BUTALBITAL

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

Structure Search

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)

HIDE SMILES / InChI

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 189 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11606331	Positive Allosteric Modulator 155

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 7997	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
Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography.	2003	12845581
Distribution of butalbital in postmortem tissues and fluids from non-overdose cases.	2003 Apr	12731655
Effects of barbiturates on human platelet aggregation differ depending on their chemical structures.	2003 Aug	12897810
Mixed drug intoxication involving zaleplon ("Sonata").	2003 Jul 8	12850405
Oral phenobarbital loading: a safe and effective method of withdrawing patients with headache from butalbital compounds.	2003 Sep	12940814
Weight restoration in a patient with anorexia nervosa on dialysis.	2005 Dec	16261601
Glomerular tip lesion associated with nonsteroidal anti-inflammatory drug-induced nephrotic syndrome.	2005 Oct	16183408
Eletriptan treatment of migraine in patients switching from barbiturate-containing analgesics: results from a multiple-attack study.	2005 Sep	16109055
Occurrence and fate of barbiturates in the aquatic environment.	2006 Dec 1	17180967
Patterns of medical diagnosis and treatment of migraine and probable migraine in a health plan.	2006 Jan	16396665
A categorical structure-activity relationship analysis of the developmental toxicity of antithyroid drugs.	2009	20111734
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Quantitation of amobarbital, butalbital, pentobarbital, phenobarbital, and secobarbital in urine, serum, and plasma using gas chromatography-mass spectrometry (GC-MS).	2010	20077060
Breaking the cycle of medication overuse headache.	2010 Apr	20360117
Acute treatment of migraine headaches.	2010 Apr	20352584
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

Name

Type

Language

BUTALBITAL

Official Name

English

ALLYLBARBITURIC ACID

Systematic Name

English

BUTALBITAL COMPONENT OF FEMCET

Common Name

English

BUTALBITAL [MART.]

Common Name

English

5-ALLYL-5-ISOBUTYLBARBITURIC ACID

Systematic Name

English

TRIAD COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL [USP]

Common Name

English

BUTALBITAL [USP MONOGRAPH]

Common Name

English

BUTALBITAL [VANDF]

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-(2-METHYLPROPYL)-5-(2-PROPENYL)-

Systematic Name

English

BUTALBITAL [WHO-DD]

Common Name

English

BUTALBITAL COMPONENT OF TRIAPRIN

Common Name

English

BUTALBITAL COMPONENT OF SEDAPAP

Common Name

English

BUTALBITAL COMPONENT OF FIORICET

Common Name

English

BUTALBITAL [MI]

Common Name

English

TENCON COMPONENT BUTALBITAL

Common Name

English

TRIAPRIN COMPONENT BUTALBITAL

Common Name

English

LANORINAL COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL [USAN]

Common Name

English

BUTALBITAL [ORANGE BOOK]

Common Name

English

FIORINAL COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL COMPONENT OF FIORINAL

Common Name

English

BUTALBITAL COMPONENT OF BUCET

Common Name

English

PHRENILIN COMPONENT BUTALBITAL

Common Name

English

BANCAP COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL [HSDB]

Common Name

English

BUTALBITAL COMPONENT OF MEDIGESIC PLUS

Common Name

English

BUTALBITAL COMPONENT OF ESGIC

Common Name

English

BUTALBITAL COMPONENT OF BUTAPAP

Common Name

English

BUTALBITAL [INN]

Common Name

English

BUTALBITAL COMPONENT OF BANCAP

Common Name

English

BUTALBITAL COMPONENT OF ANOQUAN

Common Name

English

FIORICET COMPONENT BUTALBITAL

Common Name

English

SANDOPTAL

Brand Name

English

BUTALBITAL COMPONENT OF LANORINAL

Common Name

English

AXOTAL COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL CIII

Common Name

English

BUTALBITAL COMPONENT OF PHRENILIN

Common Name

English

SEDAPAP COMPONENT BUTALBITAL

Common Name

English

ESGIC COMPONENT BUTALBITAL

Common Name

English

BUCET COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL COMPONENT OF TENCON

Common Name

English

ANOQUAN COMPONENT BUTALBITAL

Common Name

English

BUTAPAP COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL CIII [USP-RS]

Common Name

English

FEMCET COMPONENT BUTALBITAL

Common Name

English

BUTALBITAL COMPONENT OF TRIAD

Common Name

English

BUTALBITAL COMPONENT OF AXOTAL

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 1308.32

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

NDF-RT

N0000175693

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

NCI_THESAURUS

C67084

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

DEA NO.

2100

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

NDF-RT

N0000008016

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

LIVERTOX

131

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

Code System Code Type Description

HSDB

7853

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

INN

7

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

DRUG BANK

DB00241

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

PRIMARY

IUPHAR

7138

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

EPA CompTox

77-26-9

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

MERCK INDEX

M2784

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

Merck Index

ECHA (EC/EINECS)

201-017-8

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

LACTMED

Butalbital

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

USP_CATALOG

1081002

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

USP-RS

DRUG CENTRAL

441

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

PRIMARY

RXCUI

19860

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

RxNorm

MESH

C004470

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

ChEMBL

CHEMBL454

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

PRIMARY

NCI_THESAURUS

C47425

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

CAS

77-26-9

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

PRIMARY

FDA UNII

KHS0AZ4JVK

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

PUBCHEM

2481

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

WIKIPEDIA

Butalbital

Created by admin on Fri Jun 25 20:58:37 UTC 2021 , Edited by admin on Fri Jun 25 20:58:37 UTC 2021

PRIMARY

EVMPD

SUB05999MIG

Created by admin on Fri Jun 25 20:58:36 UTC 2021 , Edited by admin on Fri Jun 25 20:58:36 UTC 2021

PRIMARY

ACTIVE MOIETY


					KHS0AZ4JVK

BUTALBITAL

SALT/SOLVATE (PARENT)


					BBH31P2ABJ

BUTALBITAL SODIUM

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020232s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11279945

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020232s033lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/11279945

C_max

T_1/2

F_unbound