NAV

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
Similar Structures
Weight
Average: 1131.38
Monoisotopic: 1130.48301423
Chemical Formula
C57H70N12O9S2
Synonyms
  • Vapreotida
  • Vapreotide
  • Vapreotidum
External IDs
  • BMY 41606
  • BMY-41606
  • RC-160
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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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Contraindications & Blackbox Warnings
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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).

TargetActionsOrganism
ASomatostatin receptor type 2
inducer
Humans
ASomatostatin receptor type 5
agonist
Humans
UNeurokinin 1 receptor
antagonist
Humans
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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Vapreotide.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Vapreotide.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Vapreotide.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Vapreotide.
AlectinibThe metabolism of Alectinib can be decreased when combined with Vapreotide.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Vapreotide acetate5562377HFV849479-74-9KBIZSMHYSQUHDH-NCACADTJSA-N
International/Other Brands
Octastatin / Sanvar / Sanvar IR

Categories

ATC Codes
H01CB04 — Vapreotide
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 / 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
  1. 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]
  2. Authors unspecified: Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. [Article]
  3. Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. [Article]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
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);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentGastric Varices / Hemorrhage Esophageal / Portal Hypertension / Varices, Esophageal1
3TerminatedSupportive CarePancreatic Cancer / Perioperative/Postoperative Complications1

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
PropertyValueSource
Water Solubility0.00401 mg/mLALOGPS
logP2.69ALOGPS
logP1.07Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)9.43Chemaxon
pKa (Strongest Basic)10.26Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count13Chemaxon
Polar Surface Area350.64 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity306.22 m3·mol-1Chemaxon
Polarizability118.22 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9656
Blood Brain Barrier-0.9221
Caco-2 permeable-0.7899
P-glycoprotein substrateSubstrate0.8572
P-glycoprotein inhibitor INon-inhibitor0.9346
P-glycoprotein inhibitor IINon-inhibitor0.9514
Renal organic cation transporterNon-inhibitor0.8571
CYP450 2C9 substrateNon-substrate0.8172
CYP450 2D6 substrateNon-substrate0.7495
CYP450 3A4 substrateSubstrate0.5808
CYP450 1A2 substrateNon-inhibitor0.8063
CYP450 2C9 inhibitorNon-inhibitor0.638
CYP450 2D6 inhibitorNon-inhibitor0.8286
CYP450 2C19 inhibitorNon-inhibitor0.6249
CYP450 3A4 inhibitorNon-inhibitor0.739
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5526
Ames testNon AMES toxic0.7151
CarcinogenicityNon-carcinogens0.8667
BiodegradationNot ready biodegradable0.9935
Rat acute toxicity2.7335 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.973
hERG inhibition (predictor II)Inhibitor0.6667
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/MSsplash10-001i-1900000000-b5141e6eaf3638706265
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fs-2900000001-91b21299d72d925bbf20
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00m0-7900000005-755a379504e92eafb657
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01r6-8900000016-8c192e38c05a71d48d7d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k9x-5900000000-dd19468a68132b8a770a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-059x-5900000011-7d5af25a8276a3d83c62
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-307.61215
predicted
DeepCCS 1.0 (2019)
[M+H]+309.33588
predicted
DeepCCS 1.0 (2019)
[M+Na]+315.66483
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Somatostatin receptor type 2
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
  1. 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]
Details2. Somatostatin receptor type 5
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
  1. 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]
Details3. Neurokinin 1 receptor
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
  1. 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]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Details1. Cytochrome P450 3A4
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