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butalbital

Trade name: fiornal

Small moleculeapproved

Approved

May 4, 1976

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. — NCATS

Clinical trial activity

2 trials · 3 clinical orgs · 55 marketing orgs

Phase 1
0
Phase 2
2
Phase 3
2
Phase 4
0

Earliest trial started Feb 1, 2008 (NCT00573170)

Timeline

1970s

  1. May 4, 1976

    Sandoz — Earliest FDA Approval

  2. May 4, 1976

    Sandoz — NDA Organization

  3. May 4, 1976

    Allergan — NDA Secondary Org

  4. Feb 21, 1979

    Watson Pharmaceuticals — Marketing Organization

  5. Jun 5, 1979

    Hikma — Marketing Organization

  6. Jul 25, 1979

    Actavis — Marketing Organization

1980s

  1. Apr 30, 1980

    Puracap Pharmaceutical — Marketing Organization

  2. Jul 30, 1980

    Fosun — Marketing Organization

  3. Dec 28, 1981

    Lannett Company, Inc. — Marketing Organization

  4. Nov 9, 1984

    Actavis — NDA Secondary Org

  5. Jan 24, 1985

    Specgx Llc — Marketing Organization

  6. Mar 27, 1985

    Graham Dm — Marketing Organization

  7. Mar 27, 1985

    Mallinckrodt — Marketing Organization

  8. Mar 27, 1985

    Avon Products — Marketing Organization

  9. Jun 19, 1985

    Bausch Health Companies — Marketing Organization

  10. Oct 17, 1985

    Mayrand — Marketing Organization

  11. Mar 17, 1986

    Mayne Pharma — Marketing Organization

  12. Mar 17, 1986

    Dr. Reddy's Laboratories — Marketing Organization

  13. Oct 1, 1986

    Shire — Marketing Organization

  14. Jan 21, 1987

    Mikart — Marketing Organization

  15. Jul 2, 1987

    Dunhall Pharmaceuticals — Marketing Organization

1990s

  1. May 15, 1990

    International Minerals and Chemical Corporation — Marketing Organization

  2. Oct 26, 1990

    SmithKline Beecham — NDA Secondary Org

  3. Aug 31, 1998

    Jerome Stevens Pharmaceuticals — Marketing Organization

2000s

  1. Jul 23, 2001

    Able Laboratories — Marketing Organization

  2. Nov 30, 2001

    LGM Pharma — Marketing Organization

  3. Apr 22, 2002

    Vintage — Marketing Organization

  4. Jul 29, 2005

    Sun Pharmaceuticals — Marketing Organization

  5. Jun 13, 2007

    Nostrum Laboratories — Marketing Organization

  6. Jan 1, 2008

    Earliest Phase 3 Sponsor(trial)

  7. Dec 1, 2008

    Novast Labs — Marketing Organization

  8. Dec 23, 2008

    Mirror Pharms — Marketing Organization

  9. Nov 16, 2009

    Nexgen Pharma, Inc — Marketing Organization

2010s

  1. Oct 30, 2015

    County Line — Marketing Organization

  2. Oct 30, 2015

    Alvogen — Marketing Organization

  3. Dec 4, 2015

    Larken Labs Inc — Marketing Organization

  4. Sep 22, 2016

    Pharmaceutics International, Inc. — Marketing Organization

  5. Sep 22, 2016

    Esteve Labs — Marketing Organization

  6. Sep 22, 2016

    Strides Pharma Science — Marketing Organization

  7. Oct 28, 2016

    Nuvo Research Inc. — Marketing Organization

  8. Aug 4, 2017

    Xspire Pharma — Marketing Organization

  9. Aug 4, 2017

    Wraser Pharmaceuticals — Marketing Organization

  10. Sep 26, 2018

    Abhai LLC — Marketing Organization

  11. Sep 26, 2018

    Aurobindo Pharma — Marketing Organization

  12. Nov 22, 2019

    Granules India — Marketing Organization

2020s

  1. Jul 1, 2020

    Taro Pharmaceuticals — Marketing Organization

  2. Jul 17, 2020

    Nesher Pharms — Marketing Organization

  3. Jul 17, 2020

    Zydus Discovery DMCC — Marketing Organization

  4. Aug 13, 2021

    Senores Pharms — Marketing Organization

  5. Nov 17, 2021

    RiconPharma — Marketing Organization

  6. Aug 16, 2022

    AACE PHARMS — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

Approval history

  • approvedMay 4, 1976

Chemistry & pharmacology

Loading structure…

SMILES

CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O
Mol. weight
224.2563 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 5-(2-methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
  • 5-(2-methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
  • 5-allyl-5-(2'-methyl-n-propyl) barbituric acid
  • 5-allyl-5-(2'-methyl-n-propyl) barbituric acid
  • 5-allyl-5-(2-methylpropyl)barbituric acid
  • 5-allyl-5-(2-methylpropyl)barbituric acid
  • 5-allyl-5-isobutyl-2,4,6(1h,3h,5h)-pyrimidinetrione
  • 5-allyl-5-isobutyl-2,4,6(1h,3h,5h)-pyrimidinetrione
  • 5-allyl-5-isobutylbarbituric acid
  • 5-allyl-5-isobutylbarbituric acid
  • 5-allyl-5-isobutylbarbituric acid
  • 5-allyl-5-isobutyl-pyrimidine-2,4,6-trione
  • 5-allyl-5-isobutyl-pyrimidine-2,4,6-trione
  • alisobumal
  • alisobumal
  • alisobumal
  • alisobumal
  • alisobumal
  • allylbarbital
  • allylbarbital
  • allylbarbital
  • allylbarbital
  • allylbarbitone
  • allylbarbitone
  • allylbarbitone
  • allylbarbituric acid
  • allylbarbituric acid
  • allylbarbituric acid
  • allylisobutylbarbital
  • allylisobutylbarbituric acid
  • butalbarbital
  • butalbarbital
  • butalbarbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital
  • butalbital, monosodium salt
  • butalbitalum
  • butalbitalum
  • iso-butylallylbarbituric acid
  • iso-butylallylbarbituric acid
  • isobutylallylbarbituric acid
  • itobarbital
  • itobarbital
  • itobarbital
  • itobarbital
  • sandoptal
  • sandoptal
  • tetrallobarbital
  • tetrallobarbital
  • tetrallobarbital

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07093697Phase 3Mar 28, 2024Daewon Pharmaceutical Co., Ltd., Korea University
NCT00573170Phase 3Feb 1, 2008GlaxoSmithKline
Showing 2 of 2 trials
Page 1 / 1

Organizations

Research & Development (3)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Daewon Pharmaceutical Co., Ltd.For profit1112024
GlaxoSmithKlineFor profit1112008
Korea UniversityAcademic/Hospital1012024
3 organizations
Page 1 / 1

Marketing (63)

OrganizationOrg typeRelationshipDate
AACE PHARMSFor profitMKTGAug 16, 2022
Abhai LLCFor profitMKTGSep 26, 2018
Able LaboratoriesFor profitMKTGJul 23, 2001
ActavisFor profitNDA2Nov 9, 1984
ActavisFor profitMKTGJul 25, 1979
AllerganFor profitNDA2May 4, 1976
AlvogenFor profitMKTGOct 30, 2015
Aurobindo PharmaFor profitMKTGSep 26, 2018
Avon ProductsFor profitMKTGMar 27, 1985
Bausch Health CompaniesFor profitMKTGJun 19, 1985
County LineFor profitMKTGOct 30, 2015
Dr. Reddy's LaboratoriesFor profitMKTGMar 17, 1986
Dunhall PharmaceuticalsFor profitMKTGJul 2, 1987
Esteve LabsFor profitMKTGSep 22, 2016
Forest LaboratoriesFor profitMKTG—
FosunFor profitMKTGJul 30, 1980
Graham DmFor profitMKTGMar 27, 1985
Granules IndiaFor profitSYNDec 1, 2008
Granules IndiaFor profitMKTGNov 22, 2019
HalseyFor profitMKTG—
HikmaFor profitSYNOct 28, 1998
HikmaFor profitMKTGJun 5, 1979
HikmaFor profitSYNJun 12, 1995
International Minerals and Chemical CorporationFor profitMKTGMay 15, 1990
IvaxFor profitMKTG—
Jerome Stevens PharmaceuticalsFor profitMKTGAug 31, 1998
LGM PharmaFor profitMKTGNov 30, 2001
Laboratoires GilbertFor profitMKTG—
Lannett Company, Inc.For profitMKTGDec 28, 1981
Lannett Company, Inc.For profitSYNSep 13, 2012
Larken Labs IncFor profitMKTGDec 4, 2015
MallinckrodtFor profitMKTGMar 27, 1985
Mayne PharmaFor profitMKTGMar 17, 1986
MayrandFor profitMKTGOct 17, 1985
MikartFor profitMKTGJan 21, 1987
Mirror PharmsFor profitMKTGDec 23, 2008
Nesher PharmsFor profitMKTGJul 17, 2020
Nexgen Pharma, IncFor profitMKTGNov 16, 2009
Nexgen Pharma, IncFor profitSYNNov 30, 2001
Nostrum LaboratoriesFor profitMKTGJun 13, 2007
Novast LabsFor profitMKTGDec 1, 2008
Nuvo Research Inc.For profitMKTGOct 28, 2016
Pharmaceutics International, Inc.For profitMKTGSep 22, 2016
Puracap PharmaceuticalFor profitMKTGApr 30, 1980
Quantum PharmaceuticalFor profitMKTG—
RiconPharmaFor profitMKTGNov 17, 2021
SandozFor profitNDAMay 4, 1976
Savage LabsFor profitMKTG—
Senores PharmsFor profitMKTGAug 13, 2021
ShireFor profitMKTGOct 1, 1986
SmithKline BeechamFor profitNDA2Oct 26, 1990
Specgx LlcFor profitMKTGJan 24, 1985
Strides Pharma ScienceFor profitMKTGSep 22, 2016
Sun PharmaceuticalsFor profitMKTGJul 29, 2005
Taro PharmaceuticalsFor profitMKTGJul 1, 2020
Taro PharmaceuticalsFor profitSYNJul 1, 2020
US CHEMFor profitMKTG—
VintageFor profitMKTGApr 22, 2002
VintageFor profitSYNMar 5, 1999
Watson PharmaceuticalsFor profitMKTGFeb 21, 1979
Wraser PharmaceuticalsFor profitMKTGAug 4, 2017
Xspire PharmaFor profitMKTGAug 4, 2017
Zydus Discovery DMCCFor profitMKTGJul 17, 2020