Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H44O |
Molecular Weight | 384.6377 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
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)CCCC(C)C
InChI
InChIKey=QYSXJUFSXHHAJI-YRZJJWOYSA-N
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00169
Curator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00169
Cholecalciferol (/ˌkoʊləkælˈsɪfərɒl/) (vitamin D3) is one of the five forms of vitamin D. Cholecalciferol is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of Vitamin A. The classical manifestation of vitamin D deficiency is rickets, which is seen in children and results in bony deformities including bowed long bones. Most people meet at least some of their vitamin D needs through exposure to sunlight. Ultraviolet (UV) B radiation with a wavelength of 290–320 nanometers penetrates uncovered skin and converts cutaneous 7-dehydrocholesterol to previtamin D3, which in turn becomes vitamin D3. In supplements and fortified foods, vitamin D is available in two forms, D2 (ergocalciferol) and D3 (cholecalciferol) that differ chemically only in their side-chain structure. Vitamin D2 is manufactured by the UV irradiation of ergosterol in yeast, and vitamin D3 is manufactured by the irradiation of 7-dehydrocholesterol from lanolin and the chemical conversion of cholesterol. The two forms have traditionally been regarded as equivalent based on their ability to cure rickets and, indeed, most steps involved in the metabolism and actions of vitamin D2 and vitamin D3 are identical. Both forms (as well as vitamin D in foods and from cutaneous synthesis) effectively raise serum 25(OH) D levels. Firm conclusions about any different effects of these two forms of vitamin D cannot be drawn. However, it appears that at nutritional doses, vitamins D2 and D3 are equivalent, but at high doses, vitamin D2 is less potent. The American Academy of Pediatrics (AAP) recommends that exclusively and partially breastfed infants receive supplements of 400 IU/day of vitamin D shortly after birth and continue to receive these supplements until they are weaned and consume ≥1,000 mL/day of vitamin D-fortified formula or whole milk. Cholecalciferol is used in diet supplementary to treat Vitamin D Deficiency. Cholecalciferol is inactive: it is converted to its active form by two hydroxylations: the first in the liver, the second in the kidney, to form calcitriol, whose action is mediated by the vitamin D receptor, a nuclear receptor which regulates the synthesis of hundreds of enzymes and is present in virtually every cell in the body. Calcitriol increases the serum calcium concentrations by increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20435140 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18326608/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CALCIDIOL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
968.6 nM × day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18326608/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CALCIDIOL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.5 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18326608/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CALCIDIOL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100000 unit single, oral Highest studied dose Dose: 100000 unit Route: oral Route: single Dose: 100000 unit Sources: |
healthy, 27-84 years n = 30 Health Status: healthy Age Group: 27-84 years Sex: M+F Population Size: 30 Sources: |
|
200 ug 1 times / day multiple, oral Highest studied dose Dose: 200 ug, 1 times / day Route: oral Route: multiple Dose: 200 ug, 1 times / day Sources: |
healthy, 33.4 ± 6.6 years n = 25 Health Status: healthy Age Group: 33.4 ± 6.6 years Sex: M+F Population Size: 25 Sources: |
|
100000 unit single, intramuscular Dose: 100000 unit Route: intramuscular Route: single Dose: 100000 unit Sources: |
healthy, 34.9 ± 9.1 years n = 12 Health Status: healthy Age Group: 34.9 ± 9.1 years Sex: M+F Population Size: 12 Sources: |
|
2000000 unit single, oral Overdose Dose: 2000000 unit Route: oral Route: single Dose: 2000000 unit Sources: |
unhealthy, 90-95 years n = 2 Health Status: unhealthy Age Group: 90-95 years Sex: M+F Population Size: 2 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/10219964/ Page: 3.0 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10219964/ Page: 3.0 |
yes [Ki 10 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10219964/ Page: 3.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15353333/ Page: 2.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15353333/ Page: 2.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15353333/ Page: 2.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15353333/ Page: 2.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15353333/ Page: 2.0 |
yes |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23612780
Purified T lymphocytes from 14 patients with systemic lupus erythematosus (SLE) and 13 healthy controls were cultured for 48 h in the presence and absence of 1 and 100 nM doses of vitamin D3.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
M05BB03
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NCI_THESAURUS |
C941
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WHO-ATC |
M05BB05
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EMA ASSESSMENT REPORTS |
ADROVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
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EMA ASSESSMENT REPORTS |
FOSAVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
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LOINC |
33958-0
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DSLD |
207 (Number of products:385)
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WHO-ATC |
M05BB08
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WHO-VATC |
QM05BB03
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WHO-VATC |
QM05BX53
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CFR |
21 CFR 172.380
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WHO-ATC |
M05BX53
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LOINC |
87671-4
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EMA ASSESSMENT REPORTS |
VANTAVO (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
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LOINC |
1990-1
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FDA ORPHAN DRUG |
348111
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WHO-ESSENTIAL MEDICINES LIST |
27
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FDA ORPHAN DRUG |
342911
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WHO-VATC |
QM05BB05
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NDF-RT |
N0000006277
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WHO-ATC |
A11CC05
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WHO-ATC |
A11CC55
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EPA PESTICIDE CODE |
202901
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DSLD |
2297 (Number of products:7402)
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NDF-RT |
N0000175952
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WHO-ATC |
M05BB04
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WHO-VATC |
QM05BB04
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WHO-VATC |
QA11CC05
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LIVERTOX |
NBK548094
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WHO-ATC |
M05BB07
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Code System | Code | Type | Description | ||
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DB00169
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PRIMARY | |||
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CHEMBL1042
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PRIMARY | |||
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1244014
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ALTERNATIVE | |||
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2840
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PRIMARY | |||
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1C6V77QF41
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PRIMARY | |||
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CHOLECALCIFEROL
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odourless.Solubility: Practically insoluble in water; soluble in ethanol (~750 g/l) TS, ether R.Category: Vitamin, antirachitic.Storage: Colecalciferol should be kept in a hermetically closed container, in an inert atmosphere, protected from light and storedat a temperature between 2? and 8?C.Additional information: Even in the absence of light, Colecalciferol is gradually degraded on exposure to a humid atmosphere, thedecomposition being faster at higher temperatures. | ||
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C48194
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PRIMARY | |||
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200-673-2
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PRIMARY | |||
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5280795
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PRIMARY | |||
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820
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PRIMARY | |||
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1497
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PRIMARY | |||
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D002762
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PRIMARY | |||
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CHOLECALCIFEROL
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PRIMARY | |||
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1131009
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PRIMARY | |||
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28940
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PRIMARY | |||
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cholecalciferol
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PRIMARY | |||
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100000092724
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PRIMARY | |||
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m11486
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PRIMARY | Merck Index | ||
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DTXSID6026294
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PRIMARY | |||
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2747
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PRIMARY | |||
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67-97-0
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PRIMARY | |||
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SUB06794MIG
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PRIMARY | |||
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2418
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PRIMARY | |||
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1C6V77QF41
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PRIMARY | |||
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375571
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PRODRUG)