Home Other Building Blocks Tacalcitol

Tacalcitol

CAS No.:
57333-96-7
Catalog Number:
AG00EBMC
Molecular Formula:
C27H44O3
Molecular Weight:
416.6365
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$291
- +
5mg
≥98%
1 week
United States
$1046
- +
10mg
98%
1 week
United States
$1890
- +
25mg
98%
1 week
United States
$4057
- +
Product Description
Catalog Number:
AG00EBMC
Chemical Name:
Tacalcitol
CAS Number:
57333-96-7
Molecular Formula:
C27H44O3
Molecular Weight:
416.6365
MDL Number:
MFCD13184757
IUPAC Name:
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
InChI:
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
SMILES:
O[C@H]1C[C@H](O)C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CC[C@H](C(C)C)O)C)C)/C1
UNII:
C2W72OJ5ZU
Properties
Complexity:
676  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
2  
Exact Mass:
416.329g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
416.646g/mol
Monoisotopic Mass:
416.329g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
60.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.3  
Literature
Title Journal
Interleukin-17- and protease-activated receptor 2-mediated production of CXCL1 and CXCL8 modulated by cyclosporine A, vitamin D3 and glucocorticoids in human keratinocytes. The Journal of dermatology 20120701
Topical vitamin D₃ analogues induce thymic stromal lymphopoietin and cathelicidin in psoriatic skin lesions. The British journal of dermatology 20120701
Effects of rotation of topical vitamin D3 in chronic plaque-type psoriasis. The Journal of dermatology 20120301
The in-vitro antiproliferative effect of PRI-2191 and imatinib applied in combined treatment with cisplatin, idarubicin, or docetaxel on human leukemia cells. Anti-cancer drugs 20120101
Dexamethasone enhances 1alpha,25-dihydroxyvitamin D3 effects by increasing vitamin D receptor transcription. The Journal of biological chemistry 20111021
The separate daily application of tacalcitol 4 µg/g ointment and budesonide 0.25 mg/g cream is more effective than the single daily application of a two compound ointment containing calcipotriol 50 µg/g and betamethasone dipropionate 0.5 mg/g. Giornale italiano di dermatologia e venereologia : organo ufficiale, Societa italiana di dermatologia e sifilografia 20110801
Vitamin D: a novel therapeutic approach for keloid, an in vitro analysis. The British journal of dermatology 20110401
Calcipotriol plus betamethasone dipropionate gel compared with tacalcitol ointment and the gel vehicle alone in patients with psoriasis vulgaris: a randomized, controlled clinical trial. Dermatology (Basel, Switzerland) 20110101
Stereoselective synthesis of C24-hydroxylated vitamin D3 analogs: a practical and expeditius route to calcipotriol. The Journal of steroid biochemistry and molecular biology 20100701
Vitamin D derivatives: calcitriol and tacalcitol inhibits interleukin-6 and interleukin-8 expression in human nasal polyp fibroblast cultures. Advances in medical sciences 20100101
Biopsy proven morphea treated with tacalcitol ointment: case report. Acta dermatovenerologica Croatica : ADC 20100101
Clinical evaluation of topical tacalcitol efficacy in extending the remission period between nb-UVB phototherapy cycles in psoriatic patients. Acta bio-medica : Atenei Parmensis 20090401
Tacalcitol ointment for the treatment of nail psoriasis. The Journal of dermatological treatment 20090101
Influence of vitamin D(3) analogues in combination with budesonid R on proliferation of nasal polyp fibroblasts. Acta biochimica Polonica 20090101
Toxicity and antitumor activity of the vitamin D analogs PRI-1906 and PRI-1907 in combined treatment with cyclophosphamide in a mouse mammary cancer model. Cancer chemotherapy and pharmacology 20081001
The influence of 1,25-dihydroxyvitamin D3 and 1,24-dihydroxyvitamin D3 on alphavbeta3 integrin expression in cancer cell lines. Oncology reports 20081001
Nail psoriasis: a combined treatment with 8% clobetasol nail lacquer and tacalcitol ointment. Journal of the European Academy of Dermatology and Venereology : JEADV 20080801
Efficacy of high-concentration tacalcitol ointment in psoriasis vulgaris after changing from other high-concentration vitamin D3 ointments. Dermatology online journal 20080227
Inhibitory effects of 1,25-dihydroxyvitamin D3 and its low-calcemic analogues on staurosporine-induced apoptosis. Pharmacological reports : PR 20070101
The effect of combined treatment on head and neck human cancer cell lines with novel analogs of calcitriol and cytostatics. Oncology research 20070101
[The change of proliferative potential of fibroblasts derived of nasal polyps in vitro cultured, influenced by derivatives vitamins D]. Otolaryngologia polska = The Polish otolaryngology 20070101
Daily versus intermittent application of high-concentration tacalcitol ointment in combination with low-dose cyclosporin for psoriasis vulgaris. The Journal of dermatology 20060201
Antiproliferative activity of vitamin D compounds in combination with cytostatics. Anticancer research 20060101
Involvement of PI3-K in neuroprotective effects of the 1,25-dihydroxyvitamin D3 analogue - PRI-2191. Pharmacological reports : PR 20060101
Presence of a truncated form of the vitamin D receptor (VDR) in a strain of VDR-knockout mice. Endocrinology 20051201
Profile of clinical efficacy and safety of topical tacalcitol. Acta bio-medica : Atenei Parmensis 20050401
Effects of PRI-2191--a low-calcemic analog of 1,25-dihydroxyvitamin D3 on the seizure-induced changes in brain gene expression and immune system activity in the rat. Brain research 20050328
Does the determination of the Bb vitamin D receptor genotype identify psoriasis vulgaris patients responsive to topical tacalcitol? Journal of dermatological science 20050301
Cost-effectiveness of once-daily treatment with calcipotriol/betamethasone dipropionate followed by calcipotriol alone compared with tacalcitol in the treatment of Psoriasis vulgaris. Dermatology (Basel, Switzerland) 20050101
Correlation between VDR expression and antiproliferative activity of vitamin D3 compounds in combination with cytostatics. Anticancer research 20050101
Tolerance to calcitriol and tacalcitol in three patients with allergic contact dermatitis to calcipotriol. Journal of drugs in dermatology : JDD 20050101
Non-invasive evaluation of tacalcitol plus puva versus tacalcitol plus UVB-NB in the treatment of psoriasis: 'right-left intra-individual pre/post comparison design'. International journal of immunopathology and pharmacology 20050101
Toxicity and antineoplastic effect of (24R)-1,24-dihydroxyvitamin D3 (PRI-2191). Steroids 20040901
Neuroprotective effects of (24R)-1,24-dihydroxycholecalciferol in human neuroblastoma SH-SY5Y cell line. The Journal of steroid biochemistry and molecular biology 20040501
Anti-inflammatory effects of tacalcitol (1,24(R)(OH)2D3, TV-02) in the skin of TPA-treated hairless mice. The Journal of dermatology 20040301
[Treatment of scalp psoriasis. An effective and safe tacalcitol emulsion]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete 20040201
Efficacy of treatment with calcipotriol/betamethasone dipropionate followed by calcipotriol alone compared with tacalcitol for the treatment of psoriasis vulgaris: a randomised, double-blind trial. Dermatology (Basel, Switzerland) 20040101
Iatrogenic hypercalcemia due to vitamin D3 ointment (1,24(OH)2D3) combined with thiazide diuretics in a case of psoriasis. The Journal of dermatology 20031101
Pharmacological profiles of high-concentration (20 microg/g) tacalcitol ointment: effects on cutaneous inflammation, epidermal proliferation, and differentiation in mice. The Journal of dermatology 20030701
Similarly potent action of 1,25-dihydroxyvitamin D3 and its analogues, tacalcitol, calcipotriol, and maxacalcitol on normal human keratinocyte proliferation and differentiation. Journal of dermatological science 20030201
A systematic review of adverse effects associated with topical treatments for psoriasis. Dermatology online journal 20030201
Histometric assessment of psoriatic plaques treated by vitamin D3 derivatives. Dermatology (Basel, Switzerland) 20030101
Steroid hormone action in musculoskeletal cells involves membrane receptor and nuclear receptor mechanisms. Connective tissue research 20030101
The third multidisciplinary conference on drug research, Piła 2002. Effects of 1alpha,25-dihydroxyvitamin D3 and some putative steroid neuroprotective agents on the hydrogen peroxide-induced damage in neuroblastoma-glioma hybrid NG108-15 cells. Acta poloniae pharmaceutica 20030101
Polymorphisms of vitamin D receptor gene in Japanese patients with psoriasis vulgaris. Journal of dermatological science 20021101
Novel detection and differential utilization of a c-myc transcriptional block in colon cancer chemoprevention. Cancer research 20021101
A comparison of psoralen plus ultraviolet A (PUVA) monotherapy, tacalcitol plus PUVA and tazarotene plus PUVA in patients with chronic plaque-type psoriasis. The British journal of dermatology 20021001
Long-term efficacy and safety of tacalcitol ointment in patients with chronic plaque psoriasis. The British journal of dermatology 20020301
Confluent and reticulated papillomatosis (Gougerot-Carteaud) successfully treated with tacalcitol. The Journal of dermatological treatment 20020301
[1 alpha, 25-dihydroxyvitamin D3 and its analogues modulate the phagocytosis of human monocyte-derived dendritic cells]. Yao xue xue bao = Acta pharmaceutica Sinica 20020201
Vascular variant of keratosis lichenoides chronica associated with hypothyroidism and response to tacalcitol and acitretin. Acta dermato-venereologica 20020101
Explosive diaper pustular psoriasis. Pediatric dermatology 20020101
24-Oxo metabolites of vitamin D3 analogues: disassociation of their prominent antileukemic effects from their lack of calcium modulation. Cancer research 20010415
Dimer and superstructure of the active form of a vitamin D3; 1 alpha,24(R)dihydroxy-vitamin D3 monohydrate, C27O3H44.H2O. Chemical & pharmaceutical bulletin 20010301
The safety of calcitriol 3 microg/g ointment. Evaluation of cutaneous contact sensitization, cumulative irritancy, photoallergic contact sensitization and phototoxicity. European journal of dermatology : EJD 20010101
Hyperkeratosis lenticularis perstans (Flegel's disease)--lack of response to treatment with tacalcitol and calcipotriol. Dermatology (Basel, Switzerland) 20010101
New developments in the treatment of psoriasis. Skin pharmacology and applied skin physiology 20010101
Enhancement of the antiparakeratotic potency of calcitriol and tacalcitol in liposomal preparations in the mouse tail test. Skin pharmacology and applied skin physiology 20010101
Effects of calcitriol and its analogues on interaction of MCP-1 and monocyte derived dendritic cells in vitro. Acta pharmacologica Sinica 20010101
Comparison of the relative effects of 1,24-dihydroxyvitamin D(2) [1, 24-(OH)(2)D(2)], 1,24-dihydroxyvitamin D(3) [1,24-(OH)(2)D(3)], and 1,25-dihydroxyvitamin D(3) [1,25-(OH)(2)D(3)] on selected vitamin D-regulated events in the rat. Biochemical pharmacology 20000901
Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25-dihydroxyvitamin D3 and its analogs. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 19940801
1 alpha,24R-dihydroxyvitamin D3 has an ability comparable to that of 1 alpha,25-dihydroxyvitamin D3 to induce keratinocyte differentiation. The Journal of dermatology 19901101
Properties