Pasireotide

Pasireotide, sold under the brand name Signifor, is an orphan drug approved in the United States^[1] and the European Union^[2][3] for the treatment of Cushing's disease in patients who fail or are ineligible for surgical therapy.^[4][5][6] 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.

Trade namesSignifor, Signifor LAR

Other namesSOM230

AHFS/Drugs.comMonograph

License data

• US DailyMed: Pasireotide

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Pasireotide

Clinical data
Trade names	Signifor, Signifor LAR
Other names	SOM230
AHFS/Drugs.com	Monograph
License data	US DailyMed: Pasireotide
Pregnancy category	AU: B3
Routes of administration	Subcutaneous injection, intramuscular injection
ATC code	H01CB05 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Identifiers
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
CAS Number	396091-73-9 Y
PubChem CID	9941444
IUPHAR/BPS	2018
DrugBank	DB06663 N
ChemSpider	8117062 N
UNII	98H1T17066
KEGG	D10147 N
ChEBI	CHEBI:72312 N
ECHA InfoCard	100.211.883
Chemical and physical data
Formula	C58H66N10O9
Molar mass	1047.227 g·mol−1
3D model (JSmol)	Interactive image
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
InChI InChI=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 N Key:VMZMNAABQBOLAK-DBILLSOUSA-N N
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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.^[2][7][8]

Pasireotide was approved for Cushing's disease by the European Medicines Agency (EMA) in April 2012^[2][9] and by the U.S. Food and Drug Administration (FDA) in December 2012.^[1][10]

Pasireotide LAR (the long-acting-release formulation) was approved by the FDA for treatment of acromegaly in December 2014,^[11] and had been approved for this indication by the EMA in September 2014.^[2][12]