U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H16N2O3
Molecular Weight 224.2568
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTALBITAL

SMILES

C=CCC1(CC(C)C)C(=NC(=O)N=C1O)O

InChI

InChIKey=UZVHFVZFNXBMQJ-UHFFFAOYSA-N
InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)

HIDE SMILES / InChI
Butalbital, 5-allyl-5-isobutylbarbituric acid, is a barbiturate with an intermediate duration of action. The different combinations with butalbital is approved. One of them is fioricet with codeine (butalbital, ccetaminophen, caffeine, and codeine phosphate) which is indicated for the relief of the symptom complex of tension (or muscle contraction) headache. Evidence supporting the efficacy and safety of fioricet with codeine in the treatment of multiple recurrent headaches is unavailable. Butalbital is well absorbed from the gastrointestinal tract and is expected to distribute to most tissues in the body. This compound in general may appear in breast milk and readily cross the placental barrier. Monoamine oxidase (MAO) inhibitors may enhance the CNS effects. The mechanism of action for butalbital is proposed the following: this compound 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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FIORICET W/ CODEINE

Approved Use

Fioricet with Codeine is indicated for the relief of the symptom complex of tension (or muscle contraction) headache. Evidence supporting the efficacy and safety of Fioricet with Codeine in the treatment of multiple recurrent headaches is unavailable. Caution in this regard is required because codeine and butalbital are habit-forming and potentially abusable.

Launch Date

7.1245437E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1 μg/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
BUTALBITAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
26.9 μg/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
BUTALBITAL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
35 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
BUTALBITAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
BUTALBITAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Co-administed with::
acetylsalicylic acid(660 mg oral)
caffeine(80 mg oral)
Sources:
healthy, 27-41
n = 5
Health Status: healthy
Age Group: 27-41
Population Size: 5
Sources:
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
acetylsalicylic acid(13000 mg oral; single)
caffeine(1600 mg oral; single)
codeine(1200 mg oral; single)
Sources: Page: p.1,2
unhealthy, 67
n = 1
Health Status: unhealthy
Condition: Headache
Age Group: 67
Sex: F
Population Size: 1
Sources: Page: p.1,2
Other AEs: Coma...
Other AEs:
Coma
Sources: Page: p.1,2
AEs

AEs

AESignificanceDosePopulation
Coma
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
acetylsalicylic acid(13000 mg oral; single)
caffeine(1600 mg oral; single)
codeine(1200 mg oral; single)
Sources: Page: p.1,2
unhealthy, 67
n = 1
Health Status: unhealthy
Condition: Headache
Age Group: 67
Sex: F
Population Size: 1
Sources: Page: p.1,2
PubMed

PubMed

TitleDatePubMed
Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography.
2003
Distribution of butalbital in postmortem tissues and fluids from non-overdose cases.
2003 Apr
Effects of barbiturates on human platelet aggregation differ depending on their chemical structures.
2003 Aug
Mixed drug intoxication involving zaleplon ("Sonata").
2003 Jul 8
Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds.
2003 Sep
Weight restoration in a patient with anorexia nervosa on dialysis.
2005 Dec
Glomerular tip lesion associated with nonsteroidal anti-inflammatory drug-induced nephrotic syndrome.
2005 Oct
Eletriptan treatment of migraine in patients switching from barbiturate-containing analgesics: results from a multiple-attack study.
2005 Sep
Occurrence and fate of barbiturates in the aquatic environment.
2006 Dec 1
Patterns of medical diagnosis and treatment of migraine and probable migraine in a health plan.
2006 Jan
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.
2009
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Quantitation of amobarbital, butalbital, pentobarbital, phenobarbital, and secobarbital in urine, serum, and plasma using gas chromatography-mass spectrometry (GC-MS).
2010
Breaking the cycle of medication overuse headache.
2010 Apr
Acute treatment of migraine headaches.
2010 Apr
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.
2010 Feb 18
Why do migraineurs abuse butalbital-containing combination analgesics?
2010 Jul
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents.
2010 Jul 1
Patents

Sample Use Guides

Fioricet with Codeine (Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate): One or 2 capsules every 4 hours. Total daily dosage should not exceed 6 capsules. Extended and repeated use of this product is not recommended because of the potential for physical dependence.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
BUTALBITAL
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
ALLYLBARBITURIC ACID
Systematic Name English
BUTALBITAL COMPONENT OF FEMCET
Common Name English
BUTALBITAL [MART.]
Common Name English
5-ALLYL-5-ISOBUTYLBARBITURIC ACID
Systematic Name English
TRIAD COMPONENT BUTALBITAL
Common Name English
BUTALBITAL [USP]
Common Name English
BUTALBITAL [USP MONOGRAPH]
Common Name English
BUTALBITAL [VANDF]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-(2-METHYLPROPYL)-5-(2-PROPENYL)-
Systematic Name English
BUTALBITAL [WHO-DD]
Common Name English
BUTALBITAL COMPONENT OF TRIAPRIN
Common Name English
BUTALBITAL COMPONENT OF SEDAPAP
Common Name English
BUTALBITAL COMPONENT OF FIORICET
Common Name English
BUTALBITAL [MI]
Common Name English
TENCON COMPONENT BUTALBITAL
Common Name English
TRIAPRIN COMPONENT BUTALBITAL
Common Name English
LANORINAL COMPONENT BUTALBITAL
Common Name English
BUTALBITAL [USAN]
Common Name English
BUTALBITAL [ORANGE BOOK]
Common Name English
FIORINAL COMPONENT BUTALBITAL
Common Name English
BUTALBITAL COMPONENT OF FIORINAL
Common Name English
BUTALBITAL COMPONENT OF BUCET
Common Name English
PHRENILIN COMPONENT BUTALBITAL
Common Name English
BANCAP COMPONENT BUTALBITAL
Common Name English
BUTALBITAL [HSDB]
Common Name English
BUTALBITAL COMPONENT OF MEDIGESIC PLUS
Common Name English
BUTALBITAL COMPONENT OF ESGIC
Common Name English
BUTALBITAL COMPONENT OF BUTAPAP
Common Name English
BUTALBITAL [INN]
Common Name English
BUTALBITAL COMPONENT OF BANCAP
Common Name English
BUTALBITAL COMPONENT OF ANOQUAN
Common Name English
FIORICET COMPONENT BUTALBITAL
Common Name English
SANDOPTAL
Brand Name English
BUTALBITAL COMPONENT OF LANORINAL
Common Name English
AXOTAL COMPONENT BUTALBITAL
Common Name English
BUTALBITAL CIII
USP-RS  
Common Name English
BUTALBITAL COMPONENT OF PHRENILIN
Common Name English
SEDAPAP COMPONENT BUTALBITAL
Common Name English
ESGIC COMPONENT BUTALBITAL
Common Name English
BUCET COMPONENT BUTALBITAL
Common Name English
BUTALBITAL COMPONENT OF TENCON
Common Name English
ANOQUAN COMPONENT BUTALBITAL
Common Name English
BUTAPAP COMPONENT BUTALBITAL
Common Name English
BUTALBITAL CIII [USP-RS]
Common Name English
FEMCET COMPONENT BUTALBITAL
Common Name English
BUTALBITAL COMPONENT OF TRIAD
Common Name English
BUTALBITAL COMPONENT OF AXOTAL
Common Name English
Classification Tree Code System Code
CFR 21 CFR 1308.32
Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021
NDF-RT N0000175693
Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021
NCI_THESAURUS C67084
Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021
DEA NO. 2100
Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021
NDF-RT N0000008016
Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021
LIVERTOX 131
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Code System Code Type Description
HSDB
7853
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PRIMARY
INN
7
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PRIMARY
DRUG BANK
DB00241
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PRIMARY
IUPHAR
7138
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PRIMARY
EPA CompTox
77-26-9
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PRIMARY
MERCK INDEX
M2784
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PRIMARY Merck Index
ECHA (EC/EINECS)
201-017-8
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PRIMARY
LACTMED
Butalbital
Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021
PRIMARY
USP_CATALOG
1081002
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PRIMARY USP-RS
DRUG CENTRAL
441
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PRIMARY
RXCUI
19860
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PRIMARY RxNorm
MESH
C004470
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PRIMARY
ChEMBL
CHEMBL454
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PRIMARY
NCI_THESAURUS
C47425
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PRIMARY
CAS
77-26-9
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PRIMARY
FDA UNII
KHS0AZ4JVK
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PRIMARY
PUBCHEM
2481
Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021
PRIMARY
WIKIPEDIA
Butalbital
Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021
PRIMARY
EVMPD
SUB05999MIG
Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021
PRIMARY