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

• ChemBase编号: 536
• 分子式: C26H40O5
• 平均质量: 432.5928
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: isopropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; latanaprost
• 商标名: Xalatan; Xalatan Fixed Flow Device
• 别名: (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

登记号

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

理论计算性质

JChem

• Acid pKa: 14.468507
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 3.9810123
• LogD (pH = 7.4): 3.9810123
• Log P: 3.9810123
• 摩尔折射率: 124.3376 cm^3
• 极化性: 48.735634 Å^3
• 极化表面积: 86.99 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.16
• LOG S: -4.53
• 溶解度: 1.29e-02 g/l

分子性质

理化性质

• 溶解度: 8 mg/mL; Chloroform; DMSO: freely soluble; methanol: soluble
• 外观: Colourless Oil; pale yellow oil
• 疏水性(logP): 4.4

安全信息

• 保存条件: -80°C Freezer
• RTECS编号: MJ9669550
• 德国WGK号: 3
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C26H40O5

详细说明

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.

参考文献

• 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)