Vapreotide
Identification
- Generic Name
- Vapreotide
- DrugBank Accession Number
- DB04894
- Background
Vapreotide is a synthetic octapeptide somatostatin analog. It was being studied for the treatment of cancer.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 1131.38
Monoisotopic: 1130.48301423 - Chemical Formula
- C57H70N12O9S2
- Synonyms
- Vapreotida
- Vapreotide
- Vapreotidum
- External IDs
- BMY 41606
- BMY-41606
- RC-160
Pharmacology
- Indication
For the treatment of esophageal variceal bleeding in patients with cirrhotic liver disease and has also shown efficacy in the treatment of patients with AIDS-related diarrhea.
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- Pharmacodynamics
Vapreotide is a somatostatin analog with a higher metabolic stability than the parent hormone. Vapreotide reduces splanchnic blood flow; inhibits growth hormone release, and inhibits the release of peptides and vasoactive compounds from neuroendocrine tumors.
- Mechanism of action
The exact mechanism of action is unknown, although one study has provided in vitro and in vivo evidence for a tachykinin NK1 receptor antagonist effect in the analgesic effects of vapreotide (PMID: 7556407).
Target Actions Organism ASomatostatin receptor type 2 inducerHumans ASomatostatin receptor type 5 agonistHumans UNeurokinin 1 receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Vapreotide is 76% eliminated in bile. The remainder is renally eliminated.
- Half-life
30 minutes
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Safety data are limited, however, headache, fatigue, diarrhea, nausea, vomiting, and abdominal pain have been reported commonly with the use of vapreotide.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be decreased when combined with Vapreotide. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Vapreotide. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Vapreotide. Albendazole The metabolism of Albendazole can be decreased when combined with Vapreotide. Alectinib The metabolism of Alectinib can be decreased when combined with Vapreotide. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Vapreotide acetate 5562377HFV 849479-74-9 KBIZSMHYSQUHDH-NCACADTJSA-N - International/Other Brands
- Octastatin / Sanvar / Sanvar IR
Categories
- ATC Codes
- H01CB04 — Vapreotide
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Analgesics
- Antineoplastic Agents
- Central Nervous System 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
- Hypothalamic Hormones
- Nerve Tissue Proteins
- Neuropeptides
- Pancreatic Hormones
- Peptide Hormones
- Peptides
- Peripheral Nervous System Agents
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormone Release Inhibiting Hormones
- Proteins
- Sensory System Agents
- Somatostatin and Analogues
- 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 / Phenylalanine and derivatives / Macrolactams / N-acyl-alpha amino acids and derivatives / Tryptamines and derivatives / Alpha amino acid amides / 3-alkylindoles / Amphetamines and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines show 13 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 3-alkylindole / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic heteropolycyclic compound show 33 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 2PK59M9GFF
- CAS number
- 103222-11-3
- InChI Key
- SWXOGPJRIDTIRL-DOUNNPEJSA-N
- InChI
- InChI=1S/C57H70N12O9S2/c1-32(2)49-57(78)68-48(55(76)64-44(50(60)71)26-35-28-61-41-16-8-6-14-38(35)41)31-80-79-30-47(67-51(72)40(59)24-33-12-4-3-5-13-33)56(77)65-45(25-34-19-21-37(70)22-20-34)53(74)66-46(27-36-29-62-42-17-9-7-15-39(36)42)54(75)63-43(52(73)69-49)18-10-11-23-58/h3-9,12-17,19-22,28-29,32,40,43-49,61-62,70H,10-11,18,23-27,30-31,58-59H2,1-2H3,(H2,60,71)(H,63,75)(H,64,76)(H,65,77)(H,66,74)(H,67,72)(H,68,78)(H,69,73)/t40-,43+,44+,45+,46-,47+,48+,49+/m1/s1
- IUPAC Name
- (2R)-2-amino-N-[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-4-{[(1S)-1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-[(1H-indol-3-yl)methyl]-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-phenylpropanamide
- SMILES
- CC(C)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(N)=O)NC(=O)[C@H](N)CC1=CC=CC=C1
References
- Synthesis Reference
Venkata Raghavendra Palle, Maheedhara Reddy Challa, "PROCESS FOR PREPARING VAPREOTIDE." U.S. Patent US20070111930, issued May 17, 2007.
US20070111930- General References
- Sarr MG: The potent somatostatin analogue vapreotide does not decrease pancreas-specific complications after elective pancreatectomy: a prospective, multicenter, double-blinded, randomized, placebo-controlled trial. J Am Coll Surg. 2003 Apr;196(4):556-64; discussion 564-5; author reply 565. [Article]
- Authors unspecified: Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. [Article]
- Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. [Article]
- Betoin F, Ardid D, Herbet A, Aumaitre O, Kemeny JL, Duchene-Marullaz P, Lavarenne J, Eschalier A: Evidence for a central long-lasting antinociceptive effect of vapreotide, an analog of somatostatin, involving an opioidergic mechanism. J Pharmacol Exp Ther. 1994 Apr;269(1):7-14. [Article]
- Girard PM, Goldschmidt E, Vittecoq D, Massip P, Gastiaburu J, Meyohas MC, Coulaud JP, Schally AV: Vapreotide, a somatostatin analogue, in cryptosporidiosis and other AIDS-related diarrhoeal diseases. AIDS. 1992 Jul;6(7):715-8. [Article]
- Stiefel F, Morant R: Vapreotide, a new somatostatin analogue in the palliative management of obstructive ileus in advanced cancer. Support Care Cancer. 1993 Jan;1(1):57-8. [Article]
- Betoin F, Eschalier A, Duchene-Marullaz P, Lavarenne J: Seven-day antinociceptive effect of a sustained release vapreotide formulation. Neuroreport. 1994 Jan 31;5(5):642-4. [Article]
- External Links
- KEGG Drug
- D06281
- PubChem Compound
- 6918026
- PubChem Substance
- 46506923
- ChemSpider
- 5293243
- ChEMBL
- CHEMBL3349523
- Therapeutic Targets Database
- DAP001242
- PharmGKB
- PA164743146
- Wikipedia
- Vapreotide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Gastric Varices / Hemorrhage Esophageal / Portal Hypertension / Varices, Esophageal 1 3 Terminated Supportive Care Pancreatic Cancer / Perioperative/Postoperative Complications 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00401 mg/mL ALOGPS logP 2.69 ALOGPS logP 1.07 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 9.43 Chemaxon pKa (Strongest Basic) 10.26 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 13 Chemaxon Polar Surface Area 350.64 Å2 Chemaxon Rotatable Bond Count 18 Chemaxon Refractivity 306.22 m3·mol-1 Chemaxon Polarizability 118.22 Å3 Chemaxon Number of Rings 7 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 + 0.9656 Blood Brain Barrier - 0.9221 Caco-2 permeable - 0.7899 P-glycoprotein substrate Substrate 0.8572 P-glycoprotein inhibitor I Non-inhibitor 0.9346 P-glycoprotein inhibitor II Non-inhibitor 0.9514 Renal organic cation transporter Non-inhibitor 0.8571 CYP450 2C9 substrate Non-substrate 0.8172 CYP450 2D6 substrate Non-substrate 0.7495 CYP450 3A4 substrate Substrate 0.5808 CYP450 1A2 substrate Non-inhibitor 0.8063 CYP450 2C9 inhibitor Non-inhibitor 0.638 CYP450 2D6 inhibitor Non-inhibitor 0.8286 CYP450 2C19 inhibitor Non-inhibitor 0.6249 CYP450 3A4 inhibitor Non-inhibitor 0.739 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5526 Ames test Non AMES toxic 0.7151 Carcinogenicity Non-carcinogens 0.8667 Biodegradation Not ready biodegradable 0.9935 Rat acute toxicity 2.7335 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.973 hERG inhibition (predictor II) Inhibitor 0.6667
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 307.61215 predictedDeepCCS 1.0 (2019) [M+H]+ 309.33588 predictedDeepCCS 1.0 (2019) [M+Na]+ 315.66483 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inducer
- 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
- Fortune BE, Jackson J, Leonard J, Trotter JF: Vapreotide: a somatostatin analog for the treatment of acute variceal bleeding. Expert Opin Pharmacother. 2009 Oct;10(14):2337-42. doi: 10.1517/14656560903207019. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- 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
- Fortune BE, Jackson J, Leonard J, Trotter JF: Vapreotide: a somatostatin analog for the treatment of acute variceal bleeding. Expert Opin Pharmacother. 2009 Oct;10(14):2337-42. doi: 10.1517/14656560903207019. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Tachykinin receptor activity
- Specific Function
- This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of aff...
- Gene Name
- TACR1
- Uniprot ID
- P25103
- Uniprot Name
- Substance-P receptor
- Molecular Weight
- 46250.5 Da
References
- Betoin F, Advenier C, Fardin V, Wilcox G, Lavarenne J, Eschalier A: In vitro and in vivo evidence for a tachykinin NK1 receptor antagonist effect of vapreotide, an analgesic cyclic analog of somatostatin. Eur J Pharmacol. 1995 Jun 12;279(2-3):241-9. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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 at October 21, 2007 22:23 / Updated at November 03, 2023 23:48