Latanoprost acid
Grundinformationen
- CAS
41639-83-2- Standard-SMILES
O=C(O)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O- InChIKey
HNPFPERDNWXAGS-NFVOFSAMSA-N- Summenformel
- C23H34O5
- Durchschnittliche Molmasse
- 390,5 g/mol
- Monoisotopische Masse
- 390,24062419
Überblick
Latanoprost free acid is a prostaglandin Falpha that is an analogue of prostaglandin F2alpha in which the pentyl group has been replaced by 2-phenylethyl and where the the 13,14-double bond has undergone formal hydrogenation. Its isopropyl ester prodrug, latanoprost, is used in the treatment of open-angle glaucoma and ocular hypertension. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, an antihypertensive agent and an antiglaucoma drug. It is a hydroxy monocarboxylic acid and a prostaglandins Falpha.
Namen und Bezeichner
- Bevorzugter Name
- Latanoprost acid
- IUPAC
- (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
- Englischer Name
- Latanoprost acid
- Summenformel
- C23H34O5
- Molmasse
- 390.51
Namen und Synonyme
Latanoprost acid(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoic acidLATANOPROST IMPURITY H [EP IMPURITY](5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid13,14-DIHYDRO-17-PHENYL TRINOR PGF2.ALPHA.5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((3R)-3-HYDROXY-5-PHENYLPENTYL)CYCLOPENTYL)-, (5Z)-LATANOPROST IMPURITY H (EP IMPURITY)(5Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoic acidRefChem:79853213,14-DIHYDRO-17-PHENYL TRINOR PGF2ALPHA682-021-041639-83-2
Weitere Namen anzeigen
(5Z)-LAT-FALT-AcidlatanoprostfreeaciLatanoprost acid 95%LATANOPROST (FREE ACID)Latanoprost Impurity 23
Phxa 85LatanoprostacidPhxa-85latanoprost-free acid(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoic acidMFCD08056084latanoprost free acidLatanoprost impurity H CRS
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 98 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 12
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 472
Physikochemische Eigenschaften
- Siedepunkt
- 609.1 · 609.1±50.0 °C(Predicted)
- Dichte
- 1.159 · 1.159±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- DMSO: freely soluble
- Aggregatzustand
- Oil
- pka
- 4.76 · 4.76±0.10(Predicted)
- Farbe
- pale yellow, oil
- Stabilität
- Hygroscopic
- InChIKey
- HNPFPERDNWXAGS-NFVOFSAMSA-N
- SMILES
- C(O)(=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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Danger
H301 (33.3%): Toxic if swallowed [Danger Acute toxicity, oral]
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 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (33.3%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2937500000
- Speicherklasse
- 10 - Combustible liquids
Chemie und Industrie
Anwendungen
BeschreibungLatanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (free acid) by endogenous esterase enzymes. The free acid form is 200 times more potent than latanoprost as an FP receptor ligand for the human recombinant FP receptor. Latanoprost is the isopropyl ester of a PGF2α analog containing an aromatic group (17-phenyl) in the ω-chain. Lat-FA is the corresponding carboxylic acid of this analog. Lat-FA is a potent FP receptor agonist with an EC50 of 3.6 nM for human FP receptors, which is twice the potency of PGF2α. The efficacy of PG analog esters for the treatment of glaucoma correlates closely with the FP receptor binding affinity of the free acid. However, Lat-FA is more irritating and less effective than the prodrug latanoprost when applied directly to the eyes of human glaucoma patients.
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Anbieter89 Anbieter
国药集团化学试剂有限公司86-21-63210123 · [email protected]
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
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