liarozole: inhibits all-trans-retinoic acid 4-hydroxylase; effective against hormone-dependent and hormone-independent tumors; R 75251 is chlorohydrate of R 61405; a potent inhibitor of retinoic acid metabolism; USAN name - liarozole fumarate [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 60652 |
| CHEMBL ID | 389433 |
| CHEBI ID | 135316 |
| SCHEMBL ID | 18597 |
| SCHEMBL ID | 15944205 |
| MeSH ID | M0169552 |
| Synonym |
|---|
| liazal |
| r-75251 |
| liarozole |
| NCGC00181034-01 |
| r 61405 |
| r 085246 |
| r085246 , |
| liarozol [inn-spanish] |
| liarozolum [inn-latin] |
| r-085246 |
| liarozole [inn:ban] |
| r-61405 |
| 1h-benzimidazole, 5-((3-chlorophenyl)-1h-imidazol-1-ylmethyl)- |
| 115575-11-6 |
| CHEBI:135316 |
| CHEMBL389433 , |
| 6-[(3-chlorophenyl)-imidazol-1-ylmethyl]-1h-benzimidazole |
| 5-[(3-chlorophenyl)(1h-imidazol-1-yl)methyl]-1h-benzimidazole |
| UGFHIPBXIWJXNA-UHFFFAOYSA-N |
| 6-((3-chlorophenyl)(1h-imidazol-1-yl)methyl)-1h-benzo[d]imidazole |
| bdbm50176808 |
| 5-[(3-chloro-phenyl)-imidazol-1-yl-methyl]-1h-benzoimidazole |
| unii-k0q29tgv9y |
| liarozolum |
| k0q29tgv9y , |
| liarozol |
| gtpl5210 |
| 5-[(3-chlorophenyl)(1h-imidazol-1-yl)methyl]-1h-1,3-benzodiazole |
| SCHEMBL18597 |
| 1h-benzimidazole, 5-((3-chlorophenyl)-1h-imidazol-1-ylmethyl)-, (+/-)- |
| 6-((3-chlorophenyl)-1h-imidazol-1-ylmethyl)-1h-benzimidazole |
| liarozole [mi] |
| liarozole [mart.] |
| liarozole [inn] |
| liarozole [who-dd] |
| (+/-)-5-(m-chloro-.alpha.-imidazol-1-ylbenzyl)benzimidazole |
| DTXSID9048277 |
| SCHEMBL15944205 |
| r75251 |
| unii-17nyd2210b |
| unii-090y06w08h |
| bdbm50157605 |
| 172282-43-8 |
| liarozole, (+)- |
| 1h-benzimidazole, 5-((3-chlorophenyl)-1h-imidazol-1-ylmethyl)-, (-)- |
| 171849-18-6 |
| 1h-benzimidazole, 5-((3-chlorophenyl)-1h-imidazol-1-ylmethyl)-, (+)- |
| liarozole, (-)- |
| 17NYD2210B , |
| 090Y06W08H , |
| liarozole dihydrochloride, >=98% (hplc) |
| DB13066 |
| 5-((3-chlorophenyl)(1h-imidazol-1-yl)methyl)-1h-benzo[d]imidazole |
| FT-0745508 |
| Q15633974 |
| F81706 |
| MS-24483 |
| r75251 dihydrochloride |
| 1h-benzimidazole, 6-[(3-chlorophenyl)-1h-imidazol-1-ylmethyl]- |
| HY-106019 |
| CS-0024635 |
| AKOS040733598 |
Liarozole is an imidazole derivative that has been identified as an inhibitor of the cytochrome P450-dependent all-trans retinoid acid (RA) breakdown. Liarozole appears to be a promising treatment option in prostate cancer.
Liarozole has been reported to inhibit P450 enzymes responsible for the catabolism of retinoic acid. Liarozole was found to be effective in the treatment of chronic plaque psoriasis and ichthyoses.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Liarozole has been reported to inhibit P450 enzymes responsible for the catabolism of retinoic acid. " | ( Liarozole potentiates the cancer chemopreventive activity of and the up-regulation of gap junctional communication and connexin43 expression by retinoic acid and beta-carotene in 10T1/2 cells. Acevedo, P; Bertram, JS, 1995) | 3.18 |
| "Liarozole has been postulated by others (R." | ( Liarozole and 13-cis-retinoic acid anti-prostatic tumor activity. Fudge, K; Stearns, ME; Wang, M, 1993) | 2.45 |
| "Liarozole has already been found to be effective in the treatment of retinoid-responsive conditions such as chronic plaque psoriasis and ichthyoses." | ( Oral liarozole in the treatment of palmoplantar pustular psoriasis: a randomized, double-blind, placebo-controlled study. Bhushan, M; Burden, AD; Griffiths, CE; James, R; McElhone, K; Vanhoutte, FP, 2001) | 1.55 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Liarozole promotes differentiation of cancer cells by increasing the intratumoral levels of retinoic acid." | ( Liarozole--a novel treatment approach for advanced prostate cancer: results of a large randomized trial versus cyproterone acetate. Liarozole Study Group. Boccardo, F; Brune, D; Bruynseels, J; De Porre, P; Debruyne, FJ; Denis, L; Fradet, Y; Janssens, M; Johansson, JE; Marberger, JM; Murray, R; Rassweiler, J; Tyrrell, C; Vangeneugden, T, 1998) | 2.46 |
Lierozole fumarate (40 mg/kg, -60 min) reduced the elimination rate of 4-keto-RA. It prolonged the plasma half-life of the retinoid to 12 min, without affecting its distribution volume.
Liarozole's antitumor effects on ER positive mammary tumors merit further studies. In combination with tamoxifen, liarozole had neither an additive nor an antagonistic effect.
| Excerpt | Relevance | Reference |
|---|---|---|
| " Moreover, liarozole possessed antikeratinizing activity: when dosed subchronically (5-20 mg/kg, once daily for 3 days) to ovariectomized rats, the compound reversed the vaginal keratinization induced in these animals by estrogenic stimulation." | ( Liarozole, an inhibitor of retinoic acid metabolism, exerts retinoid-mimetic effects in vivo. Borghgraef, P; Coene, MC; Cools, W; Goossens, J; Janssen, PA; Stoppie, P; Van Nyen, G; Van Wauwe, J, 1992) | 2.12 |
| " injected RA from plasma: the half-life of RA increased from 27 min in control-treated animals to 43 min and 76 min after dosing with ketoconazole and R 75 251, respectively." | ( Effects of cytochrome P-450 inhibitors on the in vivo metabolism of all-trans-retinoic acid in rats. Coene, MC; Cools, W; Goossens, J; Monbaliu, J; Van Wauwe, JP, 1990) | 0.28 |
| "Continuous oral dosing with all-trans retinoic acid (RA) is associated with a progressive decrease in plasma drug concentrations that has been linked to relapse and retinoid resistance in patients with acute promyelocytic leukemia (APL)." | ( Modulation of all-trans retinoic acid pharmacokinetics by liarozole. Kris, MG; Miller, VA; Muindi, JR; Rigas, JR; Tong, WP; Venkatraman, E; Warrell, RP, 1994) | 0.53 |
| Class | Description |
|---|---|
| benzimidazoles | An organic heterocyclic compound containing a benzene ring fused to an imidazole ring. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 2.8184 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 25.1189 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Cytochrome P450 26A1 | Homo sapiens (human) | IC50 (µMol) | 3.2900 | 0.0051 | 3.4125 | 7.8000 | AID1191997; AID1248100; AID1290556; AID241210; AID282734; AID363251; AID593893; AID619521 |
| Cytochrome P450 1A2 | Homo sapiens (human) | IC50 (µMol) | 0.5400 | 0.0001 | 1.7740 | 10.0000 | AID619521 |
| Cytochrome P450 3A4 | Homo sapiens (human) | IC50 (µMol) | 0.3540 | 0.0001 | 1.7536 | 10.0000 | AID1248107; AID1290555 |
| Cytochrome P450 2D6 | Homo sapiens (human) | IC50 (µMol) | 4.7600 | 0.0000 | 2.0151 | 10.0000 | AID1248108 |
| Aromatase | Homo sapiens (human) | IC50 (µMol) | 0.0248 | 0.0000 | 1.2904 | 10.0000 | AID282900; AID479369 |
| 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial | Homo sapiens (human) | IC50 (µMol) | 0.0023 | 0.0023 | 0.3666 | 0.5200 | AID1160913 |
| Cytochrome P450 26B1 | Homo sapiens (human) | IC50 (µMol) | 0.0180 | 0.0005 | 1.9728 | 5.9000 | AID1290555 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Cytochrome P450 26A1 | Homo sapiens (human) | EC50 (µMol) | 7.0000 | 0.0050 | 3.5025 | 7.0000 | AID1799732 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1248100 | Inhibition of CYP26A1 in ATRA-induced human HL60 cell microsomes incubated for 30 mins in dark condition with NADPH and ATRA by HPLC method | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID1079949 | Proposed mechanism(s) of liver damage. [column 'MEC' in source] | |||
| AID1079943 | Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source] | |||
| AID1248103 | Growth inhibition of human HL60 cells at 10 uM incubated for 48 hrs in presence of 0.1 uM ATRA by MTT assay | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID593893 | Inhibition of CYP26A1 in human MCF7 cell microsomes using [3H]ATRA after 1 hr by scintillation counting | 2011 | Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8 | Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates. |
| AID763092 | Cytotoxicity against human NB4 cells assessed as growth inhibition at 10 uM after 96 hrs by hemocytometry relative to control | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1192002 | Induction of cell differentiation of human HL60 cells at 10 uM after 72 hrs by NBT dye based assay | 2015 | Bioorganic & medicinal chemistry, Mar-15, Volume: 23, Issue:6 | Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1). |
| AID1079948 | Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source] | |||
| AID763087 | Potentiation of ATRA-induced human NB4 cell differentiation at 10 uM after 96 hrs by nitroblue tetrazolium assay (Rvb = 29.44 +/- 2.03%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1079946 | Presence of at least one case with successful reintroduction. [column 'REINT' in source] | |||
| AID1079933 | Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is | |||
| AID1248108 | Inhibition of CYP2D6 (unknown origin) incubated for 45 mins using NADPH and ATRA by HPLC assay | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID1192000 | Growth inhibition of human HL60 cells at 10 uM in presence of 0.1 uM ATRA after 48 hrs by MTT assay | 2015 | Bioorganic & medicinal chemistry, Mar-15, Volume: 23, Issue:6 | Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1). |
| AID1290556 | Inhibition of microsomal fraction of human CYP26A1 expressed in Sf9 cells using 9-cis-RA as substrate preincubated for 5 mins followed by NADPH addition measured after 1 min by HPLC analysis in presence of rat P450 reductase | 2016 | Journal of medicinal chemistry, Mar-24, Volume: 59, Issue:6 | Development and Characterization of Novel and Selective Inhibitors of Cytochrome P450 CYP26A1, the Human Liver Retinoic Acid Hydroxylase. |
| AID1079940 | Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source] | |||
| AID282900 | Inhibition of human placental microsome CYP19 | 2005 | Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23 | Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. |
| AID763091 | Potentiation of ATRA-induced human NB4 cell growth inhibition at 5 uM after 96 hrs by hemocytometry (Rvb = 32.70 +/- 2.25%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1192003 | Induction of cell differentiation of human HL60 cells at 10 uM in presence of 0.1 uM ATRA after 72 hrs by NBT dye based assay | 2015 | Bioorganic & medicinal chemistry, Mar-15, Volume: 23, Issue:6 | Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1). |
| AID1248102 | Growth inhibition of human HL60 cells at 10 uM incubated for 48 hrs by MTT assay | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID1079945 | Animal toxicity known. [column 'TOXIC' in source] | |||
| AID1191999 | Growth inhibition of human HL60 cells at 10 uM after 48 hrs by MTT assay | 2015 | Bioorganic & medicinal chemistry, Mar-15, Volume: 23, Issue:6 | Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1). |
| AID763088 | Potentiation of ATRA-induced human NB4 cell differentiation at 5 uM after 96 hrs by nitroblue tetrazolium assay (Rvb = 29.44 +/- 2.03%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1079938 | Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source] | |||
| AID282371 | Inhibition of ATRA-induced CYP26 in human T47D cells assessed as ATRA metabolism using [11.12-3H]-ATRA up to 10 uM | 2004 | Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27 | Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. |
| AID1079947 | Comments (NB not yet translated). [column 'COMMENTAIRES' in source] | |||
| AID763086 | Cytotoxicity against human NB4 cells assessed as growth inhibition at 0.5 uM after 96 hrs by hemocytometry relative to control | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID282733 | Inhibition of all-trans retinoic acid metabolism in rat liver microsomes | 2005 | Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23 | Novel tetralone-derived retinoic acid metabolism blocking agents: synthesis and in vitro evaluation with liver microsomal and MCF-7 CYP26A1 cell assays. |
| AID1079939 | Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source] | |||
| AID763085 | Potentiation of ATRA-induced human NB4 cell growth inhibition at 0.5 uM after 96 hrs by hemocytometry (Rvb = 32.42 +/- 3.98%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID241210 | Potency towards cytochrome P 450 26 enzyme activity | 2005 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6 | Potent and selective [2-imidazol-1-yl-2-(6-alkoxy-naphthalen-2-yl)-1-methyl-ethyl]-dimethyl-amines as retinoic acid metabolic blocking agents (RAMBAs). |
| AID1248105 | Induction of cell differentiation in human HL60 cells at 10 uM incubated for 72 hrs by NBT dye based assay | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID593894 | Induction of CYP26A1 mRNA expression in human SH-SY5Y cells at 1 uM after 72 hrs by RT-PCR analysis | 2011 | Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8 | Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates. |
| AID479369 | Inhibition of human placental microsome CYP19 | 2010 | Bioorganic & medicinal chemistry letters, May-15, Volume: 20, Issue:10 | Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). |
| AID1079931 | Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source] | |||
| AID763082 | Inhibition of CYP26A1 in human NB4 cells assessed as ATRA level in medium at 5 uM after 12 hrs by LC-MS/MS analysis (Rvb = 27.05 +/- 1.34 ng/ml) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID763089 | Induction of human NB4 cell differentiation at 0.5 to 10 uM after 96 hrs by nitroblue tetrazolium assay relative to control | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1079934 | Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source] | |||
| AID282366 | Inhibition of ATRA hydroxylase in Syrian golden hamster liver microsome assessed ATRA metabolism using [11.12-3H]-ATRA | 2004 | Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27 | Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. |
| AID763083 | Potentiation of ATRA-induced human NB4 cell differentiation at 0.5 uM after 96 hrs by nitroblue tetrazolium assay (Rvb = 29.93 +/- 0.73%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID763081 | Potentiation of ATRA-induced human NB4 cell growth inhibition at 1 uM after 96 hrs by hemocytometry (Rvb = 32.42 +/- 3.98%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID763090 | Potentiation of ATRA-induced human NB4 cell growth inhibition at 10 uM after 96 hrs by hemocytometry (Rvb = 32.70 +/- 2.25%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1290555 | Inhibition of microsomal fraction of human CYP26B1 expressed in Sf9 cells using 9-cis-RA as substrate preincubated for 5 mins followed by NADPH addition measured after 5 mins by HPLC analysis in presence of rat P450 reductase | 2016 | Journal of medicinal chemistry, Mar-24, Volume: 59, Issue:6 | Development and Characterization of Novel and Selective Inhibitors of Cytochrome P450 CYP26A1, the Human Liver Retinoic Acid Hydroxylase. |
| AID1248107 | Inhibition of CYP3A4 (unknown origin) incubated for 45 mins using NADPH by fluorescence assay | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID763080 | Potentiation of ATRA-induced human NB4 cell differentiation at 1 uM after 96 hrs by nitroblue tetrazolium assay (Rvb = 29.93 +/- 0.73%) | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID619521 | Inhibition of human CYP26A1 assessed using [11,12-3H]ATRA as substrate by scintillation counting | 2011 | Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19 | Synthesis and biological evaluation of 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26). |
| AID1079944 | Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source] | |||
| AID1191997 | Inhibition of CYP26A1 in ATRA-induced human HL60 cell microsomes incubated for 30 mins using ATRA and NADPH by HPLC method | 2015 | Bioorganic & medicinal chemistry, Mar-15, Volume: 23, Issue:6 | Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1). |
| AID282369 | Inhibition of ATRA-induced CYP26 in human T47D cell microsome assessed as ATRA metabolism using [11.12-3H]-ATRA | 2004 | Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27 | Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. |
| AID1079937 | Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source] | |||
| AID282370 | Inhibition of ATRA-induced CYP26 in human MCF7 cells assessed as ATRA metabolism using [11.12-3H]-ATRA up to 10 uM | 2004 | Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27 | Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. |
| AID593895 | Induction of CYP26A1 mRNA expression in human SH-SY5Y cells at 1 uM after 72 hrs by RT-PCR analysis in presence of 0.1 uM of all-trans retinoic acid | 2011 | Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8 | Small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26): synthesis and biological evaluation of imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates. |
| AID763093 | Cytotoxicity against human NB4 cells assessed as growth inhibition at 5 uM after 96 hrs by hemocytometry relative to control | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID1079932 | Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source] | |||
| AID1079935 | Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source] | |||
| AID282734 | Inhibition of CYP26A1 in human MCF7 cells assessed as all-trans retinoic acid metabolism | 2005 | Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23 | Novel tetralone-derived retinoic acid metabolism blocking agents: synthesis and in vitro evaluation with liver microsomal and MCF-7 CYP26A1 cell assays. |
| AID1160913 | Inhibition of human MBP-tagged CYP24A1 expressed in Escherichia coli using 1,25(OH)2D3 substrate in presence of bovine adrenodoxin, adrenodoxin reductase and NADPH incubated at 37 degC for 25 mins by HPLC method | 2014 | Journal of medicinal chemistry, Sep-25, Volume: 57, Issue:18 | Small-molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): synthesis and biological evaluation. |
| AID1079941 | Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source] | |||
| AID1079936 | Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source] | |||
| AID1079942 | Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source] | |||
| AID1248106 | Induction of cell differentiation in human HL60 cells at 10 uM incubated for 72 hrs in presence of 0.1 uM ATRA by NBT dye based assay | 2015 | Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20 | Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors. |
| AID243542 | Potency (30 mg/kg, bid) was determined towards AT 6.1 cell | 2005 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 15, Issue:6 | Potent and selective [2-imidazol-1-yl-2-(6-alkoxy-naphthalen-2-yl)-1-methyl-ethyl]-dimethyl-amines as retinoic acid metabolic blocking agents (RAMBAs). |
| AID763084 | Cytotoxicity against human NB4 cells assessed as growth inhibition at 1 uM after 96 hrs by hemocytometry relative to control | 2013 | Bioorganic & medicinal chemistry, Jun-01, Volume: 21, Issue:11 | 2-(2-Methylfuran-3-carboxamido)-3-phenylpropanoic acid, a potential CYP26A1 inhibitor to enhance all-trans retinoic acid-induced leukemia cell differentiation based on virtual screening and biological evaluation. |
| AID619522 | Increase in CYP26A1 mRNA expression in human SH-SY5Y cells after 72 hrs by RT-PCR analysis in the presence of 0.1 uM all-trans-retinoic acid | 2011 | Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19 | Synthesis and biological evaluation of 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26). |
| AID363251 | Inhibition of CYP26A1 in human MCF7 cells | 2008 | Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17 | Novel azolyl-(phenylmethyl)]aryl/heteroarylamines: potent CYP26 inhibitors and enhancers of all-trans retinoic acid activity in neuroblastoma cells. |
| AID1799732 | Cell Assay from Article 10.1080/14756360802218334: \\Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26.\\ | 2009 | Journal of enzyme inhibition and medicinal chemistry, Apr, Volume: 24, Issue:2 | Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26. |
| AID504749 | qHTS profiling for inhibitors of Plasmodium falciparum proliferation | 2011 | Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043 | Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets. |
| AID1347411 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary | 2020 | ACS chemical biology, 07-17, Volume: 15, Issue:7 | High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (1.03) | 18.7374 |
| 1990's | 52 (53.61) | 18.2507 |
| 2000's | 29 (29.90) | 29.6817 |
| 2010's | 14 (14.43) | 24.3611 |
| 2020's | 1 (1.03) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (27.83) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 23 (22.77%) | 5.53% |
| Reviews | 13 (12.87%) | 6.00% |
| Case Studies | 2 (1.98%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 63 (62.38%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
| Trial | Phase | Enrollment | Study Type | Start Date | Status | ||
|---|---|---|---|---|---|---|---|
| A Randomized, Double-blind, Placebo-controlled Phase II/III Trial to Evaluate the Efficacy and Safety of 2 Doses of Oral Liarozole (75 mg od and 150 mg od) Given During 12 Weeks in Lamellar Ichthyosis [NCT00282724] | Phase 2/Phase 3 | 98 participants (Actual) | Interventional | 2006-01-31 | Completed | ||
| [information is prepared from clinicaltrials.gov, extracted Sep-2024] | |||||||