Tacalcitol

Last updated
Tacalcitol
Tacalcitol.svg
Clinical data
Other names(1α,24R)-1,24-Dihydroxyvitamin D3
AHFS/Drugs.com International Drug Names
Routes of
administration
Topical
ATC code
Identifiers
  • (1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.220.855 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H44O3
Molar mass 416.646 g·mol−1
3D model (JSmol)
  • O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CC[C@@H](O)C(C)C)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 X mark.svgN
  • Key:BJYLYJCXYAMOFT-RSFVBTMBSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Tacalcitol (1,24-dihydroxyvitamin D3) is a synthetic vitamin D3 analog. [1] Tacalcitol is marketed under several names, including Curatoderm and Bonalfa.

Contents

It is on the World Health Organization's List of Essential Medicines. [2]

Mechanism

Tacalcitol reduces excessive cell turnover in the epidermis by interacting with vitamin D receptors on keratinocytes. [3] [4]

Uses

It is usually prescribed by a general practitioner or dermatologist for the treatment of psoriasis, chronic chapped lips and other severe dry skin conditions because of its ability to reduce excessive skin cell turnover. [1] It is available as an ointment or lotion.

It has also been used for vitiligo [5] [6] and Hailey-Hailey disease. [7]

Related Research Articles

<span class="mw-page-title-main">Vitiligo</span> Skin condition where patches lose pigment

Vitiligo is a chronic autoimmune disorder that causes patches of skin to lose pigment or color. The cause of vitiligo is unknown, but it may be related to immune system changes, genetic factors, stress, or sun exposure. Treatment options include topical medications, light therapy, surgery and cosmetics. The condition can show up on any skin type as a light peachy color and can appear on any place on the body in all sizes. The spots on the skin known as vitiligo are also able to “change” as spots lose and regain pigment; they will stay in relatively the same areas but can move over time and some big patches can move through the years but never disappear overnight.

<span class="mw-page-title-main">Keratinocyte</span> Primary type of cell found in the epidermis

Keratinocytes are the primary type of cell found in the epidermis, the outermost layer of the skin. In humans, they constitute 90% of epidermal skin cells. Basal cells in the basal layer of the skin are sometimes referred to as basal keratinocytes. Keratinocytes form a barrier against environmental damage by heat, UV radiation, water loss, pathogenic bacteria, fungi, parasites, and viruses. A number of structural proteins, enzymes, lipids, and antimicrobial peptides contribute to maintain the important barrier function of the skin. Keratinocytes differentiate from epidermal stem cells in the lower part of the epidermis and migrate towards the surface, finally becoming corneocytes and eventually being shed, which happens every 40 to 56 days in humans.

<span class="mw-page-title-main">Cholecalciferol</span> Vitamin D3, a chemical compound

Cholecalciferol, also known as vitamin D3 and colecalciferol, is a type of vitamin D that is made by the skin when exposed to UV-B light; it is found in some foods and can be taken as a dietary supplement.

<span class="mw-page-title-main">Keratin 2A</span>

Keratin 2A also known as keratin 2E or keratin 2 is a protein that in humans is encoded by the KRT2A gene.

<span class="mw-page-title-main">Keratin 16</span> Protein-coding gene in the species Homo sapiens

Keratin 16 is a protein that in humans is encoded by the KRT16 gene.

Darier's disease (DD) is a rare, genetic skin disorder. It is an autosomal dominant disorder, that is, if one parent has DD, there is a 50% chance than a child will inherit DD. It was first reported by French dermatologist Ferdinand-Jean Darier in 1889.

<span class="mw-page-title-main">Calcitriol</span> Active form of vitamin D

Calcitriol is the active form of vitamin D, normally made in the kidney. It is also known as 1,25-dihydroxycholecalciferol. It is a hormone which binds to and activates the vitamin D receptor in the nucleus of the cell, which then increases the expression of many genes. Calcitriol increases blood calcium (Ca2+) mainly by increasing the uptake of calcium from the intestines.

<span class="mw-page-title-main">Calcipotriol</span> Chemical compound

Calcipotriol, also known as calcipotriene, is a synthetic derivative of calcitriol, a form of vitamin D. It is used in the treatment of psoriasis. It is safe for long-term application in psoriatic skin conditions.

<span class="mw-page-title-main">Skin whitening</span> Practice of using chemical substances to lighten the skin

Skin whitening, also known as skin lightening and skin bleaching, is the practice of using chemical substances in an attempt to lighten the skin or provide an even skin color by reducing the melanin concentration in the skin. Several chemicals have been shown to be effective in skin whitening, while some have proven to be toxic or have questionable safety profiles. This includes mercury compounds which may cause neurological problems and kidney problems.

<span class="mw-page-title-main">Vitamin D receptor</span> Transcription factor activated by vitamin D

The vitamin D receptor (VDR also known as the calcitriol receptor) is a member of the nuclear receptor family of transcription factors. Calcitriol (the active form of vitamin D, 1,25-(OH)2vitamin D3) binds to VDR, which then forms a heterodimer with the retinoid-X receptor. The VDR heterodimer then enters the nucleus and binds to Vitamin D responsive elements (VDRE) in genomic DNA. VDR binding results in expression or transrepression of many specific gene products. VDR is also involved in microRNA-directed post transcriptional mechanisms. In humans, the vitamin D receptor is encoded by the VDR gene located on chromosome 12q13.11.

Corneocytes are terminally differentiated keratinocytes and compose most of the stratum corneum, the outermost layer of the epidermis. They are regularly replaced through desquamation and renewal from lower epidermal layers and are essential for its function as a skin barrier.

<span class="mw-page-title-main">CYP24A1</span>

Cytochrome P450 family 24 subfamily A member 1 (abbreviated CYP24A1) is a member of the cytochrome P450 superfamily of enzymes encoded by the CYP24A1 gene. It is a mitochondrial monooxygenase which catalyzes reactions including 24-hydroxylation of calcitriol (1,25-dihydroxyvitamin D3). It has also been identified as vitamin D3 24-hydroxylase.(EC 1.14.15.16)

<span class="mw-page-title-main">Loricrin</span> Protein-coding gene in the species Homo sapiens

Loricrin is a protein that in humans is encoded by the LOR gene.

<span class="mw-page-title-main">HR (gene)</span> Protein-coding gene in the species Homo sapiens

HR is a gene encoding Protein hairless.

UV-B lamps are lamps that emit a spectrum of ultraviolet light with wavelengths ranging from 290–320 nanometers. This spectrum is also commonly called the biological spectrum due to the human body's sensitivity to light of such a wavelength. UV-B light does not tan the skin very much, compared to the UV-A lamps that are used in tanning beds.

<span class="mw-page-title-main">24,25-Dihydroxycholecalciferol</span> Chemical compound

24,25-Dihydroxycholecalciferol, also known as 24,25-dihydroxyvitamin D3 and (24R)-hydroxycalcidiol (abbreviated as 24(R),25-(OH)2D3), is a compound which is closely related to 1,25-dihydroxyvitamin D3, the active form of vitamin D3. Like vitamin D3 itself and calcifediol (25-hydroxyvitamin D3), it is inactive as a hormone both in vitro and in vivo. It was first identified in 1972 in the laboratory of Hector DeLuca and Michael F. Holick.

<span class="mw-page-title-main">Vitamin D deficiency</span> Human disorder

Vitamin D deficiency or hypovitaminosis D is a vitamin D level that is below normal. It most commonly occurs in people when they have inadequate exposure to sunlight, particularly sunlight with adequate ultraviolet B rays (UVB). Vitamin D deficiency can also be caused by inadequate nutritional intake of vitamin D; disorders that limit vitamin D absorption; and disorders that impair the conversion of vitamin D to active metabolites, including certain liver, kidney, and hereditary disorders. Deficiency impairs bone mineralization, leading to bone-softening diseases, such as rickets in children. It can also worsen osteomalacia and osteoporosis in adults, increasing the risk of bone fractures. Muscle weakness is also a common symptom of vitamin D deficiency, further increasing the risk of fall and bone fractures in adults. Vitamin D deficiency is associated with the development of schizophrenia.

<span class="mw-page-title-main">Arsenical keratosis</span> Medical condition

An arsenical keratosis is a growth of keratin on the skin caused by arsenic, which occurs naturally in the Earth's crust and is widely distributed in the environment, Arsenical compounds are used in industrial, agricultural, and medicinal substances. Arsenic is also found to be an environmental contaminant in drinking water and an occupational hazard for miners and glass workers. Arsenic may also causes other conditions including: Bowen's disease, cardiovascular diseases, developmental abnormalities, neurologic and neurobehavioral disorders, diabetes, hearing loss, hematologic disorders, and various types of cancer. Arsenical keratoses may persist indefinitely, and some may develop into invasive squamous cell carcinoma. Metastatic arsenic squamous cell carcinoma and arsenic-induced malignancies in internal organs such as the bladder, kidney, skin, liver, and colon, may result in death.

<span class="mw-page-title-main">Michael F. Holick</span> American physician–scientist

Michael F. Holick is an American adult endocrinologist, specializing in vitamin D, such as the identification of both calcidiol, the major circulating form of vitamin D, and calcitriol, the active form of vitamin D. His work has been the basis for diagnostic tests and therapies for vitamin D-related diseases. He is a professor of medicine at the Boston University Medical Center and editor-in-chief of the journal Clinical Laboratory.

HaCaT is a spontaneously transformed aneuploid immortal keratinocyte cell line from adult human skin, widely used in scientific research. HaCaT cells are utilized for their high capacity to differentiate and proliferate in vitro. Their use in research allows for the characterization of human keratinocyte using a model that is reproducible and addresses issues such as short culture lifespan and variations between cell lines that would otherwise be encountered. These cells have allowed the characterization of several processes, such as their utilization as a model system for vitamin D3 metabolism in the skin.

References

  1. 1 2 Peters DC, Balfour JA (August 1997). "Tacalcitol". Drugs. 54 (2): 265–71, discussion 272. doi:10.2165/00003495-199754020-00005. PMID   9257082. S2CID   263503145.
  2. World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl: 10665/345533 . WHO/MHP/HPS/EML/2021.02.
  3. Matsumoto K, Hashimoto K, Kiyoki M, Yamamoto M, Yoshikawa K (February 1990). "Effect of 1,24R-dihydroxyvitamin D3 on the growth of human keratinocytes". The Journal of Dermatology. 17 (2): 97–103. doi:10.1111/j.1346-8138.1990.tb03714.x. PMID   2158504. S2CID   38248260.
  4. Fukuoka M, Sakurai K, Ohta T, Kiyoki M, Katayama I (2001). "Tacalcitol, an active vitamin D3, induces nerve growth factor production in human epidermal keratinocytes". Skin Pharmacol. Appl. Skin Physiol. 14 (4): 226–33. doi:10.1159/000056351. PMID   11464105. S2CID   24302198.
  5. Leone G, Pacifico A, Iacovelli P, Paro Vidolin A, Picardo M (March 2006). "Tacalcitol and narrow-band phototherapy in patients with vitiligo". Clin. Exp. Dermatol. 31 (2): 200–5. doi:10.1111/j.1365-2230.2005.02037.x. PMID   16487090. S2CID   39021489.
  6. Birlea SA, Costin GE, Norris DA (April 2008). "Cellular and molecular mechanisms involved in the action of vitamin D analogs targeting vitiligo depigmentation". Current Drug Targets. 9 (4): 345–59. doi:10.2174/138945008783954970. PMID   18393827.
  7. Aoki T, Hashimoto H, Koseki S, Hozumi Y, Kondo S (November 1998). "1alpha,24-dihydroxyvitamin D3 (tacalcitol) is effective against Hailey-Hailey disease both in vivo and in vitro". Br. J. Dermatol. 139 (5): 897–901. doi:10.1046/j.1365-2133.1998.02522.x. PMID   9892963. S2CID   72418207.