Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H44O |
Molecular Weight | 396.6484 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 3 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C)[C@H](C)\C=C\[C@H](C)C(C)C
InChI
InChIKey=MECHNRXZTMCUDQ-RKHKHRCZSA-N
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
DescriptionSources: http://www.drugbank.ca/drugs/DB00153Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/ergocalciferol.html
Sources: http://www.drugbank.ca/drugs/DB00153
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/ergocalciferol.html
Ergoalcifediol (Vitamin D2) is a fat soluble steroid hormone precursor of vitamin D. The principal biologic function of vitamin D is the maintenance of normal levels of serum calcium and phosphorus in the bloodstream by enhancing the efficacy of the small intestine to absorb these minerals from the diet. Cholecalciferol is synthesized within our bodies naturally, but if UV exposure is inadequate or the metabolism of cholecalciferol is abnormal, then an exogenous source is required. Vitamin D2 is converted to 25-hydroxyvitamin D (25OHD) in the liver, and then to the active form, 1,25-dihydroxyvitamin D (1,25(OH)2D), in the kidney. Once transformed, it binds to the vitamin D receptor, which leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Very few foods naturally contain vitamin D. Sources that contain the vitamin include fatty fish, the liver and fat of aquatic mammals (e.g., seals, polar bears), and eggs from chickens fed vitamin D-fortified feed. As such, many countries have instituted policies to fortify certain foods with vitamin D to compensate for the potentially low exposures of skin to sunlight. Vitamin D deficiency results in inadequate mineralization of bone or compensatory skeletal demineralization and causes decreased ionized calcium concentrations in blood and a resultant increase in the production and secretion of PTH. Increase in PTH stimulates the mobilization of skeletal calcium, inhibits renal excretion of calcium, and stimulates renal excretion of phosphorus. This results in normal fasting serum calcium concentrations and low or near-normal serum phosphorus. The enhanced mobilization of skeletal calcium induced by this secondary hyperparathyroidism leads porotic bone. Ergoalcifediol is used for use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin D resistant rickets). This drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis). Ergocalciferol is manufactured and marketed under various names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo) and Calcidol (Patrin Pharma).
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24466410
Curator's Comment: Discovered in 1932
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1977 Sources: http://www.drugbank.ca/drugs/DB00153 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Ergocalciferol Approved UseErgocalciferol 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 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 is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia. Launch Date2009 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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46.92 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25782422/ |
125 μg 1 times / day multiple, oral dose: 125 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
CALCIFEDIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2324.1 ng × day/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25782422/ |
125 μg 1 times / day multiple, oral dose: 125 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
CALCIFEDIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25782422/ |
125 μg 1 times / day multiple, oral dose: 125 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
CALCIFEDIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
15 mg multiple, oral (total) Highest studied dose |
unknown, 7 months n = 1 Health Status: unknown Age Group: 7 months Sex: M Population Size: 1 Sources: |
Other AEs: Renal failure... |
0.5 mg 1 times / week multiple, oral Highest studied dose Dose: 0.5 mg, 1 times / week Route: oral Route: multiple Dose: 0.5 mg, 1 times / week Sources: |
unknown, 80.1 ± 10.0 years n = 70 Health Status: unknown Age Group: 80.1 ± 10.0 years Sex: M+F Population Size: 70 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Renal failure | 1 patient | 15 mg multiple, oral (total) Highest studied dose |
unknown, 7 months n = 1 Health Status: unknown Age Group: 7 months Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
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Progressively increased serum 1,25-dihydroxyvitamin D2 concentration in a hypoparathyroid patient with protracted hypercalcemia due to vitamin D2 intoxication. | 1994 Aug |
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Nonhypercalcemic vitamin D analogs: interactions with the vitamin D-binding protein. | 1996 |
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Steroids as possible inhibitors of HIV-1 protease. | 1998 Apr 16 |
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Comparative effects of vitamin K2 and vitamin E on experimental arteriosclerosis. | 1999 Jan |
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Vitamin D receptor as an intestinal bile acid sensor. | 2002 May 17 |
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The prostate 25-hydroxyvitamin D-1 alpha-hydroxylase is not influenced by parathyroid hormone and calcium: implications for prostate cancer chemoprevention by vitamin D. | 2004 Jun |
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The role of vitamin D in the prevention of osteoporosis. | 2005 |
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Spotlight on paricalcitol in secondary hyperparathyroidism. | 2005 |
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The high prevalence of inadequate serum vitamin D levels and implications for bone health. | 2005 Apr |
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Serum parathyroid hormone (PTH) levels in smokers and non-smokers. The fifth Tromsø study. | 2005 Jan |
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Failure of high-dose ergocalciferol to correct vitamin D deficiency in adults with cystic fibrosis. | 2005 Jul 15 |
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Prevalence and correction of 25(OH) vitamin D deficiency in peritoneal dialysis patients. | 2005 Jul-Aug |
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Estimates of beneficial and harmful sun exposure times during the year for major Australian population centres. | 2006 Apr 3 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/ergocalciferol.html
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/20650254
Ergoalcifediol (1.2 nm) stimulated synthesis and intercellular deposition of rat elastic fibres and had a stabilizing effect on the musculo-elastic multilayer formed by the cultured cells.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C941
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DSLD |
2476 (Number of products:490)
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NDF-RT |
N0000006337
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LIVERTOX |
361
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NDF-RT |
N0000175909
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NDF-RT |
N0000006337
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CFR |
21 CFR 172.379
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NDF-RT |
N0000006337
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EPA PESTICIDE CODE |
202900
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WHO-VATC |
QA11CC01
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DSLD |
206 (Number of products:56)
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NDF-RT |
N0000006337
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WHO-ESSENTIAL MEDICINES LIST |
27
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WHO-ATC |
A11CC01
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100000090229
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m11485
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C29029
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819
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5280793
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ERGOCALCIFEROL
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PRIMARY | Other name: Vitamin D2.Description: Colourless or slightly yellowish crystals or a white or slightly yellowish, crystalline powder; odourless or almost odourless.Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R and ether R.Category: Vitamin, antirachitic.Storage: Ergocalciferol should be kept in a hermetically closed container, preferably in an inert atmosphere, such as nitrogen,protected from light and stored at a temperature between 2 and 8 ?C.Additional information: Ergocalciferol is affected by air and by light. Even in the absence of light, it is gradually degraded onexposure to a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Ergocalciferol contains not less than 95.0% and not more than 105.0% of C28H44O. | ||
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ERGOCALCIFEROL
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DTXSID5020233
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200-014-9
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SUB06596MIG
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28934
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ergocalciferol
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DB00153
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2838
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CHEMBL1536
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62792
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382
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VS041H42XC
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4018
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50-14-6
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1239005
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VS041H42XC
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SUB127287
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)