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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyButabarbital
Identification
- Name
- Butabarbital
- Accession Number
- DB00237 (APRD00752)
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Description
Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia]
- Structure
Structure for Butabarbital (DB00237)
- Synonyms
- 5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
- 5-Ethyl-5-(1-methylpropyl)barbituric acid
- 5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
- 5-Sec-butyl-5-ethylbarbituric acid
- 5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione
- Butabarbital
- Secbutabarbital
- Product Ingredients
Ingredient UNII CAS InChI Key Butabarbital Sodium 9WTD50I918 143-81-7 QORQZMBCPRBCAB-UHFFFAOYSA-M - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Butisol Sodium Tablet 50 mg/1 Oral MedPointe Pharmaceuticals 2007-08-02 2007-08-02 US 
Butisol Sodium Tablet 30 mg/1 Oral MEDA Pharmaceuticals 1939-08-01 2020-01-31 US Butisol Sodium Solution 30 mg/5mL Oral MedPointe Pharmaceuticals 2007-08-02 2007-08-02 US Butisol Sodium Tab 100mg Tablet 100 mg Oral Carter Horner Corp. 1982-12-31 2001-01-02 Canada 
Butisol Sodium Tab 15mg Tablet 15 mg Oral Carter Horner Corp. 1982-12-31 2001-01-02 Canada Butisol Sodium Tab 30mg Tablet 30 mg Oral Carter Horner Corp. 1982-12-31 2001-01-02 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Phenazopyridine Hydrochloride, Hyoscyamine Hydrobromide, and Butabarbital Butabarbital (15 mg/1) + Hyoscyamine hydrobromide (0.3 mg/1) + Phenazopyridine hydrochloride (150 mg/1) Tablet, coated Oral Physicians Total Care, Inc. 2004-09-03 2011-06-30 US Phenazopyridine Plus Butabarbital (15 mg/1) + Hyoscyamine hydrobromide (0.3 mg/1) + Phenazopyridine hydrochloride (150 mg/1) Tablet, coated Oral Breckenridge Pharmaceutical, Inc. 2005-03-01 2011-02-28 US Pyrelle H.B. Butabarbital (15 mg/1) + Hyoscyamine hydrobromide (0.3 mg/1) + Phenazopyridine hydrochloride (150 mg/1) Tablet Oral Azur Pharma, Inc. 2004-01-01 2010-06-01 US - International/Other Brands
- Butalan / Butisol / Sarisol No. 2
- Categories
- UNII
- P0078O25A9
- CAS number
- 125-40-6
- Weight
- Average: 212.2456
Monoisotopic: 212.116092388 - Chemical Formula
- C10H16N2O3
- InChI Key
- ZRIHAIZYIMGOAB-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
- IUPAC Name
- 5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
- SMILES
- CCC(C)C1(CC)C(=O)NC(=O)NC1=O
Pharmacology
- Indication
For short-term treatment of insomnia and anxiety disorders
- Associated Conditions
- Pharmacodynamics
Butabarbital, a barbiturate, is used for the treatment of short term insomnia. It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
- Mechanism of action
Butabarbital 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.
Target Actions Organism AGABA-A receptor (anion channel) positive allosteric modulatorHuman UNeuronal acetylcholine receptor subunit alpha-4 antagonistHuman UNeuronal acetylcholine receptor subunit alpha-7 antagonistHuman UGlutamate receptor 2 antagonistHuman UGlutamate receptor ionotropic, kainate 2 antagonistHuman - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and most metabolic products are excreted in the urine.
- Half life
- Not Available
- 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
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 1,10-Phenanthroline The therapeutic efficacy of Butabarbital can be decreased when used in combination with 1,10-Phenanthroline. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Butabarbital is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3,4-Methylenedioxyamphetamine The risk or severity of adverse effects can be increased when Butabarbital is combined with 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when Butabarbital is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when Butabarbital is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of adverse effects can be increased when Butabarbital is combined with 5-methoxy-N,N-dimethyltryptamine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Butabarbital is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Butabarbital is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Abacavir Butabarbital may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Butabarbital may decrease the excretion rate of Acarbose which could result in a higher serum level. - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014382
- KEGG Drug
- D03180
- KEGG Compound
- C07827
- PubChem Compound
- 2479
- PubChem Substance
- 46505051
- ChemSpider
- 2385
- ChEBI
- 3228
- ChEMBL
- CHEMBL449
- Therapeutic Targets Database
- DAP000667
- PharmGKB
- PA164743463
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Butabarbital
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Medpointe pharmaceuticals medpointe healthcare inc
- Alpharma us pharmaceuticals division
- Wockhardt eu operations (swiss) ag
- Lannett co inc
- Meda pharmaceuticals inc
- Halsey drug co inc
- Cm bundy co
- Sandoz inc
- Solvay pharmaceuticals
- Teva pharmaceuticals usa inc
- Watson laboratories inc
- Whiteworth towne paulsen inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Marshall pharmacal corp
- West ward pharmaceutical corp
- Packagers
- C.O. Truxton Inc.
- Chattem Chemicals Inc.
- Meda AB
- Dosage forms
Form Route Strength Solution Oral 30 mg/5mL Tablet Oral 30 mg/1 Tablet Oral 50 mg/1 Tablet Oral 100 mg Tablet Oral 15 mg Tablet Oral 30 mg Tablet, coated Oral Tablet Oral - Prices
Unit description Cost Unit Butisol sodium 50 mg tablet 2.46USD tablet Butisol sodium 30 mg tablet 1.89USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 166.5 °C PhysProp water solubility 1360 mg/L Not Available logP 1.65 WONG,O & MCKEOWN,RH (1988) - Predicted Properties
Property Value Source Water Solubility 1.39 mg/mL ALOGPS logP 1.7 ALOGPS logP 1.45 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 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 53.4 m3·mol-1 ChemAxon Polarizability 21.41 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9324 Blood Brain Barrier + 0.9782 Caco-2 permeable - 0.6013 P-glycoprotein substrate Substrate 0.5938 P-glycoprotein inhibitor I Non-inhibitor 0.617 P-glycoprotein inhibitor II Non-inhibitor 0.961 Renal organic cation transporter Non-inhibitor 0.9465 CYP450 2C9 substrate Non-substrate 0.7719 CYP450 2D6 substrate Non-substrate 0.9014 CYP450 3A4 substrate Non-substrate 0.7098 CYP450 1A2 substrate Non-inhibitor 0.8775 CYP450 2C9 inhibitor Non-inhibitor 0.821 CYP450 2D6 inhibitor Non-inhibitor 0.933 CYP450 2C19 inhibitor Non-inhibitor 0.7828 CYP450 3A4 inhibitor Non-inhibitor 0.9203 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9458 Ames test Non AMES toxic 0.6458 Carcinogenicity Non-carcinogens 0.8533 Biodegradation Not ready biodegradable 0.9759 Rat acute toxicity 3.6803 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.99 hERG inhibition (predictor II) Non-inhibitor 0.9233
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0a4l-6900000000-6e0cbc3d26c5541ad8eb Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Barbituric acid derivatives
- Alternative Parents
- N-acyl ureas / Diazinanes / Dicarboximides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Barbiturate / N-acyl urea / Ureide / 1,3-diazinane / Dicarboximide / Urea / Carbonic acid derivative / Carboxylic acid derivative / Azacycle / Organic nitrogen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- barbiturates (CHEBI:3228)
Targets
- Kind
- Protein group
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
- 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:11264449]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- 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 permeabl...
- Gene Name
- CHRNA4
- Uniprot ID
- P43681
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-4
- Molecular Weight
- 69956.47 Da
References
- 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:11264449]
- 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:16248797]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Toxic substance binding
- Specific Function
- 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. The cha...
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- 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:11264449]
- 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:16248797]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ionotropic glutamate receptor activity
- Specific Function
- Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
- Gene Name
- GRIA2
- Uniprot ID
- P42262
- Uniprot Name
- Glutamate receptor 2
- Molecular Weight
- 98820.32 Da
References
- 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:11264449]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Kainate selective glutamate receptor activity
- Specific Function
- Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
- Gene Name
- GRIK2
- Uniprot ID
- Q13002
- Uniprot Name
- Glutamate receptor ionotropic, kainate 2
- Molecular Weight
- 102582.475 Da
References
- 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:11264449]
- Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 08:37