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Butalbital

HCID 2481
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Grundinformationen

CAS
77-26-9
Standard-SMILES
C=CCC1(CC(C)C)C(=O)NC(=O)NC1=O
InChIKey
UZVHFVZFNXBMQJ-UHFFFAOYSA-N
Summenformel
C11H16N2O3
Durchschnittliche Molmasse
224,26 g/mol
Monoisotopische Masse
224,11609238

Überblick

Butalbital is a member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are substituted by an allyl group and an isobutyl group. Frequently combined with other medicines, such as aspirin, paracetamol and codeine, it is used for treatment of pain and headache. It has a role as an analgesic and a sedative. It is functionally related to a barbituric acid.

Namen und Bezeichner

Bevorzugter Name
Butalbital
IUPAC
5-(2-methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Lokaler Name
Butalbital
Englischer Name
BUTALBITAL
Summenformel
C11H16N2O3
Molmasse
224.26

Namen und Synonyme

butalbitalAllylbarbitalItobarbitalTetrallobarbitalAllylbarbitoneButalbarbitalAlisobumalAllylbarbituric acidSandoptal77-26-9ProfundalAllylisobutylbarbital
Weitere Namen anzeigen
D03182TechnalFioricetOptalidonMedigesicPhrenilin
5-Allyl-5-isobutylbarbituric acidAlisobumalumButalbitalumIso-butylallylbarbituric acidButalbitaleAllylisobutylbarbiturate2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(2-methylpropyl)-5-(2-propenyl)-Butalbital ciii

Datenbank-Bezeichner

CAS
77-26-9
PubChem CID
2481
DTXSID
DTXSID6022711
ChEMBL
CHEMBL454
ChEBI
CHEBI:102524
UNII
KHS0AZ4JVK
EC Number
201-017-8
Nikkaji
J4.555A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,7
Polarare Oberfläche (TPSA)
75,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
16
Formalladung
0
Komplexität
327

Experimentelle und physikochemische Eigenschaften

Drugs · 4 Einträge

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

SpringerMaterials PropertiesDensity
LogP · 2 Einträge

1.7

1.48

TasteSlightly bitter
Color/FormPrisms
Solubility · 5 Einträge

Soluble in ethanol, ethyl ether, acetone, chloroform; insoluble in ligands

Slightly soluble in deuterated DSMO

Practically insoluble in petroleum ether; soluble in glacial acetic acid, also in solutions of fixed alkali hydroxides

In water, 1.70X10+3 mg/L at 25 °C

2.23e+00 g/L

Human Drugs · 4 Einträge

Breast Feeding; Lactation; Milk, Human; Barbiturates; GABA Modulators; Hypnotics and Sedatives

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (91.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(2-methylpropyl)-5-(2-propenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(2-methylpropyl)-5-(2-propenyl)-: Environment tier I assessment
FDA Requirements · 2 Einträge

The compounds, mixtures, or preparations that contain a nonnarcotic controlled substance listed in part 1308.12(e) or in part1308.13(b) or (c) or in part 1308.14 or in part 1308.15 listed in the Table of Exempted Prescription Products have been exempted by the Administrator from the application of sections 302 through 305, 307 through 309, and 1002 through 1004 of the Act (21 U.S.C. 822-825, 827-829, and 952-954) and parts 1301.13, 1301.22, and parts 1301.71 through 1301.76 of this chapter for administrative purposes only. An exception to the above is that those products containing butalbital shall not be exempt from the requirement of 21 U.S.C. 952-954 concerning importation, exportation, transshipment and in-transit shipment of controlled substances. Any deviation from the quantitative composition of any of the listed drugs shall require a petition of exemption in order for the product to be exempted. A listing of the Exempted Prescription Products may be obtained by submitting a written request to the Drug and Chemical Evaluation Section, Drug Enforcement Administration.

Chemie und Industrie

Pharmakologische Informationen

Protein Binding · 1 Eintrag

The _in vitro_ plasma protein binding of butalbital is 45% over the concentration range of 0.5-20 mcg/mL. This falls within the range of plasma protein binding (20%-45%) reported with other barbiturates such as phenobarbital, pentobarbital, and secobarbital sodium.

Pharmacodynamics · 1 Eintrag

Butalbital is a short to intermediate-acting barbiturate that reversibly depresses the activity of excitable tissues, including the central nervous system in a nonselective manner. Barbiturates exhibit muscle-relaxing and anti-anxiety properties and they are capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. The sedative dose of butalbital in nontolerant individuals is 5-100 mg and the hypnotic dose is 100-200 mg. Pain perception and reaction are relatively unimpaired until the moment of unconsciousness. In some cases, an unwanted paradoxical response of excitement may be observed instead of sedation with barbiturate treatment, which may be due to their depressant effects on inhibitory centers of the CNS. At sufficiently high therapeutic doses, barbiturates induce anesthesia; however, barbiturates are reported to lose their effectiveness for sleep induction and sleep maintenance after 2 weeks. Barbiturates are habit-forming; they can produce tolerance and both dependence and addiction, which is partly explained by decreased drug concentration at the site of action due to enhanced drug metabolism by induced enzymes, or to cellular adaptive changes. In addition, butalbital may lead to analgesic overuse headache. While butalbital is expected to mediate similar actions as other members of the barbiturate drug class, the effects of butalbital in isolation are not well understood. It is suggested that butalbital is added in combination products to antagonize the unwanted central stimulating effect of stimulatory ingredients such as caffeine. Butalbital may decrease blood pressure and heart rate when administered at sedative and hypnotic doses.

Mechanism of Action · 2 Einträge

Butalbital is a CNS depressant that suppresses neuronal excitability, impulse conduction, and the release of neurotransmitters, similar to actions of other barbiturates. Barbiturates primarily mediate suppressive actions on polysynaptic neuronal responses by diminishing facilitation while enhancing inhibition. Inhibition occurs at GABAergic synapses that express GABA-A receptors, which are transmembrane chloride ion channels that bind an inhibitory neurotransmitter GABA, barbiturates, benzodiazepines, neurosteroids, and ethanol. Upon activation, GABA-A receptors allow Cl- influx and K+ efflux into the postjunctional terminal, resulting in inhibition of the postsynaptic neuron. It is suggested that barbiturates, including butalbital, enhances GABA binding to the GABA-A receptors by binding to the α+/β− interface in the intracellular domain (ICD) as an allosteric modulator. Additionally, barbiturates promote benzodiazepine binding to the receptor. Barbiturates potentiate GABA-induced increases in chloride conductance and depress voltage-activated calcium currents while prolonging the duration of GABA-induced chloride channel opening. Butalbital may also inhibit the excitatory effects mediated by AMPA receptors by reducing glutamate-induced depolarizations of the receptor. It is also proposed that barbiturates and opioids may potentiate the analgesic effects of each other when co-administered, although there are inconsistencies across preclinical data.

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Pharmaceuticals

Melting Point · 2 Einträge

138.5 °C

138 - 139 °C

Physical DescriptionSolid
Other Experimental PropertiesA saturated solution is acid to litmus

Physikochemische Eigenschaften

Schmelzpunkt
139 · 139-140 °C
Siedepunkt
365.66 °C · 365.66°C (rough estimate)
Dichte
1.1672 · 1.1672 (rough estimate)
Brechungsindex
1.5 · 1.5000 (estimate)
Flammpunkt
11 °C · 11 °C
storage temp.
2 · 2-8°C
Löslichkeit
soluble in DMSO, Methanol
Aggregatzustand
Solid
pka
12.36 · pKa 12.36±0.05(H2O t=38.0 I=0.1) (Uncertain)
Farbe
White
Wasserlöslichkeit
1.702 g/L · 1.702g/L(25 ºC)
BRN
202119 · 202119
Henry's Law Constant
1.6 · 1.6×107 mol/(m3Pa) at 25℃, HSDB (2015)
EPA chemische Informationen
2 · 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(2-methylpropyl)-5-(2-propen-1-yl)- (77-26-9)

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including butalbital, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Hazard Classes and CategoriesAcute Tox. 4 (91.3%)

Sicherheit und Schutzausrüstung

Disposal Methods · 2 Einträge

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Toxikologische Informationen

Interactions · 2 Einträge

The CNS effects of butalbital may be enhanced by monoamine oxidase (MAO) inhibitors.

A 44-year-old woman was admitted to the psychiatric unit for exacerbation of her depressive disorder. Blood concentrations of her antidepressant, imipramine, were within normal range and consistent with past concentrations. Her medical history was significant for a chronic headache disorder for which she was given a prescription containing butalbital on admission. The patient's depressive disorder was quickly controlled but relapsed 2 weeks later. Concentrations of imipramine showed a decrease of approximately 50%. Imipramine is metabolized in the liver by the cytochrome P-450 (CYP 1A2) system, and barbiturates are known inducers of this enzyme subset.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 26(SRC), determined from a structure estimation method(2), indicates that butalbital is expected to have very high mobility in soil(SRC). Volatilization of butalbital from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3)). Butalbital is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2011).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 26(SRC), determined from a structure estimation method(2), indicates that butalbital is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.3X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 8(SRC), from an estimated log Kow of 1.87(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butalbital, which has an estimated vapor pressure of 1.5X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase butalbital may be removed from the air by wet or dry deposition(SRC). Butalbital contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Effluent Concentrations · 1 Eintrag

Butalbital was detected in three wastewater treatment plant effluents associated with facilities involved in the manufacture of pharmaceuticals in New York; 35-38 samples were collected from each plant between 2004 and 2009. The maximum concentrations of butalbital were 0.9 (78% detection); 50 ug/L (97% detection) and 30 ug/L (100% detection) in the three New York samples, respectively; the latter receives 20% of its discharge from a pharmaceutical formulation facility. It was detected in 83% of samples (maximum concentration = 0.08 ug/L) from twenty-three plants across the US that were analyzed once between 2004 and 2009 as part of a National Survey; more than half of these plants receive hospital discharge. Detection limit = 0.011 ug/L. These findings suggest that current manufacturing practices at pharmaceutical formulation facilities can result in pharmaceuticals concentrations from 10 to 1000 times higher than those typically found in wastewater treatment plant effluents(1).

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of butalbital can be estimated to be 26(SRC). According to a classification scheme(2), this estimated Koc value suggests that butalbital is expected to have very high mobility in soil.

Human Toxicity Excerpts · 5 Einträge

/SIGNS AND SYMPTOMS/ Barbiturates may be habit-forming: Tolerance, psychological dependence, and physical dependence may occur especially following prolonged use of high doses of barbiturates. The average daily dose for the barbiturate addict is usually about 1500 mg. As tolerance to barbiturates develops, the amount needed to maintain the same level of intoxication increases; tolerance to a fatal dosage, however, does not increase more than two-fold. As this occurs, the margin between an intoxication dosage and fatal dosage becomes smaller. The lethal dose of a barbiturate is far less if alcohol is also ingested. Major withdrawal symptoms (convulsions and delirium) may occur within 16 hours and last up to 5 days after abrupt cessation of these drugs. Intensity of withdrawal symptoms gradually declines over a period of approximately 15 days. Treatment of barbiturate dependence consists of cautious and gradual withdrawal of the drug. Barbiturate-dependent patients can be withdrawn by using a number of different withdrawal regimens. One method involves initiating treatment at the patient's regular dosage level and gradually decreasing the daily dosage as tolerated by the patient.

/SIGNS AND SYMPTOMS/ Toxicity from barbiturate poisoning include drowsiness, confusion, and coma; respiratory depression; hypotension; and hypovolemic shock.

/CASE REPORTS/ ... The case of a 54-year-old woman who developed a barbiturate abstinence syndrome when she suspended self-administration of a drug containing butalbital /is reported/. The patient had been using barbiturates, 900 mg/day, for 2+ years for persistent headache. She was admitted to the hospital because of seizures, hallucinations and delirium not controlled by benzodiazepine and phenothiazine administration. Her symptoms resolved after parenteral phenobarbital administration.

/CASE REPORTS/ The patient was a 37-year-old woman with a history of depression and migraine headaches but not drug abuse. She developed a florid withdrawal delirium following the discontinuation of a drug she purchased online. The medication, which contained butalbital, was self-administered in escalating doses for the treatment of chronic headaches. Daily doses of up to 750 mg to 1000 mg were reported. The patient was admitted to the hospital for the treatment of unexplained seizures that were followed by several days of an intense withdrawal syndrome. Little improvement was noted after the administration of benzodiazepines and phenothiazine. After parenteral phenobarbital administration, her symptoms resolved. The withdrawal state from barbiturates is similar to that from ethanol. Tolerance can develop with prolonged abuse, leading to escalating drug doses to achieve the desired effect.

For more Human Toxicity Excerpts (Complete) data for Butalbital (6 total), please visit the HSDB record page.

Artificial Pollution SourcesButalbital's production and use as a component in some analgesics(1) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Butalbital

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 8 was calculated in fish for butalbital(SRC), using an estimated log Kow of 1.87(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for butalbital is estimated as 6.3X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that butalbital is expected to be essentially nonvolatile from water and moist soil surfaces(2). Butalbital is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-10 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1 Eintrag

Butalbital is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Butalbital contains chromophores that absorb at wavelengths >290 nm(1), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1 Eintrag

NIOSH (NOES Survey 1981-1983) has statistically estimated that 284 workers (144 of these were female) were potentially exposed to butalbital in the US(1). Occupational exposure to butalbital may occur through inhalation and dermal contact with this compound at workplaces where butalbital is produced or used. Limited monitoring data indicate that the general population may be exposed to butalbital via ingestion of contaminated drinking water. Exposure to butalbital among the general population may be limited to those administered the analgesic drugs containing this compound(SRC).

Environmental Fate/Exposure Summary · 1 Eintrag

Butalbital's production and use as a component in some analgesics may result in its release to the environment through various waste streams. If released to air,an estimated vapor pressure of 2.6X10-10 mm Hg at 25 °C indicates butalbital will exist solely in the particulate phase in the atmosphere. Particulate-phase butalbital will be removed from the atmosphere by wet or dry deposition. Butalbital does contains chromophores that absorb at wavelengths >290 nm, and therefore may be susceptible to direct photolysis by sunlight. If released to soil, butalbital is expected to have very high mobility based upon an estimated Koc of 26. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 6.3X10-13 atm-cu m/mole. Boidegradation data were not available. If released into water, butalbital is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 8 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to butalbital may occur through inhalation and dermal contact with this compound at workplaces where butalbital is produced or used. Limited monitoring data indicate that the general population may be exposed to butalbital via ingestion of contaminated drinking water. Exposure to butalbital among the general population may be limited to those administered the analgesic drugs containing this compound. (SRC)

Regulatorische Informationen

FDA Requirements · 2 Einträge

The compounds, mixtures, or preparations that contain a nonnarcotic controlled substance listed in part 1308.12(e) or in part1308.13(b) or (c) or in part 1308.14 or in part 1308.15 listed in the Table of Exempted Prescription Products have been exempted by the Administrator from the application of sections 302 through 305, 307 through 309, and 1002 through 1004 of the Act (21 U.S.C. 822-825, 827-829, and 952-954) and parts 1301.13, 1301.22, and parts 1301.71 through 1301.76 of this chapter for administrative purposes only. An exception to the above is that those products containing butalbital shall not be exempt from the requirement of 21 U.S.C. 952-954 concerning importation, exportation, transshipment and in-transit shipment of controlled substances. Any deviation from the quantitative composition of any of the listed drugs shall require a petition of exemption in order for the product to be exempted. A listing of the Exempted Prescription Products may be obtained by submitting a written request to the Drug and Chemical Evaluation Section, Drug Enforcement Administration.

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including butalbital, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Sicherheitsdaten

wgk
3
ridadr
UN 1230 3/PG 2
hs_code
2933530000
RTECS-Nr.
CP8750000
risk_code
22-43-39/23/24/25-23/24/25-11
Toxizität
LD50 oral in bird - wild: 75mg/kg
hazard_code
Xn,T,F
safety_code
36-45-36/37-16
hazard_class
6.1(b)
packing_group
III
Giftige Stoffe Daten
77-26-9(Hazardous Substances Data)

The effects of butalbital (30, 100, and 1000 ug/kg) on the number of cells expressing c-fos-like immunoreactivity (c-fos-LI), a marker of neuronal activation, within lamina I, IIo of the trigeminal nucleus caudalis and the nucleus of the solitary tract 2 hours after the intracisternal injection of capsaicin (0.1 mL; 15.25 mg/mL) or vehicle in urethane-anesthetized guinea pigs (N = 45) /was examined/. Robust c-fos-LI was observed within nuclei of cells in the trigeminal nucleus caudalis after capsaicin (329 +/- 35). Butalbital dose-dependently reduced the number of labeled cells to a maximum of 66% (1000 micrograms/kg intraperitoneally [i.p.], P < .01) in lamina I, IIo but not within area postrema, medial reticular nucleus, or the nucleus of the solitary tract. Pretreatment with bicuculline (30 micrograms/kg i.p.) blocked the effect of butalbital, thereby suggesting the importance of the GABAA receptor to activation involved in the transmission of nociceptive information. Our studies suggest the possibility that GABAA receptors might provide an important therapeutic target in migraine and related headache disorders.

Biological Half-Life · 3 Einträge

The plasma half-life is about 35 hours. In a study of 5 healthy volunteers receiving 100 mg butalbital in combination with aspirin and caffeine, the mean plasma elimination half-life of butalbital was 61 hours, with the range of 35 to 88 hours.

Elimination of butalbital is primarily via the kidney (59% to 88% of the dose) as unchanged drug or metabolites. The plasma half-life is about 35 hours.

Blood and plasma concentrations of butalbital were determined in a small group of healthy volunteers after single oral doses of 100 mg of butalbital. ... The half-lives in blood were between 35 and 87.5 hr with a mean of 61 hr.

Metabolism/Metabolites · 3 Einträge

Butalbital is expected to undergo nearly complete hepatic metabolism. It primarily undergoes C5 oxidation to form 5-isobutyl-5-(2,3-dihydroxypropyl) barbituric acid, which is the major metabolite. Butalbital may also undergo omega-hydroxylation to form 5-allyl-5(3-hydroxy-2-methyl-1-propyl) barbituric acid.

Urinary excretion products include parent drug (about 3.6% of the dose), 5-isobutyl-5-(2, 3-dihydroxypropyl) barbituric acid (about 24% of the dose), 5-allyl-5(3-hydroxy-2-methyl-1-propyl) barbituric acid (about 4.8% of the dose), products with the barbituric acid ring hydrolyzed with excretion of urea (about 14% of the dose), as well as unidentified materials. Of the material excreted in the urine, 32% is conjugated.

Butalbital, 5-allyl-5-isobutylbarbituric acid, labeled in the 2-position with 14C, was administered to dogs. Ninety-two percent of the radioactivity of the dose was excreted in the urine. The drug and three major urinary metabolites were identified in the urinary excretion of the dog. The major metabolite was 5-isobutyl-5-(2,3-dihydroxypropyl)barbituric acid, which accounted for 50.2% of the dose. Smaller amounts of the unchanged drug (2.6% of the dose) and urea (8.6% of the dose) were present. 5-Allyl-5-(3-hydroxy-2-methyl-1-propyl)barbituric acid, formed by omega-hydroxylation, accounted for 10.1% of the dose; the optical rotation of the 1,3-diethyl derivative was [alpha]D20 = +10.5. Five minor and unidentified metabolities accounted for an additional 10.7% of the dose. A total of 82.2% of the dose was accounted for.

FDA Pharmacological Classification · 5 Einträge

KHS0AZ4JVK

BUTALBITAL

Established Pharmacologic Class [EPC] - Barbiturate

Chemical Structure [CS] - Barbiturates

Butalbital is a Barbiturate.

Absorption, Distribution and Excretion · 6 Einträge

Butalbital gets readily and rapidly absorbed from the gastrointestinal tract. The time to reach the peak plasma concentrations is reported to be approximately 2 hours. Typical blood concentrations of butalbital peaked at 2.1 mg/L and declined to 1.5 mg/L at 24 hr. Plasma concentrations of 10 to 20 μg/mL have been associated with toxicity; coma and fatalities have occurred with concentrations of 25 to 30 μg/mL.

Butalbital predominantly undergoes renal elimination with 59 to 88% of the total dose administered being excreted from the kidneys as unchanged parent drug or metabolites. Urinary excretion products included parent drug (about 3.6% of the dose), 5-isobutyl-5-(2,3-dihydroxypropyl) barbituric acid (about 24% of the dose), 5-allyl-5(3-hydroxy-2-methyl-1-propyl) barbituric acid (about 4.8%), products with the barbituric acid ring hydrolyzed with excretion of urea (about 14% of the dose), as well as unidentified materials. Of the material excreted in the urine, 32% is conjugated. Elimination is not complete within 24 hours, and the drug accumulates with frequent administration.

The volume of distribution of butalbital is reported to be approximately 0.8 L/kg. Butalbital is expected to distribute to most of the tissues in the body, including the mamillary glands and placenta. The plasma-to-blood concentration ratio was almost unity indicating that there is no preferential distribution of butalbital into either plasma or blood cells.

There is limited data on the clearance of butalbital.

Butalbital is well absorbed from the gastrointestinal tract and is expected to distribute to most tissues in the body. Barbiturates in general may appear in breast milk and readily cross the placental barrier. They are bound to plasma and tissue proteins to a varying degree and binding increases directly as a function of lipid solubility.

Blood and plasma concentrations of butalbital were determined in a small group of healthy volunteers after single oral doses of 100 mg of butalbital. Butalbital was quantitated by high-performance liquid chromatography with ultraviolet detection. Typical blood concentrations of butalbital peaked at 2.1 mg/L and declined to 1.5 mg/L at 24 hr.

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 2 Einträge

MEDICATION

Use (kg) in USA (2002): 13500

Methods of ManufacturingBy preparing butarbital using a method similar to that for Amobarbital, using ethyl bromide and sec-butyl bromide as the alkylating agents ... /Butabarbital sodium/
Formulations/PreparationsTable: Non-Narcotic Analgesics with Barbiturates [Table#7589]
Use ClassificationPharmaceuticals

Anwendungen

VerwendenControlled substance (depressant). Sedative, hypnotic.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

AllylbromidEthylacetatNatrium
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are substituted by an allyl group and an isobutyl group. Frequently combined with other medicines, such as aspirin, paracetamol and codeine, it is used for reatment of pain and headache.