Calcipotriene

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)
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)	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
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

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

1of3

Preparation Products

24R-Calcipotriol

Calcipotriene Suppliers

Global( 274)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Joyochem Co.,Ltd	+86-0531-82687558 +8613290333633	sales@joyochem.com	China	42	58
HangZhou RunYan Pharma Technology Co.,LTD.	+86-88660901 +86-18112526015	sales@runyanpharma.com	China	326	58
ChemExpress	+86-021-58950125	info@chemexpress.com	China	557	58
Shanghai Affida new material science and technology center	+undefined15081010295	2691956269@qq.com	China	359	58
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29797	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21695	55
Nanjing Finetech Chemical Co., Ltd.	025-85710122 17714198479	sales@fine-chemtech.com	CHINA	885	55
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Xiamen AmoyChem Co., Ltd	+86-592-6051114 +8618959220845	sales@amoychem.com	China	6387	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58

Supplier	Advantage
Joyochem Co.,Ltd	58
HangZhou RunYan Pharma Technology Co.,LTD.	58
ChemExpress	58
Shanghai Affida new material science and technology center	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

View Lastest Price from Calcipotriene manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-03-19	Calcipotriol 112965-21-6	US $0.00-0.00 / KG	1KG	99	10 tons	Shanghai Affida new material science and technology center
2023-03-13	Calcipotriene/Calcipotriol 112965-21-6	US $0.00 / kg	1kg	99.0%min. HPLC	1000kg	HangZhou RunYan Pharma Technology Co.,LTD.
2023-01-11	Calcipotriene 112965-21-6	US $0.00 / KG	1KG	98%min	30tons/month	WUHAN FORTUNA CHEMICAL CO., LTD

Calcipotriol
112965-21-6
US $0.00-0.00 / KG
99
Shanghai Affida new material science and technology center

Calcipotriene/Calcipotriol
112965-21-6
US $0.00 / kg
99.0%min. HPLC
HangZhou RunYan Pharma Technology Co.,LTD.

Calcipotriene
112965-21-6
US $0.00 / KG
98%min
WUHAN FORTUNA CHEMICAL CO., LTD

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

1of3

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 112965-21-6 112905-21-6 2965-21-6 Isotope Labelled Compounds Intermediates & Fine Chemicals Pharmaceuticals API chemical

Calcipotriene Properties

SAFETY

Risk and Safety Statements

Calcipotriene price More Price(30)

Calcipotriene Chemical Properties,Uses,Production

Description

Chemical Properties

Originator

Uses

Preparation

Definition

Indications

Manufacturing Process

brand name

Therapeutic Function

Biological Activity

Biochem/physiol Actions

Pharmacology

Side effects

storage

Calcipotriene synthesis

Calcipotriene Preparation Products And Raw materials

Raw materials

Preparation Products

Calcipotriene Suppliers

Related articles

View Lastest Price from Calcipotriene manufacturers

Calcipotriene Spectrum

112965-21-6(Calcipotriene)Related Search: