131918-61-1

Basic information

• Product Name: Paricalcitol
• Synonyms: PARICALCITOL (10 MG)F0E3030.997MG/MG(AI);PARICALCITOL;19-nor-1alpha,25-dihydroxyvitamin D2;(1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-6-Hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol;Zemplar;1,3-Cyclohexanediol, 5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R,2E,4S)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,3R,5Z)-;Paricalcitol (10 mg) (COLD SHIPMENT REQUIRED);(1R,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-Octahydro-1-[(1R,2E,4S)-5-hydroxy-1,4,5-triMethyl-2-hexen-1-yl]-7a-Methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
• CAS NO: 131918-61-1
• Molecular Formula: C27H44O3
• Molecular Weight: 416.64
• EINECS: 1312995-182-4
• Product Categories: Vitamin D3 analogs;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 131918-61-1.mol

Chemical Properties

• Boiling Point: 564.8 °C at 760 mmHg
• Flash Point: 14℃
• Appearance: /
• Density: 1.121 g/cm³
• Vapor Pressure: 4.13E-15mmHg at 25°C
• Refractive Index: 1.609
• PKA: 14.34±0.40(Predicted)
• CAS DataBase Reference: Paricalcitol(CAS DataBase Reference)
• NIST Chemistry Reference: Paricalcitol(131918-61-1)
• EPA Substance Registry System: Paricalcitol(131918-61-1)

Safety Data

• RIDADR: UN1170 - class 3 - PG 2 - Ethanol, solution
• Hazardous Substances Data: 131918-61-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Paricalcitol is used as an antihyperparathyroid agent for the prevention and treatment of secondary hyperparathyroidism associated with chronic renal failure. It is particularly effective in reducing levels of parathyroid hormone (PTH) without significantly increasing the incidence rate for hypercalcemia or hyperphosphatemia when compared to a placebo.
Used in Renal Patient Care:
Paricalcitol is used as a synthetic analog of vitamin D in renal patients to manage secondary hyperparathyroidism, a condition that arises due to vitamin D deficiency associated with chronic kidney disease. By blocking the overproduction of parathyroid hormone, paricalcitol helps maintain the balance of calcium and phosphorus in the body, thus improving the overall health and well-being of patients with chronic renal failure.
Brand Name and Availability:
Paricalcitol is marketed under the brand name Zemplar by Abbott, making it the first vitamin D analogue to be specifically designed and marketed for the treatment of secondary hyperparathyroidism in patients with chronic renal failure.

Originator

Abbott (US)

Clinical Use

Vitamin D analogue: Treatment and prevention of secondary hyperparathyroidism associated with chronic renal failure

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Extensively metabolised via hepatic and non-hepatic pathways to form two relatively inactive metabolites. After oral administration of 3 H-paricalcitol, only about 2% of the dose was eliminated unchanged in the faeces, and no parent drug found in the urine. Approximately 70% of the radioactivity was eliminated in the faeces and 18% was recovered in the urine. Most of the systemic exposure was from the parent drug.

InChI:InChI=1/C27H44O3/c1-18(8-9-19(2)26(3,4)30)24-12-13-25-21(7-6-14-27(24,25)5)11-10-20-15-22(28)17-23(29)16-20/h8-11,18-19,22-25,28-30H,6-7,12-17H2,1-5H3/b9-8+,21-11+/t18-,19+,22-,23-,24-,25+,27-/m1/s1

Upstream product

• 79918-70-0 [1S-[1β(R*),3aα,7aβ]]-octahydro-1-(2-hydroxy-1-methylethyl)-7a-methyl-4H-inden-4-one 
• 1263286-70-9 C₁₃H₂₃IO 
• 1263286-72-1 (7E)-(1R,3R)-24-phenylsulfonyl-1,3-bis(tert-butyldimethylsililoxy)-9,10-seco-19,22,23-trinorchola-5,7-dien 
• 185997-26-6 (1R,3aR,7aR)-1-((S)-1-hydroxypropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol 
• 94284-07-8 (S)-3-hydroxy-2,3-dimethylbutanal 
• 1477494-91-9 C₃₉H₇₂O₃Si₂ 
• 1451188-52-5 C₄₅H₇₈O₆SSi₂ 
• 116535-65-0 (1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol 
• 1263286-71-0 (7aR)-7a-methyl-1-((S)-1'-(phenylsulfonyl)propane-2'-yl)hexahydro-1H-inden-4(2H)-on 
• 145372-32-3 des-A,B-22-iodo-23,24-dinorcholan-8-one 
• 1263286-73-2 (7E)-(1R,3R)-24-phenylsulfonyl-9,10-seco-19,22,23-trinorchola-5,7-dien-1,3-diol 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 94284-08-9 (R)-3-hydroxy-2,3-dimethylbutanal 
• 1192803-39-6 C₃₉H₇₂O₃Si₂ 

Related news

Effect of Paricalcitol (cas 131918-61-1) on mineral bone metabolism in kidney transplant recipients with secondary hyperparathyroidism08/02/2019

IntroductionSecondary hyperparathyroidism is highly prevalent in kidney transplant recipients, and commonly results in hypercalcaemia; an association to osteopenia and bone fractures has also been observed. Paricalcitol has proved effective to control secondary hyperparathyroidism in chronic kid...detailed

Effects of oral Paricalcitol (cas 131918-61-1) therapy on arterial stiffness and osteopontin in hypertensive patients with chronic kidney disease and secondary hyperparathyroidism08/01/2019

BackgroundArterial stiffness is linked to the progression of atherosclerosis, while activation of vitamin D receptor exerts favorable cardiovascular effects in patients with renal insufficiency. In this study, we investigated the effects of oral treatment with paricalcitol, a potent vitamin D re...detailed

Paricalcitol (cas 131918-61-1) Versus Calcifediol for Treating Hyperparathyroidism in Kidney Transplant Recipients07/31/2019

IntroductionSecondary hyperparathyroidism (SHPT) and vitamin D deficiency are common at kidney transplantation and are associated with some early and late complications. This study was designed to evaluate whether paricalcitol was more effective than nutritional vitamin D for controlling SHPT in...detailed

Perfil antiinflamatorio del Paricalcitol (cas 131918-61-1) en el receptor de trasplante renal07/29/2019

ResumenAntecedentes y objetivosEl paricalcitol, un activador selectivo del receptor de la vitamina D, se utiliza en el tratamiento del hiperparatiroidismo secundario en el receptor de trasplante renal. Estudios tanto clínicos como experimentales realizados en pacientes renales no trasplantados ...detailed

Vitamin D receptor activation by Paricalcitol (cas 131918-61-1) and insulin resistance in CKD07/28/2019

sBackground and aimsThe nature of the link (causal vs non-causal) between low 1,25-OH vitamin D and insulin resistance (IR) in patients with chronic kidney disease (CKD) remains elusive. We have now made a post hoc analysis of the effect of vitamin D receptor activation by paricalcitol on IR in ...detailed

Paricalcitol (cas 131918-61-1) alleviates lipopolysaccharide-induced depressive-like behavior by suppressing hypothalamic microglia activation and neuroinflammation07/27/2019

Depression is highly prevalent in patients suffering from chronic inflammatory diseases. Dysregulated neuroinflammation and concomitant activated microglia play a pivotal role in the pathogenesis of depression. Paricalcitol (Pari), a vitamin D2 analogue, has been demonstrated to exert anti-infla...detailed

Anti-inflammatory profile of Paricalcitol (cas 131918-61-1) in kidney transplant recipients07/26/2019

Background and objectivesParicalcitol, a selective vitamin D receptor activator, is used to treat secondary hyperparathyroidism in kidney transplant patients. Experimental and clinical studies in non-transplant kidney disease patients have found this molecule to have anti-inflammatory properties...detailed

Relevant articles and documents

Synthesis of paricalcitol: A novel strategy combining chemical and microbial transformations

A novel strategy was developed for the preparation of paricalcitol (1α,25-dihydroxy-19-norvitamin D2) via seven-step chemical transformation and one-step microbial transformation. Using vitamin D2 as a starting material, 1α- and 25-hydroxyl groups of paricalcitol were introduced by Pseudonocardia autotrophica CGMCC5098 at the late stage of the synthesis, allowing us to avoid harsh reaction conditions and tedious steps. The overall yield of paricalcitol was 0.75%.

Preparation method of paracetamol and injection thereof

The invention provides a preparation method of paracetamol, which adopts a raw material 1 as an initial raw material to synthesize paracetamol. Meanwhile, the invention provides a paracetamol injection and a preparation method thereof. The paracetamol injection comprises a 0.0003% w/v-0.0006% w/v of paracetamol as an active ingredient; 0.05-0.1% w/v of a non-ionic active agent, 2-3% w/v of polyethylene glycol 1000 vitamin E succinate, 0.1-0.5% w/v of cholate, 3-5% v/v of ethanol, 1-3% v/v of propylene glycol and the balance of water for injection. According to the paracetamol injection prepared by the invention, the addition amount of an organic solvent can be reduced, and the paracetamol injection is safer to use.

Preparation method of paricalcitol isomer impurity PY5

The invention discloses a preparation method of paricalcitol isomer impurity PY5. The preparation method comprises the following steps: taking (1R, 3aR, 7aR)-1-((2R,5R,E)-5,6-dimethyl heptyl-3-alkene-2-yl)-7a-methyl octahydro-4H-indole-4-ketone as a start

Preparation method for paricalcitol

The invention discloses a preparation method for paricalcitol. The preparation method comprises the following steps: (1) subjecting a compound 1 to a hydrolysis reaction so as to prepare a compound 2;(2) subjecting the compound 2 to oxidation with Dess-Martin periodinane so as to prepare a compound 3; (3) subjecting the compound 3 to a reaction with a compound 4 so as to prepare a compound 5; and(4) subjecting the compound 5 to hydrolysis so as to prepare a crude paricalcitol product. Accordinccording to the method of the invention, the content of an epimer impurity B in the crude paricalcitol product is reduced from the source by selecting appropriate reaction conditions, and subsequent purification steps for paricalcitol are simplified; and the preparation method has high yield and little impurities, and is more suitable for large-scale industrial production.

Purification method for paricalcitol

The invention provides a purification method for paricalcitol. The method does not need any seed crystal; a crude paricalcitol product is dissolved in a mixed solvent of acetone and water, and heatingreflux is carried out so as to allow the crude paricalcitol product to be completely dissolved; and cooling crystallization is carried out at room temperature, wherein a ratio of the usage amounts ofparicalcitol to the mixed solvent is 1: 20 to 1: 80 (g/ml).

Synthesis process of paricalcitol

The invention discloses a synthesis process of paricalcitol. The synthesis process of the paricalcitol comprises the steps of adopting nandrolone as a raw material, oxidizing, carrying out wittig reaction, carrying out hydroxy protection, brominating, rearranging, carrying out dehydrobromination, carrying out addition, oxidizing, reducing, carrying out hydroxy deprotection, and opening ring to obtain the paricalcitol. The paricalcitol is used for preventing and treating secondary hyperthyroidism.

A new metabolite of Paricalcitol: stereoselective synthesis of (22Z)-isomer of 1α,25-dihydroxy-19-norvitamin D2

Stereoselective synthesis of (22Z)-isomer of Paricalcitol, an analog of 1,25-dihydroxyergocalciferol, an active form of vitamin D2 (Ergocalciferol) has been described. The two key critical synthetic steps involved are Julia–Lythgoe's Wittig–Hor

Synthesis and crystallographic study of 1,25-dihydroxyergocalciferol analogs

The hybrid analogs of 1,25-dihydroxyergocalciferol (PRI-5201 and PRI-5202) were synthesized as potential anticancer agents using a convergent strategy. The analogs were designed by combining a 19-nor modification of the A-ring with the homologated and rig

NEW SYNTHONES FOR PREPARATION OF 19-NOR VITAMIN D DERIVATIVES

The present invention discloses the synthone of Formula (I), wherein R1 and R2 are the same or different and represent independently hydrogen atom or hydroxyl protecting group, and its use for preparation of 19-nor vitamin D derivatives of general Formula (IV), wherein represents single or double bond, p represents an integer 0 to 3, R1 and R2 represent independently hydrogen atom or hydroxyl protecting group, R3 represents hydrogen atom, CH3 or hydroxyl group, R4, R5 and R6 represent independently hydrogen atom, C1-C3-alkyl or hydroxyl group or two of R4, R5 and R6 substituents altogether form cyclopropyl group, in particular for preparation of paricalcitol.

METHODS FOR PRODUCING PARICALCITOL

The present invention is directed to novel processes for the preparation of paricalcitol to novel intermediates used in these processes, and to processes for preparation of the novel intermediates.