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Identification
NameHeptabarbital
Accession NumberDB01354
Typesmall molecule
Groupsapproved
Description

Heptabarbital is an intermediate or short term barbiturate used mainly for sedation and hypnosis.

Structure
Thumb
Synonyms
SynonymLanguageCode
HeptabarbNot AvailableNot Available
HeptabarbitoneNot AvailableNot Available
HeptabarbumNot AvailableNot Available
HeptadormNot AvailableNot Available
HeptamalNot AvailableNot Available
HeptamalumNot AvailableNot Available
HeptbarbitalNot AvailableNot Available
MedapanNot AvailableNot Available
MedomineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
MedominGeigy
MedomineCiba
Brand mixturesNot Available
Categories
CAS number509-86-4
WeightAverage: 250.2936
Monoisotopic: 250.131742452
Chemical FormulaC13H18N2O3
InChI KeyPAZQYDJGLKSCSI-UHFFFAOYSA-N
InChI
InChI=1S/C13H18N2O3/c1-2-13(9-7-5-3-4-6-8-9)10(16)14-12(18)15-11(13)17/h7H,2-6,8H2,1H3,(H2,14,15,16,17,18)
IUPAC Name
5-(cyclohept-1-en-1-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
SMILES
CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1
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
IndicationUsed mainly for sedation and hypnosis.
PharmacodynamicsNot Available
Mechanism of actionHeptabarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Heptabarbital also appears to bind neuronal nicotinic acetylcholine receptors.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
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 + 0.9655
Blood Brain Barrier + 0.9387
Caco-2 permeable - 0.5831
P-glycoprotein substrate Substrate 0.6344
P-glycoprotein inhibitor I Non-inhibitor 0.5941
P-glycoprotein inhibitor II Non-inhibitor 0.9689
Renal organic cation transporter Non-inhibitor 0.8902
CYP450 2C9 substrate Non-substrate 0.7692
CYP450 2D6 substrate Non-substrate 0.8793
CYP450 3A4 substrate Non-substrate 0.6914
CYP450 1A2 substrate Non-inhibitor 0.7892
CYP450 2C9 substrate Non-inhibitor 0.7694
CYP450 2D6 substrate Non-inhibitor 0.9057
CYP450 2C19 substrate Non-inhibitor 0.7389
CYP450 3A4 substrate Non-inhibitor 0.9666
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8083
Ames test AMES toxic 0.5298
Carcinogenicity Non-carcinogens 0.8893
Biodegradation Not ready biodegradable 0.9686
Rat acute toxicity 1.7309 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9588
hERG inhibition (predictor II) Non-inhibitor 0.8583
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point174U.S. Patent 2,501,551.
water solubility250 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.03HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility3.24e-01 g/lALOGPS
logP2.41ALOGPS
logP1.91ChemAxon
logS-2.9ALOGPS
pKa (strongest acidic)8.14ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area75.27ChemAxon
rotatable bond count2ChemAxon
refractivity66.25ChemAxon
polarizability25.86ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,501,551.

General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC17725
PubChem Compound10518
PubChem Substance46508321
ChemSpider10081
ChEBI588074
ChEMBLCHEMBL468837
Therapeutic Targets DatabaseDAP001032
PharmGKBPA164783812
WikipediaHeptabarbital
ATC CodesN05CA11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AminophyllineThe barbiturate, heptabarbital, decreases the effect of aminophylline.
BetamethasoneThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, betamethasone.
ClomifeneThe enzyme inducer, heptabarbital, decreases the effect of the hormone agent, clomifene.
Conjugated EstrogensThe enzyme inducer, heptabarbital, decreases the effect of the hormone agent, conjugated estrogens.
CyclosporineThe barbiturate, heptabarbital, increases the effect of cyclosporine.
DexamethasoneThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, dexamethasone.
DiethylstilbestrolThe enzyme inducer, heptabarbital, decreases the effect of the hormone agent, diethylstilbestrol.
DoxycyclineThe anticonvulsant, heptabarbital, decreases the effect of doxycycline.
EstradiolThe enzyme inducer, heptabarbital, decreases the effect of the hormone agent, estradiol.
Ethinyl EstradiolThis product may cause a slight decrease of contraceptive effect
FelodipineThe barbiturate, heptabarbital, decreases the effect of felodipine.
FludrocortisoneThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, fludrocortisone.
Folic AcidFolic acid decreases the effect of anticonvulsant, heptabarbital.
GefitinibThe CYP3A4 inducer, heptabarbital, may decrease the serum concentration and therapeutic effects of gefitinib.
GriseofulvinThe barbiturate, heptabarbital, decreases the effect of griseofulvin.
HydrocortisoneThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, hydrocortisone.
LevonorgestrelPhenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone AcetateThe enzyme inducer, heptabarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol acetateThe enzyme inducer, heptabarbital, decreases the effect of the hormone agent, megestrol.
MethadoneThe barbiturate, heptabarbital, decreases the effect of methadone.
MetronidazoleThe barbiturate, heptabarbital, decreases the effect of metronidazole.
NifedipineThe barbiturate, heptabarbital, decreases the effect of the calcium channel blocker, nifedipine.
NorethindroneThis product may cause a slight decrease of contraceptive effect
OxtriphyllineThe barbiturate, heptabarbital, decreases the effect of oxtriphylline.
PrednisoloneThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, prednisolone.
PrednisoneThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, prednisone.
QuinidineThe anticonvulsant, heptabarbital, decreases the effect of quinidine.
TheophyllineThe barbiturate, heptabarbital, decreases the effect of theophylline.
TriamcinoloneThe barbiturate, heptabarbital, 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. Brunton LL, Lazo JS, Parker KL, Goodman LS and Gilman AG (2005). Goodman & Gilman’s Pharmacological Basis of Therapeutics. McGraw-Hill. ISBN 0071422803.
  2. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. Pubmed
  3. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. 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. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. 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

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Drug created on July 06, 2007 13:49 / Updated on April 28, 2014 16:20