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
C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC3
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 |
|---|---|---|
| Cloning and analysis of Trypanosoma cruzi lanosterol 14alpha-demethylase. | 2003-12 |
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| Two new 24-isopropenyl-lanostanoids from Tillandsia brachycaulos. | 2003-10-28 |
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| Combined overexpression of genes of the ergosterol biosynthetic pathway leads to accumulation of sterols in Saccharomyces cerevisiae. | 2003-10 |
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| Localization of mammalian NAD(P)H steroid dehydrogenase-like protein on lipid droplets. | 2003-09-19 |
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| Conservation in the CYP51 family. Role of the B' helix/BC loop and helices F and G in enzymatic function. | 2003-08-05 |
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| Anti-inflammatory lanostane-type triterpene acids from Piptoporus betulinus. | 2003-08 |
|
| Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii. | 2003-08 |
|
| In yeast sterol biosynthesis the 3-keto reductase protein (Erg27p) is required for oxidosqualene cyclase (Erg7p) activity. | 2003-07-04 |
|
| Revision and confirmation of the regiochemistry of isoxazoles derived from methyl oleanonate and lanost-8-en-3-one. Synthesis of a new lanostane triterpenoid with a cyano-enone functionality in ring A. | 2003-06-13 |
|
| Lanosterol metabolism and sterol regulatory element binding protein (SREBP) expression in male germ cell maturation. | 2003-06 |
|
| Phylogeny of choanozoa, apusozoa, and other protozoa and early eukaryote megaevolution. | 2003-05 |
|
| Mechanistic insights into oxidosqualene cyclizations through homology modeling. | 2003-04-30 |
|
| Saccharomyces cerevisiae Dap1p, a novel DNA damage response protein related to the mammalian membrane-associated progesterone receptor. | 2003-04 |
|
| Production of progesterone from de novo-synthesized cholesterol in cumulus cells and its physiological role during meiotic resumption of porcine oocytes. | 2003-04 |
|
| Antitumor agents 220. Antitumor-promoting effects of cimigenol and related compounds on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. | 2003-03-20 |
|
| Human serum paraoxonase 1 decreases macrophage cholesterol biosynthesis: possible role for its phospholipase-A2-like activity and lysophosphatidylcholine formation. | 2003-03-01 |
|
| Drug induced proteome changes in Candida albicans: comparison of the effect of beta(1,3) glucan synthase inhibitors and two triazoles, fluconazole and itraconazole. | 2003-03 |
|
| Structure-based de novo design, synthesis, and biological evaluation of non-azole inhibitors specific for lanosterol 14alpha-demethylase of fungi. | 2003-02-13 |
|
| Conservation and cloning of CYP51: a sterol 14 alpha-demethylase from Mycobacterium smegmatis. | 2003-02-07 |
|
| [Serum markers in relation to cognitive functioning in an aging population: results of the Maastricht Aging Study (MAAS)]. | 2003-02 |
|
| Triterpenoids from the orchids Agrostophyllum brevipes and Agrostophyllum callosum. | 2003-02 |
|
| Identification of farnesoid X receptor beta as a novel mammalian nuclear receptor sensing lanosterol. | 2003-02 |
|
| Formation of the C ring in the lanosterol biosynthesis from squalene. | 2003-01-23 |
|
| Many facets of mammalian lanosterol 14alpha-demethylase from the evolutionarily conserved cytochrome P450 family CYP51. | 2003-01-01 |
|
| Supernatant protein factor and tocopherol-associated protein: an unexpected link between cholesterol synthesis and vitamin E (review). | 2003-01 |
|
| Protein prenyltransferases. | 2003 |
|
| Identification of two proteins induced by exposure of the pathogenic fungus Candida glabrata to fluconazole. | 2002-12-25 |
|
| Serum cholesterol, precursors and metabolites and cognitive performance in an aging population. | 2002-12-21 |
|
| Creating new supramolecular materials by architecture of three-dimensional nanocrystal fiber networks. | 2002-12-18 |
|
| Desmosterolosis presenting with multiple congenital anomalies and profound developmental delay. | 2002-12-15 |
|
| Directed evolution experiments reveal mutations at cycloartenol synthase residue His477 that dramatically alter catalysis. | 2002-12-12 |
|
| A novel sterol 14alpha-demethylase/ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily. | 2002-12-06 |
|
| Evidence for multiple sterol methyl transferase pathways in Pneumocystis carinii. | 2002-12 |
|
| The role of cytochrome P450 in the regulation of cholesterol biosynthesis. | 2002-12 |
|
| Novel hydroquinone as a matrix metallo-proteinase inhibitor from the mushroom, Piptoporus betulinus. | 2002-12 |
|
| Sterol biosynthesis in Pneumocystis: unique steps that define unique targets. | 2002-12 |
|
| Nuclear receptor agonists stimulate release of arachidonic acid from rat liver cells. | 2002-12 |
|
| Is Pneumocystis a plant? | 2002-11-12 |
|
| Triterpenoid constituents isolated from the bark of Abies sachalinensis. | 2002-11 |
|
| Progesterone and 17 alpha-OH-progesterone in concentrations similar to that of preovulatory follicular fluid is without effect on resumption of meiosis in mouse cumulus enclosed oocytes cultured in the presence of hypoxanthine. | 2002-11 |
|
| Anisotropic motion and molecular dynamics of cholesterol, lanosterol, and ergosterol in lecithin bilayers studied by quasi-elastic neutron scattering. | 2002-10-29 |
|
| Complete characterisation of lanolin steryl esters by sub-ambient pressure gas chromatography-mass spectrometry in the electron impact and chemical ionisation modes. | 2002-09-13 |
|
| Concomitant C-ring Expansion and D-ring formation in lanosterol biosynthesis from squalene without violation of Markovnikov's rule. | 2002-09-04 |
|
| A cAMP-responsive element binding site is essential for sterol regulation of the human lanosterol 14alpha-demethylase gene (CYP51). | 2002-08 |
|
| Altered gene expression of hepatic lanosterol 14alpha-demethylase (CYP51) in lead nitrate-treated rats. | 2002-07 |
|
| Comprehensive and definitive structural identities of Pneumocystis carinii sterols. | 2002-07 |
|
| Abnormal sterol metabolism in a patient with Antley-Bixler syndrome and ambiguous genitalia. | 2002-06-15 |
|
| Chemopreventive effect of farnesol and lanosterol on colon carcinogenesis. | 2002 |
|
| [A new triterpene from the fruiting bodies of Ganoderma lucidum]. | 2001-08 |
|
| [Studies on quality specification standards for Saposhnicovia divaricata (Turcz.) Schischk]. | 2001-03 |
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
by
admin
on
Edited
Mon Mar 31 17:45:15 GMT 2025
by
admin
on
Mon Mar 31 17:45:15 GMT 2025
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| Record UNII |
1J05Z83K3M
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| Record Status |
Validated (UNII)
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| Record Version |
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74898-8
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LANOSTEROL
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