Page last updated: 2024-11-11

adarotene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

adarotene: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9864378
CHEMBL ID442016
SCHEMBL ID403528
SCHEMBL ID403527
MeSH IDM0575175

Synonyms (34)

Synonym
HY-14808
st 1926
3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid
st1926
(2e)-3-[4'-hydroxy-3'-(tricyclo[3.3.1.13,7]dec-1-yl)biphenyl-4-yl]prop-2-enoic acid
(e)-3-(3''-adamantan-1-yl-4''-hydroxy-biphenyl-4-yl)-acrylic acid
(e)-4-[3-(1-adamantyl)-4-hydroxyphenyl]cinnamic acid
bdbm50124518
adarotene
CHEMBL442016 ,
496868-77-0
adarotene [inn]
w6su73vg8h ,
unii-w6su73vg8h
(2e)-3-(3'-(a(4sdamantan-1-yl)-4'-hydroxy-1,1'-biphenyl-4-yl)prop-2-enoic acid
2-propenoic acid, 3-(4'-hydroxy-3'-tricyclo(3.3.1.13,7)dec-1-yl(1,1'-biphenyl)-4-yl)-, (2e)-
CS-0678
(2e)-3-(3'-(adamantan-1-yl)-4'-hydroxy-1,1'-biphenyl-4-yl)prop-2-enoic acid
adarotene [who-dd]
SCHEMBL403528
SCHEMBL403527
QAWBIEIZDDIEMW-FPYGCLRLSA-N
e-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid
DTXSID9040390
AKOS030526823
(2e)-3-[3'-(adamantan-1-yl)-4'-hydroxy-[1,1'-biphenyl]-4-yl]prop-2-enoic acid
AS-74260
NCGC00485908-01
(2e)-3-(4'-hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid
Q15633950
(e)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid
C75317
A913875
(e)-3-(3'-((3r,5r,7r)-adamantan-1-yl)-4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylic acid

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Preliminary results show low and variable drug absorption in patients, with extensive glucuroconjugation influencing the bioavailability of ST1926."( Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ST1926, a novel oral antitumor agent, adamantyl retinoid derivative, in plasma of patients in a Phase I study.
Bagnati, R; Capocasa, F; D'Incalci, M; Marangon, E; Pace, S; Sala, F; Zucchetti, M, 2009
)
0.35
" Therefore, synthetic retinoids were developed, such as the atypical adamantyl retinoid ST1926 that provides enhanced bioavailability and reduced toxicity."( The synthetic retinoid ST1926 attenuates prostate cancer growth and potentially targets prostate cancer stem-like cells.
Abdel-Samad, R; Abou-Kheir, W; Bahmad, HF; Cheaito, K; Darwiche, N; Hadadeh, O; Hayar, B; Liu, YN; Monzer, A; Msheik, H; Pisano, C; Samman, H, 2019
)
0.51
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Retinoic acid receptor betaHomo sapiens (human)EC50 (µMol)0.20000.00030.23116.9000AID240375
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
ureteric bud developmentRetinoic acid receptor betaHomo sapiens (human)
glandular epithelial cell developmentRetinoic acid receptor betaHomo sapiens (human)
growth plate cartilage developmentRetinoic acid receptor betaHomo sapiens (human)
apoptotic processRetinoic acid receptor betaHomo sapiens (human)
signal transductionRetinoic acid receptor betaHomo sapiens (human)
striatum developmentRetinoic acid receptor betaHomo sapiens (human)
neurogenesisRetinoic acid receptor betaHomo sapiens (human)
regulation of myelinationRetinoic acid receptor betaHomo sapiens (human)
negative regulation of chondrocyte differentiationRetinoic acid receptor betaHomo sapiens (human)
embryonic hindlimb morphogenesisRetinoic acid receptor betaHomo sapiens (human)
multicellular organism growthRetinoic acid receptor betaHomo sapiens (human)
positive regulation of apoptotic processRetinoic acid receptor betaHomo sapiens (human)
embryonic eye morphogenesisRetinoic acid receptor betaHomo sapiens (human)
embryonic digestive tract developmentRetinoic acid receptor betaHomo sapiens (human)
ventricular cardiac muscle cell differentiationRetinoic acid receptor betaHomo sapiens (human)
neural precursor cell proliferationRetinoic acid receptor betaHomo sapiens (human)
stem cell proliferationRetinoic acid receptor betaHomo sapiens (human)
negative regulation of stem cell proliferationRetinoic acid receptor betaHomo sapiens (human)
retinoic acid receptor signaling pathwayRetinoic acid receptor betaHomo sapiens (human)
hormone-mediated signaling pathwayRetinoic acid receptor betaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIRetinoic acid receptor betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIRetinoic acid receptor betaHomo sapiens (human)
cell differentiationRetinoic acid receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
DNA-binding transcription factor activity, RNA polymerase II-specificRetinoic acid receptor betaHomo sapiens (human)
DNA bindingRetinoic acid receptor betaHomo sapiens (human)
zinc ion bindingRetinoic acid receptor betaHomo sapiens (human)
protein-containing complex bindingRetinoic acid receptor betaHomo sapiens (human)
nuclear retinoid X receptor bindingRetinoic acid receptor betaHomo sapiens (human)
heterocyclic compound bindingRetinoic acid receptor betaHomo sapiens (human)
sequence-specific double-stranded DNA bindingRetinoic acid receptor betaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingRetinoic acid receptor betaHomo sapiens (human)
nuclear receptor activityRetinoic acid receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusRetinoic acid receptor betaHomo sapiens (human)
nucleoplasmRetinoic acid receptor betaHomo sapiens (human)
cytoplasmRetinoic acid receptor betaHomo sapiens (human)
chromatinRetinoic acid receptor betaHomo sapiens (human)
nucleusRetinoic acid receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (111)

Assay IDTitleYearJournalArticle
AID1347157Confirmatory screen GU Rhodamine qHTS for Zika virus inhibitors qHTS2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347164384 well plate NINDS Rhodamine confirmatory qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347149Furin counterscreen qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347169Tertiary RLuc qRT-PCR qHTS assay for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347153Confirmatory screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347167Vero cells viability qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347163384 well plate NINDS AMC confirmatory qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347156DAPI mCherry counterscreen qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347170Vero cells viability counterscreen for qRT-PCR qHTS assay of selected Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347152Confirmatory screen NINDS AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347168HepG2 cells viability qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347161Confirmatory screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347171Orthogonal mCherry assay for qRT-PCR qHTS of selected Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347158ZIKV-mCherry secondary qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347172Secondary qRT-PCR qHTS assay for selected Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID47357Transcriptional activation in CV-1 cells expressing RAR alpha at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID645998Induction of apoptosis in human ATRA-resistant HL60R cells at 1 uM after 24 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID650085Antiproliferative activity against human NCI-H460 cells incubated for 24 hrs drug exposure measured after 48 hrs of recovery by sulforhodamine B assay2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID1870696Inhibition of Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb InhA substrate at 20 uM by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID1870695Antimycobacterial activity against Mycobacterium tuberculosis H37Ra assessed as inhibition of growth measured after 7 days by microplate reader2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID82680Induction of apoptosis in HL60R leukemia cells after 24 hr r treatment at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID646001Induction of apoptosis in human MDA-MB-231 cells at 1 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID1870699Inhibition of Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb DHFR substrate at 20 uM by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID47358Transcriptional activation in CV-1 cells expressing RAR beta at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID650087Antitumor activity against human NCI-H460 cells xenografted in nude CD1 mouse assessed as tumor volume inhibition at 25 mg/kg, po administered qd 3 times per week for 2 weeks relative to control2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID248756Concentration of compound required for inhibition of (IGROV-1/Pt1) human cisplatin resistant ovarian carcinoma cell growth by 50%2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID299869Activation of p38 kinase in IGROV1/Pt1 cells with p53 mutation assessed as phosphorylation after 18 hrs2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID240384Effective concentration against retinoic acid receptor gamma in COS-7 cells co-expressing DR5-tk-CAT reporter; value range (0.1-0.3)2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID93490Apoptosis was determined my morphological analysis of propidium-iodide-stained cells following 72 hr exposure to IC80 (0.5 uM), value expressed as percentage of apoptotic cells versus total cell number2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID101801Induction of apoptosis in MDA-MB-231 breast cancer cells after 96 hr at 0.5E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID365035Induction of apoptosis in human MDA-MB-231 cells at 1.0 uM after 96 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID299860Antiproliferative activity against human NB4 cells after 72 hrs2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID1870697Inhibition of Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb KasA substrate at 20 uM by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID650090Antitumor activity against human A431 cells xenografted in nude CD1 mouse assessed as tumor volume inhibition at 25 mg/kg, po administered qd 3 times per week for 2 weeks relative to control2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID82679Induction of apoptosis in HL60R leukemia cells after 24 hr r treatment at 0.1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID365036Induction of apoptosis in human MDA-MB-231 cells at 2.0 uM after 96 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID58230Apoptosis was determined my morphological analysis of propidium-iodide-stained cells following 48 hr exposure to IC80 (0.5 uM), value expressed as percentage of apoptotic cells versus total cell number2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID200415Antiproliferative effect of compound on SAOS cell line2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID646002Induction of apoptosis in human MDA-MB-231 cells at 2 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID288576Antiproliferative activity against HMVE cells2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID78402Antiproliferative effect of compound on H460 cell line expressing wild-type p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID650076Chemical stability in aqueous buffer containing 5% DMSO and 5% tween 80 at pH 1.2 assessed as compound recovery in anoxic conditions after 12 hrs by UPLC analysis2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID251334Percent level of apoptosis induced by 72 hr of exposure with IC80 in (IGROV-1) human ovarian carcinoma cells2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID47359Transcriptional activation in CV-1 cells expressing RAR gamma at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID93492Antiproliferative effect of compound on IGROV-1 cell line expressing wild-type p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID78410Inhibition of H460 cell proliferation after 144 hr treatment at 0.1E-6M; - denotes not determined2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID251335Percent level of apoptosis induced by 72 hr of exposure with IC80 in (IGROV-1/Pt1) human cisplatin resistant ovarian carcinoma cells2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID101803Induction of apoptosis in MDA-MB-231 breast cancer cells after 96 hr at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID78412Inhibition of H460 cell proliferation after 144 hr treatment at 1E-6M; - denotes not determined2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID650073Chemical stability in aqueous buffer containing 5% DMSO and 5% tween 80 at pH 6.8 assessed as compound recovery in anoxic conditions after 24 hrs by UPLC analysis2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID93488Apoptosis was determined my morphological analysis of propidium-iodide-stained cells following 24 hr exposure to IC80 (0.5 uM), value expressed as percentage of apoptotic cells versus total cell number2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID645995Growth inhibition of human MDA-MB-231 cells at 1 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID645997Induction of apoptosis in human ATRA-resistant HL60R cells at 0.1 uM after 24 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID288577Inhibition of HMVE cell proliferation at 0.5 uM relative to control2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610815Transcriptional activation of human RARalpha at 1 uM by (TREpal)2-tk-CAT reporter gene assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID81694Antiproliferative effect of compound on HCT116 cell line expressing wild-type p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID650244Toxicity in iv dosed nude CD1 mouse xenografted with human A431 cells assessed as mortality administered qd 3 times per week for 2 weeks2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID650071Chemical stability in aqueous buffer containing 5% DMSO and 5% tween 80 at pH 1.2 assessed as compound recovery in anoxic conditions after 3 hrs by UPLC analysis2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID108454Antiproliferative effect of compound on Me665/2/21 cell line expressing mutant p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID650242Solubility in water2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID55803Antiproliferative effect of compound on DU145 cell line expressing mutant p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID299858Antiproliferative activity against human IGROV1 cells after 72 hrs2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID650075Chemical stability in aqueous buffer containing 5% DMSO and 5% tween 80 at pH 7.4 assessed as compound recovery in anoxic conditions after 24 hrs by UPLC analysis2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID1870698Inhibition of Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb PknB substrate at 20 uM by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID610849Transcriptional activation of human RARbeta at 1 uM by (TREpal)2-tk-CAT reporter gene assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365039Growth inhibition of HMVE cells after 72 hrs by alamar blue method2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID610813Transcriptional activation of human RARbeta at 0.1 uM by luciferase reporter gene assay relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID650088Antitumor activity against human NCI-H460 cells xenografted in nude CD1 mouse assessed as tumor volume inhibition at 13 mg/kg, iv administered qd 3 times per week for 2 weeks relative to control2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID299865Induction of DNA damage in IGROV1 cells assessed as RPA2 protein phosphorylation after 6 hrs2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID1870693Inhibition of Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb PanB substrate by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID248330Concentration of compound required for inhibition of (IGROV-1) human ovarian carcinoma cell growth by 50%2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID1870694Binding affinity to Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as increase in thermal stability at 40 uM incubated for 15 mins at 25 degC followed by incubated at 52 to 72 degC for 5 mins by CESTA analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID650243Toxicity in po dosed nude CD1 mouse xenografted with human A431 cells assessed as mortality administered qd 3 times per week for 2 weeks2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID100550Antiproliferative effect of compound on LNcaP cell line expressing wild-type p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID72881Antiproliferative effect of compound on GBM cell line expressing mutant p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID1870691Inhibition of Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb PanB substrate at 20 uM by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID248352Concentration of compound required for inhibition of (NB4) human promyelocytic leukemia cell growth by 50%2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID214257Antiproliferative effect of compound on U2OS cell line expressing wild-type p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID299861Induction of apoptosis in IGROV1 cells after 72 hrs by TUNEL assay2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID93489Apoptosis was determined my morphological analysis of propidium-iodide-stained cells following 48 hr exposure to IC80 (0.5 uM), value expressed as percentage of apoptotic cells versus total cell number2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID610850Transcriptional activation of human RARgamma at 1 uM by (TREpal)2-tk-CAT reporter gene assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID299859Antiproliferative activity against human cisplatin-resistant IGROV1/Pt1 cells with p53 mutation after 72 hrs2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID1870692Inhibition of Corynebacterium glutamicum PafA expressed in Escherichia coli BL-21(DE3) assessed as inhibition of pup-ylation using Mtb PanB substrate at 20 uM by SDS-PAGE analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID650099Toxicity in nude CD1 mouse xenografted with human NCI-H460 NSCLC cells assessed as body weight loss at 25 mg/kg, po administered qd 3 times per week for 2 weeks2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID365034Induction of apoptosis in human HL60R cells at 1.0 uM after 24 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID299866Induction of DNA damage in IGROV1 cells assessed as p53 protein phosphorylation after 6 hrs2007Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
AID610812Transcriptional activation of human RARalpha at 0.1 uM by luciferase reporter gene assay relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID240375Effective concentration against retinoic acid receptor beta in COS-7 cells co-expressing DR5-tk-CAT reporter; value range (0.1-0.3)2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID7499Antiproliferative effect of compound on A2780/DX cell line2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID650086Antiproliferative activity against human A431 cells incubated for 24 hrs drug exposure measured after 48 hrs of recovery by sulforhodamine B assay2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID365033Induction of apoptosis in human HL60R cells at 0.1 uM after 24 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID288594Inhibition of CD45 PTP at 10 uM relative to control by fluorescence spectrometry2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610855Induction of apoptosis in retinoid-resistant p53 null human HL60R cells assessed as DNA fragmentation at 0.1 uM after 24 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610856Induction of apoptosis in retinoid-resistant p53 null human HL60R cells assessed as DNA fragmentation at 1 uM after 24 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID1870700Binding affinity to Mycobacterium tuberculosis PafA expressed in Escherichia coli BL-21(DE3) assessed as increase in thermal stability by measuring change in melting temperature in at 50 uM by CESTA analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Discovery and Mechanistic Study of
AID58231Apoptosis was determined my morphological analysis of propidium-iodide-stained cells following 72 hr exposure to IC80 (0.5 uM), value expressed as percentage of apoptotic cells versus total cell number2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID645996Growth inhibition of human MDA-MB-231 cells at 2 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID650102Toxicity in nude CD1 mouse xenografted with human A431 cells assessed as body weight loss at 25 mg/kg, po administered qd 3 times per week for 2 weeks2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID650100Toxicity in nude CD1 mouse xenografted with human NCI-H460 NSCLC cells assessed as body weight loss at 13 mg/kg, iv administered qd 3 times per week for 2 weeks2012Bioorganic & medicinal chemistry, Apr-01, Volume: 20, Issue:7
New retinoid derivatives as back-ups of Adarotene.
AID58229Apoptosis was determined my morphological analysis of propidium-iodide-stained cells following 24 hr exposure to IC80 (0.5 uM), value expressed as percentage of apoptotic cells versus total cell number2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID156647Antiproliferative effect of compound on PC3 cell line2003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID7886Antiproliferative effect of compound on A431 cell line expressing mutant p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID240381Effective concentration against retinoic acid receptor alpha in COS-7 cells co-expressing DR5-tk-CAT reporter; value range (0.1-0.4)2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID610814Transcriptional activation of human RARgamma at 0.1 uM by luciferase reporter gene assay relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID102035Antiproliferative effect of compound on LoVo cell line expressing wild-type p532003Journal of medicinal chemistry, Mar-13, Volume: 46, Issue:6
A novel atypical retinoid endowed with proapoptotic and antitumor activity.
AID365040Growth inhibition of HMVE cells at 0.5 uM after 72 hrs by alamar blue method2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's17 (39.53)29.6817
2010's19 (44.19)24.3611
2020's7 (16.28)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.38

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.

MetricThis Compound (vs All)
Research Demand Index21.38 (24.57)
Research Supply Index3.81 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.38)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.33%)5.53%
Reviews1 (2.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (95.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]