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)
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 |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11606331 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | FIORICET W/ CODEINE Approved UseFioricet 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 Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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1 μg/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
BUTALBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
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35 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
BUTALBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
55% |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
BUTALBITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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Quantitative design of optimal analgesic combination of acetaminophen, caffeine, and butalbital. | 2001 Aug |
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Persistently elevated acetaminophen concentrations for two days after an initial four-hour non-toxic concentration. | 2001 Aug |
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Mechanistic studies on the use of 2H- and 13C-analogues as internal standards in selected ion monitoring GC-MS quantitative determination--butalbital example. | 2001 Nov-Dec |
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Should butalbital-containing analgesics be banned? Yes. | 2002 Apr |
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Butalbital-containing agents: should they be banned? No. | 2002 Apr |
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Do butalbital-containing products have a role in the management of migraine? | 2002 Aug |
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Isotopic analogs as internal standards for quantitative GC/MS analysis--molecular abundance and retention time difference as interference factors. | 2002 Jul |
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Health resource utilization of the emergency department headache "repeater". | 2002 Sep |
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Tension-type headache. | 2002 Sep 1 |
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Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography. | 2003 |
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Distribution of butalbital in postmortem tissues and fluids from non-overdose cases. | 2003 Apr |
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Mixed drug intoxication involving zaleplon ("Sonata"). | 2003 Jul 8 |
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A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs. | 2009 |
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Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine. | 2009 Apr 28 |
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Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
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A case of linear immunoglobulin A bullous dermatosis in a patient exposed to sun and an analgesic. | 2009 Sep |
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Quantitation of amobarbital, butalbital, pentobarbital, phenobarbital, and secobarbital in urine, serum, and plasma using gas chromatography-mass spectrometry (GC-MS). | 2010 |
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Breaking the cycle of medication overuse headache. | 2010 Apr |
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Acute treatment of migraine headaches. | 2010 Apr |
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Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal. | 2010 Feb 18 |
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Why do migraineurs abuse butalbital-containing combination analgesics? | 2010 Jul |
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Pharmaceutical formulation facilities as sources of opioids and other pharmaceuticals to wastewater treatment plant effluents. | 2010 Jul 1 |
Sample Use Guides
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
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 1308.32
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NDF-RT |
N0000175693
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NCI_THESAURUS |
C67084
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DEA NO. |
2100
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NDF-RT |
N0000008016
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LIVERTOX |
131
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DB00241
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m2784
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201-017-8
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1081002
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Butalbital
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102524
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100000092556
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C004470
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CHEMBL454
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C47425
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77-26-9
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2481
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Butalbital
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SUB05999MIG
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)