chlordiazepoxide
Trade name: librium
Approved
Feb 24, 1960
Chlordiazepoxide (trade name Librium) is a sedative and hypnotic medication of the benzodiazepine class. Chlordiazepoxide is indicated for the management of anxiety disorders or for the short-term relief of symptoms of anxiety, withdrawal symptoms of acute alcoholism, and preoperative apprehension and anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. The effectiveness of Librium in long-term use, that is, more than 4 months, has not been assessed by systematic clinical studies. Chlordiazepoxide acts on benzodiazepine allosteric sites that are part of the GABAA receptor/ion-channel complex and this results in an increased binding of the inhibitory neurotransmitter GABA to the GABAA receptor thereby producing inhibitory effects on the central nervous system and body similar to the effects of other benzodiazepines. Chlordiazepoxide act via micromolar benzodiazepine binding sites as Ca2+ channel blockers and significantly inhibit depolarization-sensitive Calcium uptake in animal nerve terminal preparations. The withdrawal of chlordiazepoxide during pregnancy and breastfeeding is recommended, as chlordiazepoxide rapidly crosses the placenta and also is excreted in breast milk. Chlordiazepoxide is a long-acting benzodiazepine drug. The half-life of Chlordiazepoxide is 5 – 30 hours but has an active benzodiazepine metabolite (desmethyldiazepam), which has a half-life of 36 – 200 hours. The necessity of discontinuing therapy because of undesirable effects has been rare. Drowsiness, ataxia and confusion have been reported in some patients — particularly the elderly and debilitated. While these effects can be avoided in almost all instances by proper dosage adjustment, they have occasionally been observed at the lower dosage ranges. In a few instances syncope has been reported. — NCATS
Clinical trial activity
4 trials · 5 clinical orgs · 47 marketing orgs
Earliest trial started Jun 1, 2002 (NCT00516854)
Timeline
1960s
- Feb 24, 1960
Earliest FDA Approval
- Feb 24, 1960
Bausch Health Companies — NDA Secondary Org
- Jul 21, 1961
Bausch Health Companies — First NDA Organization
- Jul 21, 1961
Bausch Health Companies — NDA Organization
- Jul 21, 1961
Bausch Health Companies — Marketing Organization
- Jul 28, 1966
Roche — Marketing Organization
- Jul 28, 1966
Roche — NDA Secondary Org
1970s
- Apr 21, 1976
Alta Pharma — Marketing Organization
- May 11, 1976
Rachelle Pharmaceuticals — Marketing Organization
- Jun 10, 1976
Barr Laboratories — Marketing Organization
- Jun 15, 1976
Upsher-Smith Laboratories — Marketing Organization
- Jun 15, 1976
Chartwell Pharmaceuticals — Marketing Organization
- Jul 2, 1976
Roxane Laboratories — Marketing Organization
- Aug 24, 1976
Parke-Davis — Marketing Organization
- Aug 24, 1976
Warner Lambert — Marketing Organization
- Sep 2, 1976
John J. Ferrante — Marketing Organization
- Apr 6, 1977
West-Ward Pharmaceutical — Marketing Organization
- Jun 30, 1977
Abbott — Marketing Organization
- Dec 12, 1977
Impax Laboratories — Marketing Organization
- Dec 23, 1977
Heritage Pharma — Marketing Organization
- Dec 23, 1977
Chartwell Pharmaceuticals — NDA Secondary Org
- Sep 8, 1978
Watson Pharmaceuticals — Marketing Organization
1980s
- Feb 4, 1981
Teva — Marketing Organization
- Jun 10, 1981
Mylan — Marketing Organization
- May 19, 1982
Lederle — Marketing Organization
- May 19, 1982
American Cyanamid — Marketing Organization
- Jan 3, 1983
Boehringer Ingelheim — Marketing Organization
- Mar 28, 1983
Vanguard — Marketing Organization
- Jun 9, 1983
Ascot Pharmaceuticals — Marketing Organization
- Apr 25, 1985
Superpharm — Marketing Organization
- Dec 10, 1986
Frontida BioPharm — Marketing Organization
- Dec 10, 1986
UNITED RES LABS — Marketing Organization
- Dec 10, 1986
ANDA Repository — Marketing Organization
- May 9, 1988
Par Pharmaceuticals — Marketing Organization
- May 9, 1988
Strides Pharma Science — Marketing Organization
2000s
- Jan 1, 2003
Earliest Phase 3 Sponsor(trial)
2010s
- Jan 1, 2010
Earliest Phase 2 Sponsor(trial)
2020s
- Jul 7, 2020
Sunrise Medical Research, Inc. — Marketing Organization
- Jul 7, 2020
Nuvo Research Inc. — Marketing Organization
- Jul 29, 2020
Misemer Pharmaceutical — Marketing Organization
- Oct 20, 2020
Pharma Life Sciences LLC — Marketing Organization
- Oct 20, 2020
Eci Pharmaceuticals Llc — Marketing Organization
- Apr 26, 2021
Alkem Labs Ltd — Marketing Organization
- May 10, 2021
Dr. Reddy's Laboratories — Marketing Organization
- Oct 25, 2021
Amneal Pharmaceuticals — Marketing Organization
- Feb 2, 2022
Micro Labs Ltd India — Marketing Organization
- Jul 29, 2022
Corepharma — Marketing Organization
- Sep 14, 2023
Aurobindo Pharma — Marketing Organization
- Sep 15, 2023
Alembic — Marketing Organization
- Dec 14, 2023
Torrent Pharmaceuticals Limited — Marketing Organization
- Jul 8, 2024
Winder Labs Llc — 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
Combination products
librax
with clidinium
limbitrol ds
with amitriptyline
Also known as limbitrol
menrium
Approval history
- approvedPriority reviewFeb 24, 1960
Chemistry & pharmacology
SMILES
CNC1=Nc2ccc(Cl)cc2C(c2ccccc2)=[N+]([O-])C1- Mol. weight
- 299.76 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL451 ↗
- WikipediaChlordiazepoxide ↗
- NCATS6RZ6XEZ3CR ↗
- ChEMBLCHEMBL1200703 ↗
Also known as
- 7-chloro-2-methylamino-5-phenyl-3h-1,4-benzodiazepin-4-oxide
- 7-chloro-2-methylamino-5-phenyl-3h-1,4-benzodiazepin-4-oxide
- a-poxide
- a-poxide
- chloradiazepoxide
- chloradiazepoxide
- chlordiazachel
- chlordiazachel
- chlordiazepoxid
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide
- chlordiazepoxide base
- chlordiazepoxide base
- chlordiazepoxide hcl
- chlordiazepoxide hcl
- chlordiazepoxide hcl
- chlordiazepoxide hydrochloride
- chlordiazepoxide hydrochloride
- chlordiazepoxide hydrochloride
- chlordiazepoxide hydrochloride
- chlordiazepoxidum
- chlordiazepoxidum
- chloridazepoxide
- chlorodiazepoxide
- clopoxide
- clopoxide
- clopoxide
- clopoxide chloride
- clopoxide chloride
- helogaphen
- helogaphen
- librelease
- librelease
- libritabs
- libritabs
- librium
- librium
- librium
- lygen
- lygen
- methaminodiazepoxide
- methaminodiazepoxide
- methaminodiazepoxide
- multum
- multum
- risolid
- risolid
- ro-50690
- ro-50690
- ro-5-0690
- ro-5-0690
- sarlib
- trakipeal
- trakipeal
- tropium
- tropium
- zeisin
- zeisin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01109030 | Phase 2/Phase 3 (Phase 3) | Apr 1, 2010 | Isfahan University |
| NCT01573052 | Phase 4 | Mar 1, 2004 | Department of Veteran Affairs |
| NCT00136617 | Phase 3 | Aug 1, 2003 | University of Copenhagen |
| NCT00516854 | N/A | Jun 1, 2002 | Government of Hong Kong, The University of Hong Kong |
Organizations
Research & Development (5)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Department of Veteran Affairs | Government | 1 | 1 | 1 | 2004 |
| Government of Hong Kong | Government | 1 | 1 | 1 | 2002 |
| Isfahan University | Academic/Hospital | 1 | 1 | 1 | 2010 |
| The University of Hong Kong | Academic/Hospital | 1 | 0 | 1 | 2002 |
| University of Copenhagen | Academic/Hospital | 1 | 1 | 1 | 2003 |
Marketing (60)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ANDA Repository | For profit | MKTG | Dec 10, 1986 |
| Abbott | For profit | MKTG | Jun 30, 1977 |
| Alembic | For profit | MKTG | Sep 15, 2023 |
| Alembic | For profit | SYN | Sep 15, 2023 |
| Alkem Labs Ltd | For profit | MKTG | Apr 26, 2021 |
| Alta Pharma | For profit | MKTG | Apr 21, 1976 |
| American Cyanamid | For profit | MKTG | May 19, 1982 |
| Amneal Pharmaceuticals | For profit | MKTG | Oct 25, 2021 |
| Ascot Pharmaceuticals | For profit | MKTG | Jun 9, 1983 |
| Aurobindo Pharma | For profit | MKTG | Sep 14, 2023 |
| Barr Laboratories | For profit | MKTG | Jun 10, 1976 |
| Bausch Health Companies | For profit | SYN | Sep 1, 1966 |
| Bausch Health Companies | For profit | NDA2 | Feb 24, 1960 |
| Bausch Health Companies | For profit | NDA | Jul 21, 1961 |
| Bausch Health Companies | For profit | SYN | Jul 21, 1961 |
| Bausch Health Companies | For profit | MKTG | Jul 21, 1961 |
| Boehringer Ingelheim | For profit | MKTG | Jan 3, 1983 |
| Chartwell Pharmaceuticals | For profit | MKTG | Jun 15, 1976 |
| Chartwell Pharmaceuticals | For profit | NDA2 | Dec 23, 1977 |
| Corepharma | For profit | MKTG | Jul 29, 2022 |
| Dow Chemical | For profit | MKTG | — |
| Dr. Reddy's Laboratories | For profit | MKTG | May 10, 2021 |
| Eci Pharmaceuticals Llc | For profit | MKTG | Oct 20, 2020 |
| Frontida BioPharm | For profit | MKTG | Dec 10, 1986 |
| Halsey | For profit | MKTG | — |
| Heritage Pharma | For profit | MKTG | Dec 23, 1977 |
| Heritage Pharma | For profit | SYN | Dec 16, 1988 |
| Impax Laboratories | For profit | MKTG | Dec 12, 1977 |
| John J. Ferrante | For profit | MKTG | Sep 2, 1976 |
| Lederle | For profit | MKTG | May 19, 1982 |
| MM Pharma | For profit | MKTG | — |
| Micro Labs Ltd India | For profit | MKTG | Feb 2, 2022 |
| Misemer Pharmaceutical | For profit | MKTG | Jul 29, 2020 |
| Mylan | For profit | MKTG | Jun 10, 1981 |
| Mylan | For profit | SYN | Dec 10, 1986 |
| Nuvo Research Inc. | For profit | MKTG | Jul 7, 2020 |
| Par Pharmaceuticals | For profit | MKTG | May 9, 1988 |
| Parke-Davis | For profit | MKTG | Aug 24, 1976 |
| Pharma Life Sciences LLC | For profit | MKTG | Oct 20, 2020 |
| Puracap Pharmaceutical | For profit | MKTG | — |
| Rachelle Pharmaceuticals | For profit | MKTG | May 11, 1976 |
| Roche | For profit | MKTG | Jul 28, 1966 |
| Roche | For profit | NDA2 | Jul 28, 1966 |
| Roxane Laboratories | For profit | MKTG | Jul 2, 1976 |
| Strides Pharma Science | For profit | MKTG | May 9, 1988 |
| Sunrise Medical Research, Inc. | For profit | MKTG | Jul 7, 2020 |
| Superpharm | For profit | MKTG | Apr 25, 1985 |
| Teva | For profit | MKTG | Feb 4, 1981 |
| Teva | For profit | SYN | Dec 16, 1988 |
| Teva | For profit | SYN | Nov 2, 2021 |
| Teva | For profit | SYN | Mar 7, 1975 |
| Torrent Pharmaceuticals Limited | For profit | MKTG | Dec 14, 2023 |
| UNITED RES LABS | For profit | MKTG | Dec 10, 1986 |
| Upsher-Smith Laboratories | For profit | MKTG | Jun 15, 1976 |
| Upsher-Smith Laboratories | For profit | SYN | Feb 24, 1976 |
| Vanguard | For profit | MKTG | Mar 28, 1983 |
| Warner Lambert | For profit | MKTG | Aug 24, 1976 |
| Watson Pharmaceuticals | For profit | MKTG | Sep 8, 1978 |
| West-Ward Pharmaceutical | For profit | MKTG | Apr 6, 1977 |
| Winder Labs Llc | For profit | MKTG | Jul 8, 2024 |