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Calcitriol

CAS No.
32222-06-3
Chemical Name:
Calcitriol
Synonyms
rocaltrol;Calcijex;Calcitrio;CALCITROL;Calcitriol solution;Calcitriol Impurity;1,25-dihydroxycholecalciferol;9,10-SECOCHOLESTA-5Z,7E,10(19)-TRIENE-1ALPHA,3BETA,25-TRIOL;(1R,3S,5Z)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aS)-octahydro-1-[(1R)-5-hydroxy-1,5-diMethylhexyl]-7a-Methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol;Silkis
CBNumber:
CB0171027
Molecular Formula:
C27H44O3
Molecular Weight:
416.64
MDL Number:
MFCD00867079
MOL File:
32222-06-3.mol
MSDS File:
SDS
Last updated:2024-01-30 10:02:58

Calcitriol Properties

Melting point 119-1210C
alpha D25 +48° (methanol)
Boiling point 474.91°C (rough estimate)
Density 1.0362 (rough estimate)
refractive index 1.4700 (estimate)
Flash point 14 °C
storage temp. 2-8°C
pka 14.43±0.40(Predicted)
form Solid
color White to Almost white
λmax 265nm(lit.)
Merck 14,1644
BRN 7559394
BCS Class 2,4
Stability Air and Light Sensitive
InChIKey GMRQFYUYWCNGIN-UNVJKIGWSA-N
CAS DataBase Reference 32222-06-3(CAS DataBase Reference)
NCI Dictionary of Cancer Terms calcitriol
FDA UNII FXC9231JVH
NCI Drug Dictionary calcitriol
ATC code A11CC04,D05AX03

Pharmacokinetic data

Protein binding 99.9%
Excreted unchanged in urine 7-10%
Biological half-life 9-10 / 18-20

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H300+H310+H330-H372
Precautionary statements  P260-P262-P280-P302+P352+P310-P304+P340+P310-P314
Hazard Codes  T+,Xn,F
Risk Statements  26/27/28-63-36/37/38-20/21/22-11
Safety Statements  36/37/39-45-36-26-16-7
RIDADR  UN 2811 6.1/PG 1
WGK Germany  3
RTECS  FZ4645000
8-10-19
HazardClass  6.1(a)
PackingGroup  I
HS Code  29061900
Toxicity mouse,LD50,intraperitoneal,1900ug/kg (1.9mg/kg),SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYEBEHAVIORAL: ATAXIA,Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983.
NFPA 704
0
4 0

Calcitriol price More Price(54)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D1530 1α,25-Dihydroxyvitamin D3 ≥99% (HPLC) 32222-06-3 10μG $197 2023-06-20 Buy
Sigma-Aldrich D1530 1α,25-Dihydroxyvitamin D3 ≥99% (HPLC) 32222-06-3 0.1MG $896 2023-06-20 Buy
Sigma-Aldrich 17936 1α,25-Dihydroxyvitamin D3 ≥97.0%(HPLC) 32222-06-3 100μg $840 2023-06-20 Buy
Sigma-Aldrich 17936 1α,25-Dihydroxyvitamin D3 ≥97.0%(HPLC) 32222-06-3 1mg $1900 2023-06-20 Buy
Sigma-Aldrich H-089 1α,25-Dihydroxyvitamin D3 solution 5?μg/mL in ethanol, ampule of 1?mL, certified reference material, Cerilliant? 32222-06-3 1mL $240 2022-05-15 Buy
Product number Packaging Price Buy
D1530 10μG $197 Buy
D1530 0.1MG $896 Buy
17936 100μg $840 Buy
17936 1mg $1900 Buy
H-089 1mL $240 Buy

Calcitriol Chemical Properties,Uses,Production

Introduction

Calcitriol (1,25-dihydroxylcholecaldiferol) is a steroid hormone with three hydroxyl groups, which is an active metabolite and the most effective form of vitamin D. It is produced primarily in the kidney when the blood calcium level and parathyroid hormone are low. Calcitriol promotes the calcium and phosphorus absorption in the intestine, reabsorption in the kidneys. Along with parathyroid hormone, it regulates bone growth for building and keeping strong bones. Calcitriol is used to treat and prevent low levels of calcium and bone disease in patients whose kidneys or parathyroid glands are not working normally, to treat secondary hyperparathyroidism and metabolic bone disease in people with kidney disease. Calcitriol may also be chemopreventive for colon and prostate cancers as it induces cell cycle arrest, cell differentiation, and apoptosis.

References

  1. https://pubchem.ncbi.nlm.nih.gov
  2. https://medlineplus.gov
  3. http://flexikon.doccheck.com/en/Calcitriol
  4. https://en.wikipedia.org/wiki/Calcitriol
  5. https://www.webmd.com

Description

Calcitriol is the active form of vitamin D and is also a kind of hormones in the body. It plays an important role in the regulation of calcium and phosphorus concentration. It can increase the blood calcium level by increasing the intestinal absorption of calcium and can also increase the release of the bone calcium release for increasing the blood calcium levels. This study was first conducted and reported by Michael F. Holick in 1971. The basic principle of action model of calcitriol in many cases is through binding with the vitamin D receptor (the VDR), e.g., the ligand-receptor complex forming between calcitriol and its receptor in the intestinal epithelial cells cytoplasm can be transferred to the nucleus for being as the transcriptional factor in promoting the expression of calcium-binding protein. The increased level of calcium-binding proteins can help the cell to actively transport of more calcium ions, thereby increasing the calcium absorption level. Calcium absorption while maintaining electrical neutrality also requires transporting anions, mainly the absorption of inorganic phosphate ions, so calcitriol also promote the absorption of phosphorus.
Clinically, this drug can be used in the treatment of hypocalcemia, hypoparathyroidism (adult), osteomalacia, rickets (infants), chronic kidney disease, renal osteodystrophy, osteoporosis, as well as the prevention of glucocorticoid induced osteoporosis.
Calcitriol-dimensional molecular structure
Calcitriol-dimensional molecular structure
The above information is edited by the chemicalbook of Dai Xiongfeng.

Description

Calcitriol is synthesized from 7-dehydro cholesterol in humans via a non-enzymatic photochemical reaction with 290-310 nm UV light in the skin. Hydroxylation of the resulting cholecalciferol in the liver produces 25-hydroxy vitamin D3, the principal circulating form of vitamin D. A second, tightly regulated hydroxylation in the kidney produces calcitriol. Plasma calcitriol levels range from 10-70 pg/ml and are influenced by numerous dietary and hormonal factors. The main physiologic effects of calcitriol are to increase the absorption of calcium at the level of the intestinal epithelium, and to increase the mineralization of bone via the direct stimulation of osteoblasts.

Chemical Properties

White Crystalline Powder

Originator

Rocaltrol,Roche,US,1978

Uses

Calcium regulator, anti-psoriatic

Uses

The biologically active form of vitamin D3. Calcium regulator; vitamin (antirachitic); antihyperparathyroid; antineoplastic; antipsoriatic

Uses

Calcitriol (1α,25-dihydroxy Vitamin D3) is synthesized from 7-dehydrocholesterol in humans via a non-enzymatic photochemical reaction with 290-310 nm UV light in the skin. Hydroxylation of the resulting cholecalciferol in the liver produces 25-hydroxy Vitamin D3, the principal circulating form of Vitamin D. A second, tightly regulated hydroxylation in the kidney produces calcitriol. Plasma calcitriol levels range from 10-70 pg/ml and are influenced by numerous dietary and hormonal factors. The main physiologic effects of calcitriol are to increase the absorption of calcium at the level of the intestinal epithelium, and to increase the mineralization of bone via the direct stimulation of osteoblasts.[Cayman Chemical]

Uses

Vitamin medicines; it can be used for treating the renal bone malnutrition of patients with chronic renal failure;

Definition

ChEBI: A hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group. It is the active form of vitamin D3, produced fom calciol via hydoxylation in the li er to form calcidiol, which is subsequently oxidised in the kidney to give calcitriol.

Manufacturing Process

1α,25-Dihydroxyprecholecalciferol: A solution of 1α,25- diacetoxyprecholecalciferol (0.712 g, 1.42 mmols), potassium hydroxide (2.0 g, 35.6 mmols) and methanol (40 ml) was stirred at room temperature under argon for 30 hours. The reaction mixture was concentrated under reduced pressure. Water (50 ml) was added to the residue and the mixture was extracted with methylene chloride (3 x 100 ml). The combined organic extracts were washed with saturated sodium chloride solution (3 x 50 ml), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 0.619 g of 1alpha,25-dihydroxyprecholecalciferol as a thick oil.
1α,25-Dihydroxycholecalciferol: A solution of 1α,25-dihydroxyprecholecalciferol [0.619 g in dioxane (30 ml)] was heated under reflux for 30 minutes under an atmosphere of argon. The reaction mixture was concentrated under reduced pressure and the residue was purified with a Waters Associates liquid chromatograph model 202 using a 8 foot * 3/8 inch Porasil A column and a 5:1 mixture of ethyl acetate-n-hexane as the eluent to give 0.474 g (80% yield based on 1α,25-diacetoxyprecholecalciferol) of pure 1α,25- dihydroxycholecalciferol. Recrystallization from methyl formate afforded 0.340 g of 1α,25-dihydroxcholecalciferol as colorless crystals, MP 113°-114°C.

brand name

Calcijex (Abbott); Rocaltrol (Roche.

Therapeutic Function

Calcium regulator

General Description

1α,25-Dihydroxyvitamin D3, also referred as calcitriol, is a calcitrophic hormone. It is the most biologically active metabolite of vitamin D produced in proximal tubular cells in the kidney.

Biological Activity

Active metabolite of vitamin D 3 that activates the vitamin D receptor (VDR). Displays calcemic actions; stimulates intestinal and renal Ca 2+ absorption and regulates bone Ca 2+ turnover. Exhibits antitumor activity; inhibits in vivo and in vitro cell proliferation in a wide range of cells including breast, prostate, colon, skin and brain carcinomas and myeloid leukemia cells.

Biochem/physiol Actions

Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Clinical Use

Vitamin D analogue:

Promotes intestinal calcium absorption

Suppresses PTH production and release

Veterinary Drugs and Treatments

Calcitriol may be potentially beneficial in the adjunctive treatment of chronic renal disease in dogs and cats but its use is somewhat controversial, particularly the decision on how soon in the course of chronic renal insufficiency it should employed. It may also be of benefit in treating some types of dermatopathies (primary idiopathic seborrhea).

Drug interactions

Potentially hazardous interactions with other drugs
Antiepileptics: the effects of vitamin D may be reduced in patients taking barbiturates or anticonvulsants.
Diuretics: increased risk of hypercalcaemia with thiazides.
Sevelamer: absorption may be impaired by sevelamer

Metabolism

During transport in the blood at physiological concentrations, calcitriol is mostly bound to a specific vitamin D binding protein (DBP), but also, to a lesser degree, to lipoproteins and albumin. At higher blood calcitriol concentrations, DBP appears to become saturated, and increased binding to lipoproteins and albumin occurs. Calcitriol is inactivated in both the kidney and the intestine, through the formation of a number of intermediates including the formation of the 1,24,25-trihydroxy derivatives. It is excreted in the bile and faeces and is subject to enterohepatic circulation.

storage

Desiccate at -20°C

113375-51-2
32222-06-3
Synthesis of Calcitriol from 4-Cyclohexene-1,3-diol, 5-ethynyl-4-methyl-, (1R,3S)-
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Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Inositol pictures 2023-11-27 Inositol
32222-06-3
US $0.00-0.00 / g 1g 99% 50kg Wuhan Senwayer Century Chemical Co.,Ltd
Calcitriol pictures 2023-06-26 Calcitriol
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US $200.00 / kg 1kg 99% 1000kg/Month Hebei Mingeng Biotechnology Co., Ltd
Calcitriol pictures 2023-03-13 Calcitriol
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US $0.00 / kg 1kg 99.0%min. HPLC 1000kg HangZhou RunYan Pharma Technology Co.,LTD.
  • Inositol pictures
  • Inositol
    32222-06-3
  • US $0.00-0.00 / g
  • 99%
  • Wuhan Senwayer Century Chemical Co.,Ltd
  • Calcitriol pictures
  • Calcitriol
    32222-06-3
  • US $200.00 / kg
  • 99%
  • Hebei Mingeng Biotechnology Co., Ltd
  • Calcitriol pictures
  • Calcitriol
    32222-06-3
  • US $0.00 / kg
  • 99.0%min. HPLC
  • HangZhou RunYan Pharma Technology Co.,LTD.

Calcitriol Spectrum

VITAMIN D3, 1ALPHA,25-DIHYDROXY (5z,7e)-(1s,3r)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol 1,25-(OH)2-D3 (1ALPHA,3BETA,5Z,7E)-9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-1,3,25-TRIOL 1ALPHA,25-DIHYDROXYCHOLECALCIFEROL 1ALPHA,25-DIHYDROXYVITAMIN D3 1ALPHA,25-DIHYDROXY-VITAMIN D8 1A, 25-DIHYDROXYCHOLECALCIFEROL CALCITRIOL (5z,7e)-9,10-secochesta-5,7,10(19)-triene-1-alpha,3-beta,25-triol 7,10(19)-triene-1,3,25-triol,(1-alpha,3-beta,5z,7e)-10-secocholesta-5 7,10(19)-triene-1,3,25-triol,(1alpha,3beta,5z,7e)-10-secocholesta-5 9,10seco(5z,7e)-5,7,10(19)-cholestatriene-1alpha,3beta,25-triol dihydroxyvitamind3 ro215535 1A25-dihydroxycholecalciferol(+4℃) Rocalirol (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-Methylheptan-2-yl]-7a-Methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-Methylidenecyclohexane-1,3-diol Calcitriol (Rocaltrol) Panbonis Solbone P 1a,25-Dihydroxyvitamin 1α,25-Dihydroxyvitamin D3,1α,25-Dihydroxycholecalciferol, Calcitriol Calcitriol (10 mg)F0E0620.993mg/mg(ai) Calcitriol (10 mg) (COLD SHIPMENT REQUIRED) 1,25-Dihydroxyvitamin-D3-[2H3] 1,25- DIHYDROXYVITAMIN D3 (6,19,19-D3) Solution 1,25- DIHYDROXYVITAMIN D3 (6,19,19-D3) Calcitriol-D3 (1R,3S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyl-octahydroinden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol aslpha,25-Dihydroxycholecalciferol 1α,25-Dihydroxyvitamin D3 solution (1α,3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol monohydrate 1α,25-Dihydroxycholecalciferol monohydrate 1α,25-Dihydroxyvitamin D3 monohydrate 1α,25-Dihydroxycalciferol solution 1,25-DihydroxyvitaMin D3 Calcitriol Vitamin D3, 1a,25-Dihydroxy- CALCITRIOL USP 1α,25-Dihydroxyvitamin D3 (1a,3b,5Z,7E)- 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, Silkis Soltriol Topitriol Toptriol 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta.,5Z,7E)- (5z,7e)-9,10-secocholesta-5,7,10(19)-triene-1-alpha,3-beta,25-triol 1,25-dhcc 1,25-dihydroxyvitamind 1a,25-dihydroxy-cholecalcifero 1-alpha,25-dihydroxy-cholecalcifero 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1α,3β,5Z,7E)- 1,25-DIHYROXYCHOLECALIFEROL 1ALPHA,25-DIHYDROXYVITAMIND 1,25-DIHYDROXYCHOLECALIFEROL 1,25-VITAMIND 1,25-DIHYDROXYCHOLESCALIFEROL (1R,3S,5Z)-5-[(2E)-2-[(1R,3aR,7aS)-1-[(2R)-6-hydroxy-6-methyl-heptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol CALCITRIOL(RG)