Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H16N2O3 |
Molecular Weight | 224.2568 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C=CCC1(CC(C)C)C(=NC(=O)N=C1O)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 Date7.1245437E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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) Sources: caffeine(80 mg oral) |
healthy, 27-41 n = 5 Health Status: healthy Age Group: 27-41 Population Size: 5 Sources: |
|
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Co-administed with:: acetylsalicylic acid(13000 mg oral; single) Sources: Page: p.1,2caffeine(1600 mg oral; single) codeine(1200 mg oral; single) |
unhealthy, 67 n = 1 Health Status: unhealthy Condition: Headache Age Group: 67 Sex: F Population Size: 1 Sources: Page: p.1,2 |
Other AEs: Coma... |
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) Sources: Page: p.1,2caffeine(1600 mg oral; single) codeine(1200 mg oral; single) |
unhealthy, 67 n = 1 Health Status: unhealthy Condition: Headache Age Group: 67 Sex: F Population Size: 1 Sources: Page: p.1,2 |
PubMed
Title | Date | PubMed |
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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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Effects of barbiturates on human platelet aggregation differ depending on their chemical structures. | 2003 Aug |
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Mixed drug intoxication involving zaleplon ("Sonata"). | 2003 Jul 8 |
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Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds. | 2003 Sep |
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Weight restoration in a patient with anorexia nervosa on dialysis. | 2005 Dec |
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Glomerular tip lesion associated with nonsteroidal anti-inflammatory drug-induced nephrotic syndrome. | 2005 Oct |
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Eletriptan treatment of migraine in patients switching from barbiturate-containing analgesics: results from a multiple-attack study. | 2005 Sep |
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Occurrence and fate of barbiturates in the aquatic environment. | 2006 Dec 1 |
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Patterns of medical diagnosis and treatment of migraine and probable migraine in a health plan. | 2006 Jan |
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A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs. | 2009 |
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Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
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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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7853
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7
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DB00241
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7138
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77-26-9
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M2784
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201-017-8
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Butalbital
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1081002
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441
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19860
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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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KHS0AZ4JVK
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2481
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Butalbital
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SUB05999MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)