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 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:48 UTC |
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HMDB ID | HMDB0014976 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Clocortolone |
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Description | Clocortolone is only found in individuals that have used or taken this drug. It is a medium potency corticosteroid that is often used as a topical cream for the relief of inflammatory oand pruritic (itching) arising from steroid-responsive dermatoses of the scalp.The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. These enzyme transcriptional changes are mediated by the drug binding first to the glucocorticoid receptor. This complex can migrate to the cell nucleus which then binds to DNA initiating genetic activation and repression of various genes. |
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Structure | [H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1 |
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Synonyms | Value | Source |
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9-Chloro-6alpha-fluoro-11beta,21-dihydroxy-16alpha-methyl-1,4-pregnadien-3,20-dione | ChEBI | 9-Chloro-6alpha-fluoro-16alpha-methyl-1,4-pregnadiene-11beta,21-diol-3,20-dione | ChEBI | Clocortolona | ChEBI | Clocortolonum | ChEBI | 9-Chloro-6a-fluoro-11b,21-dihydroxy-16a-methyl-1,4-pregnadien-3,20-dione | Generator | 9-Chloro-6α-fluoro-11β,21-dihydroxy-16α-methyl-1,4-pregnadien-3,20-dione | Generator | 9-Chloro-6a-fluoro-16a-methyl-1,4-pregnadiene-11b,21-diol-3,20-dione | Generator | 9-Chloro-6α-fluoro-16α-methyl-1,4-pregnadiene-11β,21-diol-3,20-dione | Generator | Clocortolone pivalate | HMDB | Clocortolone acetate | HMDB |
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Chemical Formula | C22H28ClFO4 |
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Average Molecular Weight | 410.907 |
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Monoisotopic Molecular Weight | 410.166015296 |
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IUPAC Name | (1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one |
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Traditional Name | clocortolona |
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CAS Registry Number | 34097-16-0 |
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SMILES | [H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C |
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InChI Identifier | InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1 |
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InChI Key | YMTMADLUXIRMGX-RFPWEZLHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
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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 | Hydroxysteroids |
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Direct Parent | 21-hydroxysteroids |
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Alternative Parents | |
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Substituents | - 21-hydroxysteroid
- Progestogin-skeleton
- 20-oxosteroid
- Pregnane-skeleton
- 6-halo-steroid
- Halo-steroid
- 3-oxo-delta-1,4-steroid
- 9-halo-steroid
- 3-oxosteroid
- Oxosteroid
- 11-beta-hydroxysteroid
- 11-hydroxysteroid
- Delta-1,4-steroid
- Cyclic alcohol
- Alpha-hydroxy ketone
- Halohydrin
- Chlorohydrin
- Secondary alcohol
- Ketone
- Cyclic ketone
- Organic oxygen compound
- Organohalogen compound
- Organochloride
- Organofluoride
- Organooxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- Alkyl halide
- Alkyl fluoride
- Alkyl chloride
- Alcohol
- 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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.015 g/L | Not Available | LogP | 3.8 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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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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Clocortolone,1TMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C | 3283.1 | Semi standard non polar | 33892256 | Clocortolone,1TMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=O)CO | 3247.1 | Semi standard non polar | 33892256 | Clocortolone,1TMS,isomer #3 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO)O[Si](C)(C)C | 3209.5 | Semi standard non polar | 33892256 | Clocortolone,1TMS,isomer #4 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C | 3225.7 | Semi standard non polar | 33892256 | Clocortolone,2TMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C | 3222.7 | Semi standard non polar | 33892256 | Clocortolone,2TMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C | 3163.6 | Semi standard non polar | 33892256 | Clocortolone,2TMS,isomer #3 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3214.2 | Semi standard non polar | 33892256 | Clocortolone,2TMS,isomer #4 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO)O[Si](C)(C)C | 3138.0 | Semi standard non polar | 33892256 | Clocortolone,2TMS,isomer #5 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C | 3155.5 | Semi standard non polar | 33892256 | Clocortolone,3TMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C | 3137.0 | Semi standard non polar | 33892256 | Clocortolone,3TMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C | 3216.0 | Standard non polar | 33892256 | Clocortolone,3TMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C | 3464.8 | Standard polar | 33892256 | Clocortolone,3TMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3183.5 | Semi standard non polar | 33892256 | Clocortolone,3TMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3175.2 | Standard non polar | 33892256 | Clocortolone,3TMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C | 3505.8 | Standard polar | 33892256 | Clocortolone,1TBDMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C(C)(C)C | 3510.2 | Semi standard non polar | 33892256 | Clocortolone,1TBDMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=O)CO | 3445.1 | Semi standard non polar | 33892256 | Clocortolone,1TBDMS,isomer #3 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO)O[Si](C)(C)C(C)(C)C | 3443.3 | Semi standard non polar | 33892256 | Clocortolone,1TBDMS,isomer #4 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C(C)(C)C | 3441.2 | Semi standard non polar | 33892256 | Clocortolone,2TBDMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C(C)(C)C | 3681.3 | Semi standard non polar | 33892256 | Clocortolone,2TBDMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3609.9 | Semi standard non polar | 33892256 | Clocortolone,2TBDMS,isomer #3 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3620.3 | Semi standard non polar | 33892256 | Clocortolone,2TBDMS,isomer #4 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO)O[Si](C)(C)C(C)(C)C | 3587.2 | Semi standard non polar | 33892256 | Clocortolone,2TBDMS,isomer #5 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C(C)(C)C | 3588.1 | Semi standard non polar | 33892256 | Clocortolone,3TBDMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3773.5 | Semi standard non polar | 33892256 | Clocortolone,3TBDMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3828.8 | Standard non polar | 33892256 | Clocortolone,3TBDMS,isomer #1 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3678.8 | Standard polar | 33892256 | Clocortolone,3TBDMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3813.4 | Semi standard non polar | 33892256 | Clocortolone,3TBDMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3788.8 | Standard non polar | 33892256 | Clocortolone,3TBDMS,isomer #2 | C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3709.1 | Standard polar | 33892256 |
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