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Details

Stereochemistry ABSOLUTE
Molecular Formula C58H66N10O9
Molecular Weight 1047.2062
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PASIREOTIDE

SMILES

NCCCC[C@@H]1NC(=O)[C@@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H](CC6=CC=C(OCC7=CC=CC=C7)C=C6)NC1=O)OC(=O)NCCN)C8=CC=CC=C8

InChI

InChIKey=VMZMNAABQBOLAK-DBILLSOUSA-N
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

HIDE SMILES / InChI

Molecular Formula C58H66N10O9
Molecular Weight 1047.2062
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Pasireotide is a synthetic long-acting cyclic hexapeptide with somatostatin-like activity. It is marketed as a diaspartate salt called Signifor, indicated for the treatment of adult patients with Cushing’s disease for whom pituitary surgery is not an option or has not been curative. SIGNIFOR is an injectable cyclohexapeptide somatostatin analogue. Pasireotide exerts its pharmacological activity via binding to somatostatin receptors (ssts). Pasireotide binds and activates the hsst receptors resulting in inhibition of ACTH secretion, which leads to decreased cortisol secretion.

CNS Activity

Originator

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
SOM230: a new somatostatin peptidomimetic with potent inhibitory effects on the growth hormone/insulin-like growth factor-I axis in rats, primates, and dogs.
2002 Oct
Functional activity of the multiligand analog SOM230 at human recombinant somatostatin receptor subtypes supports its usefulness in neuroendocrine tumors.
2004
Medicinal chemistry of somatostatin analogs leading to the DTPA and DOTA conjugates of the multi-receptor-ligand SOM230.
2005
New aspects in the diagnosis and treatment of Cushing disease.
2006
Agonist-biased signaling at the sst2A receptor: the multi-somatostatin analogs KE108 and SOM230 activate and antagonize distinct signaling pathways.
2010 Jan
Ligand-dependent mechanisms of sst2A receptor trafficking: role of site-specific phosphorylation and receptor activation in the actions of biased somatostatin agonists.
2011 Jun
Involvement of bone morphogenetic protein activity in somatostatin actions on ovarian steroidogenesis.
2013 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Recommended initial dosage is either 0.6 mg or 0.9 mg by subcutaneous injection twice a day; recommended dosage range is 0.3 mg to 0.9 mg twice a day
Route of Administration: subcutaneous injection
In Vitro Use Guide
Primary cultures from normal human and rat adrenals were incubated with 10-100 nM Pasireotide with and without 10nM ACTH. Dose-response studies with 1 nM-1 uM Pasireotide were performed on rat adrenals. Cortisol/corticosterone levels in medium were measured after 4 and 24h. Pasireotide (10nM) significantly increased corticosteroid levels after 24h incubation in both human (36.4 ± 0.43 ng/well vs 27.7 ± 3.17 ng/well, p<0.05) and rat (16.2 ± 1.16 ng/well vs 11.6 ± 0.92 ng/well p<0.05) adrenals; lesser effects were observed with 100 nM Pasireotide (33.4 ± 2.59 ng/well vs 27.7 ± 3.17 ng/well p<0.05; 13.4 ± 0.82 ng/well vs 11.6 ± 0.92 ng/well, N.S. vs baseline secretion for human and rat adrenals, respectively). Dose-response curves confirmed maximal effect at 10nM Pasireotide.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:51:40 UTC 2019
Edited
by admin
on Mon Oct 21 20:51:40 UTC 2019
Record UNII
98H1T17066
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PASIREOTIDE
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
PASIREOTIDE [INN]
Common Name English
CYCLO((4R)-4-(2-AMINOETHYLCARBAMOYLOXY)-L-PROLYL-L-PHENYLGLYCYL-D-TRYPTOPHYL-L-LYSYL-4-O-BENZYL-L-TYROSYL-L-PHENYLALANYL-)
Common Name English
SOM230
Code English
PASIREOTIDE [VANDF]
Common Name English
PASIREOTIDE [MI]
Common Name English
PASIREOTIDE [MART.]
Common Name English
SOM 230
Code English
PASIREOTIDE [WHO-DD]
Common Name English
PASIREOTIDE [USAN]
Common Name English
SOM-230
Code English
Classification Tree Code System Code
WHO-VATC QH01CB05
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
NCI_THESAURUS C62799
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
EU-Orphan Drug EU/3/09/671
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
FDA ORPHAN DRUG 188804
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
FDA ORPHAN DRUG 288709
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
NDF-RT N0000175904
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
EMA ASSESSMENT REPORTS SIGNIFOR (AUTHORIZED: ACROMEGALY, PITUITARY ACTH HYPERSECRETION)
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
WHO-ATC H01CB05
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
FDA ORPHAN DRUG 288609
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
Code System Code Type Description
MESH
C517782
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
DRUG BANK
DB06663
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
PUBCHEM
9941444
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
IUPHAR
2018
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
CAS
396091-73-9
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
EVMPD
SUB31564
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
INN
8384
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
ChEMBL
CHEMBL3039583
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
NCI_THESAURUS
C69131
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
WIKIPEDIA
PASIREOTIDE
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY
MERCK INDEX
M8425
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY Merck Index
RXCUI
1364105
Created by admin on Mon Oct 21 20:51:40 UTC 2019 , Edited by admin on Mon Oct 21 20:51:40 UTC 2019
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> NON-SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> NON-SUBSTRATE
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> NON-SUBSTRATE
in vitro study results indicate that pasireotide is not a substrate, inhibitor, or inducer for metabolic isozymes including UGT1A1 particularly at the proposed dosing range.
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> NON-SUBSTRATE
TRANSPORTER -> NON-SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC SC INJECTION

Biological Half-life PHARMACOKINETIC