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Identification
NameSecobarbital
Accession NumberDB00418  (APRD00497)
Typesmall molecule
Groupsapproved
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
(±)-secobarbitalNot AvailableNot Available
5-allyl-5-(1-methylbutyl)barbituric acidNot AvailableNot Available
QuinalbarbitoneNot AvailableNot Available
SecobarbitalumLatinINN
SecobarbitoneNot AvailableNot Available
Salts
Name/CAS Structure Properties
Secobarbital Sodium
Thumb
  • InChI Key: AXXJTNXVUHVOJW-UHFFFAOYNA-M
  • Monoisotopic Mass: 260.113687095
  • Average Mass: 260.2647
DBSALT000255
Brand names
NameCompany
SeconalNot Available
Brand mixturesNot Available
Categories
CAS number76-73-3
WeightAverage: 238.2829
Monoisotopic: 238.131742452
Chemical FormulaC12H18N2O3
InChI KeyInChIKey=KQPKPCNLIDLUMF-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
SMILES
CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O
Mass Specshow(9.04 KB)
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 the Short-term treatment of intractable insomnia for patients habituated to barbiturates
PharmacodynamicsSecobarbital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
Mechanism of actionSecobarbital 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 eliminationBarbiturates are metabolized primarily by the hepatic microsomal enzyme system, and the metabolic products are excreted in the urine and, less commonly, in the feces.
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 + 0.9331
Blood Brain Barrier + 0.9762
Caco-2 permeable - 0.5792
P-glycoprotein substrate Substrate 0.6367
P-glycoprotein inhibitor I Non-inhibitor 0.5256
P-glycoprotein inhibitor II Non-inhibitor 0.9756
Renal organic cation transporter Non-inhibitor 0.911
CYP450 2C9 substrate Non-substrate 0.7863
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.736
CYP450 1A2 substrate Non-inhibitor 0.8707
CYP450 2C9 substrate Non-inhibitor 0.7679
CYP450 2D6 substrate Non-inhibitor 0.9276
CYP450 2C19 substrate Non-inhibitor 0.7353
CYP450 3A4 substrate Non-inhibitor 0.8902
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9176
Ames test Non AMES toxic 0.6131
Carcinogenicity Non-carcinogens 0.8977
Biodegradation Not ready biodegradable 0.9868
Rat acute toxicity 3.0894 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9603
hERG inhibition (predictor II) Non-inhibitor 0.9471
Pharmacoeconomics
Manufacturers
  • Anabolic inc
  • Barr laboratories inc
  • Everylife
  • Halsey drug co inc
  • Ivax pharmaceuticals inc
  • Kv pharmaceutical co
  • Lannett co inc
  • Parke davis div warner lambert co
  • L perrigo co
  • Purepac pharmaceutical co
  • Valeant pharmaceuticals international
  • Vitarine pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Whiteworth towne paulsen inc
  • Wyeth ayerst laboratories
  • Ranbaxy pharmaceuticals inc
  • Elkins sinn div ah robins co inc
  • Eli lilly and co
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Seconal 100 mg capsule5.23USDcapsule
Seconal sodium 100 mg capsule4.91USDcapsule
Seconal sodium 100 mg pulvul0.93USDeach
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point100 °CPhysProp
water solubility550 mg/LNot Available
logP1.97HANSCH,C ET AL. (1995)
pKa7.8WOLLWEBER,H (1989)
Predicted Properties
PropertyValueSource
water solubility1.21e+00 g/lALOGPS
logP2.2ALOGPS
logP2.03ChemAxon
logS-2.3ALOGPS
pKa (strongest acidic)8.48ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area75.27ChemAxon
rotatable bond count5ChemAxon
refractivity62.65ChemAxon
polarizability24.33ChemAxon
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 DrugD00430
ChEBI9073
ChEMBLCHEMBL447
Therapeutic Targets DatabaseDAP000674
PharmGKBPA164784035
Drug Product Database21032
Drugs.comhttp://www.drugs.com/cdi/secobarbital.html
WikipediaSecobarbital
ATC CodesN05CA06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(48.6 KB)
Interactions
Drug Interactions
Drug
AminophyllineThe barbiturate, secobarbital, decreases the effect of aminophylline.
BendamustineCYP1A2 metabolism may result in increased levels of active metabolites, decreases levels of bendamustine.
BetamethasoneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, betamethasone.
ClomifeneThe enzyme inducer, secobarbital, decreases the effect of the hormone agent, clomifene.
Conjugated EstrogensThe enzyme inducer, secobarbital, decreases the effect of the hormone agent, conjugated estrogens.
CyclosporineThe barbiturate, secobarbital, increases the effect of cyclosporine.
DexamethasoneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, dexamethasone.
DiethylstilbestrolThe enzyme inducer, secobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
DoxycyclineThe anticonvulsant , secobarbital, decreases the effect of doxycycline.
EstradiolThe enzyme inducer, secobarbital, decreases the effect of the hormone agent, estradiol.
Ethinyl EstradiolThis product may cause a slight decrease of contraceptive effect
FelodipineThe barbiturate, secobarbital, decreases the effect of felodipine.
FludrocortisoneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, fludrocortisone.
Folic AcidFolic acid decreases the effect of anticonvulsant, secobarbital.
GefitinibThe CYP3A4 inducer, secobarbital, may decrease the serum concentration and therapeutic effects of gefitinib.
GriseofulvinThe barbiturate, secobarbital, decreases the effect of griseofulvin.
HydrocortisoneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, hydrocortisone.
LevonorgestrelPhenobarbital decreases the effect of levonorgestrel
Medroxyprogesterone AcetateThe enzyme inducer, secobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Megestrol acetateThe enzyme inducer, secobarbital, decreases the effect of the hormone agent, megestrol.
MethadoneThe barbiturate, secobarbital, decreases the effect of methadone.
MetronidazoleThe barbiturate, secobarbital, decreases the effect of metronidazole.
NifedipineThe barbiturate, secobarbital, decreases the effect of the calcium channel blocker, nifedipine.
NorethindroneThis product may cause a slight decrease of contraceptive effect
OxtriphyllineThe barbiturate, secobarbital, decreases the effect of oxtriphylline.
PrednisoloneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, prednisolone.
PrednisoneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, prednisone.
QuinidineThe anticonvulsant, secobarbital, decreases the effect of quinidine.
TheophyllineThe barbiturate, secobarbital, decreases the effect of theophylline.
TretinoinThe strong CYP2C8 inducer, Secobarbital, may increase the metabolism and clearance of oral Tretinoin. Consider alternate therapy to avoid failure of Tretinoin therapy or monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Secobarbital is initiated, discontinued or dose changed.
TriamcinoloneThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, triamcinolone.
TrimipramineThe barbiturate, Secobarbital, may increase the metabolism and clearance of Trimipramine. Monitor for changes in the therapeutics and adverse effects of Trimipramine if Secobarbital is initiated, discontinued or dose changed. Dose adjustments of Trimipramine may be required.
TriprolidineThe CNS depressants, Triprolidine and Secobarbital, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VerapamilSecobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Secobarbital is initiated, discontinued or dose changed.
WarfarinSecobarbital may decrease the serum concentration of warfarin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of warfarin if secobarbital is initiated, discontinued or dose changed.
Food InteractionsNot Available

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. 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. Peters JA, Kirkness EF, Callachan H, Lambert JJ, Turner AJ: Modulation of the GABAA receptor by depressant barbiturates and pregnane steroids. Br J Pharmacol. 1988 Aug;94(4):1257-69. Pubmed
  6. Miller LG, Deutsch SI, Greenblatt DJ, Paul SM, Shader RI: Acute barbiturate administration increases benzodiazepine receptor binding in vivo. Psychopharmacology (Berl). 1988;96(3):385-90. Pubmed
  7. Kirkness EF, Turner AJ: The gamma-aminobutyrate/benzodiazepine receptor from pig brain. Purification and characterization of the receptor complex from cerebral cortex and cerebellum. Biochem J. 1986 Jan 1;233(1):265-70. Pubmed
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  9. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  10. 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

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Visser LE, van Schaik RH, Jan Danser AH, Hofman A, Witteman JC, van Duijn CM, Uitterlinden AG, Pols HA, Stricker BH: The risk of myocardial infarction in patients with reduced activity of cytochrome P450 2C9. Pharmacogenet Genomics. 2007 Jul;17(7):473-9. Pubmed

2. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Visser LE, van Schaik RH, Jan Danser AH, Hofman A, Witteman JC, van Duijn CM, Uitterlinden AG, Pols HA, Stricker BH: The risk of myocardial infarction in patients with reduced activity of cytochrome P450 2C9. Pharmacogenet Genomics. 2007 Jul;17(7):473-9. Pubmed

3. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Sakuma T, Ohtake M, Katsurayama Y, Jarukamjorn K, Nemoto N: Induction of CYP1A2 by phenobarbital in the livers of aryl hydrocarbon-responsive and -nonresponsive mice. Drug Metab Dispos. 1999 Mar;27(3):379-84. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10