal is a schedule III drug in the U.S.

Structure
Thumb
Synonyms
SynonymLanguageCode
(RS)-5-allyl-5-sec-butylpyrimidine-2,4,6(1H,3H,5H)-trioneNot AvailableIUPAC
5-allyl-5-sec-butylbarbituric acidNot AvailableNot Available
LotusateNot AvailableNot Available
sec-Butyl allyl barbituric acidNot AvailableNot Available
TalbutaleNot AvailableDCIT
TalbutalumLatinINN
SaltsNot Available
Brand names
NameCompany
LotusateSanofi Aventis
Brand mixturesNot Available
CategoriesNot Available
CAS number115-44-6
WeightAverage: 224.2563
Monoisotopic: 224.116092388
Chemical FormulaC11H16N2O3
InChI KeyBJVVMKUXKQHWJK-UHFFFAOYSA-N
InChI
InChI=1S/C11H16N2O3/c1-4-6-11(7(3)5-2)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)
IUPAC Name
5-(butan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
SMILES
CCC(C)C1(CC=C)C(=O)NC(=O)NC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassDiazines
SubclassPyrimidines and Pyrimidine Derivatives
Direct parentBarbituric Acid Derivatives
Alternative parentsUreides; Diazinanes; N-unsubstituted Carboxylic Acid Imides; Secondary Carboxylic Acid Amides; Polyamines; Carboxylic Acids
Substituentsureide; 1,3-diazinane; carboxylic acid imide, n-unsubstituted; carboxamide group; secondary carboxylic acid amide; carboxylic acid derivative; polyamine; carboxylic acid; organonitrogen compound
Classification descriptionThis compound belongs to the barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
Pharmacology
IndicationFor use as a sedative and hypnotic.
PharmacodynamicsTalbutal is a short to intermediate-acting barbiturate. Barbiturates act as nonselective depressants of the central nervous system (CNS), capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. In sufficiently high therapeutic doses, barbiturates induce anesthesia.
Mechanism of actionTalbutal 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of acute barbiturate poisoning include drowsiness, confusion, coma, respiratory depression, hypotension, and shock.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9272
Blood Brain Barrier + 0.984
Caco-2 permeable - 0.5931
P-glycoprotein substrate Substrate 0.6383
P-glycoprotein inhibitor I Non-inhibitor 0.5341
P-glycoprotein inhibitor II Non-inhibitor 0.9761
Renal organic cation transporter Non-inhibitor 0.9352
CYP450 2C9 substrate Non-substrate 0.7904
CYP450 2D6 substrate Non-substrate 0.9009
CYP450 3A4 substrate Non-substrate 0.7245
CYP450 1A2 substrate Non-inhibitor 0.8455
CYP450 2C9 substrate Non-inhibitor 0.8308
CYP450 2D6 substrate Non-inhibitor 0.9229
CYP450 2C19 substrate Non-inhibitor 0.7692
CYP450 3A4 substrate Non-inhibitor 0.8764
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9375
Ames test Non AMES toxic 0.6105
Carcinogenicity Non-carcinogens 0.8617
Biodegradation Not ready biodegradable 0.9918
Rat acute toxicity 3.5595 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9879
hERG inhibition (predictor II) Non-inhibitor 0.9537
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point109 °CPhysProp
water solubility1810 mg/L at 25 °CMEYLAN,WM et al. (1996)
logP1.47HANSCH,C ET AL. (1995)
pKa7.79 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility2.46ALOGPS
logP1.87ALOGPS
logP1.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.05 m3·mol-1ChemAxon
Polarizability22.48 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD06887
Therapeutic Targets DatabaseDAP000670
PharmGKBPA164779051
WikipediaTalbutal
ATC CodesN05CA07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AminophyllineThe barbiturate, talbutal, decreases the effect of aminophylline.
BetamethasoneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, betamethasone.
ClomifeneThe enzyme inducer, talbutal, decreases the effect of the hormone agent, clomifene.
Conjugated EstrogensThe enzyme inducer, talbutal, decreases the effect of the hormone agent, conjugated estrogens.
CyclosporineThe sulfonamide decreases the effect of cyclosporine
DexamethasoneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, dexamethasone.
DiethylstilbestrolThe enzyme inducer, talbutal, decreases the effect of the hormone agent, diethylstilbestrol.
DoxycyclineThe anticonvulsant, talbutal, decreases the effect of doxycycline.
EstradiolThe enzyme inducer, talbutal, decreases the effect of the hormone agent, estradiol.
Ethinyl EstradiolThis product may cause a slight decrease of contraceptive effect
FelodipineThe barbiturate, talbutal, decreases the effect of felodipine.
FludrocortisoneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, fludrocortisone.
Folic AcidFolic acid decreases the effect of anticonvulsant, talbutal.
GefitinibThe CYP3A4 inducer, talbutal, may decrease the serum concentration and therapeutic effects of gefitinib.
GriseofulvinThe barbiturate, talbutal, decreases the effect of griseofulvin.
HydrocortisoneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, hydrocortisone.
LevonorgestrelPhenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone AcetateThe enzyme inducer, talbutal, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol acetateThe enzyme inducer, talbutal, decreases the effect of the hormone agent, megestrol.
MethadoneThe barbiturate, talbutal, decreases the effect of methadone.
MetronidazoleThe barbiturate, talbutal, decreases the effect of metronidazole.
NifedipineThe barbiturate, talbutal, decreases the effect of the calcium channel blocker, nifedipine.
NorethindroneThis product may cause a slight decrease of contraceptive effect
OxtriphyllineThe barbiturate, talbutal, decreases the effect of oxtriphylline.
PrednisoloneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, prednisolone.
PrednisoneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, prednisone.
QuinidineThe anticonvulsant, talbutal, decreases the effect of quinidine.
TheophyllineThe barbiturate, talbutal, decreases the effect of theophylline.
TriamcinoloneThe barbiturate, talbutal, may decrease the effect of the corticosteroid, triamcinolone.
Food InteractionsNot Available

Targets

1. Gamma-aminobutyric acid receptor subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details

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. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. Pubmed
  4. 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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  6. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  7. 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

2. Gamma-aminobutyric acid receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-4 P48169 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: potentiator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-6 Q16445 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-4 P43681 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-7 P36544 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor 2 P42262 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, kainate 2 Q13002 Details

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

11. GABA-A receptor (anion channel)

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: positive allosteric modulator

Components

Name UniProt ID Details
Gamma-aminobutyric acid receptor subunit alpha-1 P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2 P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3 P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4 P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5 P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6 Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1 P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2 P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3 P28472 Details
Gamma-aminobutyric acid receptor subunit delta O14764 Details
Gamma-aminobutyric acid receptor subunit epsilon P78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2 P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928 Details
Gamma-aminobutyric acid receptor subunit pi O00591 Details
Gamma-aminobutyric acid receptor subunit theta Q9UN88 Details

References:

  1. ChEMBL Compound Report Card (Accessed December 2013)

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09