tafluprost
Description
tafluprost: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
tafluprost : A prostaglandin Falpha that is prostaglandin F2alpha in which the carboxylic acid function has been converted to the corresponding isopropyl ester and the 3-hydroxy-1-octenyl side-chain is substituted by 3,3-difluoro-4-phenoxybut-1-enyl. Used for treatment of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. [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]
Cross-References
ID Source | ID |
---|---|
PubMed CID | 9868491 |
CHEMBL ID | 1963683 |
CHEBI ID | 66899 |
SCHEMBL ID | 1286148 |
MeSH ID | M0466141 |
Synonyms (73)
Synonym |
---|
209860-87-7 |
D06274 |
zioptan (tn) |
tafluprost (jan/usan/inn) |
tafluprost |
zioptan |
tapros |
de-085 |
saflutan |
afp-168 |
de-118 |
taflotan |
mk-2452 |
unii-1o6wq6t7g3 |
1o6wq6t7g3 , |
1-methylethyl (5z)-7-{(1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5- dihydroxycyclopentyl}hept-5-enoate |
5-heptenoic acid, 7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl)-3,5- dihydroxycyclopentyl)-, 1-methylethyl ester, (5z)- |
1-methylethyl (5z)-7-((1r,2r, 3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy -1-butenyl-3,5-dihydroxycyclopentyl)-5-heptenoate |
isopropyl (5z)-7-{(1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl}hept-5-enoate |
tafluprost [usan:inn:ban] |
mk2452 |
CHEMBL1963683 |
chebi:66899 , |
isopropyl (5z)-7-{(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate |
S4851 |
c25h34f2o5 |
AKOS025294885 |
tafluprost [usan] |
tafluprost [inci] |
5-heptenoic acid, 7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5z)- |
tafluprost [jan] |
tafluprost [orange book] |
tafluprost [mart.] |
tafluprost [who-dd] |
tafluprost [mi] |
tafluprost [vandf] |
tafluprost [inn] |
isopropyl (z)-7-[(1r,2r,3r,5s)-2-[(e)-3,3-difluoro-4-phenoxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl]hept-5-enoate |
DB08819 |
HY-B0600 |
propan-2-yl (z)-7-[(1r,2r,3r,5s)-2-[(e)-3,3-difluoro-4-(phenoxy)but-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate |
gtpl7451 |
(z)-isopropyl 7-((1r,2r,3r,5s)-2-((e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate |
J-502635 |
SCHEMBL1286148 |
(z)-isopropyl 7-((1r,2r,3r,5s)-2-((e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxy cyclopentyl)hept-5-enoate |
HMS3649F04 |
propan-2-yl (5z)-7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate |
EX-A564 |
5-heptenoic acid, 7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5z)- |
AS-75193 |
sr-01000946707 |
SR-01000946707-1 |
Q2139543 |
1-methylethyl (5-z)-7-[(1r,2r,3r,5s)-2-[(1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoate |
CCG-269257 |
propan-2-yl (z)-7-[(1r,2r,3r,5s)-2-[(e)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate |
mk2452afp-168 |
(z)-isopropyl7-((1r,2r,3r,5s)-2-((e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate |
DTXSID401021504 |
5-heptenoic acid, 7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy-1-buten-1-yl)-3,5-dihydroxycyclopentyl)-, 1-methylethyl ester, (5z)- |
tafluprostum |
1-methylethyl (5z)-7-((1r,2r, 3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy-1-butenyl)-3,5-dihydroxycyclopentyl)-5-heptenoate |
isopropyl (5z)-7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate |
isopropyl (5z)-7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoate |
tafluprost ophthalmic |
tafluprost (mart.) |
tafluprost opthalmic |
1-methylethyl (5z)-7-((1r,2r, 3r,5s)-2-((1e)-3,3-difluoro-4-phenoxy-1-butenyl-3,5-dihydroxycyclopentyl)-5-heptenoate |
1-methylethyl (5z)-7-((1r,2r,3r,5s)-2-((1e)-3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoate |
s01ee05 |
EN300-21680961 |
Z2568721846 |
Research Excerpts
Overview
Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog. It is used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers.
Treatment
Treatment with tafluprost 0.005% resulted in a significantly greater reduction in IOP, compared with either latanoprost or a placebo. Treatment did not significantly affect cell viability.
Excerpt | Reference | Relevance |
---|---|---|
"Tafluprost-free acid treatment did not significantly affect cell viability." | ( Mechanisms of benzalkonium chloride toxicity in a human trabecular meshwork cell line and the protective role of preservative-free tafluprost. Chang, C; Hutnik, CM; Kagan, DB; Liu, H; Zhang, AQ, 2015) | 1.34 |
"Treatment with tafluprost 0.005% resulted in a significantly greater reduction in IOP, compared with either latanoprost 0.005% or a placebo, at various time points during treatment." | ( A comparative, placebo-controlled study of prostanoid fluoroprostaglandin-receptor agonists tafluprost and latanoprost in healthy males. Gilvarry, A; Ropo, A; Sutton, A, 2007) | 0.9 |
Toxicity
Tafluprost showed a sustained and significant effect with tolerable adverse events in Chinese patients with POAG and OH.
Pharmacokinetics
Bioavailability
Excerpt | Reference | Relevance |
---|---|---|
"Topically administered [(3)H]tafluprost was well absorbed into the ocular and systemic tissues of the primary nonclinical species, monkey." | ( Metabolism and ocular tissue distribution of an antiglaucoma prostanoid, tafluprost, after ocular instillation to monkeys. Akaishi, T; Bezwada, P; Fukano, Y; Kawazu, K; Pellinen, P, 2011) | 0.89 |
Dosage Studied
Plasma concentrations of tafluprost acid were low, with similar levels measured subsequent to either single or repeated dosing of PF FDC and PF taf luprost.
Roles (1)
Role | Description |
---|---|
prostaglandin receptor agonist | An agonist that binds to and activates prostaglandin receptors. |
[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] |
Drug Classes (3)
Class | Description |
---|---|
prostaglandins Falpha | |
organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
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] |
Bioassays (1)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1346394 | Human FP receptor (Prostanoid receptors) | 2004 | Experimental eye research, Apr, Volume: 78, Issue:4 | Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (144)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 18 (12.50) | 29.6817 |
2010's | 102 (70.83) | 24.3611 |
2020's | 24 (16.67) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 61.31
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 very strong demand-to-supply ratio for research on this compound.
| This Compound (61.31) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 35 (23.18%) | 5.53% |
Reviews | 18 (11.92%) | 6.00% |
Case Studies | 1 (0.66%) | 4.05% |
Observational | 9 (5.96%) | 0.25% |
Other | 88 (58.28%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |