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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H44O3
Molecular Weight 416.6365
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TACALCITOL

SMILES

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

InChI

InChIKey=BJYLYJCXYAMOFT-RSFVBTMBSA-N
InChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25-,26+,27-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16116820

Talcalcitol is a synthetic analogue of vitamin D3. Tacalcitol has been developed by Teijin in Japan with the aim of maintaining the potent cell-regulating properties of calcitriol without the calcium-related adverse effects. Tacalcitol differs structurally from calcitriol by hydroxylation in the 24 position instead of the 25 position. Tacalcitol can influence the principal pathogenetic factors of psoriasis by inducing normalisation of keratinocyte differentiation, performing an anti-proliferative action and finally modulating the inflammatory response. Tacalcitol has been launched as an ointment formulation for the treatment of psoriasis in various countries. High-dose formulations (ointment and lotion) are available in Japan.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CURATODERM

Approved Use

Tacalcitol ointment/lotion has been approved for the treatment of a mild and/or moderate degree of psoriasis.
PubMed

PubMed

TitleDatePubMed
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.
1994 Aug
Profile of clinical efficacy and safety of topical tacalcitol.
2005 Apr
Vitamin D analogs in the treatment of psoriasis: Where are we standing and where will we be going?
2011 Jul
Tacalcitol in the treatment of acquired perforating collagenosis.
2014 Jan
Tacalcitol: a useful adjunct to narrow-band ultraviolet-B phototherapy in vitiligo.
2016 Sep
Patents

Patents

JP2008529964A
4
US20060106003
2
WO/2004/087170A1
2
WO/2012/128653A1
2
WO/2013/100772A1
2

Sample Use Guides

In Vivo Use Guide
Tacalcitol 4 ug/g Lotion or Ointment is applied to the affected area
Route of Administration: Transdermal
In Vitro Use Guide
NGF induction in human epidermal keratinocytes caused by tacalcitol was dose-dependent, showing an ED50 between 0.1-1 nM
Name Type Language
TACALCITOL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
TACALCITOL [MI]
Common Name English
TACALCITOL [MART.]
Common Name English
1.ALPHA.,24-DIHYDROXYCHOLECALCIFEROL
Common Name English
BONALFA
Brand Name English
Tacalcitol [WHO-DD]
Common Name English
1.ALPHA.,24-DIHYDROXYVITAMIN D3
Common Name English
(+)-(5Z,7E,24R)-9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-1.ALPHA.,3.BETA.,24-TRIOL
Common Name English
tacalcitol [INN]
Common Name English
1S,3R,5Z,7E,24R)-9,10-SECOCHOLESTA-5,7,10-TRIENE-1,3,24-TRIOL
Common Name English
Classification Tree Code System Code
WHO-VATC QD05AX04
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
WHO-ATC D05AX04
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
NCI_THESAURUS C39713
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C87292
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
MERCK INDEX
m10422
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY Merck Index
MESH
C023850
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
EVMPD
SUB10794MIG
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID90905111
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
SMS_ID
100000082993
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
PUBCHEM
5283734
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
DRUG BANK
DB13689
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
WIKIPEDIA
TACALCITOL
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105611
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
RXCUI
291204
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
4727
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
CHEBI
32176
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
INN
6822
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
FDA UNII
C2W72OJ5ZU
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
CAS
57333-96-7
Created by admin on Sat Dec 16 16:30:42 UTC 2023 , Edited by admin on Sat Dec 16 16:30:42 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of TACALCITOL
SALT/SOLVATE (PARENT)
Structure of TACALCITOL MONOHYDRATE
NIH
NCATS
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