Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H44O |
Molecular Weight | 396.6484 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C
InChI
InChIKey=DNVPQKQSNYMLRS-APGDWVJJSA-N
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
DescriptionSources: https://www.drugs.com/dosage/ergocalciferol.htmlCurator's Comment: Description was created based on several sources, including
http://www.jbc.org/content/105/4/711.full.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/20526375 |
https://www.ncbi.nlm.nih.gov/pubmed/24529992
Sources: https://www.drugs.com/dosage/ergocalciferol.html
Curator's Comment: Description was created based on several sources, including
http://www.jbc.org/content/105/4/711.full.pdf |
https://www.ncbi.nlm.nih.gov/pubmed/20526375 |
https://www.ncbi.nlm.nih.gov/pubmed/24529992
Ergosterol was discovered over 100 years ago in the plant pathogenic ergot fungus Claviceps purpurea. Ergosterol is the major fungal membrane sterol that regulates membrane fluidity, plasma membrane biogenesis and function. Antifungal drugs such as Amphotericin B exerts its action by simply binding ergosterol. Vitamin D2 (ergocalciferol) is derived from ergosterol by UVB irradiation. Ergocalciferol is used for treating low parathyroid hormone levels, rickets (a vitamin D deficiency condition), and low phosphate levels in the body.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27133301
Curator's Comment: After mice received Ergosterol-loaded poly(lactide-co-glycolide) nanoparticles (NPs/Erg), the ergosterol in NPs/Erg was rapidly distributed in stomach, kidneys, liver, brain, spleen, and virtually non-existent in heart and lungs. The presence of NPs/Erg in brain was particularly improved compared with the free ergosterol.
No human data available.
Originator
Sources: Tanret C (1889) Sur un nouveau principle immediate de l'ergot deseigle ergosterine. C.R. Seances Acad Sci 108: 98–100.
Curator's Comment: 24R-methyl-cholesta-5,7,22(E)-trienol (ergosterol) was discovered over 100 years ago in the plant pathogenic ergot fungus Claviceps purpurea reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/20526375
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24529992 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Ergocalciferol Approved UseErgocalciferol (activated ergosterol) is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia. Launch Date2009 |
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Primary | Ergocalciferol Approved UseErgocalciferol (activated ergosterol) is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia. Launch Date2009 |
|||
Primary | Ergocalciferol Approved UseErgocalciferol (activated ergosterol) is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia. Launch Date2009 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/ergocalciferol.html
Ergoalcifediol (activated ergosterol) Usual Adult Dose for Hypoparathyroidism
50,000 to 200,000 international units orally daily, concomitantly with calcium lactate 4 g, six times per day
Usual Adult Dose for Rickets
12,000 to 500,000 international units orally daily
Usual Adult Dose for Familial Hypophosphatemia
12,000 to 500,000 international units orally daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27133301
Ergosterol-loaded poly(lactide-co-glycolide) nanoparticles exerted much stronger cytotoxicity against human cancer cells than the free ergosterol, and showed significantly reduced IC50 values (14.69±0.48 μg/mL in glioma U251 cells; 9.43±0.52 μg/mL in breast cancer MCF-7 cells; 4.70±0.41 μg/mL in hepatoma HepG2 cells).
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Classification Tree | Code System | Code | ||
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LOINC |
15411-2
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NCI_THESAURUS |
C843
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C83810
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1241007
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16933
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395
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ERGOSTEROL
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200-352-7
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Z30RAY509F
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444679
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57-87-4
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DB04038
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m4986
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DTXSID90878679
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SUBSTANCE RECORD