lanreotide (CHEM045201)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 12:55:52 UTC
Update Date2016-11-09 01:23:18 UTC
Accession NumberCHEM045201
Identification
Common Namelanreotide
ClassSmall Molecule
DescriptionLanreotide is a drug employed in the management of acromegaly (a hormonal condition caused by excess growth hormone) in addition to symptoms caused by neuroendocrine tumors, especially carcinoid syndrome. This drug is a long-acting analog of the drug somatostatin, a growth hormone inhibitor. Lanreotide is manufactured by the company, _Ipsen Pharmaceuticals_ as lanreotide acetate, and marketed as _Somatuline_. It is approved in several countries worldwide, including the United Kingdom, Australia, and Canada. Lanreotide was first approved for use in the United States by the FDA on August 30, 2007.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SomatulinaMeSH
SomatulineMeSH
L-Threoninamide, 3-(2-naphthalenyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-, cyclic (2-7)-disulfideMeSH
Lanreotide acetateMeSH
Nal-cyclo(cys-tyr-TRP-lys-val-cys)THR-NH2MeSH
Lanreotide-SRMeSH
2-Naphthylalanyl-cyclo(cysteinyl-tyrosyl-tryptophyl-lysyl-valyl-cysteinyl)-threoninamideMeSH
Naphthyl-cyclo(cys-tyr-TRP-lys-val-cys)THR-NH2MeSH
Nal-cyclo(cys-tyr-TRP-lys-val-cys)-THR-NH2MeSH
SomatulinMeSH
188Re-LanreotideMeSH
Naphthalenyl-cyclo(cysteinyl-tyrosyl-tryptophyl-lysyl-valyl-cysteinyl)threoninamideMeSH
LanreotideMeSH
Lanreotide acetic acidGenerator
2-{[(19-{[2-amino-1-hydroxy-3-(naphthalen-2-yl)propylidene]amino}-10-(4-aminobutyl)-6,9,12,15,18-pentahydroxy-16-[(4-hydroxyphenyl)methyl]-13-[(1H-indol-3-yl)methyl]-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaen-4-yl)(hydroxy)methylidene]amino}-3-hydroxybutanimidateGenerator
Chemical FormulaC54H69N11O10S2
Average Molecular Mass1096.330 g/mol
Monoisotopic Mass1095.467 g/mol
CAS Registry Number108736-35-2
IUPAC Name2-({19-[2-amino-3-(naphthalen-2-yl)propanamido]-10-(4-aminobutyl)-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-4-yl}formamido)-3-hydroxybutanamide
Traditional Name2-({19-[2-amino-3-(naphthalen-2-yl)propanamido]-10-(4-aminobutyl)-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}formamido)-3-hydroxybutanamide
SMILES[H]N([H])CCCCC1N([H])C(=O)C(CC2=CN([H])C3=CC=CC=C23)N([H])C(=O)C(CC2=CC=C(O)C=C2)N([H])C(=O)C(CSSCC(N([H])C(=O)C(N([H])C1=O)C(C)C)C(=O)N([H])C(C(C)O)C(=O)N([H])[H])N([H])C(=O)C(CC1=CC2=CC=CC=C2C=C1)N([H])[H]
InChI IdentifierInChI=1S/C54H69N11O10S2/c1-29(2)45-54(75)63-44(53(74)65-46(30(3)66)47(57)68)28-77-76-27-43(62-48(69)38(56)23-32-15-18-33-10-4-5-11-34(33)22-32)52(73)60-41(24-31-16-19-36(67)20-17-31)50(71)61-42(25-35-26-58-39-13-7-6-12-37(35)39)51(72)59-40(49(70)64-45)14-8-9-21-55/h4-7,10-13,15-20,22,26,29-30,38,40-46,58,66-67H,8-9,14,21,23-25,27-28,55-56H2,1-3H3,(H2,57,68)(H,59,72)(H,60,73)(H,61,71)(H,62,69)(H,63,75)(H,64,70)(H,65,74)
InChI KeyPUDHBTGHUJUUFI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylaminobenzoic acid and derivatives
Alternative Parents
Substituents
  • Acylaminobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • Benzamide
  • Anilide
  • Benzoyl
  • Iodobenzene
  • Halobenzene
  • Aryl halide
  • Aryl iodide
  • 1,3-dicarbonyl compound
  • Tertiary carboxylic acid amide
  • Vinylogous halide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Organoiodide
  • Organohalogen compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.005 g/LALOGPS
logP1.87ALOGPS
logP-0.33ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)10.26ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area355.08 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity292.92 m³·mol⁻¹ChemAxon
Polarizability114.68 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-4340104090-6be3ea865b49f29210e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-7900000123-eaa594f5bcf0aa756dedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1965373210-454c2d978a738c9cc3e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-9070101161-e3b5852fe384fea43816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fu-9010100041-0492cc7b9a68886e29dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-4902423210-e1413c69ee0448130ed1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9100000000-3a898a1e589d05e993abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005a-9300000013-177d2fa12fa34fd00ecaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-3900000010-7b8292d3e5f67208916aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000001-3848eb09dcc7e8c585a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9510000004-df04c45dfb4d319d5344Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-1900000010-a6a2ca06bcafbc525c72Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06791
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLanreotide
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID71349
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available