Pasireotide
Identification
- Name
- Pasireotide
- Accession Number
- DB06663
- 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pasireotide (DB06663)
- Weight
- Average: 1047.2062
Monoisotopic: 1046.50142376 - Chemical Formula
- C58H66N10O9
- Synonyms
- cyclo((4R)-4-(2-aminoethylcarbamoyloxy)-L-prolyl-L-phenylglycyl-D-tryptophyl-L-lysyl-4-O-benzyl-L-tyrosyl-L- phenylalanyl-)
- Pasireotida
- Pasiréotide
- Pasireotide
- Pasireotidum
- External IDs
- SOM 230
- SOM-230
- SOM230
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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism USomatostatin receptor type 1 Not Available Humans USomatostatin receptor type 2 Not Available Humans USomatostatin receptor type 3 Not Available Humans USomatostatin receptor type 5 Not Available Humans - 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.
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbiraterone The metabolism of Abiraterone can be decreased when combined with Pasireotide. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Pasireotide. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Pasireotide. Acebutolol The risk or severity of QTc prolongation can be increased when Pasireotide is combined with Acebutolol. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Pasireotide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Pasireotide. Acrivastine The risk or severity of QTc prolongation can be increased when Pasireotide is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Pasireotide is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Pasireotide. Albendazole The metabolism of Albendazole can be decreased when combined with Pasireotide. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Pasireotide acetate 662X0VFR9L 396091-76-2 WFKFNBBHVLMWQH-QKXVGOHISA-N Pasireotide diaspartate I4P76SY3N4 820232-50-6 NEEFMPSSNFRRNC-HQUONIRXSA-N Pasireotide pamoate 04F55A7UZ3 396091-79-5 HSXBEUMRBMAVDP-QKXVGOHISA-N - International/Other Brands
- Signifor / Signifor LAR
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataSignifor Injection, solution 0.3 mg Subcutaneous Novartis Europharm Limited 2012-04-24 Not applicable EU 
Signifor Injection, solution 0.9 mg Subcutaneous Novartis Europharm Limited 2012-04-24 Not applicable EU Signifor Injection, powder, for suspension 40 mg Intramuscular Novartis Europharm Limited 2012-04-24 Not applicable EU Signifor Solution 0.6 mg Subcutaneous Novartis 2013-11-26 Not applicable Canada 
Signifor Injection 0.6 mg/1mL Subcutaneous RECORDATI RARE DISEASES, INC. 2012-12-14 Not applicable US 
Signifor Injection, solution 0.3 mg Subcutaneous Novartis Europharm Limited 2012-04-24 Not applicable EU Signifor Injection, solution 0.6 mg Subcutaneous Novartis Europharm Limited 2012-04-24 Not applicable EU Signifor Injection, solution 0.9 mg Subcutaneous Novartis Europharm Limited 2012-04-24 Not applicable EU Signifor Injection, powder, for suspension 60 mg Intramuscular Novartis Europharm Limited 2012-04-24 Not applicable EU Signifor Injection 0.6 mg/1mL Subcutaneous Novartis Pharmaceuticals Corporation 2012-12-14 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- H01CB05 — Pasireotide
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Bradycardia-Causing Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Hypoglycemia-Associated Agents
- Hypothalamic Hormones
- Nerve Tissue Proteins
- Neuropeptides
- Pancreatic Hormones
- Peptide Hormones
- Peptides
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormone Release Inhibiting Hormones
- Potential QTc-Prolonging Agents
- Proteins
- QTc Prolonging Agents
- Somatostatin Agonists
- Somatostatin and Analogues
- Somatostatin Receptor Agonists
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Chemical TaxonomyProvided by Classyfire
- 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
- 3-alkylindole / Alkyl aryl ether / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbamic acid ester show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- homodetic cyclic peptide, peptide hormone (CHEBI:72312)
Chemical Identifiers
- UNII
- 98H1T17066
- CAS number
- 396091-73-9
- 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
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
- 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
- 1364105
- ChEBI
- 72312
- ChEMBL
- CHEMBL3349607
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Pasireotide
- AHFS Codes
- 68:29.04 — Somatostatin Agonists
- FDA label
- Download (567 KB)
- MSDS
- Download (567 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Prevention Neoplasms, Pancreatic / Pancreatic Fistula 1 4 Active Not Recruiting Treatment Acromegaly / Cushing's Disease / Dumping Syndrome / Ectopic ACTH Secreting (EAS) Tumors / Melanoma Negative for bRAF / Melanoma Negative for nRAS / Neuroendocrine Tumors / Pituitary Neoplasms / Prostate Cancer 1 4 Completed Supportive Care Acromegaly / Cushing's Disease 1 4 Completed Treatment BMI >30 kg/m2 / General Surgery / Hypoglycemia 1 4 Completed Treatment Cushing's Disease 1 4 Unknown Status Treatment Acromegaly 1 4 Unknown Status Treatment Reactive Hypoglycemia 1 4 Withdrawn Treatment Gastro-enteropancreatic Neuroendocrine Tumor 1 3 Completed Treatment Acromegaly 3 3 Completed Treatment Cushing's Disease 3
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Subcutaneous 0.3 mg/1mL Injection Subcutaneous 0.6 mg/1mL Injection Subcutaneous 0.9 mg/1mL Injection, powder, for suspension Intramuscular 10 MG Injection, powder, for suspension Intramuscular 20 mg Injection, powder, for suspension Intramuscular 30 MG Injection, powder, for suspension Intramuscular 40 mg Injection, powder, for suspension Intramuscular 60 mg Injection, solution 300 mcg/1mL Injection, solution 600 mcg/1mL Injection, solution 900 mcg/1mL Injection, solution Cutaneous; Parenteral 0.3 MG Injection, solution Cutaneous; Parenteral 0.6 MG Injection, solution Cutaneous; Parenteral 0.9 MG Injection, solution Subcutaneous 0.3 mg Injection, solution Subcutaneous 0.6 mg Injection, solution Subcutaneous 0.9 mg Solution Subcutaneous 0.3 mg Solution Subcutaneous 0.6 mg Solution Subcutaneous 0.9 mg Injection 0.375 mg/ml Injection 0.6 mg/1ml Injection 0.9 mg/1ml Injection, powder, for suspension 40 mg Injection, powder, for suspension 60 mg Injection, powder, for suspension, extended release; kit Intramuscular 10 mg Injection, powder, for suspension, extended release; kit Intramuscular 20 mg Injection, powder, for suspension, extended release; kit Intramuscular 30 mg Injection, powder, for suspension, extended release; kit Intramuscular 40 mg Injection, powder, for suspension, extended release; kit Intramuscular 60 mg Kit Intramuscular 5 mg/1mL Powder Injection, powder, for suspension Intramuscular 27.42 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6225284 No 2001-05-01 2016-06-28 US US7473761 No 2009-01-06 2025-07-29 US US8299209 No 2012-10-30 2025-12-27 US US8822637 No 2014-09-02 2023-08-06 US US7759308 No 2010-07-20 2026-10-25 US US9351923 No 2016-05-31 2028-05-23 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble in water. From The Merck Index. - Predicted Properties
Property Value Source Water Solubility 0.00203 mg/mL ALOGPS logP 3.03 ALOGPS logP 2.68 ChemAxon logS -5.7 ALOGPS pKa (Strongest Acidic) 9.09 ChemAxon pKa (Strongest Basic) 10.43 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 281.2 Å2 ChemAxon Rotatable Bond Count 18 ChemAxon Refractivity 286.66 m3·mol-1 ChemAxon Polarizability 111.29 Å3 ChemAxon Number of Rings 8 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9926 Blood Brain Barrier - 0.5389 Caco-2 permeable - 0.8325 P-glycoprotein substrate Substrate 0.656 P-glycoprotein inhibitor I Non-inhibitor 0.6717 P-glycoprotein inhibitor II Non-inhibitor 0.6843 Renal organic cation transporter Non-inhibitor 0.777 CYP450 2C9 substrate Non-substrate 0.8878 CYP450 2D6 substrate Non-substrate 0.758 CYP450 3A4 substrate Substrate 0.521 CYP450 1A2 substrate Non-inhibitor 0.7641 CYP450 2C9 inhibitor Non-inhibitor 0.7676 CYP450 2D6 inhibitor Non-inhibitor 0.8704 CYP450 2C19 inhibitor Inhibitor 0.5307 CYP450 3A4 inhibitor Inhibitor 0.575 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6561 Ames test Non AMES toxic 0.7722 Carcinogenicity Non-carcinogens 0.8568 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4609 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8711 hERG inhibition (predictor II) Inhibitor 0.7476
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- 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
- Humans
- 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
- 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]
- 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
- Humans
- 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
- 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]
- 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
- Humans
- 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
- 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]
- 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]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
Drug created on March 19, 2008 10:46 / Updated on October 26, 2020 22:41
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