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Details

Stereochemistry ACHIRAL
Molecular Formula C11H16N2O3
Molecular Weight 224.2563
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTALBITAL

SMILES

CC(C)CC1(CC=C)C(=O)NC(=O)NC1=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
Molecular Formula C11H16N2O3
Molecular Weight 224.2563
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

1929
8
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
186
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
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

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
26.9 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/29124988/
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
1 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020232s041lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
ACETAMINOPHEN
 BUTALBITAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
35 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020232s041lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
ACETAMINOPHEN
 BUTALBITAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020232s041lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ACETAMINOPHEN
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/3244271
healthy, 27-41
Health Status: healthy
Age Group: 27-41
Sources:
https://pubmed.ncbi.nlm.nih.gov/3244271
Sources:
https://pubmed.ncbi.nlm.nih.gov/3244271
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
unhealthy, 67
Health Status: unhealthy
Age Group: 67
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
Other AEs: Coma...
Other AEs:
Coma
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
AEs

AEs

AESignificanceDosePopulation
Coma
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
unhealthy, 67
Health Status: unhealthy
Age Group: 67
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:102524
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102524
eMolecules
535132
https://www.emolecules.com/cgi-bin/more?vid=535132
ZINC
ZINC000003830347
http://zinc15.docking.org/substances/ZINC000003830347
PubMed

PubMed

TitleDatePubMed
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents.
2010-07-01
Why do migraineurs abuse butalbital-containing combination analgesics?
2010-07
Breaking the cycle of medication overuse headache.
2010-04
Acute treatment of migraine headaches.
2010-04
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.
2010-02-18
Quantitation of amobarbital, butalbital, pentobarbital, phenobarbital, and secobarbital in urine, serum, and plasma using gas chromatography-mass spectrometry (GC-MS).
2010
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009-10-02
A case of linear immunoglobulin A bullous dermatosis in a patient exposed to sun and an analgesic.
2009-09
Acute treatment of migraine.
2009-05
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.
2009-04-28
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.
2009
Drug-induced refractory headache.
2008-05
Determinants of migraine emergency department utilization in the georgia medicaid population.
2007-10
Acute treatment for migraine headache.
2007-02
Occurrence and fate of barbiturates in the aquatic environment.
2006-12-01
Patterns of medical diagnosis and treatment of migraine and probable migraine in a health plan.
2006-01
Weight restoration in a patient with anorexia nervosa on dialysis.
2005-12
Glomerular tip lesion associated with nonsteroidal anti-inflammatory drug-induced nephrotic syndrome.
2005-10
Eletriptan treatment of migraine in patients switching from barbiturate-containing analgesics: results from a multiple-attack study.
2005-09
Stability of barbiturates in fixed tissues and formalin solutions.
2005-04
Assay for the simultaneous determination of acetaminophen-caffeine-butalbital in human serum using a monolithic column.
2004-11-19
Barbiturate withdrawal following Internet purchase of Fioricet.
2004-07
Transformed migraine and medication overuse in a tertiary headache centre--clinical characteristics and treatment outcomes.
2004-06
Simplified butalbital withdrawal protocol.
2004-03
Effects of non-steroidal anti-inflammatory drugs on cancer sites other than the colon and rectum: a meta-analysis.
2003-10-31
Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds.
2003-09
Effects of barbiturates on human platelet aggregation differ depending on their chemical structures.
2003-08
Mixed drug intoxication involving zaleplon ("Sonata").
2003-07-08
Distribution of butalbital in postmortem tissues and fluids from non-overdose cases.
2003-04
Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography.
2003
Tension-type headache.
2002-09-01
Health resource utilization of the emergency department headache "repeater".
2002-09
Do butalbital-containing products have a role in the management of migraine?
2002-08
Isotopic analogs as internal standards for quantitative GC/MS analysis--molecular abundance and retention time difference as interference factors.
2002-07
Should butalbital-containing analgesics be banned? Yes.
2002-04
Butalbital-containing agents: should they be banned? No.
2002-04
Butalbital in the treatment of headache: history, pharmacology, and efficacy.
2002-03-21
Mechanistic studies on the use of 2H- and 13C-analogues as internal standards in selected ion monitoring GC-MS quantitative determination--butalbital example.
2002-01-05
Quantitative design of optimal analgesic combination of acetaminophen, caffeine, and butalbital.
2001-08
Persistently elevated acetaminophen concentrations for two days after an initial four-hour non-toxic concentration.
2001-08
Use of a statistically designed experimental approach to optimize the propylketal derivatization of barbiturates.
2001-04
Patents

Patents

US2016228357
2
US2016271147
2
US2016271148
2
US4175119
2
US4539198
2
US9527840
2

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:34 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:34 GMT 2025
Record UNII
KHS0AZ4JVK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTALBITAL
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
ANOQUAN COMPONENT BUTALBITAL
Preferred Name English
ALLYLBARBITURIC ACID
Systematic Name English
BUTALBITAL [MART.]
Common Name English
5-Allyl-5-isobutylbarbituric acid
Systematic Name English
TRIAD COMPONENT BUTALBITAL
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 [USP IMPURITY]
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
PHRENILIN COMPONENT BUTALBITAL
Common Name English
BANCAP COMPONENT BUTALBITAL
Common Name English
BUTALBITAL [HSDB]
Common Name English
butalbital [INN]
Common Name English
FIORICET COMPONENT BUTALBITAL
Common Name English
SANDOPTAL
Brand Name English
AXOTAL COMPONENT BUTALBITAL
Common Name English
BUTALBITAL CIII
USP-RS  
Common Name English
SEDAPAP COMPONENT BUTALBITAL
Common Name English
ESGIC COMPONENT BUTALBITAL
Common Name English
BUCET 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 [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 1308.32
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
NDF-RT N0000175693
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
NCI_THESAURUS C67084
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
DEA NO. 2100
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
NDF-RT N0000008016
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
LIVERTOX 131
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
Code System Code Type Description
HSDB
7853
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
INN
7
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
DRUG BANK
DB00241
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
IUPHAR
7138
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PRIMARY
EPA CompTox
DTXSID6022711
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
DAILYMED
KHS0AZ4JVK
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
MERCK INDEX
m2784
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
201-017-8
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PRIMARY
RS_ITEM_NUM
1081002
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
LACTMED
Butalbital
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
DRUG CENTRAL
441
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PRIMARY
RXCUI
19860
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY RxNorm
CHEBI
102524
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
SMS_ID
100000092556
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
MESH
C004470
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PRIMARY
ChEMBL
CHEMBL454
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
NCI_THESAURUS
C47425
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
CAS
77-26-9
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
FDA UNII
KHS0AZ4JVK
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
PUBCHEM
2481
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
WIKIPEDIA
Butalbital
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
EVMPD
SUB05999MIG
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
Related Record Type Details
Structure of BUTALBITAL SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of 5-ISOBUTYL-5-(2,3-DIHYDROXYPROPYL)BARBITURIC ACID
METABOLITE -> PARENT
Structure of 5-ISOBUTYL-5-(2,3-DIHYDROXYPROPYL)BARBITURIC ACID
METABOLITE -> PARENT
MAJOR
URINE
Related Record Type Details
Structure of BARBITURIC ACID, 5-ALLYL-5-(2-METHYLALLYL)-
IMPURITY -> PARENT
Related Record Type Details
Structure of BUTALBITAL
ACTIVE MOIETY
NIH
NCATS
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