chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylate

• ChemBase编号: 751
• 分子式: C24H31ClO7
• 平均质量: 466.95174
• 单一同位素质量: 466.17583101
• SMILES: ClCOC(=O)[C@]1(OC(=O)OCC)[C@@]2([C@H]([C@H]3[C@H]([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)CC3)C)CC1)C
• Canonical SMILES: ClCOC(=O)[C@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)OC(=O)OCC
• InChI: InChI=1S/C24H31ClO7/c1-4-30-21(29)32-24(20(28)31-13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)19(16)18(27)12-23(17,24)3/h7,9,11,16-19,27H,4-6,8,10,12-13H2,1-3H3/t16-,17-,18-,19+,22-,23-,24-/m0/s1
• InChIKey: DMKSVUSAATWOCU-HROMYWEYSA-N

名称和登记号

名称

• IUPAC标准名: chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylate; chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-14-carboxylate
• IUPAC传统名: loteprednol etabonate
• 商标名: Alrex; Lotemax; Zylet; Loteflam
• 别名: (11β,17α)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxo-androsta-1,4-diene-17-carboxylic Acid Chloromethyl Ester; CDDD-5604, HGP-1, P-5604, Alrex, Lotemax; Loteprednol Etabonate; Loteprednol; Alrex; Lotemax; Loteprednol Etabonate

登记号

• CAS号: 82034-46-6
• PubChem SID: 160964214
• PubChem CID: 444025

理论计算性质

JChem

• Acid pKa: 14.879642
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 3.937488
• LogD (pH = 7.4): 3.9374878
• Log P: 3.937488
• 摩尔折射率: 118.1722 cm^3
• 极化性: 46.392654 Å^3
• 极化表面积: 99.13 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.08
• LOG S: -4.83
• 溶解度: 6.93e-03 g/l

分子性质

理化性质

• 溶解度: 5 mg/mL; Chloroform
• 外观: White to Off-White Solid
• 熔点: 226-233°C
• 疏水性(logP): 3.4

安全信息

• 保存条件: -20°C; -20°C Freezer

产品相关信息

• 纯度: 97%
• 成盐信息: Free Base

详细说明

DrugBank - DB00873

• Drug Groups: approved
• Description: Loteprednol (as Loteprednol Etabonate) is a topical corticoid antiinflammatory. It is used in ophthalmic solution for the treatment of steroid responsive inflammatory conditions of the eye such as allergic conjunctivitis, uveitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, and selected infective conjunctivitides. As a nasal spray, is used for the treatment and management of seasonal allergic rhinitis.
• Indication: As an ophthalmic it is used for the treatment of steroid responsive inflammatory conditions of the eye such as allergic conjunctivitis, uveitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, and selected infective conjunctivitides. As a nasal spray, used for the treatment and management of seasonal allergic rhinitis.
• Pharmacology: Loteprednol etabonate (LE) is a "soft" steroid belonging to a unique class of glucocorticoids. LE possesses a metabolically labile 17 beta-chloromethyl ester function which was designed in order to be hydrolyzed to an inactive carboxylic acid moiety. This inactive metabolite is more hydrophilic and is thus readily eliminated from the body. Loteprednol etabonate has good ocular permeation properties and good skin permeation properties similar to "hard" steroids. It is used as a topical agent for the treatment of steroid responsive inflammatory conditions of the eye such as allergic conjunctivitis, uveitis and iritis.
• Toxicity: Adverse effects include abnormal vision / blurring, burning on instillation, chemosis, discharge, dry eyes, epiphora, foreign body sensation, itching, injection, and photophobia.
• Affected Organisms: Humans and other mammals
• Biotransformation: The drugs 17 beta-chloromethyl ester function is hydrolyzed to an inactive carboxylic acid moiety.
• Absorption: Very limited systemic absorption, but good absorption at the point of delivery.
• References: [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1669

Research Area: Inflammation
Biological Activity:
Loteprednol etabonate is an anti-inflammatory corticosteroid used in ophthalmology.It is used for the treatment of steroid responsive inflammatory conditions of the eye such as allergic conjunctivitis, uveitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis and selected infective conjunctivitides. As a nasal spray, it is used for the treatment and management of seasonal allergic rhinitis. [1]

Toronto Research Chemicals - L471400

An ophthalmic corticosteroid. Used as an anti-inflammatory.

参考文献

• Pubmed
• http://en.wikipedia.org/wiki/Loteprednol
• Alberth, M., et al.: J. Biopharm.Sci., 2, 115 (1991)
• Bodor, N., et al.: Pharm. Res., 9, 1275 (1991)
• Bartlett, J.D., et al.: J. Ocul. Pharmacol., 9, 157 (1993)