Pasireotide

Pasireotide

Systematic (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
Clinical data
Trade names	Signifor
License data	EU EMA: Signifor
Routes of administration	Subcutaneous
Legal status
Legal status	℞ (Prescription only)
Identifiers
CAS Number	396091-73-9
ATC code	H01CB05 (WHO)
PubChem	CID 9941444
IUPHAR/BPS	2018
DrugBank	DB06663
ChemSpider	8117062
UNII	98H1T17066
KEGG	D10147
ChEBI	CHEBI:72312
Synonyms	SOM230
Chemical data
Formula	C58H66N10O9
Molar mass	1047.21 g/mol[1]
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 Key:VMZMNAABQBOLAK-DBILLSOUSA-N
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Pasireotide (SOM230, trade name Signifor^[2]) is an orphan drug approved in the U.S. and Europe for the treatment of Cushing's disease and acromegaly in patients who fail or are ineligible for surgical therapy.^[3][4] 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.

Pasireotide was approved for Cushing's disease by the EMEA in October 2009^[5] and by the FDA in December 2012.^[6]

Pasireotide LAR was approved by the FDA for treatment of acromegaly in December 2014, and had been approved for this indication by the EMEA one month earlier.^[7]

References

1. Pasireotide | C58H66N10O9 - PubChem http://pubchem.ncbi.nlm.nih.gov/compound/Pasireotide
2. Signifor® (pasireotide) Official Website for healthcare professionals outside the US http://www.signifor.com/
3. "Novartis drug Signifor® approved in the EU as the first medication to treat patients with Cushing's disease". Retrieved 2012-07-08.
4. Mancini, Tatiana; Porcelli, Teresa; Giustina, Andrea (2010). "Treatment of Cushing disease: overview and recent findings". Therapeutics and Clinical Risk Management 6: 505–16. doi:10.2147/TCRM.S12952 (inactive 2015-02-01). PMC: 2963160. PMID 21063461.
5. EMEA Approval for Pasireotide
6. "FDA Approves Pasireotide for Cushing's Disease".
7. Tucker, Miriam E. FDA Approves Pasireotide for Treating Acromegaly, Medscape, December 17, 2014, Retrieved 2015-08-21