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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H44O2
Molecular Weight 400.6371
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CALCIFEDIOL ANHYDROUS

SMILES

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C

InChI

InChIKey=JWUBBDSIWDLEOM-DTOXIADCSA-N
InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1

HIDE SMILES / InChI

Description

Calcifediol (25-Hydroxyvitamin D3 or 25-hydroxycholecalciferol) is a biologically active vitamin D3 metabolite. It is concluded that the liver is the major if not the only physiologic site of hydroxylation of vitamin D3 into calcifediol. Calcifediol is a prohormone of the active form of vitamin D3, calcitriol (1,25-dihydroxyvitamin D3). Calcifediol is converted to calcitriol by cytochrome P450 27B1 (CYP27B1), also called 1-alpha hydroxylase, primarily in the kidney. Calcitriol binds to the vitamin D receptor in target tissues and activates vitamin D responsive pathways that result in increased intestinal absorption of calcium and phosphorus and reduced parathyroid hormone synthesis. RAYALDEE (calcifediol) extended-release capsules is indicated for the treatment of secondary hyperparathyroidism in adult patients with stage 3 or 4 chronic kidney disease.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Determination of vitamin D and its metabolites in plasma from normal and anephric man.
1979 Jul 15
Interrelationship of serum 25-hydroxyvitamin D3 and 1,25-dihydroxyvitamin D in juvenile renal osteodystrophy after therapy with 25-hydroxyvitamin D3.
1982
Tubular aggregates in a case of osteomalacic myopathy due to anticonvulsant drugs.
1984 Jan-Feb
Hypercalcemia in 25 OH D3 treated patients receiving a calcium exchange resin.
1985 Jun
The effect of vitamin D status on cutaneous sterologenesis in vivo and in vitro.
1987 Sep 14
Inhibition of tubercle bacilli in cultured human macrophages by chloroquine used alone and in combination with streptomycin, isoniazid, pyrazinamide, and two metabolites of vitamin D3.
1990 Nov
Vitamin D3 compounds regulate human immunodeficiency virus type 1 replication in U937 monoblastoid cells and in monocyte-derived macrophages.
1993 Feb
Proteins in the heat shock-70 family specifically bind 25-hydroxyvitamin D3 and 17beta-estradiol.
1998 Apr
Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile.
2010 Mar 30
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.
2011 Feb 3
Patents

Sample Use Guides

In Vivo Use Guide
The initial dose of RAYALDEE (calcifediol) extended-release capsules is 30 mcg administered orally once daily at bedtime. Serum calcium should be below 9.8 mg/dL before initiating treatment. Monitor serum calcium, phosphorus, 25-hydroxyvitamin D and intact parathyroid hormone (PTH) 3 months after starting therapy or changing dose. Increase the dose to 60 mcg once daily after 3 months if intact PTH is above the treatment goal. Ensure serum calcium is below 9.8 mg/dL, phosphorus is below 5.5 mg/dL and 25-hydroxyvitamin D is below 100 ng/mL before increasing the dose. Suspend dosing if intact PTH is persistently abnormally low, serum calcium is consistently above the normal range or serum 25­ hydroxyvitamin D is consistently above 100 ng/mL
Route of Administration: Oral
In Vitro Use Guide
Vitamin D metabolites down-regulated stimulated IL-8 only in those hyperinflammatory monocyte-derived macrophages, and only when used at high doses (>100 nM for Calcifediol).
Name Type Language
CALCIFEDIOL ANHYDROUS
Common Name English
CALCIFEDIOL, ANHYDROUS
Common Name English
CALCIFEDIOL,ANHYDROUS
VANDF  
Common Name English
CALCIFEDIOL [MI]
Common Name English
CALCIFEDIOL [INN]
Common Name English
CALCIFEDIOL,ANHYDROUS [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC A11CC06
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
Code System Code Type Description
INN
3057
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
MERCK INDEX
M2911
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY Merck Index
DRUG BANK
DB00146
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
PUBCHEM
5283731
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C77155
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
EVMPD
SUB06045MIG
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
EPA CompTox
19356-17-3
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
RXCUI
1855064
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
ECHA (EC/EINECS)
242-990-9
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY
CAS
19356-17-3
Created by admin on Tue Mar 06 11:00:10 UTC 2018 , Edited by admin on Tue Mar 06 11:00:10 UTC 2018
PRIMARY