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Vapreotide

July 24, 2017
Common Name

Vapreotide Description

Vapreotide is only found in individuals that have used or taken this drug. It is a synthetic octapeptide somatostatin analog. It was being studied for the treatment of cancer.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 ). Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source BMY 41606HMDB OctastatinHMDB RC-160HMDB Vapreotide acetateHMDB

Chemical Formlia

C57H70N12O9S2 Average Molecliar Weight

1131.371 Monoisotopic Molecliar Weight

1130.483013278 IUPAC Name

2-amino-N-[10-(4-aminobutyl)-4-{[1-carbamoyl-2-(1H-indol-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-phenylpropanamide Traditional Name

octastatin CAS Registry Number

103222-11-3 SMILES

CC(C)C1NC(=O)C(CCCCN)NC(=O)C(CC2=CNC3=C2C=CC=C3)NC(=O)C(CC2=CC=C(O)C=C2)NC(=O)C(CSSCC(NC1=O)C(=O)NC(CC1=CC2=CC=CC=C2N1)C(N)=O)NC(=O)C(N)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C57H70N12O9S2/c1-32(2)49-57(78)68-48(55(76)64-44(50(60)71)28-37-26-35-14-6-8-16-41(35)62-37)31-80-79-30-47(67-51(72)40(59)24-33-12-4-3-5-13-33)56(77)65-45(25-34-19-21-38(70)22-20-34)53(74)66-46(27-36-29-61-42-17-9-7-15-39(36)42)54(75)63-43(52(73)69-49)18-10-11-23-58/h3-9,12-17,19-22,26,29,32,40,43-49,61-62,70H,10-11,18,23-25,27-28,30-31,58-59H2,1-2H3,(H2,60,71)(H,63,75)(H,64,76)(H,65,77)(H,66,74)(H,67,72)(H,68,78)(H,69,73)

InChI Key

GAWXLRUZZFSQON-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives 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
  • 1-hydroxy-2-unsubstituted benzenoids
  • Aralkylamines
  • Substituted pyrroles
  • Fatty amides
  • Heteroaromatic compounds
  • Secondary carboxylic acid amides
  • Primary carboxylic acid amides
  • Organic dislifides
  • Lactams
  • Azacyclic compounds
  • Carbonyl compounds
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds

    • Substituents

  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Phenylalanine or derivatives
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty amide
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Organic dislifide
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Analgesics
  • Antineoplastic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility3.99e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.004 mg/mLALOGPS logP2.7ALOGPS logP0.76ChemAxon logS-5.5ALOGPS 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 Refractivity306.2 m3·mol-1ChemAxon Polarizability118.82 Å3ChemAxon Number of Rings7ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04894

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04894

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-1 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-0 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04894 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    26330333 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15601 Metagene Link

    HMDB15601 METLIN ID

    Not Available PubChem Compound

    23725064 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: U-73123

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General 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. [PubMed:7556407 ]
    2. 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. [PubMed:1354449 ]
    3. 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. [PubMed:7511473 ]
    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. [PubMed:7909563 ]
    5. 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. [PubMed:7912964 ]
    6. 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. [PubMed:12691930 ]
    7. Authors unspecified: Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. [PubMed:12952505 ]
    8. Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. [PubMed:16047258 ]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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 affinity of this receptor to tachykinins is:substance P > substance K > neuromedin-K
    Gene Name:
    TACR1
    Uniprot ID:
    P25103
    Molecular weight:
    46250.5
    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. [PubMed:7556407 ]
    2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for somatostatins-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 PLC via pertussis toxin insensitive as well as sensitive G proteins. In RIN-5F cells, this receptor inhibits calcium entry by suppressing voltage dependent calcium-channels
    Gene Name:
    SSTR2
    Uniprot ID:
    P30874
    Molecular weight:
    41332.4
    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. [PubMed:19708854 ]

    PMID: 22082421

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