| Identification | Back Directory | [Name]
17-PHENYL TRINOR PGF2ALPHA-IPR | [CAS]
130209-76-6 | [Synonyms]
13-trans-Latanoprost
Bimatoprost isopropyl este
imatoprost isopropyl ester
Bimatoprost isopropyl ester
17-PHENYL TRINOR PGF2ALPHA-IPR
Bimatoprost Acid Isopropyl Ester
17-phenyl trinor PGF2α isopropyl ester
17-phenyl trinor PGF2alpha isopropyl ester
17-phenyl trinor Prostaglandin F2α isopropyl ester
17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER
isopropyl phenylhydroxypentene dihydroxycyclopentylheptenate
17-phenyl-18,19,20-trinor-prostaglandinf2alpha-1-isopropylester
9ALPHA,11ALPHA,15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER
isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)hept-5-enoate
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoate
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-5-heptenoic acid propan-2-yl ester
7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-5-heptenoic acid 1-methylethyl ester
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-, 1-methylethyl ester, (5Z)- | [Molecular Formula]
C26H38O5 | [MDL Number]
MFCD00902150 | [MOL File]
130209-76-6.mol | [Molecular Weight]
430.58 |
| Chemical Properties | Back Directory | [Boiling point ]
573.4±50.0 °C(Predicted) | [density ]
1.141 | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 50 mg/ml; Ethanol:PBS (pH 7.2) (1:1): 1 mg/ml | [form ]
Solid | [pka]
14.25±0.20(Predicted) | [color ]
White to off-white | [InChIKey]
JGZRPRSJSQLFBO-FWPUOYPASA-N | [SMILES]
C(OC(C)C)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1 |
| Hazard Information | Back Directory | [Description]
17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost.1 The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost.2 This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist.3 In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost.4 At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF2α isopropyl ester was the most potent analog tested in reducing IOP, lowering the IOP 1.3 mm Hg below the level achieved by latanoprost. However, this derivative was also significantly more irritating to the eye than latanoprost.4 | [Uses]
PhDH 100A can be useful in the determination of prostaglandin analogs in cosmetic products by high performance liquid chromatography with tandem mass spectrometry. | [Definition]
ChEBI: 17-phenyl-trinor-PGF2alpha isopropyl ester is a prostanoid. | [storage]
Store at -20°C | [References]
[1] MARK ABRAMOVITZ . The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2000, 1483 2: Pages 285-293. DOI: 10.1016/s1388-1981(99)00164-x
[2] D.F WOODWARD PHD. The Pharmacology of Bimatoprost (Lumigan?)[J]. Survey of ophthalmology, 2001, 45: Pages S337-S345. DOI: 10.1016/s0039-6257(01)00224-7
[3] BAHRAM RESUL PHD Johan S M, PHD Laszlo B P Goran Selén Phd. Structure-activity relationships and receptor profiles of some ocular hypotensive prostanoids[J]. Survey of ophthalmology, 1997, 41: Pages S47-S52. DOI: 10.1016/s0039-6257(97)80007-0
[4] KIRK M MAXEY MD Jennifer L B Jennifer L Johnson MS. The Hydrolysis of Bimatoprost in Corneal Tissue Generates a Potent Prostanoid FP Receptor Agonist[J]. Survey of ophthalmology, 2002, 47: Pages S34-S40. DOI: 10.1016/s0039-6257(02)00323-5 |
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