Page last updated: 2024-12-04

butalbital

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

butalbital: management of butalbital withdrawal can be simplified by using a phenobarbital-loading protocol; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

butalbital : 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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID2481
CHEMBL ID454
CHEBI ID102524
SCHEMBL ID79820
SCHEMBL ID21065545
MeSH IDM0045538

Synonyms (117)

Synonym
AKOS003398680
2,4,6(1h,3h,5h)-pyrimidinetrione, 5-(2-methylpropyl)-5-(2-propenyl)-
barbituric acid, 5-allyl-5-isobutyl-
KBIO1_000970
DIVK1C_000970
5-(2-methylpropyl)-5-prop-2-en-1-ylpyrimidine-2,4,6(1h,3h,5h)-trione
77-26-9
butalbital (usp/inn)
sandoptal (tn)
D03182
allylbarbituric acid
butalbital
IDI1_000970
butalbitale [dcit]
einecs 201-017-8
allylisobutylbarbital
sandoptal
profundal
alisobumal
allylisobutylbarbiturate
alisobumalum
butalbitalum [inn-latin]
5-isobutyl-5-allylbarbituric acid
5-allyl-5-(2-methylpropyl)barbituric acid
5-allyl-5-isobutyl-pyrimidine-2,4,6-trione
itobarbital
allylbarbital
iso-butylallylbarbituric acid
5-allyl-5-isobutyl-2,4,6(1h,3h,5h)-pyrimidinetrione
5-allyl-5-isobutylbarbituric acid
5-allyl-5-(2'-methyl-n-propyl) barbituric acid
DB00241
butalbarbital
allylbarbitone
5-(2-methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
tetrallobarbital
NINDS_000970
butalbital ciii
CHEMBL454
HMS503A21
CHEBI:102524 ,
5-(2-methylpropyl)-5-(prop-2-en-1-yl)pyrimidine-2,4,6(1h,3h,5h)-trione
butalbitalum
butalbital [usan:usp:inn]
khs0az4jvk ,
unii-khs0az4jvk
butalbitale
hsdb 7853
butalbital [inn]
femcet component butalbital
lanorinal component butalbital
butalbital [orange book]
butalbital [usp impurity]
butalbital component of lanorinal
butalbital [hsdb]
butalbital component of bancap
phrenilin component butalbital
triad component butalbital
butalbital component of medigesic plus
triaprin component butalbital
butalbital [usp monograph]
fioricet component butalbital
esgic component butalbital
butalbital component of axotal
butalbital component of esgic
butalbital component of fioricet
butalbital component of bucet
bucet component butalbital
butalbital component of femcet
butalbital component of fiorinal
butalbital [vandf]
anoquan component butalbital
butalbital component of butapap
butalbital component of sedapap
butalbital [mi]
butalbital component of tencon
butalbital [usan]
butapap component butalbital
butalbital component of triad
butalbital component of anoquan
axotal component butalbital
tencon component butalbital
fiorinal component butalbital
sedapap component butalbital
butalbital [mart.]
bancap component butalbital
butalbital ciii [usp-rs]
butalbital [who-dd]
butalbital component of phrenilin
butalbital component of triaprin
AKOS015894376
BRD-K71350836-001-01-6
gtpl7138
4,6-dihydroxy-5-(2-methylpropyl)-5-(prop-2-en-1-yl)-2,5-dihydropyrimidin-2-one
CCG-220459
SCHEMBL79820
allylisobutylbarbituric acid
UZVHFVZFNXBMQJ-UHFFFAOYSA-N
isobutylallylbarbituric acid
isobutylallylbarturic acid
axocet (salt/mix)
W-109270
5-(2-methylpropyl)-5-(2-propen-1-l)-2,4,6(1h,3h,5h)-pyrimidinetrione
DTXSID6022711
5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
SR-01000872704-1
sr-01000872704
butalbital, united states pharmacopeia (usp) reference standard
butalbital 1.0 mg/ml in methanol
HMS3713K20
5-allyl-5-isobutylpyrimidine-2,4,6(1h,3h,5h)-trione
Q1606543
SCHEMBL21065545
5-allyl-5-isobutyl-barbitursa currencyure
NCGC00344559-01
2,4,6(1h,3h,5h)-pyrimidinetrione, 5-(2-methylpropyl)-5-(2-propen-1-yl)-
butalbital, 1mg/ml in methanol

Research Excerpts

Overview

Butalbital is a small molecule (approximately 220 Da), with 26% protein binding, a 0.8 L/kg volume of distribution, and is eliminated nearly 80% unchanged in the urine. It is a barbiturate contained in combination products with caffeine and an analgesic.

ExcerptReferenceRelevance
"Butalbital is a small molecule (approximately 220 Da), with 26% protein binding, a 0.8 L/kg volume of distribution, and is eliminated nearly 80% unchanged in the urine. "( Extracorporeal elimination of butalbital in acute aspirin-butalbital-caffeine-codeine (Fiorinal with Codeine) poisoning.
Albright, R; Barreto, EF; Clain, J; Pandompatam, G; Poyant, JO, 2018
)
2.21
"Butalbital is a barbiturate contained in combination products with caffeine and an analgesic prescribed for the treatment of migraine and tension-type headaches. "( Maternal butalbital use and selected defects in the national birth defects prevention study.
Botto, LD; Browne, ML; Druschel, CM; Louik, C; Richardson, S; Van Zutphen, AR, 2014
)
2.26

Toxicity

ExcerptReferenceRelevance
" All patients were effectively treated with no serious adverse events."( Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds.
Biondi, D; Loder, E, 2003
)
0.54

Dosage Studied

ExcerptRelevanceReference
" We recommend repeat measurement of imipramine concentrations 1 week after the start of any butalbital-containing product or barbiturate, and dosage adjustments based on the results and on the patient's response to the change."( Possible interaction between imipramine and butalbital.
Amsden, GW; Garey, KW; Johns, CA,
)
0.61
"According to the degree of importance to the combined analgesic effect, Ace > Caf > Bul; Ace showed a significant dose-response relationship, whereas in Caf and Bul, this relationship was not apparent."( Quantitative design of optimal analgesic combination of acetaminophen, caffeine, and butalbital.
Gui, CQ; Sun, RY; Wang, XW; Zheng, QS, 2001
)
0.53
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
sedativeA central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
analgesicAn agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
barbituratesMembers of the class of pyrimidones consisting of pyrimidine-2,4,6(1H,3H,5H)-trione (barbituric acid) and its derivatives. Largest group of the synthetic sedative/hypnotics, sharing a characteristic six-membered ring structure.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID169097Negative log of molar concentration (-log C) required to produce 50% inhibition of oxygen (oxygen uptake) on rat brain respiration in vitro1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID167610Negative log of minimum effective dose (moles per kilogram) in rabbits (hypnotic)1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID24211Compound is evaluated for ionization constant log k1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1145374Induction of hypnotic activity in rat1976Journal of medicinal chemistry, May, Volume: 19, Issue:5
Molecular connectivity. 6. Examination of the parabolic relationship between molecular connectivity and biological activity.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID38915Negative log of molar concentration (-log ED50) required to reduce cell division by 50% in Arbacia egg; ND = No Data1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1130943Octanol-water partition coefficient, log P of nonionized form of compound1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1130940Retention index of the compound by HPLC method1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1130944Hypnotic activity in rabbit1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID26320pKa value is evaluated1983Journal of medicinal chemistry, Jul, Volume: 26, Issue:7
A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (20.41)18.7374
1990's9 (18.37)18.2507
2000's14 (28.57)29.6817
2010's16 (32.65)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 101.25

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index101.25 (24.57)
Research Supply Index4.20 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index181.47 (26.88)
Search Engine Supply Index2.01 (0.95)

This Compound (101.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (6.45%)5.53%
Reviews8 (12.90%)6.00%
Case Studies17 (27.42%)4.05%
Observational0 (0.00%)0.25%
Other33 (53.23%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]