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
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 |
|---|---|---|
| [A new triterpene from the fruiting bodies of Ganoderma lucidum]. | 2001 Aug |
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| [Studies on quality specification standards for Saposhnicovia divaricata (Turcz.) Schischk]. | 2001 Mar |
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| Chemopreventive effect of farnesol and lanosterol on colon carcinogenesis. | 2002 |
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| A cAMP-responsive element binding site is essential for sterol regulation of the human lanosterol 14alpha-demethylase gene (CYP51). | 2002 Aug |
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| Evidence for multiple sterol methyl transferase pathways in Pneumocystis carinii. | 2002 Dec |
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| The role of cytochrome P450 in the regulation of cholesterol biosynthesis. | 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 |
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| Nuclear receptor agonists stimulate release of arachidonic acid from rat liver cells. | 2002 Dec |
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| Directed evolution experiments reveal mutations at cycloartenol synthase residue His477 that dramatically alter catalysis. | 2002 Dec 12 |
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| Desmosterolosis presenting with multiple congenital anomalies and profound developmental delay. | 2002 Dec 15 |
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| 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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| A novel sterol 14alpha-demethylase/ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily. | 2002 Dec 6 |
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| Altered gene expression of hepatic lanosterol 14alpha-demethylase (CYP51) in lead nitrate-treated rats. | 2002 Jul |
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| Comprehensive and definitive structural identities of Pneumocystis carinii sterols. | 2002 Jul |
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| Abnormal sterol metabolism in a patient with Antley-Bixler syndrome and ambiguous genitalia. | 2002 Jun 15 |
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| Triterpenoid constituents isolated from the bark of Abies sachalinensis. | 2002 Nov |
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| 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 Nov |
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| Anisotropic motion and molecular dynamics of cholesterol, lanosterol, and ergosterol in lecithin bilayers studied by quasi-elastic neutron scattering. | 2002 Oct 29 |
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| Complete characterisation of lanolin steryl esters by sub-ambient pressure gas chromatography-mass spectrometry in the electron impact and chemical ionisation modes. | 2002 Sep 13 |
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| Concomitant C-ring Expansion and D-ring formation in lanosterol biosynthesis from squalene without violation of Markovnikov's rule. | 2002 Sep 4 |
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| Is Pneumocystis a plant? | 2002 Sep-Oct |
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| Protein prenyltransferases. | 2003 |
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| Saccharomyces cerevisiae Dap1p, a novel DNA damage response protein related to the mammalian membrane-associated progesterone receptor. | 2003 Apr |
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| Production of progesterone from de novo-synthesized cholesterol in cumulus cells and its physiological role during meiotic resumption of porcine oocytes. | 2003 Apr |
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| Mechanistic insights into oxidosqualene cyclizations through homology modeling. | 2003 Apr 30 |
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| Anti-inflammatory lanostane-type triterpene acids from Piptoporus betulinus. | 2003 Aug |
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| Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii. | 2003 Aug |
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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 Aug 5 |
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| Cloning and analysis of Trypanosoma cruzi lanosterol 14alpha-demethylase. | 2003 Dec |
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| [Serum markers in relation to cognitive functioning in an aging population: results of the Maastricht Aging Study (MAAS)]. | 2003 Feb |
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| Triterpenoids from the orchids Agrostophyllum brevipes and Agrostophyllum callosum. | 2003 Feb |
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| Identification of farnesoid X receptor beta as a novel mammalian nuclear receptor sensing lanosterol. | 2003 Feb |
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| Structure-based de novo design, synthesis, and biological evaluation of non-azole inhibitors specific for lanosterol 14alpha-demethylase of fungi. | 2003 Feb 13 |
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| Conservation and cloning of CYP51: a sterol 14 alpha-demethylase from Mycobacterium smegmatis. | 2003 Feb 7 |
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| Supernatant protein factor and tocopherol-associated protein: an unexpected link between cholesterol synthesis and vitamin E (review). | 2003 Jan |
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| Many facets of mammalian lanosterol 14alpha-demethylase from the evolutionarily conserved cytochrome P450 family CYP51. | 2003 Jan 1 |
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| Formation of the C ring in the lanosterol biosynthesis from squalene. | 2003 Jan 23 |
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| Serum cholesterol, precursors and metabolites and cognitive performance in an aging population. | 2003 Jan-Feb |
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| In yeast sterol biosynthesis the 3-keto reductase protein (Erg27p) is required for oxidosqualene cyclase (Erg7p) activity. | 2003 Jul 4 |
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| Lanosterol metabolism and sterol regulatory element binding protein (SREBP) expression in male germ cell maturation. | 2003 Jun |
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| 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 Jun 13 |
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| 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 Mar |
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| Human serum paraoxonase 1 decreases macrophage cholesterol biosynthesis: possible role for its phospholipase-A2-like activity and lysophosphatidylcholine formation. | 2003 Mar 1 |
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| Antitumor agents 220. Antitumor-promoting effects of cimigenol and related compounds on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. | 2003 Mar 20 |
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| Phylogeny of choanozoa, apusozoa, and other protozoa and early eukaryote megaevolution. | 2003 May |
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| Combined overexpression of genes of the ergosterol biosynthetic pathway leads to accumulation of sterols in Saccharomyces cerevisiae. | 2003 Oct |
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| Localization of mammalian NAD(P)H steroid dehydrogenase-like protein on lipid droplets. | 2003 Sep 19 |
|
| 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.
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LOINC |
74898-8
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79-63-0
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60677
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m6681
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DB03696
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1442199
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LANOSTEROL
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1J05Z83K3M
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ACTIVE MOIETY
