BUTALBITAL SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H15N2O3.Na
Molecular Weight	246.2382
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC(C)CC1(CC=C)C(=O)NC(=O)[N-]C1=O

InChI

InChIKey=LIZXGILRVOONMO-UHFFFAOYSA-M

InChI=1S/C11H16N2O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents.	2010-07-01	20521847
Why do migraineurs abuse butalbital-containing combination analgesics?	2010-07	20649651
Breaking the cycle of medication overuse headache.	2010-04	20360117
Acute treatment of migraine headaches.	2010-04	20352584
Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal.	2010-02-18	20368903
Quantitation of amobarbital, butalbital, pentobarbital, phenobarbital, and secobarbital in urine, serum, and plasma using gas chromatography-mass spectrometry (GC-MS).	2010	20077060
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009-10-02	19798416
A case of linear immunoglobulin A bullous dermatosis in a patient exposed to sun and an analgesic.	2009-09	19843488
Acute treatment of migraine.	2009-05	19289223
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.	2009-04-28	19400959
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.	2009	20111734
Drug-induced refractory headache.	2008-05	18471123
Determinants of migraine emergency department utilization in the georgia medicaid population.	2007-10	17927649
Acute treatment for migraine headache.	2007-02	17372581
Occurrence and fate of barbiturates in the aquatic environment.	2006-12-01	17180967
Patterns of medical diagnosis and treatment of migraine and probable migraine in a health plan.	2006-01	16396665
Weight restoration in a patient with anorexia nervosa on dialysis.	2005-12	16261601
Glomerular tip lesion associated with nonsteroidal anti-inflammatory drug-induced nephrotic syndrome.	2005-10	16183408
Eletriptan treatment of migraine in patients switching from barbiturate-containing analgesics: results from a multiple-attack study.	2005-09	16109055
Stability of barbiturates in fixed tissues and formalin solutions.	2005-04	15842765
Assay for the simultaneous determination of acetaminophen-caffeine-butalbital in human serum using a monolithic column.	2004-11-19	15533665
Barbiturate withdrawal following Internet purchase of Fioricet.	2004-07	15262744
Transformed migraine and medication overuse in a tertiary headache centre--clinical characteristics and treatment outcomes.	2004-06	15154858
Simplified butalbital withdrawal protocol.	2004-03	15012672
Effects of non-steroidal anti-inflammatory drugs on cancer sites other than the colon and rectum: a meta-analysis.	2003-10-31	14588079
Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds.	2003-09	12940814
Effects of barbiturates on human platelet aggregation differ depending on their chemical structures.	2003-08	12897810
Mixed drug intoxication involving zaleplon ("Sonata").	2003-07-08	12850405
Distribution of butalbital in postmortem tissues and fluids from non-overdose cases.	2003-04	12731655
Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography.	2003	12845581
Tension-type headache.	2002-09-01	12322770
Health resource utilization of the emergency department headache "repeater".	2002-09	12390637
Do butalbital-containing products have a role in the management of migraine?	2002-08	12173787
Isotopic analogs as internal standards for quantitative GC/MS analysis--molecular abundance and retention time difference as interference factors.	2002-07	12136999
Should butalbital-containing analgesics be banned? Yes.	2002-04	11872187
Butalbital-containing agents: should they be banned? No.	2002-04	11872186
Butalbital in the treatment of headache: history, pharmacology, and efficacy.	2002-03-21	11903523
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	11765022
Quantitative design of optimal analgesic combination of acetaminophen, caffeine, and butalbital.	2001-08	11749839
Persistently elevated acetaminophen concentrations for two days after an initial four-hour non-toxic concentration.	2001-08	11474737
Use of a statistically designed experimental approach to optimize the propylketal derivatization of barbiturates.	2001-04	11318064

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:40 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:40 GMT 2025`
Record UNII	BBH31P2ABJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-ALLYL-5-ISOBUTYLBARBITURIC ACID SODIUM SALT

Preferred Name

English

BUTALBITAL SODIUM

Common Name

English

BARBITURIC ACID, 5-ALLYL-5-ISOBUTYL-, SODIUM SALT

Common Name

English

Butalbital sodium [WHO-DD]

Common Name

English

SODIUM BUTALBITAL

Common Name

English

SODIUM 5-(2-METHYLPROPYL)-4,6-DIOXO-5-PROP-2-ENYL-1H-PYRIMIDIN-2-OLATE

Systematic Name

English

Classification Tree Code System Code

DEA NO.

2100