thiopental
Trade name: pentothal
Approved
Sep 23, 1959
Sodium thiopental (also known as Sodium Pentothal, thiopental) was discovered in 1930s by investigators working for Abbott Laboratories. Thiopental sodium was used for the induction of general anesthesia and is used as an adjunct to provide hypnosis during balanced anesthesia with other anesthetic agents, including analgesics and muscle relaxants. Thiopental sodium was also used as an adjunct for control of convulsive disorders of various etiology, including those caused by local anesthetics. Finally, thiopental sodium had been used to reduce the intracranial pressure in patients with increased intracranial pressure, if controlled ventilation is provided. Nevertheless, these prescriptions of drug were discontinued. In addition, this drug was banned for use in US executions. Thiopental sodium acts through the CNS with particular activity in the mesencephalic reticular activating system. It was shown, that mechanism of action of sodium thiopental via GABAA receptor. Thiopental 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
21 trials · 38 clinical orgs · 1 marketing orgs
Earliest trial started May 1, 2002 (NCT00622570)
Timeline
Indications
Approved for
Studied for
- Amnesia · Phase 1
- Anesthesia · Phase 4
- Anesthetics · Phase 2
- Brain Injuries, Traumatic · Phase 3
- Coronary Artery Disease · Phase 4
- Drug-Related Side Effects and Adverse Reactions · Phase 3
- Heart Valve Diseases · Phase 4
- Hepatectomy · Phase 3
- Infertility · Phase 4
- Memory Disorders · Phase 1
- Neoplasms · Phase 3
- Pain · Phase 3
- Palonosetron · Phase 4
- Peripheral Nervous System Diseases · Phase 3
- Postoperative Nausea and Vomiting · Phase 4
- Postoperative Pain · Phase 4
- Shock, Septic · Phase 3
- Status Epilepticus · Phase 3
- Strabismus · Phase 2
Mechanism of action
- GABA-A receptor; anion channelPOSITIVE ALLOSTERIC MODULATOR
GABA-A receptor; anion channel positive allosteric modulator
Barbiturate site
- Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1) ↗
- Gamma-aminobutyric acid receptor subunit beta-2 (GABRB2) ↗
- Gamma-aminobutyric acid receptor subunit gamma-2 (GABRG2) ↗
- Gamma-aminobutyric acid receptor subunit beta-3 (GABRB3) ↗
- Gamma-aminobutyric acid receptor subunit alpha-4 (GABRA4) ↗
- Gamma-aminobutyric acid receptor subunit gamma-3 (GABRG3) ↗
- Gamma-aminobutyric acid receptor subunit theta (GABRQ) ↗
- Gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3) ↗
- Gamma-aminobutyric acid receptor subunit pi (GABRP) ↗
- Gamma-aminobutyric acid receptor subunit delta (GABRD) ↗
- Gamma-aminobutyric acid receptor subunit gamma-1 (GABRG1) ↗
- Gamma-aminobutyric acid receptor subunit beta-1 (GABRB1) ↗
- Gamma-aminobutyric acid receptor subunit epsilon (GABRE) ↗
- Gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2) ↗
- Gamma-aminobutyric acid receptor subunit alpha-5 (GABRA5) ↗
- Gamma-aminobutyric acid receptor subunit alpha-6 (GABRA6) ↗
- GABA receptor alpha-1 subunit
- GABA receptor beta-2 subunit
- GABA receptor alpha-4 subunit
- GABA receptor delta subunit
- GABA receptor alpha-5 subunit
- GABA receptor alpha-6 subunit
- GABA receptor beta-3 subunit
- GABA receptor alpha-3 subunit
- GABA receptor alpha-2 subunit
- GABA-A receptor; GABA-A site (alpha1/beta2 interface)
- GABA-A receptor; alpha-3/beta-3/gamma-2
- GABA-A receptor; alpha-1/beta-3/gamma-2
- GABA-A receptor; alpha-5/beta-3/gamma-2
- GABA-A receptor; alpha-2/beta-3/gamma-2
- GABA-A receptor; alpha-1/beta-2/gamma-2
- GABA-A receptor; alpha-6/beta-3/gamma-2
- GABA-A receptor; benzodiazepine site
- GABA-A receptor; agonist GABA site
- GABA A receptor alpha-2/beta-2/gamma-2
- GABA A receptor alpha-3/beta-2/gamma-2
- GABA A receptor alpha-6/beta-2/gamma-2
- GABA A receptor alpha-1/beta-1/gamma-2
- GABA A receptor alpha-4/beta-3/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta3/delta
- Gamma-aminobutyric acid receptor subunit alpha-1/ beta-1
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-3/ beta-2
- Gamma-aminobutyric acid receptor subunit alpha-3/ beta-3/gamma-3
- Gamma-aminobutyric acid receptor subunit alpha-3/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-3/beta-3/theta
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-3/gamma-3
- Gamma-aminobutyric acid receptor subunit alpha-6/beta-3
- GABA-A receptor alpha-1/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-1/beta-2/delta
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-2/delta
- Gamma-aminobutyric acid receptor subunit beta-1/beta-2
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-3
- Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-1/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-2/gamma-2
- Gamma-aminobutyric acid receptor subunit alpha-4/beta-1/delta
- Gamma-aminobutyric acid receptor subunit alpha-5/beta-2/gamma-2
- GABA receptor beta-1 subunit
- Gamma-aminobutyric acid receptor subunit alpha-2/beta-1/gamma-2
Approval history
- approvedPriority reviewSep 23, 1959
Chemistry & pharmacology
SMILES
CCCC(C)C1(CC)C(=O)NC(=S)NC1=O- Mol. weight
- 242.34 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
- Availability
- Discontinued
Oral
No
Parenteral
No
Topical
Yes
Sources
- ChEMBLCHEMBL441 ↗
- WikipediaSodium thiopental ↗
- NCATSJI8Z5M7NA3 ↗
- ChEMBLCHEMBL738 ↗
Also known as
- 2-thio-5-ethyl-5-sec-pentylbarbituric acid
- 2-thio-5-ethyl-5-sec-pentylbarbituric acid
- 5-ethyl-5-(1-methyl-butyl)-2-thioxo-dihydro-pyrimidine-4,6-dione
- 5-ethyl-5-(1-methyl-butyl)-2-thioxo-dihydro-pyrimidine-4,6-dione
- bitaryl
- bitaryl
- intraval
- intraval
- intraval sod
- omexolon
- omexolon
- penthiobarbital
- penthiobarbital
- penthiobarbital
- pentothal
- pentothal
- pentothal
- pentothal
- pentothal
- pentothal
- pentothal
- pentothal
- pentothiobarbital
- pentothiobarbital
- pentothiobarbital
- sodium pentothal
- sodium pentothal
- thiomebumal
- thiomebumal
- thiomebumal
- thiomebumal sodium
- thiomebumal sodium
- thiomebumalum
- thiomebumalum
- thionembutal
- thionembutal
- thionembutal
- thiopental
- thiopental
- thiopental
- thiopental
- thiopental
- thiopental
- thiopental
- thiopental
- thiopental
- (+-)-thiopental
- (+-)-thiopental
- thiopental sodium
- thiopental sodium
- thiopental sodium
- thiopental sodium
- thiopentobarbital
- thiopentobarbital
- thiopentobarbitone
- thiopentobarbitone
- thiopentobarbituric acid
- thiopentobarbituric acid
- thiopentone
- thiopentone
- thiopentone
- thiopentone
- tiopentale
- tiopentale
- trapanal
- trapanal
- trapanal
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT03104140 | Phase 3 | Apr 12, 2017 | Cairo University |
| NCT02813044 | N/A | Jun 1, 2016 | Yonsei University |
| NCT02809378 | Phase 4 | Jun 1, 2016 | Ajou University, CJ HealthCare Corp. |
| NCT02056236 | N/A | Apr 1, 2014 | Free University of Brussels, Medisch Spectrum Twente, Radboud University, Rijnstate Hospital, St. Antonius Hospital, Nieuwegein, University of Amsterdam, University of Groningen, University of Twente, VieCuri Medical Centre |
| NCT02486926 | N/A | Nov 1, 2012 | Hallym University |
| NCT01495949 | Phase 4 | Dec 1, 2011 | Mahidol University |
| NCT01318044 | Phase 1/Phase 2 (Phase 2) | Jan 1, 2011 | University Clinical Centre of Kosova |
| NCT01140100 | Phase 2 | Jun 8, 2010 | University of Tehran |
| NCT00965107 | Phase 4 | Sep 1, 2009 | TRYG Foundation, University of Copenhagen |
| NCT01526525 | Phase 4 | Jul 1, 2009 | Aristotle University of Thessaloniki, Gennimatas Hospital, Athens |
| NCT01930019 | N/A | Jun 1, 2009 | Government of Poland |
| NCT02377778 | Phase 4 | Jan 1, 2009 | Aristotle University of Thessaloniki |
| NCT00767767 | N/A | Oct 1, 2008 | Cornell University, National Institute of General Medical Sciences (NIGMS), National Institutes of Health (NIH) |
| NCT00471445 | Phase 3 | Oct 1, 2007 | National Cancer Institute (NCI), New York University, University of Rochester |
| NCT00265616 | Phase 3 | May 1, 2006 | Harvard University, University of Lausanne |
| NCT00611767 | N/A | Nov 1, 2005 | Department of Veteran Affairs, Yale University |
| NCT00142493 | Phase 1 | Sep 1, 2004 | Cornell University |
| NCT00219856 | Phase 3 | Aug 1, 2004 | Government of France, University of Rennes |
| NCT00478907 | Phase 2 | Mar 1, 2004 | feiz hospital, Isfahan University |
| NCT00379886 | N/A | Jan 1, 2003 | University of Copenhagen |
Organizations
Research & Development (38)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Aristotle University of Thessaloniki | Academic/Hospital | 2 | 1 | 1 | 2009 |
| Cornell University | Academic/Hospital | 2 | 2 | 2 | 2004 |
| University of Copenhagen | Academic/Hospital | 2 | 2 | 2 | 2003 |
| Ajou University | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Cairo University | Academic/Hospital | 1 | 1 | 1 | 2017 |
| CJ HealthCare Corp. | For profit | 1 | 0 | 1 | 2016 |
| Department of Veteran Affairs | Government | 1 | 0 | 1 | 2005 |
| feiz hospital | Academic/Hospital | 1 | 0 | 1 | 2004 |
| Fondo de Investigacion Sanitaria | Academic/Hospital | 1 | 0 | 1 | 2002 |
| Free University of Brussels | Academic/Hospital | 1 | 0 | 1 | 2014 |
| Gennimatas Hospital, Athens | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Government of France | Government | 1 | 0 | 1 | 2004 |
| Government of Poland | Government | 1 | 1 | 1 | 2009 |
| Hallym University | Academic/Hospital | 1 | 1 | 1 | 2012 |
| Harvard University | Academic/Hospital | 1 | 1 | 1 | 2006 |
| Hospital Universitari Son Dureta | Academic/Hospital | 1 | 1 | 1 | 2002 |
| Isfahan University | Academic/Hospital | 1 | 1 | 1 | 2004 |
| Mahidol University | Academic/Hospital | 1 | 1 | 1 | 2011 |
| Medisch Spectrum Twente | Academic/Hospital | 1 | 0 | 1 | 2014 |
| National Cancer Institute (NCI) | Government | 1 | 0 | 1 | 2007 |