Compounds > n-(2-hydroxyethyl)retinamide
Page last updated: 2024-12-11

n-(2-hydroxyethyl)retinamide

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

Description

N-(2-hydroxyethyl)retinamide: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6437840
CHEMBL ID60405
SCHEMBL ID2467990
MeSH IDM0077843

Synonyms (20)

Synonym
retinoic acid 2-hydroxyethylamide
retinamide, n-(2-hydroxyethyl)-
brn 2161307
2-hydroxyethyl retinamide
n-2-hydroxyethyl retinamide
hydroxyethyl retinamide
ro 8-4969
n-(2-hydroxyethyl)retinamide
ccris 4284
CHEMBL60405 ,
(2e,4e,6e,8e)-n-(2-hydroxyethyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
33631-47-9
bdbm50347597
SCHEMBL2467990
ro-8-4969
DTXSID801309774
hydroxyethyl)retinamide, all-trans-4-n-(2-
ZBJ8HC23XW
(2e,4e,6e,8e)-n-(2-hydroxyethyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
2-hydroxyethylretinamide

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Based on the lethality data, all-trans-retinoic acid was most toxic followed by all-trans-HER greater than all-trans-HPR greater than all-trans-ER."( Subacute toxicity of all-trans- and 13-cis-isomers of N-ethyl retinamide, N-2-hydroxyethyl retinamide, and N-4-hydroxyphenyl retinamide.
Meeks, RG; Sani, BP, 1983)		0.27

Dosage Studied

ExcerptRelevanceReference
"6 hr) in the plasma of mice dosed orally."( The pharmacokinetics of all-trans-retinoic acid and N-(2-hydroxyethyl)retinamide in mice as determined with a sensitive and convenient procedure. Solid-phase extraction and reverse-phase high performance liquid chromatography.
Hill, DL; Kalin, JR; McPhillips, DM, )		0.38
"The concentrations of 13-cis-retinoic acid and N-(2-hydroxyethyl)retinamide in serum and tissues from mice were measured after oral dosing with 10 mg/kg."( Disposition of 13-cis-retinoic acid and N-(2-hydroxyethyl)retinamide in mice after oral doses.
Hill, DL; Kalin, JR; Wells, MJ, )		0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Retinol-binding protein 4Homo sapiens (human)EC50 (µMol)0.14500.14501.25852.3720AID606066
Retinol-binding protein 4Homo sapiens (human)Kd0.21400.15600.18400.2140AID606062
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
eye developmentRetinol-binding protein 4Homo sapiens (human)
positive regulation of immunoglobulin productionRetinol-binding protein 4Homo sapiens (human)
gluconeogenesisRetinol-binding protein 4Homo sapiens (human)
heart developmentRetinol-binding protein 4Homo sapiens (human)
visual perceptionRetinol-binding protein 4Homo sapiens (human)
maintenance of gastrointestinal epitheliumRetinol-binding protein 4Homo sapiens (human)
lung developmentRetinol-binding protein 4Homo sapiens (human)
positive regulation of insulin secretionRetinol-binding protein 4Homo sapiens (human)
response to retinoic acidRetinol-binding protein 4Homo sapiens (human)
retinol transportRetinol-binding protein 4Homo sapiens (human)
retinol metabolic processRetinol-binding protein 4Homo sapiens (human)
glucose homeostasisRetinol-binding protein 4Homo sapiens (human)
embryonic organ morphogenesisRetinol-binding protein 4Homo sapiens (human)
embryonic skeletal system developmentRetinol-binding protein 4Homo sapiens (human)
cardiac muscle tissue developmentRetinol-binding protein 4Homo sapiens (human)
female genitalia morphogenesisRetinol-binding protein 4Homo sapiens (human)
negative regulation of cardiac muscle cell proliferationRetinol-binding protein 4Homo sapiens (human)
embryonic retina morphogenesis in camera-type eyeRetinol-binding protein 4Homo sapiens (human)
uterus developmentRetinol-binding protein 4Homo sapiens (human)
vagina developmentRetinol-binding protein 4Homo sapiens (human)
urinary bladder developmentRetinol-binding protein 4Homo sapiens (human)
heart trabecula formationRetinol-binding protein 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
protein bindingRetinol-binding protein 4Homo sapiens (human)
retinal bindingRetinol-binding protein 4Homo sapiens (human)
retinol bindingRetinol-binding protein 4Homo sapiens (human)
retinol transmembrane transporter activityRetinol-binding protein 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
extracellular regionRetinol-binding protein 4Homo sapiens (human)
extracellular spaceRetinol-binding protein 4Homo sapiens (human)
extracellular exosomeRetinol-binding protein 4Homo sapiens (human)
extracellular spaceRetinol-binding protein 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID606163Binding affinity to immobilized His-tagged recombinant human sRBP assessed as inhibition of sRBP and detergent treated HEK293 membrane interaction at 100 uM after 1 hr by surface plasmon resonance assay2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor.
AID606064Binding affinity to His-tagged recombinant human sRBP expressed in Escherichia coli BL21(DE3) assessed as disruption of sRBP-TTR protein interaction after 1 hr by SDS-PAGE and silver staining method2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor.
AID606161Antagonist activity at His-tagged recombinant human sRBP expressed in Escherichia coli BL21(DE3) assessed as disruption of ROH-sRBP-TTR protein interaction after 2 hr by TR-FRET assay relative to control2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor.
AID606062Binding affinity to His-tagged recombinant human sRBP expressed in Escherichia coli BL21(DE3) assessed as apparent dissociation constant after 5 mins by fluorescence spectrophotometric analysis2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor.
AID84861Reversal of keratinization in vitamin A deficient hamster trachea culture1988Journal of medicinal chemistry, Jan, Volume: 31, Issue:1
N-(Retinoyl)amino acids. Synthesis and chemopreventive activity in vitro.
AID606066Antagonist activity at His-tagged recombinant human sRBP expressed in Escherichia coli BL21(DE3) assessed as disruption of ROH-sRBP-TTR protein interaction after 2 hr by TR-FRET assay2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (90.91)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's1 (9.09)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.55

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.55 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thiazoles
[no description available]		1.96101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
methylnitrosourea
Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.		1.9610N-nitrosoureasalkylating agent;
carcinogenic agent;
mutagen;
teratogenic agent
butylhydroxybutylnitrosamine
Butylhydroxybutylnitrosamine: A substituted carcinogenic nitrosamine.. N-butyl-N-(4-hydroxybutyl)nitrosamine : A nitrosamine that has butyl and 4-hydroxybutyl substituents. In mice, it causes high-grade, invasive cancers in the urinary bladder, but not in any other tissues.		2.3620nitrosamine;
primary alcohol		carcinogenic agent
fanft
FANFT: A potent nitrofuran derivative tumor initiator. It causes bladder tumors in all animals studied and is mutagenic to many bacteria.		1.9610
nitrosobis(2-oxopropyl)amine
nitrosobis(2-oxopropyl)amine: structure. nitrosobis(2-oxopropyl)amine : A nitrosamine that is iminodiacetone that is substituted by a nitroso group at the N-atom. It induces pancreatic ductal adenocarcinomas in Syrian golden hamsters (other rodents are not susceptible).		2.3620ketone;
nitrosamine		carcinogenic agent
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		3.66100retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
retinol
Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).		2.0610retinol;
vitamin A		human metabolite;
mouse metabolite;
plant metabolite
azaserine
Azaserine: Antibiotic substance produced by various Streptomyces species. It is an inhibitor of enzymatic activities that involve glutamine and is used as an antineoplastic and immunosuppressive agent.. azaserine : A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species.		1.9610carboxylic ester;
diazo compound;
L-serine derivative;
non-proteinogenic L-alpha-amino acid		antifungal agent;
antimetabolite;
antimicrobial agent;
antineoplastic agent;
glutamine antagonist;
immunosuppressive agent;
metabolite
isotretinoin
Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.		2.8840retinoic acidantineoplastic agent;
keratolytic drug;
teratogenic agent
vitamin a acid ethylamide
vitamin A acid ethylamide: ethylamide of all-trans B-retinoic acid; RN given refers to cpd without isomeric designation		3.4680
fenretinide
Fenretinide: A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.. 4-hydroxyphenyl retinamide : A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.		2.8940monocarboxylic acid amide;
retinoid		antineoplastic agent;
antioxidant
retinylidene dimedone
retinylidene dimedone: retinoid which prevents transformation of mammary gland by DMBA in mouse whole organ culture		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Metaplasia
A condition in which there is a change of one adult cell type to another similar adult cell type.		01.9710
Anemia
A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.		01.9610
Carcinoma, Anaplastic
[description not available]		02.3620
Experimental Neoplasms
[description not available]		02.8740
Cancer of Pancreas
[description not available]		02.6530
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		02.3620
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.6530
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.3620
Benign Neoplasms
[description not available]		01.9610
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		01.9610
Atrophy
Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.		01.9510
Condition, Preneoplastic
[description not available]		01.9610
Tracheal Neoplasms
New abnormal growth of tissue in the TRACHEA.		01.9610
Amyloidosis
A group of sporadic, familial and/or inherited, degenerative, and infectious disease processes, linked by the common theme of abnormal protein folding and deposition of AMYLOID. As the amyloid deposits enlarge they displace normal tissue structures, causing disruption of function. Various signs and symptoms depend on the location and size of the deposits.		01.9610
Precancerous Conditions
Pathological conditions that tend eventually to become malignant.		01.9610
Bladder Cancer
[description not available]		02.6530
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		02.6530
Carcinoma, Transitional Cell
A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.		01.9610