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| 化学名: | ラタノプロスト | | 英語化学名: | Latanoprost | | 别名: | ISOPROPYL (5Z, 9A,11A,15R)-9,11,15-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROST-5Z-EN-1-OATE;LATANOPROST;[1R-[1α(Z)，2β(R^<*>^)，3α，5α]]-7-[3，5-Dihydroxy-2-(3-hydroxy-5-phenyl-pentyl)cyclopentyl]-5-heptenoic acid 1-methylethyl ester;Xalata;Isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoat;Latanopros;Isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate;Latanoprost ,98% | | CAS番号: | 130209-82-4 | | 分子式: | C26H40O5 | | 分子量: | 432.59 | | EINECS: | 634-172-9 | | カテゴリ情報: | Prostaglandin;Prostaglandins;Active Pharmaceutical Ingredients;Other APIs;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors;Key Products;130209-82-4;API | | Mol File: | 130209-82-4.mol |  |
| 比旋光度 | D20 +31.57° (c = 0.91 in acetonitrile) | | 沸点 | 583.8±50.0 °C(Predicted) | | 比重(密度) | 1.093±0.06 g/cm3(Predicted) | | 貯蔵温度 | -20°C | | 溶解性 | DMSO: freely soluble | | 外見 | oil | | 酸解離定数(Pka) | 14.84±0.70(Predicted) | | 色 | pale yellow | | Merck | 14,5376 | | BCS Class | 2 | | InChIKey | GGXICVAJURFBLW-RDSJPUOVSA-N | | CAS データベース | 130209-82-4(CAS DataBase Reference) |
| WGK Germany | 3 | | RTECS 番号 | MJ9669550 | | HSコード | 2937500000 |
| | ラタノプロスト Usage And Synthesis |
| 外観 | 無色～うすい黄色透明液体 | | 用途 | PGF2α 誘導体です。プロス
ラグンジン作用を示します。 | | 効能 | 抗緑内障薬, プロスタグランジンF受容体作動薬 | | 商品名 | キサラタン (ファイザー) | | 説明 | Xalatan was launched in Sweden, Switzerland and the US for the treatment
of glaucoma. It can be synthesized, from the Corey lactone, using standard
prostaglandin chemistry. Latanoprost is a PGF2α, analog that is more lipophilic thus
is better able to penetrate the cornea. The (15R)-diastereomer has only 10% of the
activity compared to the (15S)-diastereomer. It is a selective FP receptor agonist
with little or no effect on the other prostanoid receptors. The antiglaucoma effects
are the result of reduced intraocular pressure arising by increasing uveoscleral
outflow with little or no effect on trabeculo-canalicular aqueous outflow and no effect
on retinal vasculation or permeability of the blood-aqueous barrier. The topical
application is sufficient for a single daily dosage and is well tolerated with no
detectible conjunctival hyperaemia. | | 化学的特性 | Light Yellow Thick Oil | | Originator | Pharmacia & pjohn (UK) | | 使用 | antifungal polyene macrolide that is active in the cell membrane soluble 5% Acetic acid | | 使用 | Prostanoid receptor ligand | | 使用 | Prostaglandin analog, used to treat glaucoma and other degenerative diseases of the eye. | | 使用 | Latanoprost is the isopropyl ester of 17-phenyl-13,14-dihydro prostaglandin F2α (17-phenyl-13,14-dihydro PGF2α). It is a prodrug form of the free acid, which is a potent agonist of the FP receptor in the eye. Latanoprost reduces intraocular pressure in glaucoma patients with few side effects. The EC50 value of latanoprost (tested as the free acid) for FP receptors is 3.6 nM. | | 定義 | ChEBI: A prostaglandin Falpha that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension. | | Manufacturing Process | Manufacturing process for Latanoprost includes these steps as follows: Synthesis of [3aR-[3aα,4α(E),5β,6aα]]-5-(benzoyloxy)
hexahydro-4-(3-oxo-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4a(1E,3S),5β,6aα]]-5-(benzoyloxy)hexahydro-
4-(3 -hydroxy-5-phenyl-1-pentenyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4a(1E,3S),5β,6aα]]-
5-(benzoyloxy)hexahydro-4-(3-hydroxy-5-phenyl-1-pentyl)-2Hcyclopenta[b]furan-2-one, synthesis of 2-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-
phenylpentyl]cyclopentyl]acetic acid, synthesis of [3aR-[3aα,4α(R),5β,6aα]]-hexahydro-5-hydroxy-4-(3-hydroxy-5-
phenylpentyl)-2H-cyclopenta[b]furan-2-one, synthesis of [3aR-[3aα,4α(R),5β,6aα]]-
hexahydro-5-hydroxy-4-(3-hydroxy-5-phenylpentyl)-2H-cyclopenta[b]furan-2-one;synthesis of (3aR,4R,5R,6aS)-5-
(1-ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2Hcyclopenta[b]furan-2-ol;synthesis of 7-[(1R,2R,3R,5S)-3-(1-ethoxyethoxy)-5-
hydroxy-2-[(3R)-3-(1-ethoxyethoxy)-5- phenylpentyl]cyclopentyl-5-heptenoic acid; synthesis of (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-
phenylpentyl]cyclopentyl]-5-heptenoic acid (Latanoprost Acid); At last, Latanoprost acid is dissolved in DMF (10 mL) and added to a slurry of cesium
carbonate (1.6 g) in DMF (10 mL). 2-Iodopropane (0.49 mL) is added and the
slurry is heated to 45°C for about 6 hours. When the reaction is complete,
MTBE (40 mL) and water (50 mL) are added and the mixture is stirred for 15
min. The phases are separated and the aqueous phase is washed with MTBE
(20 mL). The organic phases are combined and concentrated. The concentrate
is chromatographed (silica gel) eluting with MTBE. The appropriate fractions
are pooled and concentrated to give (5Z)-(9CI)-7-[(1R,2R,3R,5S)-3,5-
Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl ]cyclopentyl]-5-heptenoic acid 1-
methylethyl ester (Latanoprost). | | brand name | Xalatan (Pharmacia & Upjohn). | | Therapeutic Function | Antiglaucoma | | 一般的な説明 | Latanoprost (Xalatan) is available as a 0.005% sterileophthalmic solution in a 2.5-mL dispenser bottle.Latanoprost is also marketed as a combination ophthalmicproduct with the β-adrenergic blocking agent, timolol,which apparently enhances IOP-lowering by decreasing theproduction of aqueous humor. Cautions and side effects aresimilar to those for other ophthalmic prostanoids. | | Biochem/physiol Actions | Latanoprost is a potent, selective prostaglandin F2α?analog receptor agonist. It is hydrolyzed by esterases into its biologically active form latanoprost acid in the cornea. Latanoprostplays a role in reducing the intraocular pressure (IOP) due to which it has therapeutic effects in treating glaucoma. | | 安全性プロファイル | A poison by ingestion
and intravenous route. Human systemic
effects. When heated to decomposition it
emits acrid smoke and irritating vapors. |
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