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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:2024-11-18 17:01:59

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 $205 2024-03-01 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 $270 2024-03-01 Buy
Sigma-Aldrich D1530 1α,25-Dihydroxyvitamin D3 ≥99% (HPLC) 32222-06-3 0.1MG $932 2024-03-01 Buy
Sigma-Aldrich 679101 Vitamin D₃, 1α, 25-Dihydroxy- - CAS 32222-06-3 - Calbiochem CAS 32222-06-3 prevents the development of clinical diabetes in NOD mice, an animal model of human autoimmune diabetes. 32222-06-3 50μg $449 2024-03-01 Buy
Sigma-Aldrich 17936 1α,25-Dihydroxyvitamin D3 ≥97.0%(HPLC) 32222-06-3 100μg $874 2024-03-01 Buy
Product number Packaging Price Buy
D1530 10μG $205 Buy
H-089 1mL $270 Buy
D1530 0.1MG $932 Buy
679101 50μg $449 Buy
17936 100μg $874 Buy

Calcitriol Chemical Properties,Uses,Production

Introduction

Calcitriol (1,25-dihydroxylcholecaldiferol,32222-06-3) 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. Plasma levels of calcitriol range from 10-70 pg/ml. 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
Calcitriol-dimensional molecular structure
The above information is edited by the chemicalbook of Dai Xiongfeng.

Chemical Properties

White Crystalline Powder

Originator

Rocaltrol,Roche,US,1978

Uses

Calcitriol is the biologically active form of vitamin D3, and its primary physiological effects are to increase calcium absorption by intestinal epithelial cells and increase bone mineralization by directly stimulating osteoblasts. It is therefore also used as a calcium regulator to treat symptoms of low calcium levels caused by kidney disease. It can also treat parathyroid disease. Calcitriol can regulate parathyroid levels by increasing the amount of calcium (vitamin D) in the body.

Definition

ChEBI: Calcitriol is 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 liver to form calcidiol, which is subsequently oxidised in the kidney to give calcitriol. It has a role as a bone density conservation agent, an antipsoriatic, an immunomodulator, an antineoplastic agent, a calcium channel modulator, a nutraceutical, a calcium channel agonist, a metabolite, a hormone, a human metabolite and a mouse metabolite. It is a hydroxycalciol, a member of D3 vitamins and a triol.

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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View Lastest Price from Calcitriol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Calcitriol pictures 2024-12-09 Calcitriol
32222-06-3
US $0.00-0.00 / g 1g 99%min;EP 100G WUHAN FORTUNA CHEMICAL CO., LTD
Calcitriol pictures 2024-12-09 Calcitriol
32222-06-3
US $0.00-0.00 / g 1g 99.0%min. HPLC 10000 HangZhou RunYan Pharma Technology Co.,LTD.
Calcitriol pictures 2024-11-18 Calcitriol
32222-06-3
US $66.00-197.00 / mg 99.64% 10g TargetMol Chemicals Inc.
  • Calcitriol pictures
  • Calcitriol
    32222-06-3
  • US $0.00-0.00 / g
  • 99%min;EP
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Calcitriol pictures
  • Calcitriol
    32222-06-3
  • US $0.00-0.00 / g
  • 99.0%min. HPLC
  • HangZhou RunYan Pharma Technology Co.,LTD.
  • Calcitriol pictures
  • Calcitriol
    32222-06-3
  • US $66.00-197.00 / mg
  • 99.64%
  • TargetMol Chemicals Inc.

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)