General Information of Drug (ID: DMAQBKX)

Drug Name
Alpha-Hydroxy-Midazolam Drug Info
Synonyms
1'-hydroxymidazolam; 1-Hydroxymidazolam; alpha-Hydroxymidazolam; 1-Hydroxymethylmidazolam; 59468-90-5; UNII-E5142BN92Z; ALPHA-HYDROXY-MIDAZOLAM; CHEMBL1188; QHSMEGADRFZVNE-UHFFFAOYSA-N; E5142BN92Z; C18H13ClFN3O; 1-OH-Mdz; 8-Chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-1-methanol; [8-chloro-6-(2-fluorophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepin-1-yl]methanol; 8-Chloro-6-(2-fluorophenyl)-4H-imidazo(1,5-a)(1,4)benzodiazepine-1-methanol; 1'-Hydroxy Midazolam; AC1L32ZB; SCHEMBL7310758; DTXSID50208175
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
107917
ChEBI ID
CHEBI:145330
CAS Number
CAS 59468-90-5
TTD Drug ID
DMAQBKX

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Clinical Trial Drug(s)
Investigative Drug(s)
Approved Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [4]
PMX-53 DMZUAJ4 Atopic dermatitis EA80 Phase 2 [5]
BMS-536924 DMXJB4N Discovery agent N.A. Investigative [6]
Heme DMGC287 Discovery agent N.A. Investigative [7]
ML-3163 DM3S5UC Discovery agent N.A. Investigative [8]
6-(3-Hydroxy-phenyl)-naphthalen-2-ol DMH8WA2 Discovery agent N.A. Investigative [9]
2-(2-(4-tert-Butylphenylthio)ethyl)-1H-imidazole DMZVBPG Discovery agent N.A. Investigative [10]
ML-3375 DMXJY6W Discovery agent N.A. Investigative [8]
ML-3403 DMTQWI8 Discovery agent N.A. Investigative [8]
4-[5-(3-Hydroxyphenyl)-3-thienyl]-2-methylphenol DM7ERYJ Discovery agent N.A. Investigative [11]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [12]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [13]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [14]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [15]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [16]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [16]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [17]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [18]
Capsaicin DMGMF6V Back pain ME84.Z Approved [19]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [20]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 3A5 (CYP3A5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [12]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [13]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [18]
Ritonavir DMU764S Human immunodeficiency virus infection 1C62 Approved [18]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [21]
Omeprazole DM471KJ Cystic fibrosis CA25 Approved [22]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [23]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [24]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [25]
Hydrocortisone DMGEMB7 Acne vulgaris ED80 Approved [26]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Albendazole monooxygenase (CYP3A4) TTXV4FI CP3A4_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Regulation of Drug Effects [2]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Biotransformations [3]

References

1 Design and synthesis of a new fluorescent probe for cytochrome P450 3A4 (CYP 3A4). Bioorg Med Chem Lett. 2003 Nov 3;13(21):3643-5.
2 Expression of the human CYP3A4 gene in the small intestine of transgenic mice: in vitro metabolism and pharmacokinetics of midazolam. Drug Metab Dispos. 2003 May;31(5):548-58. doi: 10.1124/dmd.31.5.548.
3 Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes. Biochem Pharmacol. 2008 Mar 15;75(6):1426-37. doi: 10.1016/j.bcp.2007.11.012. Epub 2007 Dec 4.
4 Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues. Eur J Med Chem. 2008 Aug;43(8):1621-31.
5 Peptidomimetic C5a receptor antagonists with hydrophobic substitutions at the C-terminus: increased receptor specificity and in vivo activity. Bioorg Med Chem Lett. 2006 Oct 1;16(19):5088-92.
6 Discovery and evaluation of 4-(2-(4-chloro-1H-pyrazol-1-yl)ethylamino)-3-(6-(1-(3-fluoropropyl)piperidin-4-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)py... J Med Chem. 2008 Oct 9;51(19):5897-900.
7 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
8 Novel substituted pyridinyl imidazoles as potent anticytokine agents with low activity against hepatic cytochrome P450 enzymes. J Med Chem. 2003 Jul 17;46(15):3230-44.
9 Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: potent and selective nonsteroidal inhibitors... J Med Chem. 2008 Apr 10;51(7):2158-69.
10 Role of hydrophobic substituents on the terminal nitrogen of histamine in receptor binding and agonist activity: development of an orally active hi... J Med Chem. 2010 May 13;53(9):3840-4.
11 New insights into the SAR and binding modes of bis(hydroxyphenyl)thiophenes and -benzenes: influence of additional substituents on 17beta-hydroxyst... J Med Chem. 2009 Nov 12;52(21):6724-43.
12 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
13 Characterization of the structural determinants required for potent mechanism-based inhibition of human cytochrome P450 1A1 by cannabidiol. Chem Biol Interact. 2014 May 25;215:62-8.
14 Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells. Toxicol Sci. 2006 Jul;92(1):51-60.
15 The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. Antimicrob Agents Chemother. 2004 Sep;48(9):3272-8.
16 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
17 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
18 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
19 Studies of the toxicological potential of capsinoids, XIII: inhibitory effects of capsaicin and capsinoids on cytochrome P450 3A4 in human liver microsomes. Int J Toxicol. 2010 Mar;29(2 Suppl):22S-6S.
20 Investigation of the effects of axitinib on the pharmacokinetics of loperamide and its main metabolite N-demethylated loperamide in rats by UPLC-MS/MS. Chem Biol Interact. 2019 Sep 1;310:108744. doi: 10.1016/j.cbi.2019.108744. Epub 2019 Jul 9.
21 Contribution of CYP3A5 to hepatic and renal ifosfamide N-dechloroethylation. Drug Metab Dispos. 2005 Jul;33(7):1074-81. doi: 10.1124/dmd.104.002279. Epub 2005 Apr 8.
22 Use of mRNA expression to detect the induction of drug metabolising enzymes in rat and human hepatocytes. Toxicol Appl Pharmacol. 2009 Feb 15;235(1):86-96.
23 Induction of human cytochrome P450 3A enzymes in cultured placental cells by thalidomide and relevance to bioactivation and toxicity. J Toxicol Sci. 2017;42(3):343-348.
24 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
25 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
26 Induction of hepatic CYP3A enzymes by pregnancy-related hormones: studies in human hepatocytes and hepatic cell lines. Drug Metab Dispos. 2013 Feb;41(2):281-90.