4-oxoretinoic acid: RN given refers to cpd without isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
all-trans-4-oxoretinoic acid : A retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 6437063 |
| CHEMBL ID | 104049 |
| CHEBI ID | 80656 |
| SCHEMBL ID | 161113 |
| MeSH ID | M0042706 |
| Synonym |
|---|
| ro 12-4824 |
| 4-oxo-tretinoin |
| 4-oxo-all-trans-retinoic acid |
| 4-oxoretinoic acid |
| (e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid |
| 4-ketoretinoic acid |
| all-trans-4-oxo-retinoic acid |
| retinoic acid, 4-oxo- |
| gtpl2741 |
| (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid |
| all-trans-4-oxoretinoic acid |
| LMPR01090026 |
| 38030-57-8 |
| 4-oxo-atra |
| CHEMBL104049 |
| chebi:80656 , |
| all-trans 4-keto retinoic acid |
| 4-oxotretinoin |
| all-trans 4-keto retinoic acid-(9-methyl)-d3 |
| ro 11-4824 |
| 4-keto-retinoic acid |
| (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid |
| unii-cjn45g18ua |
| cjn45g18ua , |
| SCHEMBL161113 |
| 4-oxo-retinoic acid |
| ro-12-4824 |
| ro-11-4824 |
| 4-oxoretinoic acid, analytical standard |
| 4-ketoretinoate |
| 4-keto-retinoate |
| (11-cis,13-cis)-4-oxoretinoic acid |
| DTXSID20865895 |
| 1346606-26-5 |
| CS-0065386 |
| HY-107494A |
| GGCUJPCCTQNTJF-FRCNGJHJSA-N |
| Q27074387 |
| MS-24622 |
| 4-eto 13-is-etinoic acid; 4-oxoisotretinoin |
| A936796 |
| (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)nona-2,4,6,8-tetraenoicacid |
| 4-oxo-(9-cis,13-cis)-retinoicacid |
| (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid |
| AKOS040759128 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "" Therefore, the sea urchin model might serve as a discriminating and rapid screening test for identifying other potential developmentally toxic retinoids." | ( Screening for the developmental toxicity of retinoids: use of the sea urchin model. Bickers, DR; Blumer, J; Kahn, TA; Silverman, RA, 1988) | 0.27 |
| " This study suggests that a greater variability exists in the safe time after discontinuation of the drug for onset of conception." | ( Steady-state pharmacokinetics of isotretinoin and its 4-oxo metabolite: implications for fetal safety. Berkovitch, M; Klein, J; Koren, G; Lester, RS; Nulman, I; Pastuszak, A; Shear, N, 1998) | 0.3 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Maternal peak circulating concentrations of the parent retinoids, total radioactivity, plasma pharmacokinetic parameters or the total concentrations of residual radioactivity in fetal tissues could not be correlated with the differential teratogenic potencies of these retinoids." | ( Comparative distribution, pharmacokinetics and placental permeabilities of all-trans-retinoic acid, 13-cis-retinoic acid, all-trans-4-oxo-retinoic acid, retinyl acetate and 9-cis-retinal in hamsters. Howard, WB; Omaye, ST; Sharma, RP; Willhite, CC, 1989) | 0.28 |
| " To assess if such metabolic conversions diminished teratogenic potency, one of the major metabolites (4-oxo-all-trans-retinoic acid) was tested for its teratogenic activity in pregnant ICR mice and further investigated for its pharmacokinetic features to determine if it accumulated in the embryo in concentrations sufficient to elicit a teratogenic response." | ( Pharmacokinetic assessment of teratologically effective concentrations of an endogenous retinoic acid metabolite. Kochhar, DM; Penner, JD; Satre, MA, 1989) | 0.28 |
| "The clinical pharmacokinetic profiles of two orally administered retinoids, isotretinoin and etretinate, are discussed and compared." | ( Pharmacokinetics of the retinoids isotretinoin and etretinate. A comparative review. Brazzell, RK; Colburn, WA, 1982) | 0.26 |
| "A pharmacokinetic profile of isotretinoin and its major dermatologically active blood metabolite, 4-oxo-isotretinoin, was developed following a single 80 mg oral suspension dose of isotretinoin to 15 normal male subjects." | ( Pharmacokinetics of isotretinoin and its major blood metabolite following a single oral dose to man. Colburn, WA; Shorter, HJ; Vane, FM, 1983) | 0.27 |
| " Pharmacokinetic studies with both dosing regimens of 13-cis-RA in pregnant rabbits showed that on Day 11 of gestation, high concentrations of parent compound, 13-cis-RA, and its major metabolite, 13-cis-4-oxoRA, existed in maternal plasma." | ( Teratogenicity and transplacental pharmacokinetics of 13-cis-retinoic acid in rabbits. Agnish, N; Chari, S; Eckhoff, C; Juhasz, L; Kromka, M; Rudiger, H; Staudner, H, 1994) | 0.29 |
| "A double-blind, placebo-controlled, randomized study using single ascending oral doses of 5 mg, 15 mg, 40 mg, 80 mg, and 150 mg of 9-cis-retinoic acid was performed to assess the single-dose pharmacokinetics, tolerability, and pharmacodynamic effects of 9-cis-retinoic acid in healthy men." | ( Pharmacokinetics and pharmacodynamics of 9-cis-retinoic acid in healthy men. Dumont, E; Weber, C, 1997) | 0.3 |
| " Values for elimination half-life (t1/2) of isotretinoin and its metabolite were 29+/-40 hours and 22+/-10 hours, respectively." | ( Steady-state pharmacokinetics of isotretinoin and its 4-oxo metabolite: implications for fetal safety. Berkovitch, M; Klein, J; Koren, G; Lester, RS; Nulman, I; Pastuszak, A; Shear, N, 1998) | 0.3 |
| " In addition, pharmacokinetic parameters of the parent drug and its 4-oxo metabolite were determined." | ( The metabolism and pharmacokinetics of isotretinoin in patients with acne and rosacea are not influenced by ethanol. Grønhøj Larsen, C; Grønhøj Larsen, F; Heidenheim, M; Held, E; Jakobsen, P; Nielsen-Kudsk, F, 2009) | 0.35 |
| " Multiple dose pharmacokinetic data for the parent drug and its main metabolite were comparable to previous studies." | ( The metabolism and pharmacokinetics of isotretinoin in patients with acne and rosacea are not influenced by ethanol. Grønhøj Larsen, C; Grønhøj Larsen, F; Heidenheim, M; Held, E; Jakobsen, P; Nielsen-Kudsk, F, 2009) | 0.35 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " During multiple dosing of etretinate, a very slow terminal elimination phase is observed which is not detected after single-dose administration." | ( Pharmacokinetics of the retinoids isotretinoin and etretinate. A comparative review. Brazzell, RK; Colburn, WA, 1982) | 0.26 |
| " The results of the 2 studies suggest that no significant changes in the pharmacokinetics of isotretinoin occur during multiple dosing and that the multiple dose pharmacokinetic profile is predictable and can be described using a linear pharmacokinetic model." | ( Pharmacokinetics of isotretinoin during repetitive dosing to patients. Brazzell, RK; Colburn, WA; Ehmann, CW; Vane, FM, 1983) | 0.27 |
| " Pharmacokinetic studies with both dosing regimens of 13-cis-RA in pregnant rabbits showed that on Day 11 of gestation, high concentrations of parent compound, 13-cis-RA, and its major metabolite, 13-cis-4-oxoRA, existed in maternal plasma." | ( Teratogenicity and transplacental pharmacokinetics of 13-cis-retinoic acid in rabbits. Agnish, N; Chari, S; Eckhoff, C; Juhasz, L; Kromka, M; Rudiger, H; Staudner, H, 1994) | 0.29 |
| Role | Description |
|---|---|
| human xenobiotic metabolite | Any human metabolite produced by metabolism of a xenobiotic compound in humans. |
| [role 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] | |
| Class | Description |
|---|---|
| retinoid | Oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. |
| enone | An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position. |
| [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] | |
| Pathway | Proteins | Compounds |
|---|---|---|
| Retinol Metabolism | 37 | 30 |
| Vitamin A Deficiency | 37 | 30 |
| 22q11.2 copy number variation syndrome | 2 | 28 |
| Retinol metabolism | 18 | 12 |
| Vitamin A and carotenoid metabolism | 0 | 20 |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID150571 | In vivo inhibition of ornithine de-carboxylase (ODC) activity induced by 12-0-tetradecanoylphorbol 13-acetate (TPA) in mouse skin | 1994 | Journal of medicinal chemistry, Sep-16, Volume: 37, Issue:19 | Cancer chemopreventive 3-substituted-4-oxoretinoic acids. |
| AID150573 | Inhibition of TPA-induced ODC activity as percentage of the average no. of papillomas / mouse in groups of control mice was determined using papilloma assay | 1994 | Journal of medicinal chemistry, Sep-16, Volume: 37, Issue:19 | Cancer chemopreventive 3-substituted-4-oxoretinoic acids. |
| AID1346777 | Human RAR-related orphan receptor-beta (1F. Retinoic acid-related orphans) | 2003 | Nature structural biology, Oct, Volume: 10, Issue:10 | All-trans retinoic acid is a ligand for the orphan nuclear receptor ROR beta. |
| AID1346159 | Human alpha2C-adrenoceptor (Adrenoceptors) | 2005 | Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6 | Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 17 (23.61) | 18.7374 |
| 1990's | 36 (50.00) | 18.2507 |
| 2000's | 15 (20.83) | 29.6817 |
| 2010's | 4 (5.56) | 24.3611 |
| 2020's | 0 (0.00) | 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 weak demand-to-supply ratio for research on this compound.
| This Compound (10.03) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 2 (2.63%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 74 (97.37%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||