Pasireotide

Identification

Name
Pasireotide
Accession Number
DB06663
Type
Small Molecule
Groups
Approved
Description

Pasireotide is a synthetic long-acting cyclic hexapeptide with somatostatin-like activity. It is marketed as a diaspartate salt called Signifor, which is used in the treatment of Cushing's disease.

Structure
Thumb
Synonyms
  • cyclo((4R)-4-(2-aminoethylcarbamoyloxy)-L-prolyl-L-phenylglycyl-D-tryptophyl-L-lysyl-4-O-benzyl-L-tyrosyl-L- phenylalanyl-)
  • Pasireotida
  • Pasiréotide
  • Pasireotidum
External IDs
SOM 230 / SOM-230 / SOM230
Product Ingredients
IngredientUNIICASInChI Key
Pasireotide diaspartateI4P76SY3N4820232-50-6NEEFMPSSNFRRNC-HQUONIRXSA-N
Pasireotide pamoate04F55A7UZ3396091-79-5HSXBEUMRBMAVDP-QKXVGOHISA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SigniforInjection, powder, for suspension40 mgIntramuscularNovartis Europharm Limited2012-04-24Not applicableEu
SigniforSolution0.3 mgSubcutaneousNovartis2013-11-26Not applicableCanada
SigniforInjection, solution0.6 mgSubcutaneousNovartis Europharm Limited2012-04-24Not applicableEu
SigniforInjection, solution0.3 mgSubcutaneousNovartis Europharm Limited2012-04-24Not applicableEu
SigniforInjection.6 mg/mLSubcutaneousNovartis2012-12-14Not applicableUs
SigniforInjection, solution0.9 mgSubcutaneousNovartis Europharm Limited2012-04-24Not applicableEu
SigniforInjection, solution0.6 mgSubcutaneousNovartis Europharm Limited2012-04-24Not applicableEu
SigniforInjection.3 mg/mLSubcutaneousNovartis2012-12-14Not applicableUs
SigniforInjection, solution0.3 mgSubcutaneousNovartis Europharm Limited2012-04-24Not applicableEu
SigniforInjection, powder, for suspension20 mgIntramuscularNovartis Europharm Limited2012-04-24Not applicableEu
Categories
UNII
98H1T17066
CAS number
396091-73-9
Weight
Average: 1047.2062
Monoisotopic: 1046.50142376
Chemical Formula
C58H66N10O9
InChI Key
VMZMNAABQBOLAK-DBILLSOUSA-N
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
IUPAC Name
(3S,6R,9S,12S,15S,19R,20aS)-9-(4-aminobutyl)-15-benzyl-12-{[4-(benzyloxy)phenyl]methyl}-6-(1H-indol-3-ylmethyl)-1,4,7,10,13,16-hexaoxo-3-phenyl-icosahydropyrrolo[1,2-a]1,4,7,10,13,16-hexaazacyclooctadecan-19-yl N-(2-aminoethyl)carbamate
SMILES
NCCCC[[email protected]@H]1NC(=O)[[email protected]@H](CC2=CNC3=C2C=CC=C3)NC(=O)[[email protected]@H](NC(=O)[[email protected]@H]2C[[email protected]](CN2C(=O)[[email protected]](CC2=CC=CC=C2)NC(=O)[[email protected]](CC2=CC=C(OCC3=CC=CC=C3)C=C2)NC1=O)OC(=O)NCCN)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of Cushing’s disease, specifically for those patients whom pituitary surgery has not been curative or is not an option.

Structured Indications
Pharmacodynamics

Signifor® is an analogue of somatostatin that promotes reduced levels of cortisol secretion in Cushing's disease patients.

Mechanism of action

Pasireotide activates a broad spectrum of somatostatin receptors, exhbiting a much higher binding affinity for somatostatin receptors 1, 3, and 5 than octreotide in vitro, as well as a comparable binding affinity for somatostatin receptor 2. The binding and activation of the somatostatin receptors causes inhibition of ACTH secretion and results in reduced cortisol secretion in Cushing's disease patients. Also this agent is more potent than somatostatin in inhibiting the release of human growth hormone (HGH), glucagon, and insulin.

TargetActionsOrganism
USomatostatin receptor type 1Not AvailableHuman
USomatostatin receptor type 2Not AvailableHuman
USomatostatin receptor type 3Not AvailableHuman
USomatostatin receptor type 5Not AvailableHuman
Absorption

The peak plasma concentration of pasireotide occurs in 0.25-0.5 hours. After administration of single and multiple doses, there is dose-proportionoal increases in Cmax and AUC.

Volume of distribution

Pasireotide is widely distributed and has a volume of distribution of >100L.

Protein binding

Plasma protein binding is 88%.

Metabolism

Metabolism is minimal.

Route of elimination

Pasireotide is eliminated mostly by hepatic clearance (biliary excretion)(about 48%) with some minor renal clearance (about 7.63%).

Half life

The half-life is 12 hours.

Clearance

The clearance in healthy patient is ~7.6 L/h and in Cushing’s disease patients is ~3.8 L/h.

Toxicity

The most common toxic effects observed are hyperglycemia, cholelithiasis, diarrhea, nausea, headache, abdominal pain, fatigue, and diabetes mellitus.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Pasireotide.Investigational
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Pasireotide.Approved, Investigational
AcebutololAcebutolol may increase the bradycardic activities of Pasireotide.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Pasireotide.Investigational, Withdrawn
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Pasireotide.Experimental, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Pasireotide.Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Pasireotide.Approved
AmiodaronePasireotide may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AnagrelidePasireotide may increase the QTc-prolonging activities of Anagrelide.Approved
Arsenic trioxidePasireotide may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherPasireotide may increase the QTc-prolonging activities of Artemether.Approved
AsenapinePasireotide may increase the QTc-prolonging activities of Asenapine.Approved
AtenololAtenolol may increase the bradycardic activities of Pasireotide.Approved
AzithromycinPasireotide may increase the QTc-prolonging activities of Azithromycin.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Pasireotide.Investigational
BedaquilinePasireotide may increase the QTc-prolonging activities of Bedaquiline.Approved
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Pasireotide.Investigational
BendroflumethiazideBendroflumethiazide may increase the bradycardic activities of Pasireotide.Approved
BeractantPasireotide may increase the bradycardic activities of Beractant.Approved
BetaxololBetaxolol may increase the bradycardic activities of Pasireotide.Approved
BisoprololBisoprolol may increase the bradycardic activities of Pasireotide.Approved
BretyliumBretylium may increase the bradycardic activities of Pasireotide.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Pasireotide.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Pasireotide.Investigational, Withdrawn
CalfactantCalfactant may increase the bradycardic activities of Pasireotide.Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Pasireotide.Approved
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Pasireotide.Experimental
CarteololCarteolol may increase the bradycardic activities of Pasireotide.Approved
CarvedilolCarvedilol may increase the bradycardic activities of Pasireotide.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Pasireotide.Experimental
CeritinibPasireotide may increase the bradycardic activities of Ceritinib.Approved
ChloroquinePasireotide may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorpromazinePasireotide may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorpropamideChlorpropamide may increase the hypoglycemic activities of Pasireotide.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Pasireotide.Experimental
CiprofloxacinPasireotide may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisapridePasireotide may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramPasireotide may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinPasireotide may increase the QTc-prolonging activities of Clarithromycin.Approved
ClonidineClonidine may increase the bradycardic activities of Pasireotide.Approved
ClozapinePasireotide may increase the QTc-prolonging activities of Clozapine.Approved
CodeineThe metabolism of Codeine can be decreased when combined with Pasireotide.Approved, Illicit
CrizotinibPasireotide may increase the QTc-prolonging activities of Crizotinib.Approved
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Pasireotide.Approved, Investigational, Vet Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Pasireotide.Investigational
DexmedetomidineDexmedetomidine may increase the bradycardic activities of Pasireotide.Approved, Vet Approved
DigoxinDigoxin may increase the bradycardic activities of Pasireotide.Approved
DiltiazemDiltiazem may increase the bradycardic activities of Pasireotide.Approved
DisopyramidePasireotide may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilidePasireotide may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronPasireotide may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidonePasireotide may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DonepezilDonepezil may increase the bradycardic activities of Pasireotide.Approved
DronedaronePasireotide may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolPasireotide may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Pasireotide.Approved
EliglustatPasireotide may increase the QTc-prolonging activities of Eliglustat.Approved
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Pasireotide.Approved
ErythromycinPasireotide may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramPasireotide may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EsmololEsmolol may increase the bradycardic activities of Pasireotide.Approved
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Pasireotide.Approved, Investigational
FingolimodPasireotide may increase the bradycardic activities of Fingolimod.Approved, Investigational
FlecainidePasireotide may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluoxetinePasireotide may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolPasireotide may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
Gadobenic acidPasireotide may increase the QTc-prolonging activities of Gadobenic acid.Approved
GalantamineGalantamine may increase the bradycardic activities of Pasireotide.Approved
GemifloxacinPasireotide may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Pasireotide.Investigational, Withdrawn
GliclazideGliclazide may increase the hypoglycemic activities of Pasireotide.Approved
GlimepirideGlimepiride may increase the hypoglycemic activities of Pasireotide.Approved
GlipizideGlipizide may increase the hypoglycemic activities of Pasireotide.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Pasireotide.Approved, Investigational
GlyburideGlyburide may increase the hypoglycemic activities of Pasireotide.Approved
GoserelinPasireotide may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronPasireotide may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
GuanfacineGuanfacine may increase the bradycardic activities of Pasireotide.Approved, Investigational
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Pasireotide.Investigational
HaloperidolPasireotide may increase the QTc-prolonging activities of Haloperidol.Approved
IbutilidePasireotide may increase the QTc-prolonging activities of Ibutilide.Approved
IloperidonePasireotide may increase the QTc-prolonging activities of Iloperidone.Approved
Insulin AspartInsulin Aspart may increase the hypoglycemic activities of Pasireotide.Approved
Insulin DetemirInsulin Detemir may increase the hypoglycemic activities of Pasireotide.Approved
Insulin GlargineInsulin Glargine may increase the hypoglycemic activities of Pasireotide.Approved
Insulin GlulisineInsulin Glulisine may increase the hypoglycemic activities of Pasireotide.Approved
Insulin HumanInsulin Human may increase the hypoglycemic activities of Pasireotide.Approved, Investigational
Insulin LisproInsulin Lispro may increase the hypoglycemic activities of Pasireotide.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Pasireotide.Approved
IvabradinePasireotide may increase the bradycardic activities of Ivabradine.Approved
LabetalolLabetalol may increase the bradycardic activities of Pasireotide.Approved
LacosamidePasireotide may increase the atrioventricular blocking (AV block) activities of Lacosamide.Approved
LanreotidePasireotide may increase the hypoglycemic activities of Lanreotide.Approved
LenvatinibPasireotide may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolidePasireotide may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevobunololLevobunolol may increase the bradycardic activities of Pasireotide.Approved
LevofloxacinPasireotide may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Pasireotide.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Pasireotide.Approved
LopinavirPasireotide may increase the QTc-prolonging activities of Lopinavir.Approved
LucinactantLucinactant may increase the bradycardic activities of Pasireotide.Approved, Investigational
LumefantrinePasireotide may increase the QTc-prolonging activities of Lumefantrine.Approved
MecaserminMecasermin may increase the hypoglycemic activities of Pasireotide.Approved, Investigational
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Pasireotide.Approved
MethadonePasireotide may increase the QTc-prolonging activities of Methadone.Approved
MethyldopaMethyldopa may increase the bradycardic activities of Pasireotide.Approved
MetipranololMetipranolol may increase the bradycardic activities of Pasireotide.Approved
MetoprololMetoprolol may increase the bradycardic activities of Pasireotide.Approved, Investigational
MifepristoneMifepristone may increase the QTc-prolonging activities of Pasireotide.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Pasireotide.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Pasireotide.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Pasireotide.Approved, Investigational
MoxifloxacinPasireotide may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NadololNadolol may increase the bradycardic activities of Pasireotide.Approved
NateglinideNateglinide may increase the hypoglycemic activities of Pasireotide.Approved, Investigational
NebivololNebivolol may increase the bradycardic activities of Pasireotide.Approved, Investigational
NilotinibPasireotide may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
OctreotideOctreotide may increase the hypoglycemic activities of Pasireotide.Approved, Investigational
OfloxacinPasireotide may increase the QTc-prolonging activities of Ofloxacin.Approved
OndansetronPasireotide may increase the QTc-prolonging activities of Ondansetron.Approved
PaliperidonePasireotide may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatPasireotide may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PazopanibPasireotide may increase the QTc-prolonging activities of Pazopanib.Approved
PegvisomantThe risk or severity of adverse effects can be increased when Pasireotide is combined with Pegvisomant.Approved
PenbutololPenbutolol may increase the bradycardic activities of Pasireotide.Approved, Investigational
PentamidinePasireotide may increase the QTc-prolonging activities of Pentamidine.Approved
PerflutrenPasireotide may increase the QTc-prolonging activities of Perflutren.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Pasireotide.Approved, Investigational, Withdrawn
PimozidePasireotide may increase the QTc-prolonging activities of Pimozide.Approved
PindololPindolol may increase the bradycardic activities of Pasireotide.Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Pasireotide.Approved, Investigational
Poractant alfaPasireotide may increase the bradycardic activities of Poractant alfa.Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Pasireotide.Approved, Investigational
PrimaquinePasireotide may increase the QTc-prolonging activities of Primaquine.Approved
ProcainamidePasireotide may increase the QTc-prolonging activities of Procainamide.Approved
PromazinePasireotide may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenonePasireotide may increase the QTc-prolonging activities of Propafenone.Approved
PropranololPropranolol may increase the bradycardic activities of Pasireotide.Approved, Investigational
QuetiapinePasireotide may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidinePasireotide may increase the QTc-prolonging activities of Quinidine.Approved
QuininePasireotide may increase the QTc-prolonging activities of Quinine.Approved
RepaglinideRepaglinide may increase the hypoglycemic activities of Pasireotide.Approved, Investigational
RivastigmineRivastigmine may increase the bradycardic activities of Pasireotide.Approved, Investigational
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Pasireotide.Approved, Investigational
RuxolitinibRuxolitinib may increase the bradycardic activities of Pasireotide.Approved
SaquinavirPasireotide may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Pasireotide.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Pasireotide.Approved, Investigational
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Pasireotide.Investigational
SotalolPasireotide may increase the QTc-prolonging activities of Sotalol.Approved
SufentanilSufentanil may increase the bradycardic activities of Pasireotide.Approved, Investigational
SulfadiazineSulfadiazine may increase the hypoglycemic activities of Pasireotide.Approved, Vet Approved
SulfamethoxazoleSulfamethoxazole may increase the hypoglycemic activities of Pasireotide.Approved
SulfisoxazolePasireotide may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Pasireotide.Approved, Investigational
SunitinibSunitinib may increase the hypoglycemic activities of Pasireotide.Approved, Investigational
TelavancinPasireotide may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinPasireotide may increase the QTc-prolonging activities of Telithromycin.Approved
TetrabenazinePasireotide may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThioridazinePasireotide may increase the QTc-prolonging activities of Thioridazine.Approved, Withdrawn
TimololTimolol may increase the bradycardic activities of Pasireotide.Approved
TizanidineTizanidine may increase the bradycardic activities of Pasireotide.Approved
TofacitinibTofacitinib may increase the bradycardic activities of Pasireotide.Approved, Investigational
TolazamideTolazamide may increase the hypoglycemic activities of Pasireotide.Approved
TolbutamideTolbutamide may increase the hypoglycemic activities of Pasireotide.Approved
ToremifenePasireotide may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Pasireotide.Investigational, Withdrawn
VandetanibPasireotide may increase the QTc-prolonging activities of Vandetanib.Approved
VemurafenibPasireotide may increase the QTc-prolonging activities of Vemurafenib.Approved
VerapamilVerapamil may increase the bradycardic activities of Pasireotide.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Pasireotide.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Pasireotide.Approved, Investigational
ZiprasidonePasireotide may increase the QTc-prolonging activities of Ziprasidone.Approved
ZuclopenthixolPasireotide may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
  • Since Signifor® is administered subcutaneously, food has no effect.

References

Synthesis Reference

Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G: SOM230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (SRIF) receptor binding and a unique antisecretory profile. Eur J Endocrinol. 2002 May;146(5):707-16.

General References
  1. Weckbecker G, Briner U, Lewis I, Bruns C: SOM230: a new somatostatin peptidomimetic with potent inhibitory effects on the growth hormone/insulin-like growth factor-I axis in rats, primates, and dogs. Endocrinology. 2002 Oct;143(10):4123-30. [PubMed:12239124]
External Links
KEGG Drug
D10147
PubChem Compound
9941444
PubChem Substance
175427082
ChemSpider
8117062
ChEBI
72312
ChEMBL
CHEMBL3349607
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pasireotide
ATC Codes
H01CB05 — Pasireotide
AHFS Codes
  • 68:29.04 — Somatostatin Agonists
FDA label
Download (567 KB)
MSDS
Download (567 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentNeuroendocrine Tumors2
1CompletedNot AvailableAlcoholism / Hepatic Cirrhosis1
1CompletedTreatmentAcromegaly / Carcinoid Tumors1
1CompletedTreatmentCarcinoid Tumors / Neuroendocrine Tumors / Progressive Neuroendocrine Tumors of pancreatic origin1
1CompletedTreatmentImpaired Renal Function1
1CompletedTreatmentMalignant Neoplasm of Pancreas1
1CompletedTreatmentNeuroendocrine Tumors1
1, 2Active Not RecruitingTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
1, 2Active Not RecruitingTreatmentCastration Resistant Prostate Cancer (CRPC)1
2Active Not RecruitingTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD) / Autosomal Dominant Polycystic Liver Disease / Polycystic Liver Disease (PLD) / Somatostatin Analogs1
2Active Not RecruitingTreatmentCarcinoid Tumors / Neuroendocrine Tumors1
2Active Not RecruitingTreatmentThyroid Cancers1
2CompletedPreventionCancer, Breast1
2CompletedTreatmentAcromegaly1
2CompletedTreatmentAdvanced Adult Hepatocellular Carcinoma1
2CompletedTreatmentAngiodysplasia1
2CompletedTreatmentCarcinoid Tumors1
2CompletedTreatmentCushing's Disease1
2CompletedTreatmentDumping Syndrome Patients1
2CompletedTreatmentHepatocellular,Carcinoma1
2CompletedTreatmentHyperglycemias1
2CompletedTreatmentLocal Recurrent Thymoma / Primary Inoperable Thymoma1
2CompletedTreatmentPostoperative Dumping Syndrome1
2Not Yet RecruitingTreatmentCongenital Hyperinsulinism / Hyperinsulinism / Insulinoma1
2Not Yet RecruitingTreatmentEnterostomy1
2RecruitingTreatmentACTH-producing pituitary tumour / Pituitary Neoplasms1
2RecruitingTreatmentCluster Headache - Episodic and Chronic1
2RecruitingTreatmentEctopic Corticotropin Syndrome1
2RecruitingTreatmentHaematological Malignancies1
2TerminatedTreatmentCancers1
2TerminatedTreatmentCastrate Resistant Prostate Cancer (CRPC) / Chemotherapy Naive Prostate Cancer / Prostate Cancer1
2TerminatedTreatmentEctopic Corticotropin Syndrome / Nelson Syndrome / Neoplasms, Pancreatic / Pituitary Neoplasms1
2TerminatedTreatmentGonadotroph Adenomas1
2TerminatedTreatmentNelson Syndrome1
2Unknown StatusTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
2WithdrawnTreatmentMultiple Myeloma (MM)1
2WithdrawnTreatmentMultiple Myeloma (MM) / Multiple Myeloma in Relapse1
2, 3CompletedTreatmentNon-functioning Pituitary Adenomas / Prolactinomas1
3Active Not RecruitingTreatmentAcromegaly2
3CompletedTreatmentAcromegaly1
3CompletedTreatmentCushing's Disease1
3CompletedTreatmentMalignant Neoplasm of Pancreas1
3CompletedTreatmentSymptomatic Refractory Resistant Carcinoid Disease1
4Active Not RecruitingTreatmentAcromegaly1
4CompletedTreatmentCushing's Disease1
4Enrolling by InvitationTreatmentBMI >30 kg/m2 / General Surgery / Hypoglycemia1
4RecruitingPreventionNeoplasms, Pancreatic / Pancreatic Fistula1
4RecruitingTreatmentAcromegaly / Cushing's Disease / Dumping Syndrome / Ectopic ACTH Secreting (EAS) Tumors / Melanoma Negative for bRAF / Melanoma Negative for nRAS / Neuroendocrine Tumors / Pituitary Neoplasms / Prostate Cancer1
4WithdrawnTreatmentGastro-enteropancreatic Neuroendocrine Tumor1
Not AvailableAvailableNot AvailableCongenital Hyperinsulinism1
Not AvailableRecruitingNot AvailableCushings Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InjectionSubcutaneous.3 mg/mL
InjectionSubcutaneous.6 mg/mL
InjectionSubcutaneous.9 mg/mL
Injection, powder, for suspensionIntramuscular20 mg
Injection, powder, for suspensionIntramuscular40 mg
Injection, powder, for suspensionIntramuscular60 mg
Injection, solutionSubcutaneous0.3 mg
Injection, solutionSubcutaneous0.6 mg
Injection, solutionSubcutaneous0.9 mg
SolutionSubcutaneous0.3 mg
SolutionSubcutaneous0.6 mg
SolutionSubcutaneous0.9 mg
Kit
Kit; powder, for suspensionIntramuscular20 mg
Kit; powder, for suspensionIntramuscular40 mg
Kit; powder, for suspensionIntramuscular60 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6225284No1996-06-282016-06-28Us
US7473761No2005-07-292025-07-29Us
US8299209No2005-12-272025-12-27Us
US8822637No2003-08-062023-08-06Us
US7759308No2006-10-252026-10-25Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble in water.From The Merck Index.
Predicted Properties
PropertyValueSource
Water Solubility0.00203 mg/mLALOGPS
logP3.03ALOGPS
logP2.68ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)10.43ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area281.2 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity286.66 m3·mol-1ChemAxon
Polarizability111.29 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9926
Blood Brain Barrier-0.5389
Caco-2 permeable-0.8325
P-glycoprotein substrateSubstrate0.656
P-glycoprotein inhibitor INon-inhibitor0.6717
P-glycoprotein inhibitor IINon-inhibitor0.6843
Renal organic cation transporterNon-inhibitor0.777
CYP450 2C9 substrateNon-substrate0.8878
CYP450 2D6 substrateNon-substrate0.758
CYP450 3A4 substrateSubstrate0.521
CYP450 1A2 substrateNon-inhibitor0.7641
CYP450 2C9 inhibitorNon-inhibitor0.7676
CYP450 2D6 inhibitorNon-inhibitor0.8704
CYP450 2C19 inhibitorInhibitor0.5307
CYP450 3A4 inhibitorInhibitor0.575
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6561
Ames testNon AMES toxic0.7722
CarcinogenicityNon-carcinogens0.8568
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4609 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8711
hERG inhibition (predictor II)Inhibitor0.7476
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Macrolactams / 3-alkylindoles / Alpha amino acids and derivatives / Phenol ethers / Phenoxy compounds / Alkyl aryl ethers / Substituted pyrroles / Pyrrolidines / Heteroaromatic compounds
show 11 more
Substituents
Alpha-oligopeptide / Cyclic alpha peptide / Macrolactam / Alpha-amino acid or derivatives / 3-alkylindole / Indole or derivatives / Indole / Phenoxy compound / Phenol ether / Alkyl aryl ether
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
homodetic cyclic peptide, peptide hormone (CHEBI:72312)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Somatostatin receptor activity
Specific Function
Receptor for somatostatin with higher affinity for somatostatin-14 than -28. This receptor is coupled via pertussis toxin sensitive G proteins to inhibition of adenylyl cyclase. In addition it stim...
Gene Name
SSTR1
Uniprot ID
P30872
Uniprot Name
Somatostatin receptor type 1
Molecular Weight
42685.77 Da
References
  1. Zatelli MC, Piccin D, Vignali C, Tagliati F, Ambrosio MR, Bondanelli M, Cimino V, Bianchi A, Schmid HA, Scanarini M, Pontecorvi A, De Marinis L, Maira G, degli Uberti EC: Pasireotide, a multiple somatostatin receptor subtypes ligand, reduces cell viability in non-functioning pituitary adenomas by inhibiting vascular endothelial growth factor secretion. Endocr Relat Cancer. 2007 Mar;14(1):91-102. [PubMed:17395978]
  2. Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G: SOM230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (SRIF) receptor binding and a unique antisecretory profile. Eur J Endocrinol. 2002 May;146(5):707-16. [PubMed:11980628]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Somatostatin receptor activity
Specific Function
Receptor for somatostatin-14 and -28. This receptor is coupled via pertussis toxin sensitive G proteins to inhibition of adenylyl cyclase. In addition it stimulates phosphotyrosine phosphatase and ...
Gene Name
SSTR2
Uniprot ID
P30874
Uniprot Name
Somatostatin receptor type 2
Molecular Weight
41332.37 Da
References
  1. Zatelli MC, Piccin D, Vignali C, Tagliati F, Ambrosio MR, Bondanelli M, Cimino V, Bianchi A, Schmid HA, Scanarini M, Pontecorvi A, De Marinis L, Maira G, degli Uberti EC: Pasireotide, a multiple somatostatin receptor subtypes ligand, reduces cell viability in non-functioning pituitary adenomas by inhibiting vascular endothelial growth factor secretion. Endocr Relat Cancer. 2007 Mar;14(1):91-102. [PubMed:17395978]
  2. Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G: SOM230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (SRIF) receptor binding and a unique antisecretory profile. Eur J Endocrinol. 2002 May;146(5):707-16. [PubMed:11980628]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Somatostatin receptor activity
Specific Function
Receptor for somatostatin-14 and -28. This receptor is coupled via pertussis toxin sensitive G proteins to inhibition of adenylyl cyclase.
Gene Name
SSTR3
Uniprot ID
P32745
Uniprot Name
Somatostatin receptor type 3
Molecular Weight
45846.995 Da
References
  1. Zatelli MC, Piccin D, Vignali C, Tagliati F, Ambrosio MR, Bondanelli M, Cimino V, Bianchi A, Schmid HA, Scanarini M, Pontecorvi A, De Marinis L, Maira G, degli Uberti EC: Pasireotide, a multiple somatostatin receptor subtypes ligand, reduces cell viability in non-functioning pituitary adenomas by inhibiting vascular endothelial growth factor secretion. Endocr Relat Cancer. 2007 Mar;14(1):91-102. [PubMed:17395978]
  2. Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G: SOM230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (SRIF) receptor binding and a unique antisecretory profile. Eur J Endocrinol. 2002 May;146(5):707-16. [PubMed:11980628]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Somatostatin receptor activity
Specific Function
Receptor for somatostatin 28 and to a lesser extent for somatostatin-14. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Increases cell growth inhibition act...
Gene Name
SSTR5
Uniprot ID
P35346
Uniprot Name
Somatostatin receptor type 5
Molecular Weight
39201.925 Da
References
  1. Zatelli MC, Piccin D, Vignali C, Tagliati F, Ambrosio MR, Bondanelli M, Cimino V, Bianchi A, Schmid HA, Scanarini M, Pontecorvi A, De Marinis L, Maira G, degli Uberti EC: Pasireotide, a multiple somatostatin receptor subtypes ligand, reduces cell viability in non-functioning pituitary adenomas by inhibiting vascular endothelial growth factor secretion. Endocr Relat Cancer. 2007 Mar;14(1):91-102. [PubMed:17395978]
  2. Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G: SOM230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (SRIF) receptor binding and a unique antisecretory profile. Eur J Endocrinol. 2002 May;146(5):707-16. [PubMed:11980628]

Drug created on March 19, 2008 10:46 / Updated on November 14, 2017 08:11