temazepam
Trade name: restoril
Approved
Feb 27, 1981
Temazepam is a benzodiazepine used as a hypnotic agent in the management of insomnia. Temazepam produces CNS depression at limbic, thalamic, and hypothalamic levels of the CNS. Temazepam increases the affinity of the neurotransmitter gamma-aminobutyric acid (GABA) for GABA receptors by binding to benzodiazepine receptors. Results are sedation, hypnosis, skeletal muscle relaxation, anticonvulsant activity, and anxiolytic action. Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. Temazepam is used for the short-term treatment of insomnia (generally 7-10 days). — NCATS
Clinical trial activity
6 trials · 7 clinical orgs · 17 marketing orgs
Earliest trial started Oct 1, 2005 (NCT00245661)
Timeline
1980s
- Feb 27, 1981
American Home Products — Earliest FDA Approval
- Feb 27, 1981
Specgx Llc — NDA Secondary Org
- Feb 27, 1981
American Home Products — NDA Organization
- Jul 10, 1986
Mylan — Marketing Organization
- Jul 10, 1986
Sun Pharmaceuticals — Marketing Organization
- Jul 10, 1986
Aurobindo Pharma — Marketing Organization
- Apr 21, 1987
Novel Anti-Infective Technologies, LLC — Marketing Organization
- Aug 7, 1987
Actavis — Marketing Organization
- Jan 12, 1988
Sandoz — Marketing Organization
- Jan 12, 1988
Chartwell Pharmaceuticals — Marketing Organization
- Sep 29, 1988
Duramed Research — Marketing Organization
1990s
- May 21, 1993
Watson Pharmaceuticals — Marketing Organization
2010s
- Jun 4, 2015
Prinston Inc — Marketing Organization
- May 23, 2016
Amneal Pharmaceuticals — Marketing Organization
- Nov 23, 2018
Alembic — Marketing Organization
2020s
- Aug 24, 2023
Alkem Labs Ltd — Marketing Organization
Indications
Mechanism of action
- GABA-A receptor; anion channelPOSITIVE ALLOSTERIC MODULATOR
GABA-A receptor; anion channel positive allosteric modulator
Benzodiazepine 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
- approvedFeb 27, 1981
Chemistry & pharmacology
SMILES
CN1C2=CC=C(Cl)C=C2C(=NC(O)C1=O)C3=CC=CC=C3- Mol. weight
- 300.74 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaTemazepam ↗
- NCATSCHB1QD2QSS ↗
- ChEMBLCHEMBL967 ↗
Also known as
- kentepam
- levanxene
- levanxol
- normison
- normison
- restoril
- restoril
- restoril
- (rs)-temazepam
- temaz
- temaz
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- temazepam
- wy-3917
- wy-3917
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT02374567 | Phase 3 | Jan 1, 2015 | Gottfried Wilhelm Leibniz Universität Hannover |
| NCT01519544 | N/A | Mar 1, 2012 | Harvard University |
| NCT02153788 | Phase 4 | Sep 1, 2009 | Duke University |
| NCT00940550 | Phase 1 | Jul 1, 2009 | Lundbeck, University of London |
| NCT00465972 | Phase 4 | Mar 1, 2007 | Duke University |
| NCT00245661 | Phase 3 | Oct 1, 2005 | Radboud University, Rijnstate Hospital |
Organizations
Research & Development (7)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Duke University | Academic/Hospital | 2 | 2 | 1 | 2007 |
| Gottfried Wilhelm Leibniz Universität Hannover | Academic/Hospital | 1 | 1 | 1 | 2015 |
| Harvard University | Academic/Hospital | 1 | 1 | 1 | 2012 |
| Lundbeck | For profit | 1 | 0 | 1 | 2009 |
| Radboud University | Academic/Hospital | 1 | 0 | 1 | 2005 |
| Rijnstate Hospital | Academic/Hospital | 1 | 1 | 1 | 2005 |
| University of London | Academic/Hospital | 1 | 1 | 1 | 2009 |
Marketing (18)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Actavis | For profit | MKTG | Aug 7, 1987 |
| Alembic | For profit | MKTG | Nov 23, 2018 |
| Alembic | For profit | SYN | Nov 23, 2018 |
| Alkem Labs Ltd | For profit | MKTG | Aug 24, 2023 |
| American Home Products | For profit | NDA | Feb 27, 1981 |
| Amneal Pharmaceuticals | For profit | MKTG | May 23, 2016 |
| Aurobindo Pharma | For profit | MKTG | Jul 10, 1986 |
| Chartwell Pharmaceuticals | For profit | MKTG | Jan 12, 1988 |
| Duramed Research | For profit | MKTG | Sep 29, 1988 |
| Mylan | For profit | MKTG | Jul 10, 1986 |
| Novel Anti-Infective Technologies, LLC | For profit | MKTG | Apr 21, 1987 |
| Prinston Inc | For profit | MKTG | Jun 4, 2015 |
| Quantum Pharmaceutical | For profit | MKTG | — |
| Sandoz | For profit | MKTG | Jan 12, 1988 |
| Specgx Llc | For profit | NDA2 | Feb 27, 1981 |
| Sun Pharmaceuticals | For profit | MKTG | Jul 10, 1986 |
| Upsher-Smith Laboratories | For profit | MKTG | — |
| Watson Pharmaceuticals | For profit | MKTG | May 21, 1993 |