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

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	MOL RATIO 1 MOL RATIO (average)

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

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tension or muscle contraction headache 2	Palliative		Approved 8,429	FIORICET W/ CODEINE

C_max

Value	Dose	Co-administered	Analyte	Population
26.9 μg/mL	2 g single, oral		BUTALBITAL plasma	Homo sapiens
1 μg/mL	50 mg single, oral	ACETAMINOPHEN	BUTALBITAL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
35 h	50 mg single, oral	ACETAMINOPHEN	BUTALBITAL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
55%	50 mg single, oral	ACETAMINOPHEN	BUTALBITAL plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
100 mg single, oral Recommended	healthy, 27-41
2000 mg single, oral Overdose	unhealthy, 67	Other AEs: Coma...

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AEs

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AE	Significance	Dose	Population
Coma		2000 mg single, oral Overdose	unhealthy, 67

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Butalbital-containing agents: should they be banned? No.	2002 Apr	11872186
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
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

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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