U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of Cholecalciferol

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
42 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
968.6 nM × day
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

T1/2

ValueDoseCo-administeredAnalytePopulation
15.5 day
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

Doses

DosePopulationAdverse 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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
strong
yes [Ki 10 uM]
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Vitamin D and the Pathogenesis of Inflammatory Bowel Disease.
2016 Oct
Human cytomegalovirus infection downregulates vitamin-D receptor in mammalian cells.
2017 Jan
Patents

Patents

Sample Use Guides

200,000 IU injection within 12 weeks.
Route of Administration: Intramuscular
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.
Name Type Language
Cholecalciferol
EP   HSDB   INCI   ISO   ORANGE BOOK   USP   VANDF  
INCI  
Official Name English
FOSAMAX PLUS D COMPONENT CHOLECALCIFEROL
Common Name English
9,10-SECOCHOLESTA-5,7,10(19)-TRIEN-3-OL, (3.BETA.,5Z,7E)-
Common Name English
COLECALCIFEROL [MART.]
Common Name English
CHOLECALCIFEROL COMPONENT OF FOSAMAX PLUS D
Common Name English
VITAMIN D (CHOLECALCIFEROL)
Common Name English
VITAMIN D ASSAY SYSTEM SUITABILITY
USP-RS  
Common Name English
Cyclohexanol, 3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-, (1S,3Z)-
Systematic Name English
COLECALCIFEROL [EMA EPAR]
Common Name English
EBIVIT
Brand Name English
colecalciferol [INN]
Common Name English
DELTA-D
Brand Name English
CHOLECALCIFEROL [ORANGE BOOK]
Common Name English
CHOLECALCIFEROL [VANDF]
Common Name English
7-DEHYDROCHOLESTEROL, ACTIVATED
Common Name English
VIGANTOL
Brand Name English
CHOLECALCIFEROL [EP MONOGRAPH]
Common Name English
VITAMIN D ASSAY SYSTEM SUITABILITY [USP-RS]
Common Name English
NSC-375571
Code English
VITAMIN D3 (AS CHOLECALCIFEROL)
Common Name English
DELSTEROL
Brand Name English
CHOLECALCIFEROL [JAN]
Common Name English
(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
Systematic Name English
COLECALCIFEROL [WHO-IP]
Common Name English
VITAMIN D3 [MI]
Common Name English
CHOLECALCIFEROL [INCI]
Common Name English
CHOLECALCIFEROL [USP-RS]
Common Name English
RICKETON
Common Name English
VITAMIN D3
FCC   MI  
Common Name English
DEPARAL
Brand Name English
DP-R206 COMPONENT VITAMIN D3
Common Name English
(3.BETA.,5Z,7E)-9,10-SECOCHOLESTA-5,7,10(19)-TRIEN-3-OL
Common Name English
VITAMIN D3 [FCC]
Common Name English
VIGANTOLETTEN
Common Name English
CHOLECALCIFEROL [USP MONOGRAPH]
Common Name English
COLECALCIFEROL
EMA EPAR   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
Colecalciferol [WHO-DD]
Common Name English
AK R215 COMPONENT COLECALCIFEROL
Code English
AK-R215 COMPONENT COLECALCIFEROL
Code English
PROVITINA
Brand Name English
CHOLECALCIFEROL [ISO]
Common Name English
COLECALCIFEROLUM [WHO-IP LATIN]
Common Name English
VITAMIN D-3
Common Name English
CHOLECALCIFEROL [HSDB]
Common Name English
Classification Tree Code System Code
WHO-ATC M05BB03
Created by admin on Sat Dec 16 17:56:36 UTC 2023 , Edited by admin on Sat Dec 16 17:56:36 UTC 2023
NCI_THESAURUS C941
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ATC M05BB05
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
EMA ASSESSMENT REPORTS ADROVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
EMA ASSESSMENT REPORTS FOSAVANCE (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
LOINC 33958-0
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
DSLD 207 (Number of products:385)
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ATC M05BB08
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-VATC QM05BB03
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-VATC QM05BX53
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
CFR 21 CFR 172.380
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ATC M05BX53
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
LOINC 87671-4
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
EMA ASSESSMENT REPORTS VANTAVO (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
LOINC 1990-1
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
FDA ORPHAN DRUG 348111
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 27
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
FDA ORPHAN DRUG 342911
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-VATC QM05BB05
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
NDF-RT N0000006277
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ATC A11CC05
Created by admin on Sat Dec 16 17:56:36 UTC 2023 , Edited by admin on Sat Dec 16 17:56:36 UTC 2023
WHO-ATC A11CC55
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
EPA PESTICIDE CODE 202901
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
DSLD 2297 (Number of products:7402)
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
NDF-RT N0000175952
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ATC M05BB04
Created by admin on Sat Dec 16 17:56:36 UTC 2023 , Edited by admin on Sat Dec 16 17:56:36 UTC 2023
WHO-VATC QM05BB04
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-VATC QA11CC05
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
LIVERTOX NBK548094
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
WHO-ATC M05BB07
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
Code System Code Type Description
DRUG BANK
DB00169
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1042
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
RXCUI
1244014
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
ALTERNATIVE
DRUG CENTRAL
2840
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
FDA UNII
1C6V77QF41
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHOLECALCIFEROL
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
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.
NCI_THESAURUS
C48194
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-673-2
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
PUBCHEM
5280795
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
HSDB
820
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
INN
1497
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
MESH
D002762
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
WIKIPEDIA
CHOLECALCIFEROL
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
RS_ITEM_NUM
1131009
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
CHEBI
28940
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
ALANWOOD
cholecalciferol
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
SMS_ID
100000092724
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
MERCK INDEX
m11486
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6026294
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
IUPHAR
2747
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
CAS
67-97-0
Created by admin on Sat Dec 16 17:56:36 UTC 2023 , Edited by admin on Sat Dec 16 17:56:36 UTC 2023
PRIMARY
EVMPD
SUB06794MIG
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
RXCUI
2418
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
DAILYMED
1C6V77QF41
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY
NSC
375571
Created by admin on Sat Dec 16 17:56:37 UTC 2023 , Edited by admin on Sat Dec 16 17:56:37 UTC 2023
PRIMARY