Latanoprost
Latanopros · LATANAPROST · 17-PHENYL-13,14-DIHYDRO TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER · Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate · xa41 · Xalata · phxa41 · LATANOPROST
Identifikatoren & physikalische Daten
| CAS No. | 130209-82-4 |
|---|---|
| Summenformel | C26H40O5 |
| Durchschnittliche Molmasse | 432,6 g/mol |
| Monoisotopische Masse | 432,28757437 g/mol |
| SMILES | CC(C)OC(=O)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O |
| InChIKey | GGXICVAJURFBLW-CEYXHVGTSA-N |
| PubChem CID | 5311221 |
| ChEMBL | CHEMBL1051 |
| ChEBI | CHEBI:6384 |
| EC No. | 634-172-9 |
| DTXSID | DTXSID1041057 |
Chemische & physikalische Eigenschaften
| XLogP | 4,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 87 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 14 |
| Schwere Atome | 31 |
| Formalladung | 0 |
| Komplexität | 526 |
| LogP (Verteilungskoeffizient) | 3.984.4 |
| Löslichkeit | 1.29e-02 g/LDMSO: freely soluble |
| Siedepunkt | 583.8583.8±50.0 °C(Predicted) |
| Physical Description | Liquid |
| Dissociation Constants | 4.88 |
| Dichte | 1.093±0.06 g/cm3(Predicted) |
| Lagerbedingungen | -20°C |
| Aggregatzustand | oil |
| pKa (Säurekonstante) | 14.84±0.70(Predicted) |
| Farbe | pale yellow |
| Merck | 14,5376 |
| BCS Class | 2 |
| InChIKey | GGXICVAJURFBLW-RDSJPUOVSA-N |
| SMILES | C(OC(C)C)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 |
| CAS Datenbank | 130209-82-4(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.7% (1 of 145) of reports.DangerH300 (63.4%): Fatal if swallowed [Danger Acute toxicity, oral]H301 (11%): Toxic if swallowed [Danger Acute toxicity, oral]H361 (62.1%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 145 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 145 reports by companies.There are 15 notifications provided by 144 of 145 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 1 (63.4%)Acute Tox. 3 (11%)Repr. 2 (62.1%) |
| Unerwünschte Wirkungen | The primary adverse effects of latanoprost include eyelid edema, blurred vision, dry eyes, itching, redness, the growth of eyelashes, change in eyelid pigmentation (may become darker), iris, and eyelash. Other adverse effects of latanoprost include contact dermatitis/allergic conjunctivitis and an iris cyst. See specific adverse effects listed below.Conjunctival hyperemia: Conjunctival hyperemia is among the most common side effects noted in 5% to 15% of patients, more than in timolol-treated eyes. Latanoprost with a preservative (benzalkonium chloride) may reduce the goblet cell density. The conjunctival redness usually appears within 2 to 3 days of initiation of the topical treatment, reduces within 1 month, and is typically mild with prolonged use.Hypertrichosis: Hypertrichosis is an increase in the thickness, length, and number of eyelashes. Although this is preferred from a cosmetic point of view in some patients, the unilateral occurrence can be undesirable. The changes in the eyelashes are usually reversible after discontinuing the drugthis is due to the stimulation of the growth phase of the hair cycle. |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.