BUTALBITAL

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020232s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11279945

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

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11606331	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tension or muscle contraction headache 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020232s033lbl.pdf	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Quantitative design of optimal analgesic combination of acetaminophen, caffeine, and butalbital.	2001 Aug	11749839
Persistently elevated acetaminophen concentrations for two days after an initial four-hour non-toxic concentration.	2001 Aug	11474737
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	11765022
Should butalbital-containing analgesics be banned? Yes.	2002 Apr	11872187
Butalbital-containing agents: should they be banned? No.	2002 Apr	11872186
Do butalbital-containing products have a role in the management of migraine?	2002 Aug	12173787
Isotopic analogs as internal standards for quantitative GC/MS analysis--molecular abundance and retention time difference as interference factors.	2002 Jul	12136999
Health resource utilization of the emergency department headache "repeater".	2002 Sep	12390637
Tension-type headache.	2002 Sep 1	12322770
Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography.	2003	12845581
Distribution of butalbital in postmortem tissues and fluids from non-overdose cases.	2003 Apr	12731655
Mixed drug intoxication involving zaleplon ("Sonata").	2003 Jul 8	12850405
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.	2009	20111734
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.	2009 Apr 28	19400959
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
A case of linear immunoglobulin A bullous dermatosis in a patient exposed to sun and an analgesic.	2009 Sep	19843488
Quantitation of amobarbital, butalbital, pentobarbital, phenobarbital, and secobarbital in urine, serum, and plasma using gas chromatography-mass spectrometry (GC-MS).	2010	20077060
Breaking the cycle of medication overuse headache.	2010 Apr	20360117
Acute treatment of migraine headaches.	2010 Apr	20352584
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.	2010 Feb 18	20368903
Why do migraineurs abuse butalbital-containing combination analgesics?	2010 Jul	20649651
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents.	2010 Jul 1	20521847

Patents

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

Name

Type

Language

BUTALBITAL

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

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