Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:49 UTC |
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HMDB ID | HMDB0015011 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Loteprednol |
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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. |
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Structure | [H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C InChI=1S/C21H27ClO5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,18(25)27-11-22)20(15,2)10-16(24)17(14)19/h5,7,9,14-17,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17+,19-,20-,21-/m0/s1 |
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Synonyms | Value | Source |
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Loteprednol etabonate | HMDB | CEHOAC | HMDB | Chloromethyl 17 ethoxycarbonyloxy 11 hydroxy 3 oxoandrosta 1,4 diene 17 carboxylate | HMDB | Etabonate, loteprednol | HMDB | Chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate | HMDB | 17-Ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate, chloromethyl | HMDB | Lotemax | HMDB | Alrex | HMDB |
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Chemical Formula | C21H27ClO5 |
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Average Molecular Weight | 394.889 |
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Monoisotopic Molecular Weight | 394.154701681 |
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IUPAC Name | chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate |
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Traditional Name | loteprednol |
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CAS Registry Number | 82034-46-6 |
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SMILES | [H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C |
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InChI Identifier | InChI=1S/C21H27ClO5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,18(25)27-11-22)20(15,2)10-16(24)17(14)19/h5,7,9,14-17,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17+,19-,20-,21-/m0/s1 |
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InChI Key | YPZVAYHNBBHPTO-MXRBDKCISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- 3-oxo-delta-1,4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- 11-hydroxysteroid
- 11-beta-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-1,4-steroid
- Tertiary alcohol
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Carboxylic acid ester
- Ketone
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organochloride
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Alkyl halide
- Alkyl chloride
- Alcohol
- Organohalogen compound
- Organic oxide
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 220 - 224 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.034 g/L | Not Available | LogP | 3.4 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Loteprednol,1TMS,isomer #1 | C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)OCCl | 3334.1 | Semi standard non polar | 33892256 | Loteprednol,1TMS,isomer #2 | C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)OCCl | 3222.5 | Semi standard non polar | 33892256 | Loteprednol,2TMS,isomer #1 | C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)OCCl | 3262.7 | Semi standard non polar | 33892256 | Loteprednol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@]1(C(=O)OCCl)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | 3602.7 | Semi standard non polar | 33892256 | Loteprednol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O)C(=O)OCCl)[C@@H]2CCC3=CC(=O)C=C[C@]3(C)[C@@H]12 | 3487.3 | Semi standard non polar | 33892256 | Loteprednol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)OCCl)[C@@H]2CCC3=CC(=O)C=C[C@]3(C)[C@@H]12 | 3765.0 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Loteprednol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0v7i-1893000000-682774df467cdebbec3b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Loteprednol GC-MS (2 TMS) - 70eV, Positive | splash10-00di-4839780000-d51f7f1f3e7bf65172bc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Loteprednol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Loteprednol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 10V, Positive-QTOF | splash10-004j-0019000000-25a9a1528f2869a02f3a | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 20V, Positive-QTOF | splash10-004i-0229000000-0aac7fbe4742db297f38 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 40V, Positive-QTOF | splash10-001i-0691000000-0ee7c0d161653ecef2f7 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 10V, Negative-QTOF | splash10-0006-0009000000-8a39d043964bd24e691c | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 20V, Negative-QTOF | splash10-002f-1019000000-006d094367c84d7fdc6d | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 40V, Negative-QTOF | splash10-0002-4091000000-cb6ff84a4e686bd3ebb2 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 10V, Positive-QTOF | splash10-0002-0009000000-a0ac3be7c2d25192a078 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 20V, Positive-QTOF | splash10-08fs-1912000000-0c6368a24232c8f7e898 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 40V, Positive-QTOF | splash10-05di-3390000000-2940c512e174324e33e3 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 10V, Negative-QTOF | splash10-0006-0009000000-6de0933cc349eb685660 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 20V, Negative-QTOF | splash10-001i-9037000000-68cdcec02980ed86b9a9 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Loteprednol 40V, Negative-QTOF | splash10-001r-1191000000-a2b788885ecb2baf3516 | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00873 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00873 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00873 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8041134 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Loteprednol |
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METLIN ID | Not Available |
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PubChem Compound | 9865442 |
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PDB ID | Not Available |
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ChEBI ID | 50848 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Pavesio CE, Decory HH: Treatment of ocular inflammatory conditions with loteprednol etabonate. Br J Ophthalmol. 2008 Apr;92(4):455-9. doi: 10.1136/bjo.2007.132621. Epub 2008 Feb 1. [PubMed:18245274 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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