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	22.9898
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 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 7.1245437E11

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
Health resource utilization of the emergency department headache "repeater".	2002 Sep	12390637
Eletriptan treatment of migraine in patients switching from barbiturate-containing analgesics: results from a multiple-attack study.	2005 Sep	16109055
Determinants of migraine emergency department utilization in the georgia medicaid population.	2007 Oct	17927649
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.	2009 Apr 28	19400959
Breaking the cycle of medication overuse headache.	2010 Apr	20360117
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:52:24 UTC 2023` Edited by `admin` on `Fri Dec 15 15:52:24 UTC 2023`
Record UNII	BBH31P2ABJ
Record Status	`Validated (UNII)`
Record Version

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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