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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H44O
Molecular Weight 396.6494
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of ERGOCALCIFEROL

SMILES

CC(C)[C@@]([H])(C)/C(/[H])=C(\[H])/[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])/C(=C(\[H])/C(/[H])=C\3/C[C@]([H])(CCC3=C)O)/CCC[C@]12C

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

HIDE SMILES / InChI

Description
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).

Originator

Curator's Comment:: Discovered in 1932

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ergocalciferol

Approved Use

Ergocalciferol is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia.

Launch Date

1.24269114E12
Primary
Ergocalciferol

Approved Use

Ergocalciferol is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia.

Launch Date

1.24269114E12
Primary
Ergocalciferol

Approved Use

Ergocalciferol is indicated for use in the treatment of hypoparathyroidism, refractory rickets, also known as vitamin D resistant rickets, and familial hypophosphatemia.

Launch Date

1.24269114E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
46.92 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2324.1 ng × day/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
33 day
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

Doses

DosePopulationAdverse events​
15 mg multiple, oral (total)
Highest studied dose
Dose: 15 mg
Route: oral
Route: multiple
Dose: 15 mg
Sources:
unknown, 7 months
n = 1
Health Status: unknown
Age Group: 7 months
Sex: M
Population Size: 1
Sources:
Other AEs: Renal failure...
Other AEs:
Renal failure (1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
Renal failure 1 patient
15 mg multiple, oral (total)
Highest studied dose
Dose: 15 mg
Route: oral
Route: multiple
Dose: 15 mg
Sources:
unknown, 7 months
n = 1
Health Status: unknown
Age Group: 7 months
Sex: M
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The effect of cortisone on vitamin D2-induced nephrocalcinosis in the rat.
1957 Feb
Degranulation of the parafollicular cells of the rat thyroid by vitamin-D2-induced hypercalcemia.
1968 Jul
Chlorothiazide-induced hypercalcemia in juvenile osteoporosis and hyperparathyroidism.
1969 Jul 10
Myopathy associated with anticonvulsant osteomalacia.
1973 Dec 1
Determination of vitamin D and its metabolites in plasma from normal and anephric man.
1979 Jul 15
Does somatostatin in each organ act specifically on that particular organ?
1979 Sep
Inhibition of vitamin D2-induced arteriosclerosis in rats by depletion of complement with cobra venom factor.
1980
Prevention of osteonecrosis following renal transplantation by using vitamin D2 (ergocalciferol).
1983
Reversal of vitamin-D2-induced hypercalciuria by chlorothiazide.
1983 Feb
Vitamin D2-induced arteriosclerosis in spontaneously hypertensive rats and protection by diltiazem, a calcium antagonist.
1984 Jun
Vitamin D2-induced hypercalcemia in rat lens.
1986 Mar
Altered vasoconstrictor responsiveness in vitamin D-induced arteriosclerotic rat aortas.
1993 Apr
Progressively increased serum 1,25-dihydroxyvitamin D2 concentration in a hypoparathyroid patient with protracted hypercalcemia due to vitamin D2 intoxication.
1994 Aug
Nonhypercalcemic vitamin D analogs: interactions with the vitamin D-binding protein.
1996
X-linked hypophosphatemia: normal renal function despite medullary nephrocalcinosis 25 years after transient vitamin D2-induced renal azotemia.
1997 Dec
Steroids as possible inhibitors of HIV-1 protease.
1998 Apr 16
Current understanding of the molecular actions of vitamin D.
1998 Oct
Perinatal metabolism of vitamin D.
2000 May
In situ detection of 1,25-dihydroxyvitamin D3 receptor in human skeletal muscle tissue.
2001 Jan
A novel mutation in helix 12 of the vitamin D receptor impairs coactivator interaction and causes hereditary 1,25-dihydroxyvitamin D-resistant rickets without alopecia.
2002 Nov
[Disturbances of calcium-PTH-vitamin D axis in chronic liver diseases].
2004 Aug
Overview of general physiologic features and functions of vitamin D.
2004 Dec
Vitamin D receptor expression in human muscle tissue decreases with age.
2004 Feb
Both high and low levels of blood vitamin D are associated with a higher prostate cancer risk: a longitudinal, nested case-control study in the Nordic countries.
2004 Jan 1
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
The role of vitamin D in the prevention of osteoporosis.
2005
The high prevalence of inadequate serum vitamin D levels and implications for bone health.
2005 Apr
Serum parathyroid hormone (PTH) levels in smokers and non-smokers. The fifth Tromsø study.
2005 Jan
Failure of high-dose ergocalciferol to correct vitamin D deficiency in adults with cystic fibrosis.
2005 Jul 15
Prevalence and correction of 25(OH) vitamin D deficiency in peritoneal dialysis patients.
2005 Jul-Aug
Estimates of beneficial and harmful sun exposure times during the year for major Australian population centres.
2006 Apr 3
Vitamin D and calcium receptors: links to hypercalciuria.
2006 Jul
Renal osteodystrophy in children: a systemic disease associated with cardiovascular manifestations.
2006 Jul
Severe hypercalcemia after transition from calcium carbonate to calcium citrate in an elderly woman treated with ergocalciferol 50,000 IU per day.
2006 Mar
Protective effect of lysozyme chloride on gastric oxidative stress and hemorrhagic ulcers in severe atherosclerotic rats.
2007 Dec
Patents

Sample Use Guides

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
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.
Name Type Language
ERGOCALCIFEROL
EP   HSDB   INCI   INN   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
ERGOCALCIFEROLUM [WHO-IP LATIN]
Common Name English
(5Z,7E,22E)-(3S)-9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3-OL
Common Name English
ERGOCALCIFEROL [VANDF]
Common Name English
VIOSTEROL
Common Name English
ERGOCALCIFEROL [EP]
Common Name English
ERGOCALCIFEROL, (+)-
Common Name English
ERGOCALCIFEROL [USP]
Common Name English
ERGOCALCIFEROL [USP-RS]
Common Name English
ERGOCALCIFEROL [INCI]
Common Name English
ERGOCALCIFEROL [WHO-DD]
Common Name English
DRISDOL
Brand Name English
OSTELIN
Brand Name English
ERGOCALCIFEROL [ORANGE BOOK]
Common Name English
ERGOCALCIFEROL [INN]
Common Name English
ERGOCALCIFEROL [EP MONOGRAPH]
Common Name English
VITAMIN D2
FCC   MI   WHO-IP  
Common Name English
ERGOCALCIFEROL [HSDB]
Common Name English
(3.BETA.,5Z,7E,22E)-9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3-OL
Common Name English
NSC-62792
Code English
24-METHYL-9,10-SECOCHOLESTA-5,7,10( 19),22-TETRAENE-3.BETA.-OL [WHO-IP]
Systematic Name English
9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3-OL, (3.BETA.,5Z,7E,22E)-
Common Name English
VITAMIN D2 [MI]
Common Name English
ERGOCALCIFEROL [MART.]
Common Name English
VITAMIN D2 [WHO-IP]
Common Name English
VITAMIN D2 [FCC]
Common Name English
VITAMIN D (ERGOCALCIFEROL)
Common Name English
ERGOCALCIFEROL [WHO-IP]
Common Name English
ERGORONE
Common Name English
DELTALIN
Brand Name English
Classification Tree Code System Code
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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Code System Code Type Description
MERCK INDEX
M11485
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PRIMARY Merck Index
NCI_THESAURUS
C29029
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PRIMARY
HSDB
819
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PRIMARY
PUBCHEM
5280793
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ERGOCALCIFEROL
Created by admin on Fri Jun 25 21:09:43 UTC 2021 , Edited by admin on Fri Jun 25 21:09:43 UTC 2021
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.
WIKIPEDIA
ERGOCALCIFEROL
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PRIMARY
EPA CompTox
50-14-6
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PRIMARY
USP_CATALOG
1239005
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PRIMARY USP-RS
ECHA (EC/EINECS)
200-014-9
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PRIMARY
EVMPD
SUB06596MIG
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PRIMARY
DRUG BANK
DB00153
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PRIMARY
DRUG CENTRAL
2838
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PRIMARY
ChEMBL
CHEMBL1536
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PRIMARY
INN
382
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PRIMARY
FDA UNII
VS041H42XC
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PRIMARY
RXCUI
4018
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PRIMARY RxNorm
CAS
50-14-6
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PRIMARY
EVMPD
SUB127287
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PRIMARY