Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H50O |
| Molecular Weight | 426.7174 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC3)[C@H](C)CCC=C(C)C
InChI
InChIKey=CAHGCLMLTWQZNJ-BQNIITSRSA-N
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
| Molecular Formula | C30H50O |
| Molecular Weight | 426.7174 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Lanosterol represents the first step in sterol formation and can be converted by lanosterol 14 α-demethylase (CYP51, a member of the cytochrome P450 family), to follicular fluid meiosis activating factor (FF-MAF), a sterol intermediate that has been extensively studied and shown to activate meiosis in gametes. Lanosterol modulates TLR4-mediated innate immune responses in macrophages. Lanosterol accumulation increases membrane fluidity and ROS production, thus potentiating phagocytosis and the ability to kill bacteria. Preliminary studies in dogs and rabbits have shown that lanosterol can prevent and even reverse cataract formation. However, Lanosterol 25 mM solution did not reverse opacification of human age-related cataractous nuclei. Lanosterol induces mitochondrial uncoupling and protects dopaminergic neurons from cell death in a model for Parkinson's disease.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Localisation of lanosterol 14alpha-demethylase in round and elongated spermatids of the mouse testis: an immunoelectron microscopic and stereological study. | 2001 |
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| Molecular dynamics simulation of the structure of dimyristoylphosphatidylcholine bilayers with cholesterol, ergosterol, and lanosterol. | 2001 Apr |
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| Anaerobiosis induces complex changes in sterol esterification pattern in the yeast Saccharomyces cerevisiae. | 2001 Apr 1 |
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| [A new triterpene from the fruiting bodies of Ganoderma lucidum]. | 2001 Aug |
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| Cholesterol biosynthesis from lanosterol: molecular cloning, chromosomal localization, functional expression and liver-specific gene regulation of rat sterol delta8-isomerase, a cholesterogenic enzyme with multiple functions. | 2001 Feb 1 |
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| LDL downregulates CYP51 in porcine vascular endothelial cells and in the arterial wall through a sterol regulatory element binding protein-2-dependent mechanism. | 2001 Feb 16 |
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| Molecular cloning and expression in yeast of 2,3-oxidosqualene-triterpenoid cyclases from Arabidopsis thaliana. | 2001 Jan |
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| Role of meiosis-activating sterols in rat oocyte maturation: effects of specific inhibitors and changes in the expression of lanosterol 14alpha-demethylase during the preovulatory period. | 2001 Jan |
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| Quantification of plasma membrane ergosterol of Saccharomyces cerevisiae by direct-injection atmospheric pressure chemical ionization/tandem mass spectrometry. | 2001 Jan 1 |
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| The interactions of amphotericin B with various sterols in relation to its possible use in anticancer therapy. | 2001 Jul 2 |
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| Ergosterol biosynthesis in novel melanized fungi from hypersaline environments. | 2001 Mar |
|
| Cholesterol biosynthesis from lanosterol. A concerted role for Sp1 and NF-Y-binding sites for sterol-mediated regulation of rat 7-dehydrocholesterol reductase gene expression. | 2001 May 25 |
|
| Chemopreventive effect of farnesol and lanosterol on colon carcinogenesis. | 2002 |
|
| My years with Konrad, a memoir. | 2002 Apr 19 |
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| Evidence for multiple sterol methyl transferase pathways in Pneumocystis carinii. | 2002 Dec |
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| Novel hydroquinone as a matrix metallo-proteinase inhibitor from the mushroom, Piptoporus betulinus. | 2002 Dec |
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| Sterol biosynthesis in Pneumocystis: unique steps that define unique targets. | 2002 Dec |
|
| Creating new supramolecular materials by architecture of three-dimensional nanocrystal fiber networks. | 2002 Dec 18 |
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| Identification of two proteins induced by exposure of the pathogenic fungus Candida glabrata to fluconazole. | 2002 Dec 25 |
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| New lanostanoids from the mushroom Ganoderma lucidum. | 2002 Jan |
|
| Yeast oxidosqualene cyclase (Erg7p) is a major component of lipid particles. | 2002 Jan 25 |
|
| Two-stage culture process for improved production of ganoderic acid by liquid fermentation of higher fungus Ganoderma lucidum. | 2002 Jan-Feb |
|
| Cholesterol metabolism in normal and heterozygous familial hypercholesterolemic newborns. | 2002 Jul |
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| Modeling of binding modes and inhibition mechanism of some natural ligands of farnesyl transferase using molecular docking. | 2002 Mar 28 |
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| Triterpenoid constituents isolated from the bark of Abies sachalinensis. | 2002 Nov |
|
| Production of progesterone from de novo-synthesized cholesterol in cumulus cells and its physiological role during meiotic resumption of porcine oocytes. | 2003 Apr |
|
| Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii. | 2003 Aug |
|
| Cloning and analysis of Trypanosoma cruzi lanosterol 14alpha-demethylase. | 2003 Dec |
|
| Triterpenoids from the orchids Agrostophyllum brevipes and Agrostophyllum callosum. | 2003 Feb |
|
| Identification of farnesoid X receptor beta as a novel mammalian nuclear receptor sensing lanosterol. | 2003 Feb |
|
| Structure-based de novo design, synthesis, and biological evaluation of non-azole inhibitors specific for lanosterol 14alpha-demethylase of fungi. | 2003 Feb 13 |
|
| Conservation and cloning of CYP51: a sterol 14 alpha-demethylase from Mycobacterium smegmatis. | 2003 Feb 7 |
|
| Supernatant protein factor and tocopherol-associated protein: an unexpected link between cholesterol synthesis and vitamin E (review). | 2003 Jan |
|
| Many facets of mammalian lanosterol 14alpha-demethylase from the evolutionarily conserved cytochrome P450 family CYP51. | 2003 Jan 1 |
|
| Serum cholesterol, precursors and metabolites and cognitive performance in an aging population. | 2003 Jan-Feb |
|
| Lanosterol metabolism and sterol regulatory element binding protein (SREBP) expression in male germ cell maturation. | 2003 Jun |
|
| Combined overexpression of genes of the ergosterol biosynthetic pathway leads to accumulation of sterols in Saccharomyces cerevisiae. | 2003 Oct |
|
| Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos. | 2003 Sep-Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.lanomax.com/lanomax.html
Lanosterol 10mg (2mg/ml). Use one or two drops three times a day
Route of Administration:
Topical
Two concentrations of lanosterol (0, 10 and 50 uM) were added to the IVM medium. A significantly higher rate of meiosis resumption was observed with 10 uM (72.3%) of lanosterol compared with the control (51.8%) or 50 uM of lanosterol (59.4%). A significantly higher content of lipids was also observed with 10 and 50 uM of lanosterol (7.3 ± 0.2 × 10(6) and 7.4 ± 0.2 × 10(6) arbitrary units of fluorescence) compared with the control (6.7 ± 0.2 × 10(6) arbitrary units of fluorescence). The results indicate that 10 uM lanosterol during IVM in medium without serum and based on recombinant human chorionic gonadotrophin has a positive effect on maturation of prepubertal ewe oocytes.
| Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:04:05 GMT 2023
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| Record UNII |
1J05Z83K3M
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Validated (UNII)
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74898-8
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ACTIVE MOIETY |
