Identification

Name
Octreotide
Accession Number
DB00104  (BTD00088, BIOD00088)
Type
Small Molecule
Groups
Approved, Investigational
Description

Octreotide is the acetate salt of a cyclic octapeptide. It is a long-acting octapeptide with pharmacologic properties mimicking those of the natural hormone somatostatin.

Structure
Thumb
Synonyms
  • Octreotida
  • Octreotidum
  • Octrotide
External IDs
SMS 201-995 / SMS-201-995
Product Ingredients
IngredientUNIICASInChI Key
Octreotide acetate75R0U2568I79517-01-4XQEJFZYLWPSJOV-XJQYZYIXSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OcphylSolution100 mcgIntravenous; SubcutaneousPendopharm Division Of De Pharmascience Inc2014-05-12Not applicableCanada
OcphylSolution50 mcgIntravenous; SubcutaneousPendopharm Division Of De Pharmascience Inc2014-05-12Not applicableCanada
OcphylSolution500 mcgIntravenous; SubcutaneousPendopharm Division Of De Pharmascience Inc2014-05-12Not applicableCanada
Octreotide AcetateInjection, solution200 ug/1mLIntravenous; SubcutaneousSandoz1988-10-212014-11-17Us
Octreotide AcetateInjection, solution1000 ug/1mLIntravenous; SubcutaneousSandoz1988-10-21Not applicableUs
Octreotide AcetateInjection, solution1000 ug/1mLIntravenous; SubcutaneousSandoz1988-10-212014-06-29Us
Octreotide AcetateInjection, solution200 ug/1mLIntravenous; SubcutaneousSandoz1988-10-21Not applicableUs
Octreotide Acetate Injection - 100mcg/mlSolution100 mcgIntravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada
Octreotide Acetate Injection - 200mcg/mlSolution200 mcgIntravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada
Octreotide Acetate Injection - 500mcg/mlSolution500 mcgIntravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OctreotideInjection, solution50 ug/1mLIntravenous; SubcutaneousFresenius Kabi2006-03-14Not applicableUs
OctreotideInjection, solution100 ug/1mLIntravenous; SubcutaneousFresenius Kabi2006-03-14Not applicableUs
OctreotideInjection, solution1000 ug/1mLIntravenous; SubcutaneousFresenius Kabi2006-03-14Not applicableUs
OctreotideInjection, solution500 ug/1mLIntravenous; SubcutaneousFresenius Kabi2006-03-14Not applicableUs
OctreotideInjection, solution200 ug/1mLIntravenous; SubcutaneousFresenius Kabi2006-03-14Not applicableUs
Octreotide acetateInjection200 ug/1mLIntravenous; SubcutaneousWockhardt2011-05-11Not applicableUs
Octreotide AcetateInjection, solution200 ug/1mLIntravenous; SubcutaneousBedford Pharmaceuticals2005-04-082014-12-31Us
Octreotide AcetateInjection, solution50 ug/1mLIntravenous; SubcutaneousMylan Institutional2011-04-01Not applicableUs
Octreotide AcetateInjection, solution50 ug/1mLIntravenous; SubcutaneousBedford Pharmaceuticals2005-04-042013-02-28Us
Octreotide AcetateInjection, solution500 ug/1mLIntravenous; SubcutaneousSun Pharmaceutical Industries Limited2012-08-312016-11-30Us
International/Other Brands
Sandostatin LAR (Novartis Pharmaceuticals)
Categories
UNII
RWM8CCW8GP
CAS number
83150-76-9
Weight
Average: 1019.25
Monoisotopic: 1018.440480713
Chemical Formula
C49H66N10O10S2
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][C@]1(NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N[C@H](CO)[C@@H](C)O)NC(=O)[C@H](N)CC1=CC=CC=C1)[C@@H](C)O

Pharmacology

Indication

For treatment of acromegaly and reduction of side effects from cancer chemotherapy

Associated Conditions
Pharmacodynamics

Octreotide exerts pharmacologic actions similar to the natural hormone, somatostatin. It is an even more potent inhibitor of growth hormone, glucagon, and insulin than somatostatin. Like somatostatin, it also suppresses leuteinizing hormone (LH) response to GnRH, decreases splanchnic blood flow, and inhibits release of serotonin, gastrin, vasoactive intestinal peptide, secretin, motilin, and pancreatic polypeptide. Octreotide has been used to treat the symptoms associated with metastatic carcinoid tumors (flushing and diarrhea), and Vasoactive Intestinal Peptide (VIP) secreting adenomas (watery diarrhea). Octreotide substantially reduces and in many cases can normalize growth hormone and/or IGF-1 (somatomedin C) levels in patients with acromegaly.

Mechanism of action

Octreotide binds to somatostatin receptors. These receptors are coupled via pertussis toxin sensitive G proteins which lead to inhibition of adenylyl cyclase. Octreotide binding to these receptors also stimulates phosphotyrosine phosphatase and activation of the Na(+)/H(+) exchanger via pertussis toxin insensitive G proteins.

TargetActionsOrganism
ASomatostatin receptor type 1Not AvailableHuman
ASomatostatin receptor type 5Not AvailableHuman
ASomatostatin receptor type 2
binder
Human
Absorption
Not Available
Volume of distribution
  • 13.6 L [healthy volunteers]
  • 21.6 ± 8.5 L [patients with acromegaly]
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

About 32% of the dose is excreted unchanged into the urine.

Half life
Not Available
Clearance
  • 7 – 10 L/hr [healthy after 100-mcg SC injection]
  • 18 L/hr [patients with acromegaly after 100-mcg SC injection]
  • 8.8 L/hr [mild renal impairment after 100-mcg SC injection]
  • 7.3 L/hr [moderate renal impairment after 100-mcg SC injection]
  • 7.6 L/hr [severe renal impairment after 100-mcg SC injection]
  • 4.5 L/hr [severe renal failure requiring dialysis after 100-mcg SC injection]
  • 5.9 L/hr [Patients with liver cirrhosis after 100-mcg SC injection]
  • 8.2 L/hr [patients with fatty liver disease after 100-mcg SC injection]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Octreotide.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Octreotide.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Octreotide.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Octreotide.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Octreotide.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Octreotide.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Octreotide.
AbemaciclibThe serum concentration of Octreotide can be increased when it is combined with Abemaciclib.
AbexinostatThe risk or severity of QTc prolongation can be increased when Octreotide is combined with Abexinostat.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Octreotide.
Food Interactions
Not Available

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. Uhl W, Anghelacopoulos SE, Friess H, Buchler MW: The role of octreotide and somatostatin in acute and chronic pancreatitis. Digestion. 1999;60 Suppl 2:23-31. [PubMed:10207228]
External Links
KEGG Drug
D00442
KEGG Compound
C07306
PubChem Compound
448601
PubChem Substance
46504600
ChemSpider
395352
BindingDB
50272772
ChEMBL
CHEMBL1680
Therapeutic Targets Database
DAP000397
PharmGKB
PA450678
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Octreotide
ATC Codes
H01CB02 — Octreotide
AHFS Codes
  • 92:00.00 — Miscellaneous Therapeutic Agents
FDA label
Download (69.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingBasic ScienceInsulin Sensitivity / Vascular Stiffness1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableIrritable Bowel Syndrome (IBS)1
1CompletedBasic ScienceBMI >30 kg/m2 / Hyperglucagonaemia1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentEnterocutaneous Fistulas / Intra-Abdominal Infections1
1CompletedTreatmentGastrin-Producing Neuroendocrine Tumor / Lung Carcinoid Tumor / Metastatic Digestive System Neuroendocrine Tumor G1 / Pancreatic Glucagonoma / Pancreatic Insulinoma / Pancreatic Polypeptide Tumor / Paraganglioma / Recurrent Digestive System Neuroendocrine Tumor G1 / Recurrent Merkel Cell Carcinoma / Recurrent Pancreatic Neuroendocrine Carcinoma / Regional Digestive System Neuroendocrine Tumor G1 / Somatostatin-Producing Neuroendocrine Tumor / Stage III Merkel Cell Carcinoma / Stage IV Merkel Cell Carcinoma / Thyroid Gland Medullary Carcinoma1
1CompletedTreatmentHealthy Volunteer Study1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentType 2 Diabetes Mellitus1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1RecruitingTreatmentAcromegaly1
1RecruitingTreatmentSmall Bowel Carcinoid Tumor1
1SuspendedTreatmentAcromegaly1
1, 2Active Not RecruitingTreatmentChronic Orthostatic Intolerance / Tachycardia1
1, 2CompletedPreventionLiver Cirrhosis / Portal Hypertension / Varices, Esophageal1
1, 2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
1, 2TerminatedTreatmentCarcinoid Syndrome1
1, 2Unknown StatusTreatmentMigrainous Headache1
2Active Not RecruitingTreatmentAnemias / Hemorrhage, Gastrointestinal / Hereditary Haemorrhagic Telangiectasia (HHT)1
2Active Not RecruitingTreatmentGastrin-Producing Neuroendocrine Tumor / Malignant Pancreatic Gastrinoma / Malignant Pancreatic Glucagonoma / Malignant Pancreatic Insulinoma / Malignant Pancreatic Somatostatinoma / Pancreatic Alpha Cell Adenoma / Pancreatic Beta Cell Adenoma / Pancreatic Delta Cell Adenoma / Pancreatic G-Cell Adenoma / Pancreatic Gastrinoma / Pancreatic Glucagonoma / Pancreatic Insulinoma / Pancreatic Neuroendocrine Tumor G1 / Pancreatic Neuroendocrine Tumor G2 / Pancreatic Polypeptide Tumor / Pancreatic Vipoma / Recurrent Pancreatic Carcinoma / Recurrent Pancreatic Neuroendocrine Carcinoma / Somatostatin-Producing Neuroendocrine Tumor / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer1
2CompletedSupportive CareCancer of the Ovary / Colorectal Cancers / Constipation, Impaction, and Bowel Obstruction / Extrahepatic Bile Duct Cancer / Gastrointestinal Stromal Tumors / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Nausea and vomiting / Peritoneal Cavity Cancer / Small Intestine Cancer1
2CompletedTreatmentAbdominal wall neoplasm / Carcinomatosis / Intestinal Obstruction1
2CompletedTreatmentAcromegaly4
2CompletedTreatmentAscites / Lymphangioleiomyomatosis / Lymphangiomyomas / Pleural Effusions1
2CompletedTreatmentBMI >30 kg/m2 / Primary Insulin Hypersecretion1
2CompletedTreatmentCarcinoid tumour of the gastrointestinal tract / Islet Cell Tumor / Neoplastic Syndrome1
2CompletedTreatmentCarcinoma NOS / Neuroendocrine Tumors1
2CompletedTreatmentCarcinoma, Islet Cell / Neoplasms, Pancreatic / Neuroendocrine Carcinomas / Neuroendocrine Tumors1
2CompletedTreatmentCarcinoma, Islet Cell / Neuroendocrine Carcinomas1
2CompletedTreatmentEctasia / Hereditary Haemorrhagic Telangiectasia (HHT)1
2CompletedTreatmentLiver Cancer1
2CompletedTreatmentLivers / Malignancies1
2CompletedTreatmentLocal Recurrent Thymoma / Primary Inoperable Thymoma1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentNeoplasms, Gastrointestinal1
2CompletedTreatmentNeuroendocrine Carcinomas1
2CompletedTreatmentThymoma and Thymic Carcinoma1
2CompletedTreatmentAdvanced thymic carcinoma1
2Enrolling by InvitationTreatmentOctreotide / Sputum1
2Not Yet RecruitingTreatmentAutosomal Dominant Polycystic Kidney Disease (ADPKD)1
2RecruitingSupportive CareMajor Liver Resection1
2RecruitingTreatmentCarcinoid Tumors1
2RecruitingTreatmentFibrosis / Hepatorenal Syndrome / Renal Failure1
2RecruitingTreatmentFistula; Salivary Duct or Gland1
2RecruitingTreatmentRecurrent Meningiomas / Resistant Meningiomas1
2TerminatedSupportive CareHormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Severe or persistent diarrhea / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer1
2TerminatedTreatmentHead and Neck Carcinoma / Islet Cell Tumor / Metastatic Cancers / Pheochromocytomas1
2TerminatedTreatmentMalignancies1
2TerminatedTreatmentNeuroendocrine Carcinomas1
2TerminatedTreatmentProstate Cancer1
2Unknown StatusTreatmentNeuroendocrine Carcinomas1
2WithdrawnTreatmentCarcinoid tumour of the gastrointestinal tract / Carcinoma, Islet Cell1
2, 3CompletedTreatmentAbdominal Pain (AP) / Autosomal Dominant Polycystic Kidney Disease (ADPKD) / Hepatomegaly / Kidney, Polycystic / Liver Diseases / Polycystic Liver Disease (PLD)1
2, 3CompletedTreatmentRefractory Ascites / Type 2 Hepatorenal Syndrome1
2, 3RecruitingTreatmentAnemias / Angiodysplasia / Hemorrhage, Gastrointestinal / Vascular Malformations1
2, 3RecruitingTreatmentCancer, Advanced / Neuroendocrine Tumors / Well-differentiated Non-pancreatic Neuroendocrine Carcinoma1
3Active Not RecruitingTreatmentAcromegaly2
3Active Not RecruitingTreatmentAtypical Carcinoid Tumor / Carcinoid Tumors / Colorectal Neuroendocrine Tumor G1 / Gastric Neuroendocrine Tumor G1 / Neuroendocrine Carcinomas / Neuroendocrine Neoplasms1
3Active Not RecruitingTreatmentMalignant Neoplasm of Pancreas1
3CompletedPreventionChemotherapy-induced Diarrhea1
3CompletedSupportive CareAnal Carcinoma / Colorectal Cancers / Drug/Agent Toxicity by Tissue/Organ / Radiation Enteritis1
3CompletedSupportive CareCancer of the Ovary / Cervical Cancers / Colorectal Cancers / Endometrial Cancers / Fallopian Tube Cancer / Prostate Cancer / Sarcomas / Severe or persistent diarrhea / Unspecified Adult Solid Tumor, Protocol Specific / Vaginal Cancers / Vulvar Cancers1
3CompletedSupportive CareColorectal Cancers / Severe or persistent diarrhea1
3CompletedTreatmentAcromegaly4
3CompletedTreatmentAdvanced Hepatocellular Carcinoma1
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentCarcinoid Tumors / Malignant Carcinoid Syndrome1
3CompletedTreatmentDiabetes Mellitus (DM) / Hypoglycemia1
3CompletedTreatmentHepatocellular,Carcinoma1
3CompletedTreatmentMetastatic Cancers / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentSymptomatic Refractory Resistant Carcinoid Disease1
3RecruitingTreatmentPancreatic Surgery1
3TerminatedSupportive CareColorectal Cancers / Severe or persistent diarrhea1
3TerminatedTreatmentAcromegaly3
3TerminatedTreatmentHyperphagia / Prader-Willi Syndrome1
4CompletedPreventionNeoplasms / Severe or persistent diarrhea1
4CompletedSupportive CareColonic Motility Index / Occasional Constipation1
4CompletedTreatmentAcromegaly8
4CompletedTreatmentBMI >30 kg/m21
4CompletedTreatmentGastric and Esophageal Varices1
4CompletedTreatmentHaematemesis / Liver Cirrhosis / Melena / Portal Hypertension1
4CompletedTreatmentHypothalamic Obesity1
4CompletedTreatmentPancreatic Fistula1
4CompletedTreatmentVariceal Bleeding, Cirrhosis1
4RecruitingPreventionAdenoma benign1
4RecruitingTreatmentAcromegaly1
4RecruitingTreatmentLiver Cirrhoses / Oesophageal varices haemorrhage / Upper Gastrointestinal Hemorrhage / Varices, Esophageal1
4RecruitingTreatmentNeoplasms1
4RecruitingTreatmentNeuroendocrine Tumors1
4TerminatedTreatmentAcromegaly1
4Unknown StatusTreatmentAcromegaly1
Not AvailableCompletedNot AvailableAcromegaly1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Sarcopenia1
Not AvailableCompletedBasic SciencePancreatic Fistula1
Not AvailableCompletedPreventionPeriampullary Carcinoma Resectable1
Not AvailableCompletedTreatmentGastroesophageal variceal hemorrhage prophylaxis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Severe or persistent diarrhea2
Not AvailableCompletedTreatmentPrader Willis Syndrome1
Not AvailableEnrolling by InvitationBasic ScienceDuodenal Neoplasms / Malnutrition / Neoplasms, Esophageal / Neoplasms, Pancreatic / Obese experiencing rapid weight loss / Stomach Neoplasms1
Not AvailableEnrolling by InvitationBasic ScienceMalnutrition / Neoplasms, Esophageal / Obese experiencing rapid weight loss / Stomach Neoplasms1
Not AvailableNot Yet RecruitingNot AvailableImmunosuppression / Severe or persistent diarrhea1
Not AvailableRecruitingNot AvailableAcromegaly1
Not AvailableRecruitingNot AvailableHepatocellular,Carcinoma / Neuroendocrine Tumors1
Not AvailableRecruitingHealth Services ResearchRoux-en-Y Bariatric Surgery1
Not AvailableRecruitingTreatmentAcromegaly1
Not AvailableRecruitingTreatmentPeriampullary Tumors1
Not AvailableTerminatedTreatmentPrader-Willi Syndrome1
Not AvailableUnknown StatusNot AvailableCancer, Breast1
Not AvailableUnknown StatusNot AvailableEsophageal and Gastric Varices / Hemorrhage / Liver Cirrhosis1
Not AvailableUnknown StatusBasic ScienceBMI >30 kg/m2 / General Surgery / Hypoglycemia1

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
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
SolutionIntravenous; Subcutaneous100 mcg
SolutionIntravenous; Subcutaneous500 mcg
SolutionIntravenous; Subcutaneous50 mcg
SolutionIntravenous; Subcutaneous200 mcg
PowderIntramuscular10 mg
PowderIntramuscular20 mg
PowderIntramuscular30 mg
Kit1.667 mg/1mL
Kit10 mg/1
Kit20 mg/1
Kit3.33 mg/1mL
Kit30 mg/1
Kit5 mg/1mL
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)
US5538739No1993-07-232013-07-23Us
CA1328402No1994-04-122011-04-12Canada
US5922338Yes1997-01-132017-01-13Us
US5922682Yes1997-01-132017-01-13Us
US5728396No1997-01-302017-01-30Us
US6156331No1997-01-302017-01-30Us
US6375978No1998-12-172018-12-17Us
US6235712No1997-06-132017-06-13Us
US6113938No1998-07-242018-07-24Us
US6124261No1997-06-132017-06-13Us
US6395292No1997-01-302017-01-30Us
US6132420No1997-01-302017-01-30Us
US5985305No1997-01-302017-01-30Us
US5932547No1997-06-132017-06-13Us
US5753618Yes1995-11-192015-11-19Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
logP1Not Available
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

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 / 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
Alpha-oligopeptide / Cyclic alpha peptide / Phenylalanine or derivatives / Macrolactam / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / 3-alkylindole / Indole
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
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. Wang ZZ, Qu W, Wang F, Li Y, Wang SK, Wang JQ: [Expression of somatostatin receptor reporter gene and its correlation with targeted imaging in vivo for detection of pancreas carcinoma]. Zhonghua Zhong Liu Za Zhi. 2005 Nov;27(11):663-6. [PubMed:16438887]
  2. Matrone C, Pivonello R, Colao A, Cappabianca P, Cavallo LM, Del Basso De Caro ML, Taylor JE, Culler MD, Lombardi G, Di Renzo GF, Annunziato L: Expression and function of somatostatin receptor subtype 1 in human growth hormone secreting pituitary tumors deriving from patients partially responsive or resistant to long-term treatment with somatostatin analogs. Neuroendocrinology. 2004 Mar;79(3):142-8. Epub 2004 Apr 16. [PubMed:15103227]
  3. Jaquet P, Gunz G, Saveanu A, Barlier A, Dufour H, Taylor J, Dong J, Kim S, Moreau JP, Culler MD: BIM-23A760, a chimeric molecule directed towards somatostatin and dopamine receptors, vs universal somatostatin receptors ligands in GH-secreting pituitary adenomas partial responders to octreotide. J Endocrinol Invest. 2005;28(11 Suppl International):21-7. [PubMed:16625841]
  4. Schmid HA, Silva AP: Short- and long-term effects of octreotide and SOM230 on GH, IGF-I, ACTH, corticosterone and ghrelin in rats. J Endocrinol Invest. 2005;28(11 Suppl International):28-35. [PubMed:16625842]
  5. Ruan W, Fahlbusch F, Clemmons DR, Monaco ME, Walden PD, Silva AP, Schmid HA, Kleinberg DL: SOM230 inhibits insulin-like growth factor-I action in mammary gland development by pituitary independent mechanism: mediated through somatostatin subtype receptor 3? Mol Endocrinol. 2006 Feb;20(2):426-36. Epub 2005 Oct 13. [PubMed:16223973]
Kind
Protein
Organism
Human
Pharmacological action
Yes
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. Bronstein MD: Acromegaly: molecular expression of somatostatin receptor subtypes and treatment outcome. Front Horm Res. 2006;35:129-34. [PubMed:16809928]
  2. Xie Y, Tang CW, Wang CH: [Effect of HBV X gene transfection on octreotide-inhibited growth of hepatocellular carcinoma cell line HepG2]. Ai Zheng. 2005 Aug;24(8):965-9. [PubMed:16086874]
  3. Wang ZZ, Qu W, Wang F, Li Y, Wang SK, Wang JQ: [Expression of somatostatin receptor reporter gene and its correlation with targeted imaging in vivo for detection of pancreas carcinoma]. Zhonghua Zhong Liu Za Zhi. 2005 Nov;27(11):663-6. [PubMed:16438887]
  4. Jaquet P, Gunz G, Saveanu A, Barlier A, Dufour H, Taylor J, Dong J, Kim S, Moreau JP, Culler MD: BIM-23A760, a chimeric molecule directed towards somatostatin and dopamine receptors, vs universal somatostatin receptors ligands in GH-secreting pituitary adenomas partial responders to octreotide. J Endocrinol Invest. 2005;28(11 Suppl International):21-7. [PubMed:16625841]
  5. Schmid HA, Silva AP: Short- and long-term effects of octreotide and SOM230 on GH, IGF-I, ACTH, corticosterone and ghrelin in rats. J Endocrinol Invest. 2005;28(11 Suppl International):28-35. [PubMed:16625842]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Binder
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. Yim CB, Boerman OC, de Visser M, de Jong M, Dechesne AC, Rijkers DT, Liskamp RM: Versatile conjugation of octreotide to dendrimers by cycloaddition ("click") chemistry to yield high-affinity multivalent cyclic Peptide dendrimers. Bioconjug Chem. 2009 Jul;20(7):1323-31. doi: 10.1021/bc900052n. [PubMed:19537708]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
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
Human
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 June 13, 2005 07:24 / Updated on November 13, 2018 07:44