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 ID: 751
• Molecular Formular: C24H31ClO7
• Molecular Mass: 466.95174
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: loteprednol etabonate
• Brand Name: Alrex; Lotemax; Zylet; Loteflam
• Synonyms: (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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.879642
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.937488
• LogD (pH = 7.4): 3.9374878
• Log P: 3.937488
• Molar Refractivity: 118.1722 cm^3
• Polarizability: 46.392654 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.08
• LOG S: -4.83
• Solubility (Water): 6.93e-03 g/l

PROPERTIES

Physical Property

• Solubility: 5 mg/mL; Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 226-233°C
• Hydrophobicity(logP): 3.4

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Purity: 97%
• Salt Data: Free Base

DETAILS

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.

REFERENCES

• 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)