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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
179
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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
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
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
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
Co-administed with::
acetylsalicylic acid(660 mg oral)
caffeine(80 mg oral)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3244271
healthy, 27-41
n = 5
Health Status: healthy
Age Group: 27-41
Population Size: 5
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
Co-administed with::
acetylsalicylic acid(13000 mg oral; single)
caffeine(1600 mg oral; single)
codeine(1200 mg oral; single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
Page: p.1,2
unhealthy, 67
n = 1
Health Status: unhealthy
Condition: Headache
Age Group: 67
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
Page: p.1,2
Other AEs: Coma...
Other AEs:
Coma
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
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:
https://pubmed.ncbi.nlm.nih.gov/29124988
Page: p.1,2
unhealthy, 67
n = 1
Health Status: unhealthy
Condition: Headache
Age Group: 67
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/29124988
Page: p.1,2
Sourcing

Sourcing

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

PubMed

TitleDatePubMed
Use of a statistically designed experimental approach to optimize the propylketal derivatization of barbiturates.
2001 Apr
Quantitative design of optimal analgesic combination of acetaminophen, caffeine, and butalbital.
2001 Aug
Persistently elevated acetaminophen concentrations for two days after an initial four-hour non-toxic concentration.
2001 Aug
Butalbital in the treatment of headache: history, pharmacology, and efficacy.
2001 Nov-Dec
Mechanistic studies on the use of 2H- and 13C-analogues as internal standards in selected ion monitoring GC-MS quantitative determination--butalbital example.
2001 Nov-Dec
Should butalbital-containing analgesics be banned? Yes.
2002 Apr
Butalbital-containing agents: should they be banned? No.
2002 Apr
Do butalbital-containing products have a role in the management of migraine?
2002 Aug
Isotopic analogs as internal standards for quantitative GC/MS analysis--molecular abundance and retention time difference as interference factors.
2002 Jul
Health resource utilization of the emergency department headache "repeater".
2002 Sep
Tension-type headache.
2002 Sep 1
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
Effects of non-steroidal anti-inflammatory drugs on cancer sites other than the colon and rectum: a meta-analysis.
2003 Oct 31
Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds.
2003 Sep
Barbiturate withdrawal following Internet purchase of Fioricet.
2004 Jul
Transformed migraine and medication overuse in a tertiary headache centre--clinical characteristics and treatment outcomes.
2004 Jun
Simplified butalbital withdrawal protocol.
2004 Mar
Assay for the simultaneous determination of acetaminophen-caffeine-butalbital in human serum using a monolithic column.
2004 Nov 19
Stability of barbiturates in fixed tissues and formalin solutions.
2005 Apr
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
Acute treatment for migraine headache.
2007 Feb
Determinants of migraine emergency department utilization in the georgia medicaid population.
2007 Oct
Drug-induced refractory headache.
2008 May
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.
2009
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.
2009 Apr 28
Acute treatment of migraine.
2009 May
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

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 Fri Dec 15 15:04:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:34 GMT 2023
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
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 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 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 [WHO-DD]
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 Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
NDF-RT N0000175693
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
DEA NO. 2100
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
NDF-RT N0000008016
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
LIVERTOX 131
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
Code System Code Type Description
HSDB
7853
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
INN
7
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
DRUG BANK
DB00241
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
IUPHAR
7138
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022711
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
DAILYMED
KHS0AZ4JVK
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
MERCK INDEX
m2784
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
201-017-8
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
RS_ITEM_NUM
1081002
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
LACTMED
Butalbital
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
DRUG CENTRAL
441
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
RXCUI
19860
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY RxNorm
CHEBI
102524
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
SMS_ID
100000092556
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
MESH
C004470
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL454
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
NCI_THESAURUS
C47425
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
CAS
77-26-9
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
FDA UNII
KHS0AZ4JVK
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
PUBCHEM
2481
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
WIKIPEDIA
Butalbital
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
PRIMARY
EVMPD
SUB05999MIG
Created by admin on Fri Dec 15 15:04:34 GMT 2023 , Edited by admin on Fri Dec 15 15:04:34 GMT 2023
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
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