2-({19-[2-amino-3-(naphthalen-2-yl)propanamido]-10-(4-aminobutyl)-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-4-yl}formamido)-3-hydroxybutanamide

• ChemBase ID: 130489
• Molecular Formular: C54H69N11O10S2
• Molecular Mass: 1096.32336
• Monoisotopic Mass: 1095.46702946
• SMILES: O=C(N)C(NC(=O)C1NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(N)Cc2cc3ccccc3cc2)CSSC1)Cc1ccc(O)cc1)Cc1c2ccccc2[nH]c1)CCCCN)C(C)C)C(O)C
• Canonical SMILES: NCCCCC1NC(=O)C(NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(CSSCC(NC(=O)C(NC1=O)C(C)C)C(=O)NC(C(=O)N)C(O)C)NC(=O)C(Cc1ccc2c(c1)cccc2)N)Cc1c[nH]c2c1cccc2
• InChI: InChI=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)
• InChIKey: PUDHBTGHUJUUFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({19-[2-amino-3-(naphthalen-2-yl)propanamido]-10-(4-aminobutyl)-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-4-yl}formamido)-3-hydroxybutanamide
• IUPAC Traditional name: 2-({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
• Brand Name: Somatuline
• Synonyms: Lanreotide; BIM-23014C; β-(2-Naphthyl)-D-Ala-Cys-Tyr-D-Trp-Lys-Val-Cys-Thr amide [Disulfide Bridge: 2–7]

Database IDs

• CAS Number: 108736-35-2
• MDL Number: MFCD00133121
• PubChem SID: 162224768; 24897906
• PubChem CID: 71349
• ATC CODE: H01CB03
• CHEMBL: 1201185
• Chemspider ID: 64450
• IUPHAR ligand ID: 2031
• Unique Ingredient Identifier: 0G3DE8943Y
• Wikipedia Title: Lanreotide

CALCULATED PROPERTIES

• Acid pKa: 9.426515
• H Acceptors: 12
• H Donor: 13
• LogD (pH = 5.5): -4.637945
• LogD (pH = 7.4): -2.4303243
• Log P: -0.3327617
• Molar Refractivity: 292.9234 cm^3
• Polarizability: 116.8736 Å^3
• Polar Surface Area: 355.08 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Intramuscular, subcutaneous
• Bioavailability: Approximately 80%
• Excretion: Mostly biliary
• Half Life: 2 hours (immediate release); 5 days (sustained release)
• Metabolism: In GI tract
• Protein Bound: 78%
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C (Australia); C (US)
• US Licence: Lanreotide
• Gene Information: human ... SSTR1(6751), SSTR4(6754)mouse ... Sstr3(20607)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - N9642

Biochem/physiol Actions
sst2 somatostatin receptor agonist.