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Compound Detail

CHEMBL451

CHLORDIAZEPOXIDE
💊 Approved Drug
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💊 Approved Drug
CNC1=Nc2ccc(Cl)cc2C(c2ccccc2)=[N+]([O-])C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL451
Name CHLORDIAZEPOXIDE
Phase Approved
Structure Type MOL
InChI Key ANTSCNMPPGJYLG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Chlordiazepoxide Chlordiazepoxide civ Chlordiazepoxide component of limbitrol Chlordiazepoxide component of limbitrol ds Chlordiazepoxide component of menrium Clordiazepoxido Librelease Libritabs Sarlib Trakipeal Zeisin
13
Targets
37
Activities
2
Assay Types
12
PK Parameters
20
Publications
11
Known Names
6
Indications
1
Mechanisms

Molecular Properties

299.8
MW (Da)
2.95
ALogP
3
HBA
1
HBD
50.5
PSA (Ų)
0.65
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1960
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product First in Class
USAN Year 1963

Extended Properties

Molecular Formula C16H14ClN3O
MW 299.76
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.40

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR GABA-A receptor; anion channel ✓ ✓

Indications

Alcoholism Anxiety Anxiety Anxiety Disorders Substance Withdrawal Syndrome Depressive Disorder, Major

ATC Classification

N05BA02
chlordiazepoxide
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 19 meas. best 6.68
IC50 18 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 6.7 6.4675 200.0 8
Histamine H1 receptor
CHEMBL231
 Ki 6.68 6.68 208.0 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
 Ki 6.56 6.3375 275.0 4
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
 Ki 6.5 6.41 320.0 4
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
 Ki 6.41 6.375 392.0 4
Translocator protein
CHEMBL4552
 Ki 6.36 6.36 438.0 1
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 6.25 6.2 560.0 4
GABA-A receptor; anion channel
CHEMBL2094107
 IC50 6.1 6.03 790.0 2
Unchecked
CHEMBL612545
 IC50 6.1 5.97 790.0 2
Unchecked
CHEMBL612545
 Ki 5.93 5.93 1164.0 1
Histamine H1 receptor
CHEMBL231
 IC50 5.75 5.75 1795.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.6 4.48 25000.0 2
Cholecystokinin receptor
CHEMBL2095185
 IC50 4.0 4.0 100000.0 1
Cholecystokinin receptor
CHEMBL2096986
 IC50 4.0 4.0 100000.0 1
Cavia porcellus
CHEMBL369
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.37 mL.min-1.kg-1 Homo sapiens
CL 0.37 mL.min-1.kg-1 Homo sapiens
CL 0.4 mL.min-1.kg-1 Homo sapiens
CL 0.37 mL.min-1.kg-1 Homo sapiens
CL 3.89 uL.min-1.(10^6cells)-1 Homo sapiens
CL 5.75 mL.min-1.g-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.04 - Homo sapiens
Fu 0.056 - Homo sapiens
Fu 0.056 - Homo sapiens
MRT 11.0 hr Homo sapiens
T1/2 8.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; anion channel IC50 = 200.0 nM 6.7 Inhibition of specific binding of 1.5 nM [3H]diazepam to rat brain benzodiazepin... 1967311
GABA-A receptor; anion channel IC50 = 200.0 nM 6.7 Concentration that inhibits binding of 1.5 nM [3H]diazepam to rat brain benzodia... 2540330
GABA-A receptor; anion channel IC50 = 200.0 nM 6.7 Inhibitory concentration against specific binding of [3H]diazepam to Benzodiazep... 2163452
Histamine H1 receptor Ki = 208.0 nM 6.68 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
GABA-A receptor; anion channel IC50 = 248.0 nM 6.61 In vitro for inhibition of [3H]diazepam towards Benzodiazepine receptor from rat 6113284
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 275.0 nM 6.56 Binding affinity by displacement of [3H]Ro-151788 from recombinant human gamma-a... 11960500
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 320.0 nM 6.5 Inhibition of [3H]Ro-151788 binding to human GABA A receptor (alpha-5-beta-3-gam... 11960500
GABA-A receptor; anion channel IC50 = 330.0 nM 6.48 Inhibition of [3H]flunitrazepam binding to GABA-A benzodiazepine receptor of rat... 2573731
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 368.0 nM 6.43 Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A recep... 15537339
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 368.0 nM 6.43 Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-a... 15125950
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 392.0 nM 6.41 Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A recep... 15537339
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 392.0 nM 6.41 Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-a... 15125950
GABA-A receptor; anion channel IC50 = 442.0 nM 6.36 Inhibition of binding of tritiated 3[H]diazepam radioligand to rat brain homogen... 6304314
Translocator protein Ki = 438.0 nM 6.36 Binding affinity against rat benzodiazepine (BZD) receptor 12372538
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 460.0 nM 6.34 Displacement of [3H]Ro-151788 from human Gamma-aminobutyric acid A receptor alph... 11960500
GABA-A receptor; alpha-2/beta-3/gamma-2 Ki = 460.0 nM 6.34 Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-2-beta-3-gamma-2 recept... 15084116
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 471.0 nM 6.33 Inhibition of [3H]-Ro- 15-1788 binding to recombinant human gamma-aminobutyric-a... 15125950
GABA-A receptor; alpha-3/beta-3/gamma-2 Ki = 471.0 nM 6.33 Displacement of [3H]-Ro- 15-1788 from human gamma-aminobutyric-acid GABA-A recep... 15537339
GABA-A receptor; alpha-5/beta-3/gamma-2 Ki = 520.0 nM 6.28 Displacement of [3H]-Ro- 15-1788 from human GABA-A alpha-5-beta-3-gamma-2 recept... 15084116
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 560.0 nM 6.25 Inhibition of [3H]Ro-151788 binding to human GABA A receptor (alpha-1-beta-3-gam... 11960500

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2573732 10.1021/jm00132a012 Rattus norvegicus 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
31473 10.1021/jm00208a008 Mus musculus 8
19630 10.1021/jm00218a009 Mus musculus 8
19361209 10.1021/jm900025h Rattus norvegicus 7
6131132 10.1021/jm00356a024 Mus musculus 6
7190614 10.1021/jm00181a013 Mus musculus 6
6716399 10.1021/jm00371a011 Mus musculus 6
26804 10.1021/jm00203a015 Mus musculus 5
1246046 10.1021/jm00223a041 Mus musculus 4
2836588 10.1021/jm00401a010 Mus musculus 4
15111 10.1021/jm00213a014 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
15111 10.1021/jm00213a014 Rattus norvegicus 3
6110780 10.1021/jm00133a006 Mus musculus 3
15125950 10.1016/j.bmcl.2004.03.054 GABA-A receptor; alpha-5/beta-3/gamma-2 3

Data from ChEMBL 36 via Core Engine