Chlordiazepoxide

Summary

Chlordiazepoxide (CHEMBL451) is an approved small-molecule anxiolytic drug (ATC N05BA02) targeting TRHR; indicated across 5 conditions including anxiety and alcohol abuse.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N05BA02
• Targets: 1 (TRHR)
• Indications: 5 conditions
• Clinical trials: 4
• Chemistry: 299.75 Da · C16H14ClN3O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL451
Name	Chlordiazepoxide
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	2712
ChEBI	CHEBI:3611
ATC	N05BA02
Molecular formula	C16H14ClN3O
Molecular weight	299.75
InChIKey	BUCORZSTKDOEKQ-UHFFFAOYSA-N

SMILES: CN=C1CN(C(=C2C=C(C=CC2=N1)Cl)C3=CC=CC=C3)O

IUPAC name: 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine

ChEBI definition: A benzodiazepine that is 3H-1,4-benzodiazepine 4-oxide substituted by a chloro group at position 7, a phenyl group at position 5 and a methylamino group at position 2.

Pharmacological roles (ChEBI): anxiolytic drug, sedative, anaesthesia adjuvant.

Also known as: Chlordiazepoxide, Chlordiazepoxide civ, Chlordiazepoxide component of limbitrol, Chlordiazepoxide component of menrium, Clordiazepoxido, Librelease, Libritabs, Sarlib, Trakipeal, Zeisin, chlordiazepoxide, Chlordiacepoxide

Parent form; salt/anhydrous children: CHEMBL1200703

Patent coverage: 10,256 distinct patent families (36,533 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 35,885 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
TRHR	TRH1 receptor	Antagonist	4.7	0%	P34981

Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: GABA-A receptor; anion channel, GABA-A receptor; anion channel, 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, Cholecystokinin receptor, Cholecystokinin receptor, Histamine H1 receptor, Kappa-type opioid receptor.

Bioactivity

ChEMBL activities: 33 potent at pChembl ≥ 5 of 37 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
O09028	6.7	IC50	200	nM	CHEMBL_ACT_361646
O09028	6.7	IC50	200	nM	CHEMBL_ACT_458757
O09028	6.7	IC50	200	nM	CHEMBL_ACT_890974
HRH1	6.68	Ki	208	nM	CHEMBL_ACT_7690456
O09028	6.61	IC50	248	nM	CHEMBL_ACT_1299203
GABRG2	6.56	Ki	275	nM	CHEMBL_ACT_86665
GABRG2	6.5	Ki	320	nM	CHEMBL_ACT_86666
O09028	6.48	IC50	330	nM	CHEMBL_ACT_852221
GABRG2	6.43	Ki	368	nM	CHEMBL_ACT_1126934
GABRG2	6.43	Ki	368	nM	CHEMBL_ACT_1488131
GABRG2	6.41	Ki	392	nM	CHEMBL_ACT_1126936
GABRG2	6.41	Ki	392	nM	CHEMBL_ACT_1488129
P16257	6.36	Ki	438	nM	CHEMBL_ACT_385482
O09028	6.36	IC50	442	nM	CHEMBL_ACT_664173
GABRG2	6.34	Ki	460	nM	CHEMBL_ACT_260703
GABRG2	6.34	Ki	460	nM	CHEMBL_ACT_86664
GABRG2	6.33	Ki	471	nM	CHEMBL_ACT_1126937
GABRG2	6.33	Ki	471	nM	CHEMBL_ACT_1488130
GABRG2	6.28	Ki	520	nM	CHEMBL_ACT_260705
GABRA1	6.25	Ki	560	nM	CHEMBL_ACT_86663
GABRA1	6.22	Ki	605	nM	CHEMBL_ACT_1126935
GABRA1	6.22	Ki	605	nM	CHEMBL_ACT_1488128
O09028	6.15	IC50	710	nM	CHEMBL_ACT_688942
GABRG2	6.13	Ki	740	nM	CHEMBL_ACT_260704
GABRA1	6.11	Ki	770	nM	CHEMBL_ACT_260702
P08219	6.1	IC50	790	nM	CHEMBL_ACT_105142
P62813	6.1	AC50	790	nM	CHEMBL_ACT_25130559
O09028	6.04	IC50	910	nM	CHEMBL_ACT_694167
P08219	5.96	IC50	1100	nM	CHEMBL_ACT_774551
HRH1	5.75	IC50	1795	nM	CHEMBL_ACT_7690455

Target pathways

Aggregated over 1 target gene(s): TRHR.

Top Reactome pathways

2 total, by targets touching each:

Pathway	Targets	Genes
Peptide ligand-binding receptors	1	TRHR
G alpha (q) signalling events	1	TRHR

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	1
phospholipase C-activating G protein-coupled receptor signaling pathway	1
signal transduction	1

Indications & clinical

Indications

5 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
anxiety	4	MONDO:0011918	EFO:0005230
anxiety disorder	4	MONDO:0005618	EFO:0006788
alcohol abuse	4	MONDO:0002046	MONDO:0007079
alcohol withdrawal	3	MONDO:0005433	EFO:0004777
major depressive disorder	2	MONDO:0002009	MONDO:0002009

Clinical trials

Total trials: 4.

Phase distribution

Phase	Trials
PHASE4	1
PHASE3	1
PHASE2/PHASE3	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01573052	PHASE4	COMPLETED	Gabapentin vs Chlordiazepoxide for Ambulatory Alcohol Withdrawal
NCT00136617	PHASE3	COMPLETED	Outpatient Treatment of Alcohol Withdrawal Syndrome
NCT01109030	PHASE2/PHASE3	COMPLETED	Pioglitazone as an Adjunct for Moderate to Severe Depressive Disorder
NCT00516854	Not specified	UNKNOWN	A Study of the Use of Combination of Anti-cholinergic and Minor Tranquilliser in the Treatment of Non-cardiac Chest Pain - a Double Blind Placebo Controlled Study

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

1 molecules share ≥1 primary target. Top 1 by shared-target count:

Molecule	Source	Status	Shared targets
PROTIRELIN	ChEMBL + PubChem	Phase 4 (approved)	TRHR