TACALCITOL

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 Search

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
Sources: http://adis.springer.com/drugs/800009378
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

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin D receptor 25 Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22110777 \| https://www.ncbi.nlm.nih.gov/pubmed/16116820 \| https://www.ncbi.nlm.nih.gov/pubmed/1665675	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 84 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16116820 https://www.ncbi.nlm.nih.gov/pubmed/22110777 http://adis.springer.com/drugs/800009378	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

Title	Date	PubMed
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.	1994 Aug	7976510
Profile of clinical efficacy and safety of topical tacalcitol.	2005 Apr	16116820
Vitamin D analogs in the treatment of psoriasis: Where are we standing and where will we be going?	2011 Jul	22110777
Tacalcitol in the treatment of acquired perforating collagenosis.	2014 Jan	24707254
Tacalcitol: a useful adjunct to narrow-band ultraviolet-B phototherapy in vitiligo.	2016 Sep	27552149

Patents

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

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