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SMB00579

Sigma-Aldrich

Tacalcitol

≥99% (HPLC)

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Synonym(s):
(1α,3β,5Z,7E,24R)-9,10-secocholesta-5,7,10(19)-triene-1,3,24-triol, 1α,24R-dihydroxycholecalciferol, 1α,24R-dihydroxyvitamin D3
Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
57333-96-7
Molecular Weight:
416.64
MDL number:
MFCD00866623
UNSPSC Code:
12352205
PubChem Substance ID:
329825068
NACRES:
NA.79

biological source

synthetic (organic)

Quality Level

200

Assay

≥99% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

−20°C

SMILES string

C[C@]1(CCC/2)[C@](CC[C@]1([H])[C@H](C)CC[C@@H](O)C(C)C)([H])C2=C\C=C3C[C@@H](O)C[C@H](O)C\3=C

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

InChI key

BJYLYJCXYAMOFT-RSFVBTMBSA-N

Related Categories

General description

Tacalcitol is a synthetic vitamin D3 analog. It is a vitamin D3 derivative, also known as 1α,24-dihydroxyvitamin D3.

Biochem/physiol Actions

Tacalcitol is widely used in the treatment of dermatosis due to its ability to inhibit keratinocyte proliferation and induce cell differentiation. It also has anti-inflammatory activity and has been shown to reduce cutaneous inflammation via suppression of leukocyte infiltration in skin. Tacalcitol is topically used for the treatment of psoriasis and has also been found to be effective in the treatment of acquired perforating collagenosis (APC), a rare perforating dermatosis. Studies suggest that this compound has potential for the treatment of the hereditary disorder Hailey-Hailey Disease.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 1 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tacalcitol in the treatment of acquired perforating collagenosis.
Escribano-Stable JC
Case Reports in Dermatology, 6(1), 69-73 (2014)
Hailey-hailey disease treated with topical tacalcitol.
Jeon SY et al
Annals of Dermatology, 25(3), 389-390 (2013)
M Fukuoka et al.
British journal of pharmacology, 124(7), 1433-1438 (1998-09-02)
1. The production of chemokines, RANTES and IL-8 in cultured human dermal fibroblasts and the effects of tacalcitol (1alpha,24(R)-dihydroxyvitamin D3) were studied using an enzyme-linked immunosorbent assay. 2. In the unstimulated condition, RANTES and IL-8 were at a trace level

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