isopropyl unoprostone: a safe and effective ocular hypotensive drug [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
isopropyl unoprostone : The isopropyl ester of unoprostone. [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 | 5282175 |
| CHEMBL ID | 1200661 |
| CHEBI ID | 31731 |
| SCHEMBL ID | 192726 |
| MeSH ID | M0196670 |
| Synonym |
|---|
| unoprostone isopropyl ester |
| ocuseva |
| rescula |
| uf-021 |
| 5-heptenoic acid, 7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-, 1-methylethyl ester, (5z)- |
| 13,14-dihydro-15-keto-20-ethyl-pgf2 |
| CHEBI:31731 , |
| isopropyl (5z,9alpha,11alpha)-9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5-en-1-oate |
| propan-2-yl (5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate |
| uf 021 |
| isopropyl unoprostone |
| D01452 |
| unoprostone isopropyl |
| 120373-24-2 |
| isopropyl unoprostone (jan) |
| isopropyl 20-ethyl-9alpha,11alpha-dihydroxy-15-keto-cis-delta-5-prostanoate |
| CHEMBL1200661 |
| (e)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-5-heptenoic acid propan-2-yl ester |
| A804495 |
| NCGC00183877-01 |
| unii-5m161s5o5p |
| 5m161s5o5p , |
| propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate |
| cas-120373-24-2 |
| tox21_113629 |
| dtxcid6028997 |
| dtxsid5049071 , |
| AKOS015965062 |
| unoprostone isopropyl [orange book] |
| unoprostone isopropyl [mart.] |
| isopropyl unoprostone [jan] |
| isopropyl z-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate, d- |
| isopropyl z-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate, (+)- |
| unoprostone isopropyl [who-dd] |
| unoprostone isopropyl [vandf] |
| unoprostone isopropyl ester [mi] |
| SCHEMBL192726 |
| gtpl8282 |
| rescula (proposed trade name) |
| isopropyl (z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate |
| HMS3648F04 |
| HY-109545 |
| isopropyl(z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-{3-oxo-1-decyl}cyclopentyl]-hept-5-enoate |
| XXUPXHKCPIKWLR-JHUOEJJVSA-N |
| Q27089094 |
| EX-A4108 |
| SR-01000946493-1 |
| sr-01000946493 |
| uf021 |
| CS-0031289 |
| propan-2-yl (5z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate |
| isopropyl (+)-(z)-7-((1 r, 2 r, 3 r, 5 s)-3,5-dihydroxy-2-(3-oxodecyl) cyclopentyl)-5-heptenoate |
| unoprostone isopropyl (mart.) |
| Excerpt | Reference | Relevance |
|---|---|---|
| "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 |
| Excerpt | Relevance | Reference |
|---|---|---|
| "12% reduced IOP in a dose-dependent manner with neither systemic nor local ocular controversial side effects at those dosage levels." | ( [Ocular effects of topical instillation of UF-021 ophthalmic solution in healthy volunteers]. Koyano, S; Murao, M; Okita, M; Takase, M; Ueno, R, 1992) | 0.28 |
| " Outflow facility was measured in six normal monkeys 3 hours prior to dosing and 1 hour after unilateral dosing with either drug." | ( A comparative study of latanoprost (Xalatan) and isopropyl unoprostone (Rescula) in normal and glaucomatous monkey eyes. Kitazawa, Y; Podos, SM; Serle, JB; Wang, RF, ) | 0.13 |
| " Recommended dosing is once daily at bedtime." | ( Prostaglandin analogs in the treatment of glaucoma. Camras, CB; Hejkal, TW, 1999) | 0.3 |
| " This prospective study included 59 NTG and 20 POAG patients treated with the following four dosing regimens of latanoprost: patients on no previous medication received latanoprost as initial therapy (Group 1, n=31), patients on beta-blocker therapy received latanoprost as adjunctive therapy (Group II, n=9), patients on unoprostone monotherapy were switched to latanoprost monotherapy (Group III, n=14), and patients previously on dual therapy with isopropyl unoprostone and beta-blocker were switched to a combined treatment of latanoprost and beta-blocker (Group IV, n=25)." | ( Intraocular pressure-lowering efficacy of latanoprost in patients with normal-tension glaucoma or primary open-angle glaucoma. Kitazawa, Y; Murase, H; Tamada, Y; Taniguchi, T; Yamamoto, T, 2001) | 0.31 |
| " However, unoprostone, but not brimonidine, decreased IOP over the complete 12-hour daytime dosing cycle." | ( The safety and efficacy of unoprostone 0.15% versus brimonidine 0.2%. Day, DG; Jenkins, J; Stewart, JA; Stewart, WC, 2004) | 0.32 |
| "15% unoprostone isopropyl solution induced no significant ocular side effects in normal cats when dosed over a 10-day treatment period." | ( The effects of bimatoprost and unoprostone isopropyl on the intraocular pressure of normal cats. Bartoe, JT; Brightman, AH; Davidson, HJ; Horton, MT; Jung, Y, ) | 0.13 |
| " However, the IOP-lowering effects of unoprostone do not compare with other commercially available prostanoids and it has the disadvantage of a twice-daily rather than once-daily dosing regimen." | ( Current status of unoprostone for the management of glaucoma and the future of its use in the treatment of retinal disease. Harms, NV; Toris, CB, 2013) | 0.39 |
| Role | Description |
|---|---|
| antiglaucoma drug | Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye. |
| antihypertensive agent | Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism. |
| prodrug | A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. |
| [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 |
|---|---|
| prostaglandins Falpha | |
| ketone | A compound in which a carbonyl group is bonded to two carbon atoms: R2C=O (neither R may be H). |
| isopropyl ester | Any carboxylic ester resulting from the formal condensation of a carboxylic acid with the hydroxy group of propan-2-ol. |
| [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) |
|---|---|---|---|---|---|---|---|
| TDP1 protein | Homo sapiens (human) | Potency | 7.4993 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| AR protein | Homo sapiens (human) | Potency | 9.7926 | 0.0002 | 21.2231 | 8,912.5098 | AID743035; AID743063 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 27.9238 | 0.0002 | 14.3764 | 60.0339 | AID720691; AID720692; AID720719 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 19.1165 | 0.0002 | 29.3054 | 16,493.5996 | AID743069; AID743075; AID743078 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 5.3080 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 21.5865 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743066; AID743067 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 33.4915 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID720552 |
| Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus | Potency | 39.8107 | 0.0096 | 10.5250 | 35.4813 | AID1479145 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 25.0927 | 0.0119 | 17.9420 | 71.5630 | AID651632; AID720516 |
| Ataxin-2 | Homo sapiens (human) | Potency | 29.8493 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID679955 | TP_TRANSPORTER: uptake in Xenopus laevis oocytes | 2005 | Experimental eye research, Jan, Volume: 80, Issue:1 | Localization of organic anion transporting polypeptides in the rat and human ciliary body epithelium. |
| AID682087 | TP_TRANSPORTER: uptake in Xenopus laevis oocytes | 2005 | Experimental eye research, Jan, Volume: 80, Issue:1 | Localization of organic anion transporting polypeptides in the rat and human ciliary body epithelium. |
| AID679630 | TP_TRANSPORTER: uptake in Xenopus laevis oocytes | 2005 | Experimental eye research, Jan, Volume: 80, Issue:1 | Localization of organic anion transporting polypeptides in the rat and human ciliary body epithelium. |
| AID682064 | TP_TRANSPORTER: uptake in Xenopus laevis oocytes | 2005 | Experimental eye research, Jan, Volume: 80, Issue:1 | Localization of organic anion transporting polypeptides in the rat and human ciliary body epithelium. |
| AID679644 | TP_TRANSPORTER: uptake in Xenopus laevis oocytes | 2005 | Experimental eye research, Jan, Volume: 80, Issue:1 | Localization of organic anion transporting polypeptides in the rat and human ciliary body epithelium. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 33 (24.81) | 18.2507 |
| 2000's | 81 (60.90) | 29.6817 |
| 2010's | 17 (12.78) | 24.3611 |
| 2020's | 2 (1.50) | 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 (14.76) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 48 (32.21%) | 5.53% |
| Reviews | 18 (12.08%) | 6.00% |
| Case Studies | 3 (2.01%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 80 (53.69%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||