Identification

Name
Octreotide
Accession Number
DB00104
Description

Acromegaly is a disorder caused by excess growth hormone (GH), increasing the growth of body tissues and causing metabolic dysfunction.6 In most cases, it results from an anterior pituitary growth hormone-releasing tumor. Typically, the feet, hands, and face grow abnormally large; organomegaly and insulin resistance may also occur. Acromegaly is a life-threatening disease requiring life-long management.6

Octreotide is a long-acting drug with pharmacologic activities that mimic those of the natural hormone, somatostatin, which inhibits the secretion of growth hormone.8 Additionally, it is used for the treatment of acromegaly and symptoms arising from various tumors, including carcinoid tumors and vasoactive intestinal tumors (VIPomas).8 In the past, octreotide has been administered solely by injection. On June 26, 2020, the first approved delayed-release oral somatostatin analog, Mycapssa, received FDA approval for the long term maintenance treatment of acromegaly. This drug was developed by Chiasma Inc.5,7,10

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 1019.25
Monoisotopic: 1018.440480713
Chemical Formula
C49H66N10O10S2
Synonyms
  • Octreotida
  • Octreotide
  • Octreotidum
  • Octrotide
External IDs
  • DRG-0115
  • SMS 201-995
  • SMS-201-995
  • SMS995-AAA

Pharmacology

Indication

Octreotide by injection is used for the treatment of acromegaly and the reduction of flushing and diarrhea symptoms related to carcinoid tumors and/or vasoactive intestinal peptide (VIPoma) tumors.8 The delayed-release oral formulation is used for the long-term treatment of acromegaly in patients who tolerate and respond adequately to injectable octreotide and lanreotide.7

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Octreotide mimics the naturally occurring hormone known as somatostatin. Like somatostatin, it demonstrates activity against growth hormone and glucagon, treating the disordered tissue growth and insulin regulation in patients with acromegaly.6,8 In addition, octreotide relieves the flushing and diarrhea associated with gastrointestinal tumors by reducing splanchnic blood flow4 and various gastrointestinal hormones associated with diarrhea.2

Product labeling warns that octreotide may reduce gallbladder contractility, bile secretion, and the release of thyroid-stimulating hormone (TSH) in healthy volunteers.8 In addition, reports of decreased vitamin B12 in patients treated with octreotide have been made. Ensure to monitor vitamin B12 levels in patients taking octreotide.10

Mechanism of action

Octreotide binds to somatostatin receptors coupled to phospholipase C through G proteins and leads to smooth muscle contraction in the blood vessels.9 Downstream effects that stimulate phospholipase C, the production of 1, 4,5-inositol triphosphate, and action on the L-type calcium channels lead to the inhibition of growth hormone, treating the various growth-hormone and metabolic effects of acromegaly.9

Octreotide's suppression of luteinizing hormone (LH)3, reduction in splanchnic blood flow4, and inhibition of serotonin, gastrin, vasoactive intestinal peptide, secretin, motilin, and pancreatic polypeptide provide relief for the gastrointestinal and flushing symptoms of carcinoid and/or VIPoma tumors.2

TargetActionsOrganism
ASomatostatin receptor
agonist
Humans
Absorption

After a subcutaneous dose, octreotide is absorbed completely upon administration.2,8 After the administration of an oral delayed-release capsule, peak concentrations were found to be 33% lower than after subcutaneous administration.10 The Cmax was attained at 1.67–2.5 hours after oral administration versus 30 minutes for the subcutaneous route. At 20 mg twice a day in patients with acromegaly, peak concentration was 2.5 mg/nL versus 5.30 ng/mL at 40 mg twice a day.10 AUC increases in proportion with the dose, regardless of the route.2,10

Volume of distribution

In a pharmacokinetic study, the volume of distribution was 13.6 L in healthy volunteers.10 One pharmacokinetic study revealed a volume of distribution ranging from 18.1-30.4L after intravenous administration in healthy volunteers.2

Protein binding

Approximately 65% of the dose is bound in the plasma to lipoproteins and albumin.8,10

Metabolism

Octreotide has been reported to be heavily metabolized in the liver.2

Route of elimination

About 32% of an oral octreotide dose is excreted into the urine 10 and 30-40% is excreted by the liver into the feces.2. About 11% of the unchanged parent drug is found in the urine, and 2% of the unchanged parent drug can be recovered in the feces.2

Half-life

After a subcutaneous dose, the plasma half-life is estimated to be 0.2 hours. The average elimination half-lives for subcutaneous and oral administration ranged from 2.3 - 2.7 hours and did not differ significantly.10 One pharmacokinetic study revealed a plasma half-life ranging from 72-113 minutes.2

Clearance

The total body clearance of octreotide is 7-10 L/h.10 One pharmacokinetic study revealed a total body clearance of 11.4 L/h.2

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

There is limited information regarding cases of octreotide overdose aside from case reports of an overdose with injectable octreotide. The dose ranged from 2.4 mg/day to 6 mg/day administered by continuous infusion or subcutaneous administration of 1.5 mg three times daily. Effects of an overdose with octreotide may include hypotension, brain hypoxia, arrhythmia, cardiac arrest, lactic acidosis, pancreatitis, hepatomegaly, diarrhea, flushing, lethargy, and weakness.10

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.
DrugInteraction
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Octreotide.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Octreotide.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Octreotide.
AcebutololThe serum concentration of the active metabolites of Acebutolol can be increased when Acebutolol is used in combination with Octreotide.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Octreotide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Octreotide.
AcrivastineThe risk or severity of QTc prolongation can be increased when Octreotide is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Octreotide is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Octreotide is combined with Ajmaline.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Octreotide.
Additional Data Available
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Food Interactions
  • Take on an empty stomach. The oral capsules should be taken on an empty stomach. Food reduces oral octreotide absorption by 90%.
  • Take with or without food. Octreotide injections may be taken with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Octreotide acetate75R0U2568I79517-01-4XQEJFZYLWPSJOV-XJQYZYIXSA-N
Octreotide pamoateMWH8YQ1AIO135467-16-2KFWJVABDRRDUHY-XJQYZYIXSA-N
International/Other Brands
Sandostatin LAR (Novartis Pharmaceuticals)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BYNFEZIA PenInjection2.5 mg/1mLSubcutaneousSun Pharmaceutical Industries, Inc.2020-04-29Not applicableUS flag
MycapssaCapsule, delayed release20 mg/1OralChiasma Inc.2020-07-06Not applicableUS flag
OcphylSolutionIntravenous; SubcutaneousPendopharm Division Of Pharmascience Inc2014-05-122018-06-14Canada flag
OcphylSolutionIntravenous; SubcutaneousPendopharm Division Of Pharmascience Inc2014-05-122018-06-14Canada flag
OcphylSolutionIntravenous; SubcutaneousPendopharm Division Of Pharmascience Inc2014-05-122018-06-14Canada flag
Octreotide AcetateInjection, solution200 ug/1mLIntravenous; SubcutaneousSandoz Inc1988-10-212016-11-30US flag
Octreotide AcetateInjection, solution1000 ug/1mLIntravenous; SubcutaneousSandoz1988-10-212014-06-29US flag
Octreotide AcetateInjection, solution200 ug/1mLIntravenous; SubcutaneousSandoz1988-10-212014-11-17US flag
Octreotide AcetateInjection, solution1000 ug/1mLIntravenous; SubcutaneousSandoz Inc1988-10-212016-11-30US flag
Octreotide Acetate Injection - 100mcg/mlSolutionIntravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Additional Data Available
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  • Product Code
    Product Code
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OctreotideInjection, solution100 ug/1mLIntravenous; SubcutaneousFresenius Kabi USA, LLC2006-03-14Not applicableUS flag
OctreotideInjection, solution1000 ug/1mLIntravenous; SubcutaneousFresenius Kabi USA, LLC2006-03-14Not applicableUS flag
OctreotideInjection, solution500 ug/1mLIntravenous; SubcutaneousFresenius Kabi USA, LLC2006-03-14Not applicableUS flag
OctreotideInjection, solution200 ug/1mLIntravenous; SubcutaneousFresenius Kabi USA, LLC2006-03-14Not applicableUS flag
OctreotideInjection, solution50 ug/1mLIntravenous; SubcutaneousFresenius Kabi USA, LLC2006-03-14Not applicableUS flag
Octreotide AcetateInjection, solution100 ug/1mLIntravenous; SubcutaneousUSV North America Inc.2019-02-01Not applicableUS flag
Octreotide AcetateInjection, solution500 ug/1mLIntravenous; SubcutaneousBedford Pharmaceuticals2009-03-092013-01-31US flag
Octreotide AcetateInjection, solution500 ug/1mLIntravenous; SubcutaneousTeva Parenteral Medicines, Inc.2005-11-14Not applicableUS flag
Octreotide AcetateInjection, solution200 ug/1mLIntravenous; SubcutaneousBedford Pharmaceuticals2005-04-082014-12-31US flag
Octreotide AcetateInjection200 ug/1mLIntravenousUSV North America Inc.2019-01-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
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Categories

ATC Codes
H01CB02 — Octreotide
Drug Categories
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 / Phenylalanine and derivatives / N-acyl-alpha amino acids and derivatives / Macrolactams / Alpha amino acid amides / 3-alkylindoles / Amphetamines and derivatives / Aralkylamines / Substituted pyrroles / Fatty amides
show 12 more
Substituents
3-alkylindole / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic heteropolycyclic compound
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
RWM8CCW8GP
CAS number
83150-76-9
InChI Key
DEQANNDTNATYII-OULOTJBUSA-N
InChI
InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1
IUPAC Name
(4R,7S,10S,13R,16S,19R)-19-[(2R)-2-amino-3-phenylpropanamido]-10-(4-aminobutyl)-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-[(1H-indol-3-yl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
SMILES
[H][[email protected]]1(NC(=O)[[email protected]](CCCCN)NC(=O)[[email protected]@H](CC2=CNC3=C2C=CC=C3)NC(=O)[[email protected]](CC2=CC=CC=C2)NC(=O)[[email protected]](CSSC[[email protected]](NC1=O)C(=O)N[[email protected]](CO)[[email protected]@H](C)O)NC(=O)[[email protected]](N)CC1=CC=CC=C1)[[email protected]@H](C)O

References

Synthesis Reference

Nishith Chaturvedi, "Novel process for production of the somatostatin analog, octreotide." U.S. Patent US20040225108, issued November 11, 2004.

US20040225108
General References
  1. Biermasz NR: New medical therapies on the horizon: oral octreotide. Pituitary. 2017 Feb;20(1):149-153. doi: 10.1007/s11102-016-0785-3. [PubMed:28091879]
  2. Battershill PE, Clissold SP: Octreotide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in conditions associated with excessive peptide secretion. Drugs. 1989 Nov;38(5):658-702. doi: 10.2165/00003495-198938050-00002. [PubMed:2689136]
  3. Prelevic GM, Wurzburger MI, Balint-Peric L, Nesic JS: Inhibitory effect of sandostatin on secretion of luteinising hormone and ovarian steroids in polycystic ovary syndrome. Lancet. 1990 Oct 13;336(8720):900-3. doi: 10.1016/0140-6736(90)92270-r. [PubMed:1976930]
  4. Clarke DL, McKune A, Thomson SR: Octreotide lowers gastric mucosal blood flow in normal and portal hypertensive stomachs. Surg Endosc. 2003 Oct;17(10):1570-2. doi: 10.1007/s00464-002-9274-z. Epub 2003 Jul 21. [PubMed:12874677]
  5. Bioworld: Chiasma carries new oral acromegaly treatment, Mycapssa, to FDA approval [Link]
  6. NIH StatPearls: Acromegaly [Link]
  7. FDA approval letter: Mycapssa [Link]
  8. Product monograph: Sandostatin (octreotide acetate) injection [Link]
  9. NIH StatPearls: Octreotide [Link]
  10. FDA Approved products: Mycapssa (octreotide) oral delayed-release capsules [Link]
  11. Cayman Chem MSDS: Octreotide acetate [Link]
  12. Product monograph: Octreotide injection (octreotide acetate) [Link]
KEGG Drug
D00442
KEGG Compound
C07306
PubChem Compound
448601
PubChem Substance
46504600
ChemSpider
395352
BindingDB
50272772
RxNav
7617
ChEMBL
CHEMBL1680
Therapeutic Targets Database
DAP000397
PharmGKB
PA450678
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Octreotide
AHFS Codes
  • 92:00.00 — Miscellaneous Therapeutic Agents
FDA label
Download (69.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailablePituitary Adenomas1
4CompletedPreventionDiarrhea / Neoplasms1
4CompletedSupportive CareColonic Motility Index / Constipation1
4CompletedTreatmentAcromegaly11
4CompletedTreatmentAscites / Liver Cirrhosis1
4CompletedTreatmentBMI >30 kg/m21
4CompletedTreatmentGastric and Esophageal Varices1
4CompletedTreatmentHematemesis / Liver Cirrhosis / Melena / Portal Hypertension1
4CompletedTreatmentHypothalamic Obesity1
4CompletedTreatmentNeoplasms1

Pharmacoeconomics

Manufacturers
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Sun pharmaceutical industries ltd
  • Teva parenteral medicines inc
  • Novartis pharmaceuticals corp
Packagers
  • APP Pharmaceuticals
  • Bachem Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Novartis AG
  • Polfa
  • Sandoz
  • Sicor Pharmaceuticals
  • Solvay Pharmaceuticals
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
InjectionSubcutaneous2.5 mg/1mL
Injection, powder, for suspension10 MG/2ML
Injection, powder, for suspension10 MG
Injection, powder, for suspension20 MG/2ML
Injection, powder, for suspension20 MG
Injection, powder, for suspension30 MG/2ML
Injection, powder, for suspension30 MG
Injection, solutionParenteral100 MICROGRAMMI/ML
Injection, solutionParenteral100 MICROGRAMMI/1ML
Injection, solutionParenteral1000 MICROGRAMMI/5ML
Injection, solutionParenteral50 MICROGRAMMI/ML
Injection, solutionParenteral50 MICROGRAMMI/1ML
Injection, solutionParenteral500 MICROGRAMMI/1ML
Injection, solutionParenteral500 MICROGRAMMI/ML
Capsule, delayed releaseOral20 mg/1
Injection
Injection, powder, for suspensionParenteral10 mg
Injection, powder, for suspensionParenteral20 mg
Injection, powder, for suspensionParenteral30 mg
InjectionIntravenous1000 ug/1mL
InjectionIntravenous200 ug/1mL
InjectionIntravenous; Subcutaneous100 ug/1mL
InjectionIntravenous; Subcutaneous1000 ug/1mL
InjectionIntravenous; Subcutaneous200 ug/1mL
InjectionIntravenous; Subcutaneous50 ug/1mL
InjectionIntravenous; Subcutaneous500 ug/1mL
Injection, solutionIntravenous; Subcutaneous100 ug/1mL
Injection, solutionIntravenous; Subcutaneous1000 ug/1mL
Injection, solutionIntravenous; Subcutaneous200 ug/1mL
Injection, solutionIntravenous; Subcutaneous50 ug/1mL
Injection, solutionIntravenous; Subcutaneous500 ug/1mL
PowderNot applicable1 g/1g
Injection, solutionParenteral0.05 MG/ML
Injection, solutionParenteral0.1 MG/ML
Injection, solutionParenteral0.5 MG/ML
Injection, solutionParenteral1 MG/5ML
Injection, powder, for suspension, extended release; kitIntramuscular
Injection, solutionParenteral0.2 MG/ML
Injection, solutionParenteral0.05 MG/1ML
Injection, solutionParenteral0.1 MG/1ML
Injection, solutionParenteral0.5 MG/1ML
Injection, solution100 mcg/1mL
Injection, solution50 mcg/1mL
InjectionIntravenous; Subcutaneous100 µg/ml
InjectionIntravenous; Subcutaneous50 µg/ml
InjectionIntravenous; Subcutaneous0.1 MG/ML
Injection, solution1 mg/5mL
Injection, solutionIntravenous; Subcutaneous100 mcg/1mL
Injection, solutionIntravenous; Subcutaneous200 mcg/1mL
Injection, solutionIntravenous; Subcutaneous50 mcg/1mL
Injection, solutionIntravenous; Subcutaneous500 mcg/1mL
Injection, solution0.1 mg/ml
Injection, solutionParenteral100 Mikrogramm/ml
Injection, solutionParenteral1000 Mikrogramm/5ml
SolutionIntravenous; Subcutaneous
Injection, solutionParenteral50 Mikrogramm/ml
Injection, solutionParenteral500 Mikrogramm/ml
InjectionIntravenous0.5 mg/ml
InjectionIntravenous0.1 mg/ml
Injection, powder, for solution10 mg
Injection, powder, for solution20 mg
Injection, powder, for solution30 mg
Injection, suspension10 mg
InjectionIntramuscular10 MG
Injection, powder, for suspension, extended releaseIntramuscular
Injection, suspension20 mg
InjectionIntramuscular20 MG
Injection, suspension30 mg
InjectionIntramuscular30 MG
KitIntramuscular1.667 mg/1mL
KitIntramuscular10 mg/1
KitIntramuscular20 mg/1
KitIntramuscular3.33 mg/1mL
KitIntramuscular30 mg/1
KitIntramuscular5 mg/1mL
Injection, powder, for suspensionIntramuscular30 mg
Injection, powder, for suspensionIntramuscular20 mg
Injection, solutionParenteral100 μg/ml
Injection, solutionParenteral500 μg/ml
Injection, solutionParenteral200 MICROGRAMMI/ML
Prices
Unit descriptionCostUnit
Sandostatin lar 30 mg kit3860.62USD kit
Sandostatin lar 20 mg kit2578.19USD kit
Sandostatin lar 10 mg kit1967.81USD kit
Sandostatin 1 mg/ml vial234.49USD ml
Sandostatin 0.5 mg/ml ampul111.48USD ml
Octreotide 1000 mcg/ml vial67.2USD ml
Sandostatin 0.2 mg/ml vial47.66USD ml
Octreotide acet 500 mcg/ml vial24.48USD ml
Sandostatin 0.1 mg/ml ampul23.11USD ml
Octreotide acet 100 mcg/ml vial15.36USD ml
Octreotide acet 200 mcg/ml vial14.4USD ml
Sandostatin 0.05 mg/ml ampul11.92USD ml
Octreotide acet 50 mcg/ml vial3.6USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5538739No1996-07-232013-07-23US flag
CA1328402No1994-04-122011-04-12Canada flag
US5922338Yes1999-07-132017-01-13US flag
US5922682Yes1999-07-132017-01-13US flag
US5728396No1998-03-172017-01-30US flag
US6156331No2000-12-052017-01-30US flag
US6375978No2002-04-232018-12-17US flag
US6235712No2001-05-222017-06-13US flag
US6113938No2000-09-052018-07-24US flag
US6124261No2000-09-262017-06-13US flag
US6395292No2002-05-282017-01-30US flag
US6132420No2000-10-172017-01-30US flag
US5985305No1999-11-162017-01-30US flag
US5932547No1999-08-032017-06-13US flag
US5753618Yes1998-05-192015-11-19US flag
US10342850No2019-07-092038-05-15US flag
US10695397No2016-02-032036-02-03US flag
US8535695No2009-09-172029-09-17US flag
US10238709No2016-02-032036-02-03US flag
US9566246No2009-09-172029-09-17US flag
US8329198No2009-09-172029-09-17US flag
US9265812No2009-09-172029-09-17US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)153-156https://www.chemicalbook.com/ChemicalProductProperty_US_CB0279552.aspx
boiling point (°C)1447https://www.chemenu.com/products/CM100710
logP-0.49https://books.google.ca/books?id=5wcyP2OBPhoC&pg=PA44&lpg=PA44&dq=log+P+octreotide&source=bl&ots=bD30to24y8&sig=ACfU3U3v39AWwZVvITGj1NwJtvU8Ljkp0A&hl=en&sa=X&ved=2ahUKEwiF6tWGiLnqAhVIJDQIHetABYsQ6AEwC3oECAwQAQ#v=onepage&q=log%20P%20octreotide&f=false
pKa12.60https://www.chemicalbook.com/ChemicalProductProperty_DE_CB2138033.htm
Predicted Properties
PropertyValueSource
Water Solubility0.0122 mg/mLALOGPS
logP0.42ALOGPS
logP-1.4ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)11.4ChemAxon
pKa (Strongest Basic)10.17ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area332.22 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity269.77 m3·mol-1ChemAxon
Polarizability107.65 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9239
Blood Brain Barrier-0.8738
Caco-2 permeable-0.7824
P-glycoprotein substrateSubstrate0.8557
P-glycoprotein inhibitor INon-inhibitor0.9599
P-glycoprotein inhibitor IINon-inhibitor0.969
Renal organic cation transporterNon-inhibitor0.8506
CYP450 2C9 substrateNon-substrate0.8205
CYP450 2D6 substrateNon-substrate0.7632
CYP450 3A4 substrateNon-substrate0.5268
CYP450 1A2 substrateNon-inhibitor0.7975
CYP450 2C9 inhibitorNon-inhibitor0.7743
CYP450 2D6 inhibitorNon-inhibitor0.8449
CYP450 2C19 inhibitorNon-inhibitor0.7355
CYP450 3A4 inhibitorNon-inhibitor0.8236
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.708
Ames testNon AMES toxic0.6448
CarcinogenicityNon-carcinogens0.8761
BiodegradationNot ready biodegradable0.9943
Rat acute toxicity2.6174 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9693
hERG inhibition (predictor II)Inhibitor0.6064
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

Targets

1. Somatostatin receptor
Kind
Group
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
This group is comprised of various subtypes of somatostatin receptors.
References
  1. Casarini AP, Jallad RS, Pinto EM, Soares IC, Nonogaki S, Giannella-Neto D, Musolino NR, Alves VA, Bronstein MD: Acromegaly: correlation between expression of somatostatin receptor subtypes and response to octreotide-lar treatment. Pituitary. 2009;12(4):297-303. doi: 10.1007/s11102-009-0175-1. [PubMed:19330452]
  2. Mulak A, Larauche M, Biraud M, Million M, Rivier J, Tache Y: Selective agonists of somatostatin receptor subtype 1 or 2 injected peripherally induce antihyperalgesic effect in two models of visceral hypersensitivity in mice. Peptides. 2015 Jan;63:71-80. doi: 10.1016/j.peptides.2014.10.013. Epub 2014 Nov 5. [PubMed:25451334]
  3. Product monograph: Sandostatin (octreotide acetate) injection [Link]
  4. NIH StatPearls: Octreotide [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Alatas E, Alatas O, Colak O: Octreotide inhibits myeloperoxidase activity in rat uterus. Acta Obstet Gynecol Scand. 2000 Jul;79(7):524-7. [PubMed:10929949]
  2. Alatas E, Gunal O, Alatas O, Colak O: Octreotide prevents postoperative adhesion formation by suppressing peritoneal myeloperoxidase activity. Hepatogastroenterology. 2000 Jul-Aug;47(34):1034-6. [PubMed:11020872]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
This enzyme action is based on limited findings of in vitro studies and the clinical relevance is unknown.
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
References
  1. Yilmaz B, Kemal Y, Teker F: Be careful before prescribing warfarin and octreotide together: a new drug-drug interaction report. Hippokratia. 2014 Oct-Dec;18(4):377. [PubMed:26052213]
  2. Liddle C, Goodwin BJ, George J, Tapner M, Farrell GC: Separate and interactive regulation of cytochrome P450 3A4 by triiodothyronine, dexamethasone, and growth hormone in cultured hepatocytes. J Clin Endocrinol Metab. 1998 Jul;83(7):2411-6. [PubMed:9661620]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Product monograph: Sandostatin (octreotide acetate) injection [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
P-glycoprotein is a possible transporter of octreotide, according to the findings of various in vitro studies.
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Gutmann H, Miller DS, Droulle A, Drewe J, Fahr A, Fricker G: P-glycoprotein- and mrp2-mediated octreotide transport in renal proximal tubule. Br J Pharmacol. 2000 Jan;129(2):251-6. doi: 10.1038/sj.bjp.0703003. [PubMed:10694230]
  2. Yamada T, Kato Y, Kusuhara H, Lemaire M, Sugiyama Y: Characterization of the transport of a cationic octapeptide, octreotide, in rat bile canalicular membrane: possible involvement of P-glycoprotein. Biol Pharm Bull. 1998 Aug;21(8):874-8. doi: 10.1248/bpb.21.874. [PubMed:9743261]
  3. Dietrich CG, Geier A, Oude Elferink RP: ABC of oral bioavailability: transporters as gatekeepers in the gut. Gut. 2003 Dec;52(12):1788-95. doi: 10.1136/gut.52.12.1788. [PubMed:14633964]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Octreotide is a substrate and weak inhibitor of MRP2, according to various in vitro studies.
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Gutmann H, Miller DS, Droulle A, Drewe J, Fahr A, Fricker G: P-glycoprotein- and mrp2-mediated octreotide transport in renal proximal tubule. Br J Pharmacol. 2000 Jan;129(2):251-6. doi: 10.1038/sj.bjp.0703003. [PubMed:10694230]
  2. Visentin M, Stieger B, Merz M, Kullak-Ublick GA: Octreotide inhibits the bilirubin carriers organic anion transporting polypeptides 1B1 and 1B3 and the multidrug resistance-associated protein 2. J Pharmacol Exp Ther. 2015 Nov;355(2):145-51. doi: 10.1124/jpet.115.227546. Epub 2015 Sep 1. [PubMed:26330539]
  3. Dietrich CG, Geier A, Oude Elferink RP: ABC of oral bioavailability: transporters as gatekeepers in the gut. Gut. 2003 Dec;52(12):1788-95. doi: 10.1136/gut.52.12.1788. [PubMed:14633964]

Drug created on June 13, 2005 07:24 / Updated on November 25, 2020 08:53

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