Tacalcitol

Names

[ Name ]:
Tacalcitol

[Synonym ]:
1a,24R-Dihydroxyvitamin D3
TV-02H
1,3-Cyclohexanediol, 4-methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,3S,5Z)-
(1S,3R,5Z,7E,24R)-9,10-Secocholesta-5,7,10-triene-1,3,24-triol
Bonalfa
1a,24(R)-Dihydroxycholecalciferol
Curatoderm
(1a,3b,5Z,7E,24R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol
1,24R-dihydroxyvitamin D3
TV-02
(+)-(5Z,7E,24R)-9,10-Secocholesta-5,7,10(19)-triene-1α,3β,24-triol
Tacalcitol

Biological Activity

[Description]:

Tacalcitol (1,24(R)-Dihydroxyvitamin D3; 1.alpha.,24R-Dihydroxyvitamin D3) promotes normal bone development by regulating calcium.IC50 value:Target: Tacalcitol modulates immunological and inflammatory processes. Tacalcitol induces nerve growth factor production in epidermal keratinocytes.

[Related Catalog]:

Signaling Pathways >> Vitamin D Related >> VD/VDR

Research Areas >> Metabolic Disease

[References]

[1]. Masuo Morisaki , aoyuki Koizumi , Nobuo Ikekawa et al. Synthesis of active forms of vitamin D. Part IX. Synthesis of 1α,24-dihydroxycholecalciferol. J. Chem. Soc., Perkin Trans. 1, 1975, 1421-1424

[2]. Kiyoshige Ochi , Isao Matsunaga , Hiroyuki Nagano et al. Synthetic studies of vitamin D3 analogues from bile acids. Part 3. Syntheses of 1α,25-, 1α,24R-, and 1α,24S-dihydroxycholecalciferols from lithocholic acid and their biological activities. J. Chem.

[3]. Rostowska-Nadolska et al Vitamin D derivatives: calcitriol and tacalcitol inhibits interleukin-6 and interleukin-8 expression in human nasal polyp fibroblasts. Adv.Med.Sci. (2010) 55 86.

[4]. Oiso N, Kawada A.Freckling Promoted by Topical Tacalcitol in a Japanese Boy with Left Eyelid Vitiligo.Pediatr Dermatol. 2011 Oct 20.

[5]. Kobayashi T, Okumura H, Azuma Y, Kiyoki M, Matsumoto K, Hashimoto K, Yoshikawa K.1 alpha,24R-dihydroxyvitamin D3 has an ability comparable to that of 1 alpha,25-dihydroxyvitamin D3 to induce keratinocyte differentiation.J Dermatol. 1990 Nov;17(11):707-9.

[6]. Matsumoto K, Hashimoto K, Kiyoki M, Yamamoto M, Yoshikawa K.Effect of 1,24R-dihydroxyvitamin D3 on the growth of human keratinocytes.J Dermatol. 1990 Feb;17(2):97-103.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
565.0±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₄₄O₃

[ Molecular Weight ]:
416.637

[ Flash Point ]:
238.4±24.7 °C

[ Exact Mass ]:
416.329041

[ PSA ]:
60.69000

[ LogP ]:
6.12

[ Vapour Pressure ]:
0.0±3.5 mmHg at 25°C

[ Index of Refraction ]:
1.546

[ Storage condition ]:
Store at -20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VS2882200

CHEMICAL NAME :: 9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol, (1-alpha,3-beta,5Z,7E,24R)-

CAS REGISTRY NUMBER :: 57333-96-7

LAST UPDATED :: 199806

DATA ITEMS CITED :: 7

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3279 ug/kg

TOXIC EFFECTS :: Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 ug/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Skin and Appendages - hair Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 556 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Skin and Appendages - hair Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3050 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 419 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 559 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 10 ug/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - changes in calcium

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17,4615,1989

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Hazard Codes ]:
N-T+

[ Risk Phrases ]:
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . R33:Danger of cumulative effects. R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .

[ Safety Phrases ]:
S61-S60-S45-S36-S28A-S13

[ RIDADR ]:
2025

[ RTECS ]:
OW2300000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1

Articles

Regulation of RANTES and IL-8 production in normal human dermal fibroblasts by active vitamin D3 (tacalcitol).

Br. J. Pharmacol. 124(7) , 1433-8, (1998)

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...

Tacalcitol in the treatment of acquired perforating collagenosis. Escribano-Stablé JC

Case Rep. Dermatol. 6(1) , 69-73, (2014)

Hailey-hailey disease treated with topical tacalcitol. Jeon SY et al

Ann. Dermatol. 25(3) , 389-90, (2013)