Calcipotriol
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MedKoo CAT#: 326717

CAS#: 112965-21-6

Description: Calcipotriol, a synthetic derivative of calcitriol or Vitamin D, is used in the treatment of psoriasis and marketed under the trade name Dovonex. It has comparable affinity with calcitriol (Vit. D) for the Vitamin D receptor (VDR), while being less than 1% as active as the calcitriol in regulating calcium metabolism. Chronic plaque psoriasis is the chief medical use of calcipotriol. It has also been used successfully in the treatment of alopecia areata.

Chemical Structure

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Calcipotriol
CAS# 112965-21-6
Instruction

Theoretical Analysis

MedKoo Cat#: 326717
Name: Calcipotriol
CAS#: 112965-21-6
Chemical Formula: C27H40O3
Exact Mass: 412.30
Molecular Weight: 412.614
Elemental Analysis: C, 78.60; H, 9.77; O, 11.63

Price and Availability

Size Price Availability Quantity
10mg USD 290
50mg USD 1400
100mg USD 2350
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Synonym: Calcipotriene; calcipotriol; Calciptriol; Calcitrene; CCRIS 7700; Daivonex; Dovonex; MC 903; PRI 2201; Psorcutan; Sorilux.

IUPAC/Chemical Name: (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol

InChi Key: LWQQLNNNIPYSNX-JQWURIRRSA-N

InChi Code: 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

SMILES Code: C[C@H](/C=C/[C@H](C1CC1)O)[C@H]([C@]2(CCC/3)C)CC[C@@]2([H])C3=C\C=C4C[C@H](O)C[C@@H](O)C\4=C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 412.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Queille-Roussel C, Bang B, Clonier F, Lacour JP. Enhanced vasoconstrictor potency of the fixed combination calcipotriol plus betamethasone dipropionate in an innovative aerosol foam formulation vs. other corticosteroid psoriasis treatments. J Eur Acad Dermatol Venereol. 2016 Jun 15. doi: 10.1111/jdv.13714. [Epub ahead of print] PubMed PMID: 27306589.

2: Kontochristopoulos G, Kouris A, Chantzaras A, Petridis A, Yfantopoulos J. Improvement of health-related quality of life and adherence to treatment with calcipotriol-betamethasone dipropionate gel in patients with psoriasis vulgaris. An Bras Dermatol. 2016 Apr;91(2):160-6. doi: 10.1590/abd1806-4841.20164476. PubMed PMID: 27192514; PubMed Central PMCID: PMC4861562.

3: Tan ES, Oon HH. Effective treatment of severe nail psoriasis using topical calcipotriol with betamethasone dipropionate gel. Indian J Dermatol Venereol Leprol. 2016 May-Jun;82(3):345-7. doi: 10.4103/0378-6323.174389. PubMed PMID: 27088952.

4: Tarikci N, Göncü EK, Yüksel T, Singer R, Topal İO, Şahin İM. Progressive symmetrical erythrokeratoderma on the face: A rare condition and successful treatment with calcipotriol. JAAD Case Rep. 2016 Feb 4;2(1):70-1. doi: 10.1016/j.jdcr.2015.11.010. eCollection 2016 Jan. PubMed PMID: 27051833; PubMed Central PMCID: PMC4809449.

5: Yan R, Jiang S, Wu Y, Gao XH, Chen HD. Topical calcipotriol/betamethasone dipropionate for psoriasis vulgaris: A systematic review. Indian J Dermatol Venereol Leprol. 2016 Mar-Apr;82(2):135-44. doi: 10.4103/0378-6323.175919. PubMed PMID: 26924402.

6: Tang YJ, Zhang RZ, Liu XM, Xu CX, Cheng S, Liu QI. Effect of the topical application of calcipotriol on the expression levels of zinc finger protein A20 and nuclear factor-κB in the skin lesions of patients with psoriasis vulgaris. Exp Ther Med. 2016 Jan;11(1):247-250. Epub 2015 Nov 24. PubMed PMID: 26889249; PubMed Central PMCID: PMC4726906.

7: Liu X, Liu Y, Xu M, Li J, Teng X, Cheng H, Xia Y. Zinc finger protein A20 is involved in the anti-psoriatic effect of calcipotriol. Br J Dermatol. 2016 Feb 15. doi: 10.1111/bjd.14481. [Epub ahead of print] PubMed PMID: 26875609.

8: Yan R, Jiang S, Wu Y, Gao XH, Chen HD. Topical calcipotriol/betamethasone dipropionate for psoriasis vulgaris: A systematic review. Indian J Dermatol Venereol Leprol. 2016 Feb 8. doi: 10.4103/0378-6323.175919. [Epub ahead of print] PubMed PMID: 26858069.

9: Tan ES, Oon HH. Effective treatment of severe nail psoriasis using topical calcipotriol with betamethasone dipropionate gel. Indian J Dermatol Venereol Leprol. 2016 Feb 9. doi: 10.4103/0378-6323.174389. [Epub ahead of print] PubMed PMID: 26858046.

10: Lovato P, Norsgaard H, Tokura Y, Røpke MA. Calcipotriol and betamethasone dipropionate exert additive inhibitory effects on the cytokine expression of inflammatory dendritic cell-Th17 cell axis in psoriasis. J Dermatol Sci. 2016 Mar;81(3):153-64. doi: 10.1016/j.jdermsci.2015.12.009. Epub 2015 Dec 23. PubMed PMID: 26794805.

11: Golusin Z, Jovanović M, Magda N, Stojanović S, Matić M, Petrović A. Effects of Rusanda Spa balneotherapy combined with calcipotriol on plaque psoriasis. Vojnosanit Pregl. 2015 Nov;72(11):1010-7. PubMed PMID: 26731976.

12: Bay C, Togsverd-Bo K, Lerche CM, Haedersdal M. Skin tumor development after UV irradiation and photodynamic therapy is unaffected by short-term pretreatment with 5-fluorouracil, imiquimod and calcipotriol. An experimental hairless mouse study. J Photochem Photobiol B. 2016 Jan;154:34-9. doi: 10.1016/j.jphotobiol.2015.11.009. Epub 2015 Nov 30. PubMed PMID: 26678673.

13: Yang M, Chang JM. Successful treatment of refractory chronic hand eczema with calcipotriol/betamethasone ointment: A report of three cases. Exp Ther Med. 2015 Nov;10(5):1943-1946. Epub 2015 Sep 4. PubMed PMID: 26640577; PubMed Central PMCID: PMC4665367.

14: Gual A, Pau-Charles I, Molin S. Topical treatment for scalp psoriasis: Comparison of patient preference, quality of life and efficacy for non-alcoholic mometasone emulsion versus calcipotriol/betamethasone gel in daily clinical practice. J Dermatolog Treat. 2016 Jun;27(3):228-34. doi: 10.3109/09546634.2015.1093590. Epub 2015 Oct 27. PubMed PMID: 26503824.

15: Ito K, Koga M, Shibayama Y, Tatematsu S, Nakayama J, Imafuku S. Proactive treatment with calcipotriol reduces recurrence of plaque psoriasis. J Dermatol. 2016 Apr;43(4):402-5. doi: 10.1111/1346-8138.13158. Epub 2015 Oct 5. PubMed PMID: 26434738.

16: Lambert J, Hol CW, Vink J. Real-life effectiveness of once-daily calcipotriol and betamethasone dipropionate gel vs. ointment formulations in psoriasis vulgaris: final analysis of the 52-week PRO-long study. J Eur Acad Dermatol Venereol. 2015 Dec;29(12):2349-55. doi: 10.1111/jdv.13230. Epub 2015 Sep 3. PubMed PMID: 26337069.

17: Park JM, Cho HH, Kim WJ, Mun JH, Song M, Kim HS, Ko HC, Kim BS, Kim MB. Efficacy and Safety of Calcipotriol/Betamethasone Dipropionate Ointment for the Treatment of Trachyonychia: An Open-Label Study. Ann Dermatol. 2015 Aug;27(4):371-5. doi: 10.5021/ad.2015.27.4.371. Epub 2015 Jul 29. PubMed PMID: 26273150; PubMed Central PMCID: PMC4530144.

18: Taraska V, Tuppal R, Olesen M, Bang Pedersen C, Papp K. A Novel Aerosol Foam Formulation of Calcipotriol and Betamethasone Has No Impact on HPA Axis and Calcium Homeostasis in Patients With Extensive Psoriasis Vulgaris. J Cutan Med Surg. 2016 Jan;20(1):44-51. doi: 10.1177/1203475415597094. Epub 2015 Jul 29. PubMed PMID: 26224733; PubMed Central PMCID: PMC4708614.

19: Arensman MD, Nguyen P, Kershaw KM, Lay AR, Ostertag-Hill CA, Sherman MH, Downes M, Liddle C, Evans RM, Dawson DW. Calcipotriol Targets LRP6 to Inhibit Wnt Signaling in Pancreatic Cancer. Mol Cancer Res. 2015 Nov;13(11):1509-19. doi: 10.1158/1541-7786.MCR-15-0204. Epub 2015 Jul 29. PubMed PMID: 26224368; PubMed Central PMCID: PMC4644680.

20: Zhao Y, Chen X, Li J, He Y, Su J, Chen M, Zhang W, Chen W, Zhu W. VDR gene polymorphisms are associated with the clinical response to calcipotriol in psoriatic patients. J Dermatol Sci. 2015 Sep;79(3):305-7. doi: 10.1016/j.jdermsci.2015.06.014. Epub 2015 Jul 7. PubMed PMID: 26169344.