アルファカルシドール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/05/08 18:43:59」(JST)
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Alfacalcidol
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Names |
IUPAC name
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-Methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
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Other names
Alphacalcidol; 1-Hydroxycholecalciferol
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Identifiers |
CAS Number
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3D model (Jmol)
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ChEBI |
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ChemSpider |
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DrugBank |
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ECHA InfoCard |
100.050.253 |
KEGG |
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UNII |
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InChI
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InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1 Y
Key: OFHCOWSQAMBJIW-AVJTYSNKSA-N Y
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InChI=1/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
Key: OFHCOWSQAMBJIW-AVJTYSNKBM
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SMILES
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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)CCCC(C)C)C
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Properties |
Chemical formula
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C27H44O2 |
Molar mass |
400.64 g/mol |
Pharmacology |
ATC code
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A11CC03 (WHO) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) |
Infobox references |
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Alfacalcidol (or 1-hydroxycholecalciferol) is an analogue of vitamin D used for supplementation in humans and as a poultry feed additive.
Alfacalcidol has a weaker impact on calcium metabolism[1] and parathyroid hormone levels[2] than calcitriol, however alfacalcidol has significant effects on the immune system, including regulatory T cells.[3] It is considered to be a more useful form of vitamin D supplementation, mostly due to much longer half-life and lower kidney load.[4] It is the most commonly prescribed vitamin D metabolite for patients with end stage renal disease, given that impaired renal function alters the ability to carry out the second hydroxylation step required for the formation of the physiologically active form of vitamin D, 1,25-dihydroxyvitamin D3. Alfacalcidol is an active vitamin D3 metabolite, and therefore does not require the second hydroxylation step in the kidney.[5]
Used as a poultry feed additive, it prevents tibial dyschondroplasia and increases phytate bioavailability.[6][original research?]
Trade names
Pharmaceutical trade names include AlphaD and One-Alpha.
References
- ^ "Biological effects of various regimes of 25-hydroxyvitamin D3 (calcidiol) administration on bone mineral metabolism in postmenopausal women". Clin Cases Miner Bone Metab. 6 (2): 169–173. 2009. PMC 2781231 . PMID 22461169.
- ^ "Oral calcitriol versus oral alfacalcidol for the treatment of secondary hyperparathyroidism in patients receiving hemodialysis: a randomized, crossover trial". Can J Clin Pharmacol. 15 (1): e36–e43. 2008.
- ^ Alfacalcidol treatment restores derailed immune-regulation in patients with undifferentiated connective tissue disease, Autoimmunity Reviews, August 2010;
- ^ "Superiority of alfacalcidol compared to vitamin D plus calcium in lumbar bone mineral density in postmenopausal osteoporosis". Rheumatol Int. 26 (5): 445–53. Mar 2006. doi:10.1007/s00296-005-0073-4. PMID 16283320.
- ^ "Alfacalcidol in the therapy of renal bone disease.". Int J Clin Pharmacol Ther. 39: 546–50. Dec 2001. doi:10.5414/cpp39546. PMID 11770836.
- ^ VDI Product Data
Vitamins (A11)
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Fat soluble |
A |
- α-Carotene
- β-Carotene
- Retinol#
- Tretinoin
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D |
- D2
- Ergosterol
- Ergocalciferol#
- D3
- 7-Dehydrocholesterol
- Previtamin D3
- Cholecalciferol#
- 25-hydroxycholecalciferol
- Calcitriol (1,25-dihydroxycholecalciferol)
- Calcitroic acid
- D4
- D5
- D analogues
- Alfacalcidol
- Dihydrotachysterol
- Calcipotriol
- Tacalcitol
- Paricalcitol
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E |
- Tocopherol
- Tocotrienol
- Tocofersolan
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K |
- Naphthoquinone
- Phylloquinone (K1)
- Menaquinones (K2)
- Menadione (K3)‡
- Menadiol (K4)
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Water soluble |
B |
- B1
- B1 analogues
- Acefurtiamine
- Allithiamine
- Benfotiamine
- Fursultiamine
- Octotiamine
- Prosultiamine
- Sulbutiamine
- B2
- B3
- B5
- Pantothenic acid
- Dexpanthenol
- Pantethine
- B6
- Pyridoxine#, Pyridoxal phosphate
- Pyridoxamine
- Pyritinol
- B7
- B9
- Folic acid
- Dihydrofolic acid
- Folinic acid
- Levomefolic acid
- B12
- Adenosylcobalamin
- Cyanocobalamin
- Hydroxocobalamin
- Methylcobalamin
- Choline
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C |
- Ascorbic acid#
- Dehydroascorbic acid
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Combinations |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Nuclear receptor modulators
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AhR |
Agonists |
- Arachidonic acid metabolites (e.g., lipoxin A4, prostaglandin G2)
- Dietary carotenoids
- Flutamide
- Halogenated aromatic hydrocarbons (e.g., polychlorinated dibenzodioxins (e.g., TCDD), dibenzofurans, biphenyls)
- Modified low-density lipoproteins
- Polycyclic aromatic hydrocarbons (e.g., 3-methylcholanthrene, benzo[a]pyrene, benzanthracenes, benzoflavones (e.g., beta-naphthoflavone))
- Tetrapyroles (e.g., bilirubin)
- Tryptophan derivatives (e.g., indigo dye, indirubin)
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Antagonists |
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CAR |
Agonists |
- 6,7-Dimethylesculetin
- Amiodarone
- Artemisinin
- Benfuracarb
- Carbamazepine
- Carvedilol
- Chlorpromazine
- Chrysin
- CITCO
- Clotrimazole
- Cyclophosphamide
- Cypermethrin
- DHEA
- Efavirenz
- Ellagic acid
- Griseofulvin
- Methoxychlor
- Mifepristone
- Nefazodone
- Nevirapine
- Nicardipine
- Octicizer
- Permethrin
- Phenobarbital
- Phenytoin
- Pregnanedione (5β-dihydroprogesterone)
- Reserpine
- TCPOBOP
- Telmisartan
- Tolnaftate
- Troglitazone
- Valproic acid
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Antagonists |
- 3,17β-Estradiol
- 3α-Androstanol
- 3α-Androstenol
- 3β-Androstanol
- 17-Androstanol
- AITC
- Ethinylestradiol
- Meclizine
- Nigramide J
- Okadaic acid
- PK-11195
- S-07662
- T-0901317
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ERR |
ERRα
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Agonists |
- 6,3′,4′-Trihydroxyflavone
- Biochanin A
- Cholesterol
- Daidzein
- Genistein
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Antagonists |
- Diethylstilbestrol
- XCT-790
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ERRβ
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Agonists |
- DY-131 (GSK-9089)
- GSK-4716 (GW-4716)
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Antagonists |
- 4-Hydroxytamoxifen (afimoxifene)
- Diethylstilbestrol
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ERRγ
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Agonists |
- Bisphenol A
- DY-131 (GSK-9089)
- GSK-4716 (GW-4716)
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Antagonists |
- 4-Hydroxytamoxifen (afimoxifene)
- Diethylstilbestrol
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FXR |
Agonists |
- Bile acids
- Cafestol
- Chenodeoxycholic acid
- Fexaramine
- GW-4064
- Obeticholic acid
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Antagonists |
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LXR |
Agonists |
- 22R-Hydroxycholesterol
- 24S-Hydroxycholesterol
- 27-Hydroxycholesterol
- Cholestenoic acid
- DMHCA
- GW-3965
- Hypocholamide
- T-0901317
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Antagonists |
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PPAR |
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PXR |
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RAR |
Agonists |
- 9CDHRA
- 9-cis-Retinoic acid (alitretinoin)
- AC-261066
- AC-55649
- Acitretin
- Adapalene
- all-trans-Retinoic acid (tretinoin)
- AM-580
- BMS-493
- BMS-753
- BMS-961
- CD-1530
- CD-2314
- CD-437
- Ch-55
- EC 23
- Etretinate
- Fenretinide
- Isotretinoin
- Palovarotene
- Retinoic acid
- Retinol (vitamin A)
- Tamibarotene
- Tazarotene
- Tazarotenic acid
- TTNPB
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Antagonists |
- BMS-195614
- BMS-493
- CD-2665
- ER-50891
- LE-135
- MM-11253
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Others |
- Retinoic acid metabolism inhibitors: Liarozole
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RXR |
Agonists |
- 9CDHRA
- 9-cis-Retinoic acid (alitretinoin)
- all-trans-Retinoic acid (tretinoin)
- Bexarotene
- CD 3254
- Docosahexaenoic acid
- Fluorobexarotene
- Isotretinoin
- LG-100268
- LG-101506
- LG-100754
- Retinoic acid
- Retinol (vitamin A)
- SR-11237
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Antagonists |
- HX-531
- HX-630
- LG-100754
- PA-452
- UVI-3003
- HX-603
- LE135 (RAR beta selective)
- LE-540
- CD3254
- PA-451
- PA-452
- Rhein
- HX-711
- 6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic acid
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SHR |
AR
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See here instead.
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ER
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See here instead.
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PR
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See here instead.
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GR
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See here instead.
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MR
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See here instead.
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VDR
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Agonists |
- 7-Dehydrocholesterol
- 22-Oxacalcitriol
- 25-Hydroxyergocalciferol
- Alfacalcidol
- Calcifediol
- Calciferol
- Calcipotriol
- Calcitriol
- Cholecalciferol (vitamin D3)
- Dihydrotachysterol
- Doxercalciferol
- EB-1089
- Eldecalcitol
- Ercalcidiol
- Ercalcitriol
- Ergocalciferol (vitamin D2)
- Lithocholic acid
- Paricalcitol
- Tacalcitol
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THR |
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See also: Receptor/signaling modulators
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UpToDate Contents
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English Journal
- Bone effects of vitamin D - Discrepancies between in vivo and in vitro studies.
- Suda T, Takahashi F, Takahashi N.SourceResearch Center for Genomic Medicine, Saitama Medical University, Saitama 350-1241, Japan.
- Archives of biochemistry and biophysics.Arch Biochem Biophys.2012 Jul 1;523(1):22-9. Epub 2011 Nov 15.
- Vitamin D was discovered as an anti-rachitic agent, but even at present, there is no direct evidence to support the concept that vitamin D directly stimulates osteoblastic bone formation and mineralization. It appears to be paradoxical, but vitamin D functions in the process of osteoclastic bone res
- PMID 22107950
- Successful treatment of osteomalacia caused by renal tubular acidosis associated with Sjögren's syndrome.
- Yamamoto S, Okada Y, Mori H, Hirata S, Saito K, Inokuchi N, Tanaka Y.SourceThe First Department of Internal Medicine, School of Medicine, University of Occupational and Environmental Health, Japan, 1-1 Iseigaoka, Yahatanishi-ku, Kitakyushu, 807-8555, Japan.
- Modern rheumatology / the Japan Rheumatism Association.Mod Rheumatol.2012 Jun 28. [Epub ahead of print]
- A 62-year-old woman was diagnosed with severe osteomalacia caused by renal tubular acidosis associated with Sjögren's syndrome. She was treated with sodium bicarbonate, risedronate, alfacalcidol, and prednisolone (1 mg/kg). By 24 months, renal tubular acidosis was improved and the bone density ha
- PMID 22740247
Japanese Journal
- Effect of eldecalcitol, an active vitamin D analog, on hip structure and biomechanical properties: 3D assessment by clinical CT.
- Ito Masako,Nakamura Toshitaka,Fukunaga Masao,Shiraki Masataka,Matsumoto Toshio
- Bone 49(3), 328-334, 2011-09
- … The subjects - a subgroup of a recent randomized, double-blind study comparing anti-fracture efficacy of ELD with alfacalcidol (ALF) - constituted 193 ambulatory patients with osteoporosis (189 postmenopausal women and 4 men aged 52-85years, average±SD: 70.9±6.92years) enrolled at 11 institutions. …
- NAID 120003220727
- Effects of alfacalcidol on circulating cytokines and growth factors in rat skeletal muscle
- Testerink Janwillem,Jaspers Richard T.,Rittweger Jorn [他]
- The journal of physiological sciences 61(6), 525-535, 2011-11
- NAID 40019052981
Related Links
- アルファカルシドール(Alfacalcidol)の検索ならお薬検索QLife(キューライフ)。お医者さんが処方する処方薬と、薬局で買える市販薬(OTC)、の効果と副作用、写真、添付文書、保管方法等を掲載。商品名だけでなく一般名や剤形、色など ...
- Vitamin D is important for healthy, strong bones. Alfacalcidol is a type of vitamin D. A mild lack of vitamin D may not cause any symptoms, but can cause... ... If you experience any other symptoms which you think may be due to ...
Related Pictures
![of calcitriol, its precursor alfacalcidol](https://1mg.info/0/8/h/0649.jpg)
![Alpha D3 (Alfacalcidol) - 0.25mcg (30](https://1mg.info/0/8/h/0650.jpg)
![Alfacalcidol Alfacalcidol 1mcg Caps 30](https://1mg.info/0/8/h/0651.jpg)
![Alfacalcidol.png](https://1mg.info/0/8/h/0652.jpg)
![Alfacalcidol Medice ist ein](https://1mg.info/0/8/h/0653.jpg)
★リンクテーブル★
[★]
- 英
- alfacalcidol
- 同
- 1-ヒドロキシコレカルシフェロール、1α-ヒドロキシコレカルシフェロール 1α-hydroxy cholecalciferol
- 商
- アルカドール、アルシオドール、アルファスリー、アルファロール、アロートール、エルシボン、カルシタミン、カルフィーナ、コバルファ、ディーアルファ、トヨファロール、ビタミロアルファ、プラチビット、ポロセーブ、リモデリン、ワークミン、ワンアルファ
- 関
- ビタミンD。ビタミンA及びD剤
参考文献
- アルファロールカプセル0.25μg/アルファロールカプセル0.5μg/アルファロールカプセル1μg
- http://www.info.pmda.go.jp/go/pack/3112001M1046_1_08/3112001M1046_1_08?view=body
[★]
1-ヒドロキシコレカルシフェロール
- 関
- alfacalcidol