octreotide
Octreotide is a cyclic octapeptide with a disulfide bridge between cysteine residues at positions 1 and 8, forming a macrocyclic core. It incorporates a D-phenylalanine derivative at position 2 and a C-terminal amide, conferring structural rigidity and enhanced metabolic stability compared to native somatostatin. The molecule features thioether linkages and multiple amide bonds, with a side-chain modification at position 7 enhancing receptor affinity. As an active pharmaceutical ingredient (API), it serves as a reference standard for HPLC-based quantification of octreotide analogs in drug formulation analysis.
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Molecular Formula
C49H66N10O10S2
Molecular Weight
1019.2000
CAS Number
83150-76-9
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PubChem CID
448601 ↗
IUPAC Name
(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
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📝 Synonyms
Octreotide
83150-76-9
Octreotida
Octreotidum
RWM8CCW8GP
SMS-201-995
SMS995
SMS-995
DRG-0115
DTXSID0048682
🔬 Chemical Identifiers
C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)[C@@H](CC5=CC=CC=C5)N)C(=O)N[C@H](CO)[C@@H](C)O)O
InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1
DEQANNDTNATYII-OULOTJBUSA-N
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