pasireotide

{{Short description|Pharmaceutical drug}}

{{Use dmy dates|date=March 2024}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451604097

| IUPAC_name = [(3S,6S,9S,12R,15S,18S,20R)-9-(4-aminobutyl)-3-benzyl-12-(1H-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-15-phenyl-6-[(4-phenylmethoxyphenyl)methyl]-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosan-20-yl] N-(2-aminoethyl)carbamate

| image = Pasireotide.svg

| alt =

| caption =

| tradename = Signifor, Signifor LAR

| Drugs.com = {{drugs.com|monograph|pasireotide}}

| DailyMedID = Pasireotide

| pregnancy_AU = B3

| pregnancy_category =

| routes_of_administration = Subcutaneous injection, intramuscular injection

| ATC_prefix = H01

| ATC_suffix = CB05

| legal_AU =

| legal_CA =

| legal_UK = POM

| legal_US = Rx-only

| legal_EU = Rx-only

| legal_EU_comment =

| legal_status = Rx-only

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 2018

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 396091-73-9

| PubChem = 9941444

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB06663

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 72312

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 98H1T17066

| synonyms = SOM230

| KEGG = D10147

| KEGG_Ref = {{keggcite|changed|kegg}}

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8117062

| C=58 | H=66 | N=10 | O=9

| smiles = C1[C@H](CN2[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C2=O)CC3=CC=CC=C3)CC4=CC=C(C=C4)OCC5=CC=CC=C5)CCCCN)CC6=CNC7=CC=CC=C76)C8=CC=CC=C8)OC(=O)NCCN

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C58H66N10O9/c59-27-13-12-22-46-52(69)64-47(30-38-23-25-42(26-24-38)76-36-39-16-6-2-7-17-39)53(70)66-49(31-37-14-4-1-5-15-37)57(74)68-35-43(77-58(75)61-29-28-60)33-50(68)55(72)67-51(40-18-8-3-9-19-40)56(73)65-48(54(71)63-46)32-41-34-62-45-21-11-10-20-44(41)45/h1-11,14-21,23-26,34,43,46-51,62H,12-13,22,27-33,35-36,59-60H2,(H,61,75)(H,63,71)(H,64,69)(H,65,73)(H,66,70)(H,67,72)/t43-,46+,47+,48-,49+,50+,51+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VMZMNAABQBOLAK-DBILLSOUSA-N

}}

Pasireotide, sold under the brand name Signifor, is an orphan drug approved in the United States{{cite web | title=Drug Approval Package: Signifor (pasireotide) Injection NDA #200677 | website=U.S. Food and Drug Administration (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/200677Orig1s000TOC.cfm | access-date=13 May 2020}} and the European Union{{cite web | title=Signifor EPAR | website=European Medicines Agency (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/signifor | access-date=13 May 2020}} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.{{cite web | title = Summary of Product Characteristics: Signifor | url = http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002052/WC500128056.pdf | publisher = European Medicines Agency | access-date = 27 September 2016 | archive-date = 14 June 2018 | archive-url = https://web.archive.org/web/20180614200149/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002052/WC500128056.pdf | url-status = dead }} for the treatment of Cushing's disease in patients who fail or are ineligible for surgical therapy.{{cite web | title=Pasireotide Orphan Drug Designation and Approval | website=U.S. Food and Drug Administration (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=288709 | archive-url=https://web.archive.org/web/20210821025329/https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=288709 | url-status=dead | archive-date=21 August 2021 | access-date=13 May 2020}}{{cite web | title=EU/3/09/671 | website=European Medicines Agency | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/orphan-designations/eu309671 | access-date=13 May 2020}} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.{{cite journal | vauthors = Mancini T, Porcelli T, Giustina A | title = Treatment of Cushing disease: overview and recent findings | journal = Therapeutics and Clinical Risk Management | volume = 6 | pages = 505–16 | date = October 2010 | pmid = 21063461 | pmc = 2963160 | doi = 10.2147/TCRM.S12952 | doi-access = free }} It was developed by Novartis. Pasireotide is a somatostatin analog with a 40-fold increased affinity to somatostatin receptor 5 compared to other somatostatin analogs.

The most common side effects include hyperglycaemia (high blood sugar levels), diabetes, diarrhoea, abdominal pain (stomach ache), nausea (feeling sick), cholelithiasis (gallstones), injection site reactions, and tiredness.{{cite web | title=Signifor- pasireotide injection | website=DailyMed | date=15 January 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=442f0d9d-5c7d-4b81-b329-d71be8cf2be2 | access-date=13 May 2020}}{{cite web | title=Signifor LAR- pasireotide kit | website=DailyMed | date=17 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5504116c-d531-4d47-b160-41c6671d52aa | access-date=13 May 2020}}

Pasireotide was approved for Cushing's disease by the European Medicines Agency (EMA) in April 2012{{Cite web |url=http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/orphans/2009/11/human_orphan_000677.jsp |title=EMEA Approval for Pasireotide |access-date=26 January 2014 |archive-date=4 February 2014 |archive-url=https://web.archive.org/web/20140204042347/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fmedicines%2Fhuman%2Forphans%2F2009%2F11%2Fhuman_orphan_000677.jsp |url-status=dead }} and by the U.S. Food and Drug Administration (FDA) in December 2012.{{cite web|title=FDA Approves Pasireotide for Cushing's Disease|url=http://www.medscape.com/viewarticle/776273}}

Pasireotide LAR (the long-acting-release formulation) was approved by the FDA for treatment of acromegaly in December 2014,{{cite web | title=Signifor LAR (pasireotide) for injectable suspension | website=U.S. Food and Drug Administration (FDA) | date=1 March 2016 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203255Orig1s000TOC.cfm | archive-url=https://web.archive.org/web/20201031092641/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203255Orig1s000TOC.cfm | url-status=dead | archive-date=31 October 2020 | access-date=13 May 2020}} and had been approved for this indication by the EMA in September 2014.{{cite web | last = Tucker | first = Miriam E | name-list-style = vanc | url = http://www.medscape.com/viewarticle/836728 | title = FDA Approves Pasireotide for Treating Acromegaly | work = Medscape | date = 17 December 2014 | access-date = 2 August 2015 }}