propan-2-yl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

• ChemBase ID: 536
• Molecular Formular: C26H40O5
• Molecular Mass: 432.5928
• Monoisotopic Mass: 432.28757438
• SMILES: O[C@H]1[C@@H]([C@H]([C@@H](O)C1)C/C=C/CCCC(=O)OC(C)C)CC[C@@H](O)CCc1ccccc1
• Canonical SMILES: O[C@@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C/CCCC(=O)OC(C)C)O
• InChI: InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3+/t21-,22+,23+,24-,25+/m0/s1
• InChIKey: GGXICVAJURFBLW-RDSJPUOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; propan-2-yl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• IUPAC Traditional name: isopropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; latanaprost
• Brand Name: Xalatan; Xalatan Fixed Flow Device
• Synonyms: (5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; (5E)-Latanoprost; 5,6-trans-Latanoprost; trans-Latanoprost; Isopropyl (5Z,9α,11α,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate; Xalatan; Latanoprost; latanoprost; Latanoprost

Database IDs

• CAS Number: 130209-82-4; 913258-34-1
• MDL Number: MFCD00216074
• PubChem SID: 160963999; 24724523
• PubChem CID: 5282380

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.468507
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.9810123
• LogD (pH = 7.4): 3.9810123
• Log P: 3.9810123
• Molar Refractivity: 124.3376 cm^3
• Polarizability: 48.735634 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.16
• LOG S: -4.53
• Solubility (Water): 1.29e-02 g/l

PROPERTIES

Physical Property

• Solubility: 8 mg/mL; Chloroform; DMSO: freely soluble; methanol: soluble
• Apperance: Colourless Oil; pale yellow oil
• Hydrophobicity(logP): 4.4

Safety Information

• Storage Condition: -80°C Freezer
• RTECS: MJ9669550
• German water hazard class: 3
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H40O5

DETAILS

DrugBank - DB00654

• Drug Groups: approved; investigational
• Description: Latanoprost ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.; ; It is also known by the brand name of Xalatan manufactured by Pfizer.
• Indication: For the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
• Pharmacology: Latanoprost is an isopropyl ester prodrug which is inactive but which becomes active after hydrolysis to the acid from. Latanoprost opthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.
• Toxicity: Symptoms of overdose include bloodshot eyes and eye irritation.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic (none except hydrolysis in the eye). Latanoprost is an isopropyl ester prodrug. It is hydrolyzed by esterases in the cornea to latanoprost acid, which is biologically active. The portion of the latanoprost acid that reaches the systemic circulation is metabolized primarily by the liver to 1,2-dinor and 1,2,3,4-tetranor metabolites by fatty acid beta-oxidation.
• Absorption: Latanoprost is well absorbed through the cornea where the isopropyl ester prodrug is hydrolyzed to the acid form. Peak concentration is reached 2 hrs after topical administration.
• Half Life: 17 minutes
• Clearance: * 7 mL/min/kg
• References: Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes] Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - L1167

Biochem/physiol Actions
Latanoprost is a potent, selective prostaglandin FP receptor agonist.

Toronto Research Chemicals - L177300

Prostaglandin analog; prodrug of active acid metabolite. It is a synthetic derivative of the natural prostaglandin PGF2α, used as an anti-glaucoma agent that is effective in various types of glaucoma and ocular hypertension.

REFERENCES

• Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes] Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. Pubmed
• Resul, B., et al.: J. Med. Chem., 36, 2242 (1993)
• Toris, C., et al.: Ophthalmology, 100, 1297 (1993)
• Holmstrom, S., et al.: Curr. Med. Res. Op., 21, 1875 (1993)