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

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 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11606331	Positive Allosteric Modulator 179

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 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

C_max

Value	Dose	Co-administered	Analyte	Population
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

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 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Do butalbital-containing products have a role in the management of migraine?	2002 Aug	12173787
Mixed drug intoxication involving zaleplon ("Sonata").	2003 Jul 8	12850405
Barbiturate withdrawal following Internet purchase of Fioricet.	2004 Jul	15262744
Transformed migraine and medication overuse in a tertiary headache centre--clinical characteristics and treatment outcomes.	2004 Jun	15154858
Occurrence and fate of barbiturates in the aquatic environment.	2006 Dec 1	17180967
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.	2009	20111734
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
Acute treatment of migraine headaches.	2010 Apr	20352584
Why do migraineurs abuse butalbital-containing combination analgesics?	2010 Jul	20649651

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 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

5-ALLYL-5-ISOBUTYLBARBITURIC ACID SODIUM SALT

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