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Calcipotriene

Calcipotriene Structure
Calcipotriene structure
CAS No.
112965-21-6
Chemical Name:
Calcipotriene
Synonyms
Calcipotriol anhydrous;mc903;dovonex;Daivobet;Calcipotriol hydrate;Daivonex;cipotriene;Calciptriol;Calcipotriene;Calcipotriene-d4
CBNumber:
CB4412713
Molecular Formula:
C27H40O3
Molecular Weight:
412.6
MDL Number:
MFCD00866630
MOL File:
112965-21-6.mol
MSDS File:
SDS
Last updated:2024-11-20 11:41:24
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Calcipotriene Properties

Melting point 166-168°C
Boiling point 582.0±50.0 °C(Predicted)
Density 1.12±0.1 g/cm3(Predicted)
storage temp. Desiccate at -20°C
solubility DMSO: soluble15mg/mL, clear
form powder
pka 14.29±0.20(Predicted)
color White to off-white
Stability Light and Temperature Sensitive, Light And Temperature Sensitive
InChIKey LWQQLNNNIPYSNX-HCHVWAPNSA-N
SMILES [C@@H]1(O)C/C(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)/C=C/[C@H](C2CC2)O)/C(=C)[C@@H](O)C1
CAS DataBase Reference 112965-21-6(CAS DataBase Reference)
FDA UNII 143NQ3779B
NCI Drug Dictionary Dovonex

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P264-P270-P301+P310-P405-P501
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26
RIDADR  UN 2811 6.1 / PGIII
WGK Germany  3
HS Code  2906195000
Toxicity dog,LD50,skin,> 1500ug/kg (1.5mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)MUSCULOSKELETAL: OTHER CHANGESGASTROINTESTINAL: NAUSEA OR VOMITING,Journal of Toxicological Sciences. Vol. 21(Suppl,

Calcipotriene price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C4369 Calcipotriol hydrate ≥98% (HPLC) 112965-21-6 10mg $239 2024-03-01 Buy
Sigma-Aldrich 1086141 Calcipotriol hydrate 112965-21-6 200mg $2750 2024-03-01 Buy
Sigma-Aldrich C4369 Calcipotriol hydrate ≥98% (HPLC) 112965-21-6 50mg $909 2024-03-01 Buy
TRC C144200 Calcipotriene 112965-21-6 2mg $85 2021-12-16 Buy
ChemScene CS-0387 Calcipotriol 99.77% 112965-21-6 10mg $84 2021-12-16 Buy
Product number Packaging Price Buy
C4369 10mg $239 Buy
1086141 200mg $2750 Buy
C4369 50mg $909 Buy
C144200 2mg $85 Buy
CS-0387 10mg $84 Buy

Calcipotriene Chemical Properties,Uses,Production

Description

Calcipotriene also known as Calcipotriol, is a topical vitaminD3 derivative effective in the treatment of psoriasis vulgaris. The drug acts by binding to vitamin D3 receptors in the skin keratinocytes, producing an elevation in cell differentiation and a reduction in cell proliferation. Although its efficacy is comparable to calcitriol, calcipotriol exhibits at least 100 times less effect on calcium metabolism in rats.

Chemical Properties

White Crystalline Solid

Originator

Leo Denmark (Denmark)

Uses

Calcipotriene is an antipsoriatic that is a vitamin D3 analogue with low calcemic activity. It works by regulating the production and growth of skin cells. In the United States, this drug was first marketed under the trade name Dovonex and is used mainly for the treatment of psoriasis. It is one of the most effective non glucocorticoid topical drugs for the treatment of localized psoriasis.This drug has many off-label applications that are alternative therapies for many dermatologic diseases.

Preparation

A convergent approach for the total synthesis of calcipotriol (brand name: Dovonex), a proven Vitamin D analog used for the treatment of psoriasis, and medicinally relevant synthetic analogs is described.
A Synthesis of calcipotriol via a Key Electroreductive Cross-coupling Approach
A Synthesis of calcipotriol via a Key Electroreductive Cross-coupling Approach
Calcipotriol is currently the most successful VitD analog and is prescribed for the treatment of psoriasis, an autoimmune skin disease.

Definition

ChEBI: Calcipotriol is a seco-cholestane that is 26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene carrying additional hydroxy substituents at positions 1, 3 and 24. It is used (as its hydrate) in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients. It has a role as a drug allergen and an antipsoriatic. It is a member of cyclopropanes, a secondary alcohol, a triol, a hydroxy seco-steroid and a seco-cholestane.

Indications

Calcipotriene (Dovonex), a synthetic vitamin D3 derivative, is indicated for the treatment of moderate plaque psoriasis. Its mechanism of action is unknown, although it competes for calcitriol receptors on keratinocytes and normalizes differentiation. It also has a variety of immunomodulatory effects in the skin. Although the drug can cause local irritation, the most serious toxicities are hypercalciuria and hypercalcemia, which are usually reversible.

Manufacturing Process

(1S,3R)-Bis-(t-butyldimethylsilyloxy)-(20S)-formyl-9,10-secopregna(5E,7E,10 (19))triene (Calverley Tetrahedron 43.4609 (1967) and (cyclopropyl)(tri-phenylphoshoranylidene)ketone are stirred in dimethyl sulfoxide under nitrogen. The reaction mixture is then diluted at room temperature with ethyl acetate and washed with common salt solution. The organic phase is dried on sodium sulfate and filtered. After removal of the solvent, the residue is filtered with toluene through silica gel. Evaporation of the solvent and gradient chromatography (toluene/hexane (1:1)-toluene) of the residue on silica gel yield (5E,7E,22E),(1S,3R)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-one.
(5E,7E,22E),(1S,3R)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-9,10- secochola-5,7,10(19),22-tetraene-24-one in tetrahydrofuran and methanol are mixed with a 0.4 M methanol CeCl3·7H2O solution. Sodium borohydride is added by portions under nitrogen with ice cooling. The suspension is stirred with ice cooling and then put into ice/common salt solution. The aqueous phase is extracted with ethyl acetate, the organic phase is washed neutral with water and dried on sodium sulfate. Filtration and removal of the solvent yield oil. By chromatography on silica gel with ethyl acetate/hexane (1:9). The (5E,7E,22E),(1S,3R,24S)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-ol is obtained.
(5E,7E,22E),(1S,3R,24S)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-ol is dissolved in toluene and after addition of anthracene and 1 drop of triethylamine it is radiated at room temperature with a high pressure mercury vapor lamp (Heraeus TQ 150) through Pyrex glass. The reaction mixture is concentrated by evaporation and the residue a mixture of (5Z,7E,22E),(1S,3R,24S)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene- 24-ol and anthracene - is directly reacted with tetrabutylammonium fluoride.
(5Z,7E,22E),(1S,3R,24S)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl- 9,10-secochola-5,7,10(19),22-tetraene-24-ol in tetrahydrofuran is kept with a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran under nitrogen. For working up, the cooled reaction mixture is poured into cold sodium bicarbonate solution and then extracted with ethyl acetate. After drying of the organic phase on sodium sulfate, filtration and evaporation of the solvent yields a resin-like residue. Chromatography on silica gel with ethyl acetate/hexane (2:1) yields (5Z,7E,22E),(1S,3R,24S)-24-cyclopropyl-9,10- secochola-5,7,10(19),22-tetraene-1,3,24-triol.

brand name

Dovonex (Leo);Daivonex.

Therapeutic Function

Antipsoriatic

Biological Activity

Vitamin D 3 analog that displays minimal effects on calcium homeostasis. Regulates cell differentiation and proliferation; exhibits antiproliferative activity against human HL-60, HL60/MX2, MCF-7, T47D, SCC-25 and mouse WEHI-3 cancer cell lines.

Biochem/physiol Actions

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. VDR belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. Binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation-related genes.

Pharmacology

Calcipotriene (Dovonex) enhances the effectiveness of ultraviolet B (UVB) but also increases photosensitivity in UVB-treated patients. Ultraviolet light, 6% salicylic acid, 12% lactic acid, hydrocortisone valerate 0.2% ointment, and tazarotene (Tazorac) gel degrade calcipotriene (Dovonex). Halobetasol ointment and 5% tar gel are compatible with Calcipotriene (Dovonex). A British study found calcipotriene (Dovonex) to be safe and effective in a pediatric population over the age of 3, although it is not approved by the FDA.

Side effects

Possible side effects include:
severe burning, stinging, skin rash, or other irritation after applying the medicine;
worsening of your skin condition;
high calcium levels--confusion, tiredness, nausea, vomiting, loss of appetite, constipation, increased thirst or urination, weight loss;
mild skin irritation;
skin rash;
itching.

storage

Store at -20°C

Calcipotriene synthesis

113082-99-8
112965-21-6
Synthesis of Calcipotriene from (5E)-Calcipotriene

Calcipotriene Preparation Products And Raw materials

Raw materials

Liquid sulfur dioxide tert-Butyldimethylsilyl chloride 4-METHYLMORPHOLINE-4-OXIDE SOLUTION Selenium dioxide Tetrabutylammonium fluoride
Anthracene Cyclopropylmagnesium bromide Triethylamine Sodium borohydride CERIUM(III) CHLORIDE
PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)] (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol (5E)-Calcipotriene

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Preparation Products

24R-Calcipotriol

Calcipotriene Suppliers

Global( 286)Suppliers
Supplier Tel Email Country ProdList Advantage
Joyochem Co.,Ltd
+86-0531-82687558 +8613290333633 sales@joyochem.com China 31 58
HangZhou RunYan Pharma Technology Co.,LTD.
+8618882027439 sales2@runyanpharma.com China 302 58
ChemExpress
+86-021-58950125 +86-021-58950125; info@chemexpress.com China 737 58
Capot Chemical Co.,Ltd. 		+86-（0）57185586718 +86-13336195806 sales@capot.com China 29791 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Nanjing Finetech Chemical Co., Ltd. 		025-85710122 17714198479 sales@fine-chemtech.com CHINA 885 55
career henan chemical co 		+86-0371-86658258 +8613203830695 sales@coreychem.com China 29881 58
Xiamen AmoyChem Co., Ltd 		+86-86-5926051114 +8618959220845 sales@amoychem.com China 6383 58
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd 		+86-023-6139-8061 +86-86-13650506873 sales@chemdad.com China 39894 58
Supplier Advantage
Joyochem Co.,Ltd
58
HangZhou RunYan Pharma Technology Co.,LTD.
58
ChemExpress
58
Capot Chemical Co.,Ltd. 		60
Henan Tianfu Chemical Co.,Ltd. 		55
Nanjing Finetech Chemical Co., Ltd. 		55
career henan chemical co 		58
Xiamen AmoyChem Co., Ltd 		58
BOC Sciences 		58
Chongqing Chemdad Co., Ltd 		58

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View Lastest Price from Calcipotriene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Calcipotriene/Calcipotriol pictures 2024-11-27 Calcipotriene/Calcipotriol
112965-21-6
 US $0.00-0.00 / g 1g 95.5.0%min. HPLC 1000kg HangZhou RunYan Pharma Technology Co.,LTD.
Calcipotriene pictures 2024-11-27 Calcipotriene
112965-21-6
 US $0.00 / KG 1KG 98%min 30tons/month WUHAN FORTUNA CHEMICAL CO., LTD
Calcipotriol pictures 2024-11-19 Calcipotriol
112965-21-6
 US $52.00-133.00 / mg 99.07% 10g TargetMol Chemicals Inc.
  • Calcipotriene pictures
  • Calcipotriene
    112965-21-6
  • US $0.00 / KG
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Calcipotriol pictures
  • Calcipotriol
    112965-21-6
  • US $52.00-133.00 / mg
  • 99.07%
  • TargetMol Chemicals Inc.

Calcipotriene Spectrum

Calcipotriene(112965-21-6)MS

112965-21-6(Calcipotriene)Related Search:

Tetrapropylammonium hydroxide Allyl glycidyl ether Allyl chloride Propylthiouracil Cocamidopropyl betaine
CHLOROPHOSPHONAZO III Allyl bromide N,N-Diisopropylethylamine (2E,4R)-4-[(1R,3aS,4E,7aR)-4-[(2E)-2-[(3S,5R)-3,5-Bis[[(tert-butyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethylidene]octahydro-7a-methyl-1H-inden-1-yl]-1-cyclopropyl-2-penten-1-one Carboplatin
(5Z,7E,22E)-9,10-Seco-26,27-cyclo-1α,3β-dihydroxycholesta-5,7,10(19),22-tetren-24-one CALCIPOTRIOL MONOHYDRATE (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol Calcipotriene Calcipotriene

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5z,7e,22e,24s)--bet 9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol,24-cyclopropyl-,(1-alpha,3 CALCIPOTRIOL,CALCIPOTRIENE Calciptriol, MC-903, Daivonex, Dovonex, Psorcutan (1S,3S,5Z)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(E,2S)-5-Cyclopropyl-5-hydroxy-pent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol Calcipotriene CALCIPOTRIOL - EP 24-CYCLOPROPYL-(1ALPHA,3BETA,5Z,7E,22E,24S)-9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1,3,24-TRIOL 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1-alpha,3-beta,5Z,7E,22E,24S) (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetrene-1α,3β,24-triol 1α,24(OH)2-22-Ene-24-cyclopropyl-D3 Calcipotriol hydrate, Calcipotriene 1,3-Cyclohexanediol, 5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-, (1R,3S,5Z)- Calcipotriene-d4 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1α,3β,5Z,7E,22E,24S)- Calciptriol Daivonex calcipotriol anhydre ep5.3 (1α，3β，5Z，7E，22E，24S)-24-Cyclopropyl-9，10-secochola-5，7，10(19)，22-tetraene-1，3，24-triol (1S,3R,5Z)-5-{2-[(1R,3aR,4Z,7aS)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-Methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-Methylidenecyclohexane-1,3-diol (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-Cyclopropyl-4-hydroxy-1-Methyl-2-buten-1-yl]octahydro-7a-Methyl-4H-inden-4-ylidene]ethylidene]-4-Methylene-1,3-cyclohexanediol Calcipotriol(MC 903) (1R,3S)-5-[2-[(1R,3aR,7aS)-1-[(2S)-5-cyclopropyl-5-hydroxy-pent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-Cyclopropyl-4-hydroxy-1-methylbut-2-en-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]-ethylidene]-4-methylene-1,3-cyclohexanediol Calcipotriene (1086141) calcipotriol monohydrateQ: What is calcipotriol monohydrate Q: What is the CAS Number of calcipotriol monohydrate Q: What is the storage condition of calcipotriol monohydrate Q: What are the applications of calcipotriol monohydrate Calcipotriol D4Q: What is Calcipotriol D4 Q: What is the CAS Number of Calcipotriol D4 Q: What is the storage condition of Calcipotriol D4 Q: What are the applications of Calcipotriol D4 Vitamin D (Calcipotriol) ( Under Development) cipotriene (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Calcipotriol-d4 (Calcipotriene-d4) (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,1R,4S)-4-cyclopropyl-4-hydroxy-1-methyl-but-2-enyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexane-1,3-diol dovonex mc903 Calcipotriol hydrate Daivobet Calcipotriol anhydrous 2H4]-Calcipotriol PRI 2201dene]-4-methylene-cyclohexane-1,3-diol 5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-Cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-cyclohexanediol (1R,3S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((2R,5S,E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol MC 903|||Calcipotriene 112965-21-6 112905-21-6 2965-21-6 Isotope Labelled Compounds Intermediates & Fine Chemicals Pharmaceuticals API chemical