MIDAZOLAM

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N05CD08
UNII R60L0SM5BC
EPA CompTox DTXSID5023320

Structure

InChI Key DDLIGBOFAVUZHB-UHFFFAOYSA-N
Smiles Cc1ncc2n1-c1ccc(Cl)cc1C(c1ccccc1F)=NC2
InChI
InChI=1S/C18H13ClFN3/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-9H,10H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H13ClFN3
Molecular Weight 325.77
AlogP 4.32
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 30.18
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 23.0

Bioactivity

Mechanism of Action Action Reference
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR ISBN Wikipedia Wikipedia Wikipedia
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit pi
Organism : Homo sapiens
O00591 ENSG00000094755
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit delta
Organism : Homo sapiens
O14764 ENSG00000187730
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-1
Organism : Homo sapiens
P14867 ENSG00000022355
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-1
Organism : Homo sapiens
P18505 ENSG00000163288
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-2
Organism : Homo sapiens
P18507 ENSG00000113327
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-3
Organism : Homo sapiens
P28472 ENSG00000166206
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-5
Organism : Homo sapiens
P31644 ENSG00000186297
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-3
Organism : Homo sapiens
P34903 ENSG00000011677
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-2
Organism : Homo sapiens
P47869 ENSG00000151834
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-2
Organism : Homo sapiens
P47870 ENSG00000145864
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-4
Organism : Homo sapiens
P48169 ENSG00000109158
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit epsilon
Organism : Homo sapiens
P78334 ENSG00000102287
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-6
Organism : Homo sapiens
Q16445 ENSG00000145863
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-1
Organism : Homo sapiens
Q8N1C3 ENSG00000163285
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-3
Organism : Homo sapiens
Q99928 ENSG00000182256
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit theta
Organism : Homo sapiens
Q9UN88 ENSG00000268089
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 8100 - 2470 100
Ion channel Ligand-gated ion channel GABA-A receptor
- - - 2 -
Membrane receptor
- - - 2 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 23
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 41700-41740 - - 12
Assay Description Organism Bioactivity Reference
Binding affinity against rat benzodiazepine (BZD) receptor None 2.0 nM
Binding affinity to rat benzodiazepine receptor None 2.0 nM
Inhibition of P-gp was determined using rhodamine-assay in human CaCo-2 cells None 12.0 %
Inhibition of CYP3A activity in orally dosed human Homo sapiens 95.0 %
TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical)(Digoxin: 5 uM, Midazolam: 100 uM) in Caco-2 cells None 74.0 %
Allosteric modulation of gamma-aminobutyric acid receptor A alpha1beta2gamma2S expressed in Xenopus oocytes assessed as potentiation of GABA-mediated chloride current by voltage clamp analysis None 143.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 32.9 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 6.7 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 22.7 %
Inhibition of human CYP3A4 at 10 uM Homo sapiens 99.46 %

Environmental Exposure

Environmental Exposure Map
Countries
Serbia
Slovenia

Cross References

Resources Reference
ChEBI 6931
ChEMBL CHEMBL655
DrugBank DB00683
DrugCentral 1802
FDA SRS R60L0SM5BC
Human Metabolome Database HMDB0014821
Guide to Pharmacology 3342
KEGG C07524
PDB 08J
PharmGKB PA450496
PubChem 4192
SureChEMBL SCHEMBL35061
ZINC ZINC000095626706
CONTENTS