Drug/Small Molecule:
butalbital

2D structure

Overview

Generic Names: Allylbarbital; Butalbital M (OH)
IUPAC Name: 5-(2-methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Brand Mixtures: Fiorinal C1/2 Cap (Acetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate); Fiorinal C1/4 Cap (Acetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate); Fiorinal Tab (Acetylsalicylic Acid + Butalbital + Caffeine); Ratio-Tecnal (Acetylsalicylic Acid + Butalbital + Caffeine); Ratio-Tecnal C 1/2 (Acetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate); Ratio-Tecnal C1/4 (Acetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate); Trianal Capsules (Acetylsalicylic Acid + Butalbital + Caffeine); Trianal Tablet (Acetylsalicylic Acid + Butalbital + Caffeine); Trianal-C 1/2 Capsule (Acetylsalicylic Acid + Butalbital + Caffeine + Codeine Phosphate)
PharmGKB Accession Id: PA448695

Description

Butalbital, 5-allyl-5-isobutylbarbituric acid, is a barbiturate with an intermediate duration of action. It has the same chemical formula as talbutal but a different structure. Butalbital is often combined with other medications, such as acetaminophen or aspirin, and is commonly prescribed for the treatment of pain and headache. [Wikipedia]

Indication

Used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain.

Pharmacology and Interactions

Mechanism Of Action

Butalbital 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.

Pharmacology

Butalbital is a short to intermediate-acting barbiturate. Barbiturates act as nonselective depressants of the central nervous system (CNS), capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. In sufficiently high therapeutic doses, barbiturates induce anesthesia.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic, although most of the dose is eliminated via the kidney (59 to 88%). Urinary excretion products included parent drug (about 3.6% of the dose), 5-isobutyl-5-(2,3-dihydroxypropyl) barbituric acid (about 24% of the dose), 5-allyl-5(3-hydroxy-2-methyl-1-propyl) barbituric acid (about 4.8%).

Protein Binding

45%

Absorption

Well absorbed from the gastrointestinal tract and is expected to distribute to most tissues in the body.

Half Life

35 hours

Toxicity

Symptoms of acute barbiturate poisoning include drowsiness, confusion, coma, respiratory depression, hypotension, and shock.

Chemical Properties

Chemical Formula:

C11H16N2O3

SMILES Code:

CC(C)CC1(C(=O)NC(=O)NC1=O)CC=C

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

224.2563 / 224.1161

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00241
PubChem Compound ID:
2481
PubChem Substance ID:
149431

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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