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209860-87-7 | 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)-
CAS No: 209860-87-7 Catalog No: AG002KG9 MDL No:MFCD08062150
Product Description
Catalog Number:
AG002KG9
Chemical Name:
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)-
CAS Number:
209860-87-7
Molecular Formula:
C25H34F2O5
Molecular Weight:
452.5313
MDL Number:
MFCD08062150
IUPAC Name:
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
InChI:
InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1
InChI Key:
WSNODXPBBALQOF-VEJSHDCNSA-N
SMILES:
CC(OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/C(COc1ccccc1)(F)F)O)C
UNII:
1O6WQ6T7G3
Properties
Complexity:
614
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
2
Exact Mass:
452.237g/mol
Formal Charge:
0
Heavy Atom Count:
32
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
452.539g/mol
Monoisotopic Mass:
452.237g/mol
Rotatable Bond Count:
13
Topological Polar Surface Area:
76A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.5
Literature
| Title | Journal |
|---|---|
| Corneal epithelial cell viability following exposure to ophthalmic solutions containing preservatives and/or antihypertensive agents. | Advances in therapy 20121001 |
| Drug metabolite heterogeneity in cultured single cells profiled by pico-trapping direct mass spectrometry. | Nanomedicine (London, England) 20120901 |
| Comparison of efficacy of four prostaglandin analogues by bilateral treatment in healthy subjects. | Japanese journal of ophthalmology 20120701 |
| Efficacy and ocular surface tolerability of preservative-free tafluprost 0.0015%: a 6-month, single-blind, observational study on naïve ocular hypertension or glaucoma patients. | Expert opinion on drug safety 20120701 |
| Randomized clinical trial of the efficacy and safety of preservative-free tafluprost and timolol in patients with open-angle glaucoma or ocular hypertension. | American journal of ophthalmology 20120601 |
| Spanish multicenter tafluprost tolerability study. | The British journal of ophthalmology 20120601 |
| Tafluprost (Zioptan) - a new topical prostaglandin for glaucoma. | The Medical letter on drugs and therapeutics 20120416 |
| In vitro study of antiadipogenic profile of latanoprost, travoprost, bimatoprost, and tafluprost in human orbital preadiopocytes. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20120401 |
| FDA approves glaucoma treatment. | American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20120315 |
| Ocular hypotensive effect of tafluprost in latanoprost low-responder cynomolgus monkeys. | Journal of glaucoma 20120201 |
| A prospective study evaluating IOP changes after switching from a therapy with prostaglandin eye drops containing preservatives to nonpreserved tafluprost in glaucoma patients. | TheScientificWorldJournal 20120101 |
| Clobazam, ezogabine, and tafluprost. | Journal of the American Pharmacists Association : JAPhA 20120101 |
| Efficacy and safety of tafluprost in normal-tension glaucoma with intraocular pressure of 16 mmHg or less. | Japanese journal of ophthalmology 20111101 |
| Tafluprost for glaucoma. | Expert opinion on pharmacotherapy 20111001 |
| Tafluprost: a novel prostaglandin analog for treatment of glaucoma. | Advances in therapy 20110901 |
| Preservative-free tafluprost 0.0015% in the treatment of patients with glaucoma and ocular hypertension. | Advances in therapy 20110701 |
| Toxicological evaluation of preservative-containing and preservative-free topical prostaglandin analogues on a three-dimensional-reconstituted corneal epithelium system. | The British journal of ophthalmology 20110601 |
| Metabolism and ocular tissue distribution of an antiglaucoma prostanoid, tafluprost, after ocular instillation to monkeys. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20110601 |
| Effects of prostaglandin F(2α) analogues on endothelin-1-induced impairment of rabbit ocular blood flow: comparison among tafluprost, travoprost, and latanoprost. | Experimental eye research 20101201 |
| Effects of benzalkonium chloride-preserved, polyquad-preserved, and sofZia-preserved topical glaucoma medications on human ocular epithelial cells. | Advances in therapy 20101101 |
| Effects of topical phenylephrine and tafluprost on optic nerve head circulation in monkeys with unilateral experimental glaucoma. | Investigative ophthalmology & visual science 20100801 |
| IOP-lowering efficacy and tolerability of preservative-free tafluprost 0.0015% among patients with ocular hypertension or glaucoma. | Current medical research and opinion 20100801 |
| Twenty-four-hour ocular hypotensive effects of 0.0015% tafluprost and 0.005% latanoprost in healthy subjects. | Japanese journal of ophthalmology 20100701 |
| [Optimization of benzalkonium chloride concentration in 0.0015% tafluprost ophthalmic solution from the points of ocular surface safety and preservative efficacy]. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20100601 |
| In vitro toxicity of topical ocular prostaglandin analogs and preservatives on corneal epithelial cells. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20100601 |
| A review of preserved and preservative-free prostaglandin analogues for the treatment of open-angle glaucoma and ocular hypertension. | Drugs of today (Barcelona, Spain : 1998) 20100601 |
| [Intraocular pressure lowering effect of 0.0015% tafluprost as compared to placebo in patients with normal tension glaucoma: randomized, double-blind, multicenter, phase III study]. | Nippon Ganka Gakkai zasshi 20100501 |
| Switching from a preserved to a preservative-free prostaglandin preparation in topical glaucoma medication. | Acta ophthalmologica 20100501 |
| Effects of repeated administrations of tafluprost, latanoprost, and travoprost on optic nerve head blood flow in conscious normal rabbits. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20100401 |
| A phase II study on the duration and stability of the intraocular pressure-lowering effect and tolerability of Tafluprost compared with latanoprost. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20100201 |
| Efficacy and safety of tafluprost 0.0015% versus latanoprost 0.005% eye drops in open-angle glaucoma and ocular hypertension: 24-month results of a randomized, double-masked phase III study. | Acta ophthalmologica 20100201 |
| Tafluprost protects rat retinal ganglion cells from apoptosis in vitro and in vivo. | Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie 20091001 |
| Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats. | Drug metabolism and disposition: the biological fate of chemicals 20090801 |
| Corneal penetration into rabbit aqueous humor is comparable between preserved and preservative-free tafluprost. | Ophthalmic research 20090101 |
| Adjunctive use of tafluprost with timolol provides additive effects for reduction of intraocular pressure in patients with glaucoma. | European journal of ophthalmology 20090101 |
| [Receptors involved in the mechanism of action of topical prostaglandines]. | Oftalmologia (Bucharest, Romania : 1990) 20090101 |
| Short-term effects of topical tafluprost on retinal blood flow in cats. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20081001 |
| Relaxing effect and mechanism of tafluprost on isolated rabbit ciliary arteries. | Experimental eye research 20080901 |
| Conjunctival and corneal reactions in rabbits following short- and repeated exposure to preservative-free tafluprost, commercially available latanoprost and 0.02% benzalkonium chloride. | The British journal of ophthalmology 20080901 |
| Tafluprost, a new potent prostanoid receptor agonist: a dose-response study on pharmacodynamics and tolerability in healthy volunteers. | International journal of clinical pharmacology and therapeutics 20080801 |
| In vitro effects of preservative-free tafluprost and preserved latanoprost, travoprost, and bimatoprost in a conjunctival epithelial cell line. | Current eye research 20080401 |
| In search of improved prostaglandin treatment for glaucoma. | Acta ophthalmologica. Supplement 20080101 |
| Pharmacokinetics, efficacy and safety profiles of preserved and preservative-free tafluprost in healthy volunteers. | Acta ophthalmologica. Supplement 20080101 |
| Efficacy and safety levels of preserved and preservative-free tafluprost are equivalent in patients with glaucoma or ocular hypertension: results from a pharmacodynamics analysis. | Acta ophthalmologica. Supplement 20080101 |
| [Glaucoma--strategy of treatment]. | Oftalmologia (Bucharest, Romania : 1990) 20080101 |
| A comparative, placebo-controlled study of prostanoid fluoroprostaglandin-receptor agonists tafluprost and latanoprost in healthy males. | Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20070801 |
| The IOP-lowering effects and mechanism of action of tafluprost in prostanoid receptor-deficient mice. | The British journal of ophthalmology 20070501 |
| Prostaglandin analogues and mouse intraocular pressure: effects of tafluprost, latanoprost, travoprost, and unoprostone, considering 24-hour variation. | Investigative ophthalmology & visual science 20050601 |
| Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. | Experimental eye research 20040401 |
| New fluoroprostaglandin F(2alpha) derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. | Biological & pharmaceutical bulletin 20031201 |
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