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Paricalcitol/en - Revision history
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{{short description|Chemical compound}}<br />
{{Drugbox<br />
| Verifiedfields = changed<br />
| Watchedfields = changed<br />
| verifiedrevid = 445909355<br />
| IUPAC_name = (1''R'',3''R'',7''E'',17β)-17-[(1''R'',2''E'',4''S'')-5-hydroxy-1,4,5-trimethylhex-2-en-1-yl]-9,10-secoestra-5,7-diene-1,3-diol<br />
| image = Paricalcitol.svg<br />
| width = 200px<br />
| image2 = Paricalcitol3Dan.gif<br />
| width2 = 200px<br />
<!--Clinical data--><br />
| tradename = Zemplar<br />
| Drugs.com = {{drugs.com|monograph|paricalcitol}}<br />
| MedlinePlus = a682335<br />
| pregnancy_AU = C<br />
| pregnancy_US = C<br />
| pregnancy_category = <br />
| legal_AU = S4<br />
| legal_CA = Rx-only<br />
| legal_UK = POM<br />
| legal_US = Rx-only<br />
| legal_status = <br />
| routes_of_administration = Oral, Intravenous<br />
<!--Pharmacokinetic data--><br />
| bioavailability = 72%<br />
| protein_bound = 99.8%<br />
| metabolism = [[Hepatic]]<br />
| elimination_half-life = 14-20 hours<br />
| excretion = Faeces (74%), urine (16%)<br />
<!--Identifiers--><br />
| CAS_number_Ref = {{cascite|correct|??}}<br />
| CAS_number = 131918-61-1<br />
| ATC_prefix = H05<br />
| ATC_suffix = BX02<br />
| ATC_supplemental = <br />
| ChEBI_Ref = {{ebicite|changed|EBI}}<br />
| ChEBI = 7931<br />
| PubChem = 5281104<br />
| IUPHAR_ligand = 2791<br />
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}<br />
| DrugBank = DB00910<br />
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br />
| ChemSpiderID = 4444552<br />
| UNII_Ref = {{fdacite|correct|FDA}}<br />
| UNII = 6702D36OG5<br />
| KEGG_Ref = {{keggcite|changed|kegg}}<br />
| KEGG = D00930<br />
| ChEMBL_Ref = {{ebicite|correct|EBI}}<br />
| ChEMBL = 1200622<br />
<!--Chemical data--><br />
| chemical_formula =<br />
| C=27 | H=44 | O=3<br />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChI = 1S/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<br />
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChIKey = BPKAHTKRCLCHEA-UBFJEZKGSA-N<br />
| synonyms = <small>(1''R'',3''S'')-5-[2-[(1''R'',3a''R'',7a''S'')-1-<nowiki>[</nowiki>(2''R'',5''S'')-6-hydroxy-5,6-dimethyl-3''E''-hepten-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-cyclohexane-1,3-diol</small><br />
}}<br />
<br />
'''Paricalcitol''' (chemically it is '''19-nor-1,25-(OH)<sub>2</sub>-vitamin D<sub>2</sub>'''. Marketed by [[Abbott Laboratories]] under the trade name '''Zemplar''') is a [[pharmaceutical drug|drug]] used for the prevention and treatment of [[secondary hyperparathyroidism]] (excessive secretion of [[parathyroid hormone]]) associated with [[chronic kidney failure]]. It is an [[analog (chemistry)|analog]] of 1,25-dihydroxyergocalciferol, the active form of [[Vitamin D2|vitamin D<sub>2</sub>]] (ergocalciferol).<br />
<br />
<!-- Society and culture --><br />
It was patented in 1989 and approved for medical use in 1998.<br />
<br />
==Medical uses==<br />
Its primary use in medicine is in the treatment of secondary [[hyperparathyroidism]] associated with [[chronic kidney disease]]. However current evidence is not sufficient to demonstrate an advantage of paricalcitol over non-selective vitamin D derivatives for this indication.<br />
<br />
==Adverse effects==<br />
'''Adverse effects by frequency:'''<br /><br />
'''Very common (>10% frequency):'''<br />
* Nausea<br />
<br />
'''Common (1-10% frequency):'''<br />
{{div col|colwidth=18em}}<br />
* Diarrhoea<sup>†</sup><br />
* [[Oedema]]<br />
* Allergic reaction<br />
* [[Arthritis]]<br />
* Dizziness<sup>†</sup><br />
* Stomach discomfort<sup>‡</sup><br />
* [[Gastroesophageal reflux disease]]<sup>†</sup><br />
* [[Acne]]<sup>†</sup><br />
* [[Hypercalcaemia]]<sup>†</sup><br />
* [[Hypocalcaemia]]<sup>†</sup><br />
* [[Hyperphosphataemia]]<br />
* Decreased appetite<sup>†</sup><br />
* Headache<br />
* Breast tenderness<sup>†</sup><br />
* Taste changes<br />
* [[Hypoparathyroidism]]<br />
* Vertigo<br />
* Rash<sup>‡</sup><br />
{{div col end}}<br />
<br />
'''Uncommon (0.1-1% frequency):'''<br />
{{div col|colwidth=18em}}<br />
* Abnormal hepatic enzymes<sup>‡</sup><br />
* Constipation<sup>‡</sup><br />
* Dry mouth<sup>‡</sup><br />
* [[Pruritus|Itchiness]]<sup>‡</sup><br />
* [[Urticaria|Hives]]<br />
* Hypersensitivity<sup>‡</sup><br />
* Muscle spasms<sup>‡</sup><br />
* Bleeding time prolonged<br />
* Aspartate aminotransferase increased<br />
* Laboratory test abnormal<br />
* Weight loss<br />
* Elevated blood creatinine<br />
* Cardiac arrest<br />
* Arrhythmia<br />
* Atrial flutter<br />
* [[Anaemia]]<br />
* [[Leucopenia]]<br />
* Lymphadenopathy<br />
* Coma<br />
* [[Cerebrovascular accident|Stroke]]<br />
* [[Transient ischemic attack]]<br />
* [[Vasovagal syncope|Fainting]]<br />
* [[Myoclonus]]<br />
* [[Hypoaesthesia]]<br />
* [[Paraesthesia]]<br />
* [[Glaucoma]]<br />
* [[Conjunctivitis]]<br />
* Ear disorder<br />
* Pulmonary oedema<br />
* Asthma<br />
* [[Dyspnoea|Shortness of breath]]<br />
* [[Epistaxis|Nose bleed]]<br />
* Cough<br />
* Rectal haemhorrhage<br />
* [[Colitis]]<br />
* [[Gastritis]]<br />
* [[Dyspepsia|Indigestion]]<br />
* [[Dysphagia|Difficulty swallowing]]<br />
* Gastrointestinal disorder<br />
* Gastrointestinal haemorrhage<br />
* Bullous dermatitis<br />
* [[Alopecia|Hair loss]]<br />
* [[Hirsutism]]<br />
* [[Hyperhidrosis]]<br />
* [[Arthralgia|Joint pain]]<br />
* Joint stiffness<br />
* Back pain<br />
* Muscle twitching<br />
* [[Myalgia|Muscle aches]]<br />
* [[Hyperparathyroidism]]<br />
* [[Hyperkalaemia]]<br />
* [[Hypocalcemia]]<br />
* [[Breast cancer]]<br />
* [[Sepsis]]<br />
* [[Pneumonia]]<br />
* Infection<br />
* [[Pharyngitis]]<br />
* Vaginal infection<br />
* Influenza<br />
* [[Hypertension|High blood pressure]]<br />
* [[Hypotension]]<br />
* Gait disturbance<br />
* Injection site pain<br />
* [[Pyrexia|Fever]]<br />
* Chest pain<br />
* Condition aggravated<br />
* [[Asthenia|Muscle weakness]]<br />
* [[Malaise]]<br />
* Thirst<br />
* Breast pain<br />
* [[Erectile dysfunction|Impotence]]<br />
* Confusional state<br />
* Delirium<br />
* Depersonalization<br />
* Agitation<br />
* Insomnia<br />
* Nervousness<br />
{{div col end}}<br />
<br />
<sup>‡</sup> These are adverse effects only seen in patients with grade 3 or 4 chronic kidney disease. <br />
<sup>†</sup> These are adverse effects only seen in patients with grade 5 chronic kidney disease.<br />
<br />
==Contraindications==<br />
Contraindications include:<br />
* [[Hypervitaminosis D|Vitamin D intoxication]]<br />
* [[Hypercalcaemia]]<br />
* Hypersensitivity to paricalcitol or any of its excipients<br />
<br />
whereas cautions include:<br />
* Impaired liver function<br />
* It is also advised that physicians regularly monitor their patients' [[calcium]] and [[phosphorus]] levels.<br />
<br />
==Interactions==<br />
Drugs that may interact with paricalcitol include:<br />
{{div col|colwidth=30em}}<br />
* [[Ketoconazole]], as it may interfere with paricalcitol's metabolism in the liver.<br />
* [[Digitoxin]], hypercalcaemia due to any cause can exacerbate the toxicity of digitoxin.<br />
* [[Thiazide]] diuretics or calcium supplements as [[hypercalcaemia]] may be induced by this combination<br />
* [[Magnesium]]-containing products such as [[antacids]] may increase the risk of [[hypermagnesemia]].<br />
* [[Aluminium]]-containing products such as antacids may increase the risk of [[aluminium toxicity]].<br />
* Drugs that interfere with the absorption of fat-soluble vitamins, such as [[cholestyramine]] may interfere with the absorption of paricalcitol. <br />
{{div col end}}<br />
<br />
==Overdose==<br />
Electrolyte abnormalities (e.g. [[hypercalcaemia]] and [[hyperphosphataemia]]) are common overdose symptoms. Treatment is mostly supportive, with particular attention being paid to correcting electrolyte anomalies and reducing intake of calcium in both the form of supplementation and diet. As it is so heavily bound to plasma proteins [[haemodialysis]] is unlikely to be helpful in cases of overdose.<br />
<br />
Early symptoms of overdose can include:<br />
{{div col|colwidth=18em}}<br />
* Weakness<br />
* Headache<br />
* Somnolence<br />
* Nausea<br />
* Vomiting<br />
* Dry mouth<br />
* Constipation<br />
* Muscle pain<br />
* Bone pain<br />
* Metallic taste in the mouth.<br />
{{div col end}}<br />
It is worth noting, however, that may of these symptoms are also indicative of kidney failure and hence may be masked by the patient's condition.<br />
<br />
Late symptoms of overdose include:<br />
{{div col|colwidth=18em}}<br />
* [[Anorexia (symptom)|Loss of appetite]]<br />
* Weight loss<br />
* [[Conjunctivitis]] (calcific)<br />
* [[Pancreatitis]]<br />
* Photophobia<br />
* Rhinorrhoea<br />
* Pruritus<br />
* Hyperthermia<br />
* Decreased libido<br />
* Elevated BUN<br />
* Hypercholesterolaemia<br />
* Elevated AST and ALT<br />
* Ectopic calcification<br />
* Hypertension<br />
* Cardiac arrhythmias<br />
* Somnolence<br />
* Death<br />
* Psychosis (rare)<br />
{{div col end}}<br />
<br />
==Mechanism of action==<br />
[[File:Paricalcitol structure.svg|thumb|left|3D structure of paricalcitol]]{{clear left}}<br />
Like 1,25-dihydroxyergocalciferol, paricalcitol acts as an [[agonist]] at the [[vitamin D receptor]] and thereby lowers [[parathyroid hormone]] levels in the blood.<br />
<br />
==Pharmacokinetics==<br />
The plasma concentration of paricalcitol decreases rapidly and log-linearly within two hours after initial intravenous administration. Therefore, it is not expected to accumulate with multiple dosing, since paricalcitol is usually given no more frequently than every other day (3 times per week).<br />
<br />
{{Vitamins}}<br />
{{Calcium homeostasis}}<br />
{{Vitamin D receptor modulators}}<br />
<br />
{{二次利用|date=20 December 2023}}<br />
[[Category:Secosteroids]]<br />
[[Category:Vitamin D]]<br />
[[Category:Drugs developed by AbbVie]]</div>
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