Skip to content
Vinony
English
EnglishBahasa IndonesiaDeutschEspañolFrançaisItalianoNederlandsPolskiPortuguêsSvenskaTiếng ViệtTürkçeРусскийالعربيةفارسیहिन्दी한국어中文日本語
calcitriol

Structure via PubChem · Public domain (PubChem)

EntityQ139195· pop 37· linked from 562 articles

calcitriol

Sign in to save

Also known as Calcijex®, Rocaltrol®, (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10-triene-1,3,25-triol, 1alpha,25-dihydroxyvitamin D3, (1alpha,3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol, 1,25-DHCC, (5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol, 1alpha,25-dihydroxycholecalciferol

Calcitriol is a hormone and the active form of vitamin D, normally made in the kidney. It is also known as 1,25-dihydroxycholecalciferol. It binds to and activates the vitamin D receptor in the nucleus of the cell, which then increases the expression of many genes. Calcitriol increases blood calcium mainly by increasing the uptake of calcium from the intestines.

OverviewAI-generated

Calcitriol is a chemical compound with the formula C₂₇H₄₄O₃. Its molecular mass is listed as 416.329, while its weight is recorded as 416.6. The substance has a charge of 0 and an xlogp value of 5.1. It features a topological polar surface area of 60.7, with three hydrogen bond donors and three hydrogen bond acceptors.

The compound is associated with a PubMed query count of 25028. It is referenced by 562 other encyclopedia articles.

Synthesized by Vinony from 16 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.Watchedfields
changed
Drug.verifiedrevid
460772865
Drug.image
File:Calcitriol.svg
Drug.image_class
skin-invert-image
Drug.width
250
Drug.image2
Calcitriol3Dan.gif
Drug.width2
250
Drug.tradename
Rocaltrol, Calcijex, Decostriol, others
Drug.MedlinePlus
a682335
Drug.DailyMedID
Calcitriol
Drug.pregnancy_AU
B3
Drug.routes_of_administration
By mouth, intravenous
Drug.ATC_prefix
A11
Drug.ATC_suffix
CC04
Drug.legal_AU
S4
Drug.legal_CA
Rx-only
Drug.legal_UK
POM
Drug.legal_US
Rx-only

via Wikipedia infobox

Chemical data

Formula
C27H44O3
Molecular weight
416.6 g/mol
IUPAC name
trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
SMILES
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
InChIKey
GMRQFYUYWCNGIN-NKMMMXOESA-N
XLogP
5.1
Polar surface area
60.7 Ų
H-bond donors
3
H-bond acceptors
3
Formal charge
0

via PubChem

Research

25,028 papers

via PubMed

~10 min read

Encyclopedic overview

9 sections
Contents
  • Medical use
  • Adverse effects
  • Mechanism of action
  • Biosynthesis and its regulation
  • Interactive pathway map
  • Metabolism
  • History
  • Names
  • References

Calcitriol is a hormone and the active form of vitamin D, normally made in the kidney. It is also known as 1,25-dihydroxycholecalciferol. It binds to and activates the vitamin D receptor in the nucleus of the cell, which then increases the expression of many genes. Calcitriol increases blood calcium mainly by increasing the uptake of calcium from the intestines.

Calcitriol can be given as a medication for the treatment of osteoporosis, osteomalacia, familial hypophosphatemia, low blood calcium due to hypoparathyroidism, and low blood calcium and hyperparathyroidism due to kidney disease. It can be taken by mouth or by injection into a vein. Excessive amounts or intake can result in weakness, headache, nausea, constipation, urinary tract infections, and abdominal pain. Serious side effects may include high blood calcium and anaphylaxis.

Excerpted from Wikipedia’s “calcitriol” article, available under the CC BY-SA 4.0 licence.

Gallery (3)

Available in 37 languages

Show 18 more

via Wikidata sitelinks · CC0