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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

CC(C)[C@H](O)CC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CCC\C2=C/C=C3/C[C@@H](O)C[C@H](O)C3=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
Molecular Formula C27H44O3
Molecular Weight 416.6365
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 2
Optical Activity UNSPECIFIED

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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
CURATODERM

Approved Use

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

Cmax

ValueDoseCo-administeredAnalytePopulation
25 pg/mL
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/2/470310_2691700M2025_2_002_1F.pdf#page=40
200 μg 1 times / day multiple, topical
dose: 200 μg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
TACALCITOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
25 pg/mL
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/2/470310_2691700M2025_2_002_1F.pdf#page=40
140 μg 1 times / day multiple, topical
dose: 140 μg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
TACALCITOL serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
25 pg/mL
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/2/470310_2691700M2025_2_002_1F.pdf#page=40
200 μg 1 times / day multiple, topical
dose: 200 μg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
TACALCITOL serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0%
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/2/470310_2691700M2025_2_002_1F.pdf#page=41
TACALCITOL plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
20 mg/kg 1 times / day multiple, topical
Higher than recommended
Dose: 20 mg/kg, 1 times / day
Route: topical
Route: multiple
Dose: 20 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20302582/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20302582/
Sources:
https://pubmed.ncbi.nlm.nih.gov/20302582/
4 mg/kg 1 times / day multiple, topical
Recommended
Dose: 4 mg/kg, 1 times / day
Route: topical
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
Disc. AE: Skin irritation, Skin irritation...
AEs leading to
discontinuation/dose reduction:
Skin irritation (5.9%)
Skin irritation (4.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
AEs

AEs

AESignificanceDosePopulation
Skin irritation 4.9%
Disc. AE
4 mg/kg 1 times / day multiple, topical
Recommended
Dose: 4 mg/kg, 1 times / day
Route: topical
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
Skin irritation 5.9%
Disc. AE
4 mg/kg 1 times / day multiple, topical
Recommended
Dose: 4 mg/kg, 1 times / day
Route: topical
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/11952541/
PubMed

PubMed

TitleDatePubMed
Tacalcitol: a useful adjunct to narrow-band ultraviolet-B phototherapy in vitiligo.
2016-09
Tacalcitol in the treatment of acquired perforating collagenosis.
2014-01
Vitamin D analogs in the treatment of psoriasis: Where are we standing and where will we be going?
2011-07
Profile of clinical efficacy and safety of topical tacalcitol.
2005-04
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs.
1994-08
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
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:53:50 GMT 2025
Edited
by admin
on Wed Apr 02 07:53:50 GMT 2025
Record UNII
C2W72OJ5ZU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TACALCITOL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
BONALFA
Preferred Name English
TACALCITOL [MI]
Common Name English
TACALCITOL [MART.]
Common Name English
1.ALPHA.,24-DIHYDROXYCHOLECALCIFEROL
Common 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 Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
WHO-ATC D05AX04
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
NCI_THESAURUS C39713
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C87292
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
MERCK INDEX
m10422
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY Merck Index
MESH
C023850
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
EVMPD
SUB10794MIG
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID90905111
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
SMS_ID
100000082993
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
PUBCHEM
5283734
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
DRUG BANK
DB13689
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
WIKIPEDIA
TACALCITOL
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105611
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
RXCUI
291204
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
4727
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
CHEBI
32176
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
INN
6822
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
FDA UNII
C2W72OJ5ZU
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
CAS
57333-96-7
Created by admin on Wed Apr 02 07:53:50 GMT 2025 , Edited by admin on Wed Apr 02 07:53:50 GMT 2025
PRIMARY
Related Record Type Details
Structure of TACALCITOL MONOHYDRATE
SALT/SOLVATE -> PARENT
Structure of TACALCITOL MONOHYDRATE
SOLVATE->ANHYDROUS
Related Record Type Details
Structure of TACALCITOL
ACTIVE MOIETY
NIH
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