カルシポトリエン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/07 03:14:18」(JST)
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Calcipotriol
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| Systematic (IUPAC) name |
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(1R,3S,5E)-5-{2-[(1R,3aS,4Z,7aR)-1-[(2R,3E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohyytyexane-1,3-diol
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| Clinical data |
| Trade names |
Daivobex, Dovobex, Sorilux |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a608018 |
Pregnancy
category |
- AU: B3
- US: C (Risk not ruled out)
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| Legal status |
- AU: Prescription Only (S4)
- CA: ℞-only
- UK: Prescription-only (POM)
- US: ℞-only
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Routes of
administration |
Topical |
| Pharmacokinetic data |
| Bioavailability |
5 to 6% |
| Metabolism |
Hepatic |
| Excretion |
Biliary |
| Identifiers |
| CAS Registry Number |
112965-21-6 Y |
| ATC code |
D05AX02 |
| PubChem |
CID: 5288783 |
| IUPHAR/BPS |
2778 |
| DrugBank |
DB02300 Y |
| ChemSpider |
4450880 Y |
| UNII |
143NQ3779B Y |
| KEGG |
D01125 Y |
| ChEBI |
CHEBI:50749 Y |
| ChEMBL |
CHEMBL100918 N |
| Chemical data |
| Formula |
C27H40O3 |
| Molecular mass |
412.605 g/mol |
SMILES
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O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]4([C@H]2CC[C@@H]4[C@@H](/C=C/[C@@H](O)C3CC3)C)C
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InChI
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InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1 Y
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Key:LWQQLNNNIPYSNX-UROSTWAQSA-N Y
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| N (what is this?) (verify) |
Calcipotriol (INN) or calcipotriene (USAN) is a synthetic derivative of calcitriol, a form of vitamin D. It is used in the treatment of psoriasis, marketed under the trade name "Dovonex" in the United States, "Daivonex" outside of North America, and "Psorcutan" in Germany. This medication is safe for long-term application in psoriatic skin conditions.
Contents
- 1 Medical uses
- 2 Adverse effects
- 2.1 Contraindications
- 2.2 Interactions
- 3 Mechanism
- 4 References
- 5 External links
Medical uses
Chronic plaque psoriasis is the chief medical use of calcipotriol.[1] It has also been used successfully in the treatment of alopecia areata.[2]
Adverse effects
Adverse effects by frequency:[1][3][4][5]
- Very common (> 10% frequency)
- Burning
- Itchiness
- Skin irritation
- Common (1–10% frequency)
- Dermatitis
- Dry skin
- Erythema
- Peeling
- Worsening of psoriasis including facial/scalp
- Rash
- Uncommon (0.1–1% frequency)
- Exacerbation of psoriasis
- Rare (< 0.1% frequency)
- Allergic contact dermatitis
- Hypercalcaemia
- Photosensitivity
- Changes in pigmentation
- Skin atrophy
Contraindications
Hypersensitivity, use on face, hypercalcaemia, or evidence of vitamin D toxicity are the only contraindications for calcipotriol use.[3]
Cautions include exposure to excessive natural or artificial light, due to the potential for calcipotriol to cause photosensitivity.[3]
Interactions
No drug interactions are known.[3]
Mechanism
The efficacy of calcipotriol in the treatment of psoriasis was first noticed by the observation of patients receiving various forms of vitamin D in an osteoporosis study. Unexpectedly, some patients who also suffered from psoriasis experienced dramatic reductions in lesion counts.[6]
The precise mechanism of calcipotriol in remitting psoriasis is not well understood. However, it has been shown to have comparable affinity with calcitriol for the vitamin D receptor (VDR), while being less than 1% as active as the calcitriol in regulating calcium metabolism. The vitamin D receptor belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kidney, and T cells of the immune system. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.
References
- ^ a b Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3.
- ^ Kim, D. H.; Lee, J. W.; Kim, I. S.; Choi, S. Y.; Lim, Y. Y.; Kim, H. M.; Kim, B. J.; Kim, M. N. (2012). "Successful Treatment of Alopecia Areata with Topical Calcipotriol". Annals of Dermatology 24 (3): 341–344. doi:10.5021/ad.2012.24.3.341. PMC 3412244. PMID 22879719. edit
- ^ a b c d "Dovonex, Calcitrene Ointment (calcipotriene) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 26 January 2014.
- ^ "CALCIPOTRIENE (calcipotriene) solution [E. FOUGERA & CO. A division of Fougera Pharmaceuticals Inc.]". DailyMed. E. FOUGERA & CO. A division of Fougera Pharmaceuticals Inc. May 2012. Retrieved 26 January 2014.
- ^ "PRODUCT INFORMATION DAIVONEX® CREAM Calcipotriol 50 microgram/g" (PDF). TGA eBusiness Services. LEO Pharma Pty Ltd. 28 April 2011. Retrieved 26 January 2014.
- ^ Morimoto, S., Kumahara, Y. A patient with psoriasis cured by 1-α-hydroxyvitamin D3. Med. J. Osaka Univ., 1985, 35:51–54
External links
- Leo Pharmaceuticals Product Monograph- Detailed information from the manufacturers, includes the blood testing recommendation (.pdf document).
- Calcipotriene information - U.S. NLM/NIH
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Drugs used for psoriasis (D05)
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| Topical |
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Tars
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Antracens
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Psoralens
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Other
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- Fumaric acid
- vitamin D (Calcipotriol
- Calcipotriol/betamethasone
- Calcitriol
- Tacalcitol)
- Tazarotene
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| Systemic |
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Psoralens
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- Trioxysalen
- Methoxsalen
- Bergapten
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Retinoids
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of skin
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|
| Description |
- Anatomy
- Physiology
- Development
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|
| Disease |
- Infections
- Vesiculobullous
- Dermatitis and eczema
- Papulosquamous
- Urticaria and erythema
- Radiation-related
- Pigmentation
- Mucinoses
- Keratosis, ulcer, atrophy, and necrobiosis
- Vasculitis
- Fat
- Neutrophilic and eosinophilic
- Congenital
- Neoplasms and cancer
- nevi and melanomas
- epidermis
- dermis
- Symptoms and signs
- Terminology
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| Treatment |
- Procedures
- Drugs
- antibiotics
- disinfectants
- emollients and protectives
- itch
- psoriasis
- other
- Wound and ulcer
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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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|
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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
- Cyanocobalamin
- Hydroxocobalamin
- Methylcobalamin
- Cobamamide
- 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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Index of nutrition
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| Description |
- Vitamins
- Cofactors
- Metal metabolism
- Fats
- metabolism
- intermediates
- lipoproteins
- Sugars
- Glycolysis
- Glycogenesis and glycogenolysis
- Fructose and galactose
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|
| Disease |
- Vitamins
- Carbohydrate
- Lipid
- Metals
- Other
- Symptoms and signs
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|
| Treatment |
- Drugs
- Vitamins
- Mineral supplements
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UpToDate Contents
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English Journal
- An Applicator Delivery System for Fixed-Combination Calcipotriene Plus Betamethasone Dipropionate Topical Suspension (Gel): Innovating Psoriasis Vulgaris Treatment Through Patient Collaboration.
- Rasmussen G1, Bech LL2, Nielsen TW2.
- Dermatology and therapy.Dermatol Ther (Heidelb).2015 Dec;5(4):235-246. Epub 2015 Nov 5.
- Treatment non-adherence is a complex problem encountered in all therapy areas, particularly in chronic diseases such as psoriasis vulgaris. To address adherence issues, focus is turning towards developing interventions tailored to individual patient needs. Topical therapies remain the mainstay of ps
- PMID 26541164
- Efficacy and Safety of Calcipotriene Plus Betamethasone Dipropionate Aerosol Foam in Patients With Psoriasis Vulgaris - a Randomized Phase III Study (PSO-FAST).
- Leonardi C, Bagel J, Yamauchi P, Pariser D, Xu Z, Olesen M, Osterdal ML, Stein Gold L.
- Journal of drugs in dermatology : JDD.J Drugs Dermatol.2015 Dec 1;14(12):1468-77.
- INTRODUCTION: An innovative aerosol foam formulation of calcipotriene 0.005% (Cal) plus betamethasone dipropionate 0.064% (BD) designed to improve treatment outcomes.<br/>OBJECTIVE: To compare the efficacy and safety of Cal/BD aerosol foam with aerosol foam vehicle in patients with psoriasis.&
- PMID 26659941
- Transient reactive papulotranslucent acrokeratoderma: a report of 3 cases showing excellent response to topical calcipotriene.
- Durmaz EÖ1, Sezer E1, Şahin S1, Ekici ID2, Özkan F2.
- Cutis.Cutis.2015 Nov;96(5):E13-6.
- PMID 26682562
Japanese Journal
- Calcipotriene and corticosteroid combination therapy for vitiligo
- Topical calcipotriene and narrowband ultraviolet B in the treatment of vitiligo
- KULLAVANIJAYA P
- Photodermatol Photoimmunol Photomed 20, 248-251, 2004
- NAID 30005153164
Related Links
- Consumer information about the medication CALCIPOTRIENE - TOPICAL ( Dovonex, Sorilux), includes side effects, drug interactions, recommended dosages, and storage information. Read more about the prescription drug CALCIPOTRIENE ...
- Calcipotriol (INN) or calcipotriene (USAN) is a synthetic derivative of calcitriol or vitamin D. It is used in the treatment of psoriasis, marketed under the trade name "Dovonex" in the United States, "Daivonex" outside of North America, and ...
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