Octreotide

ID: ALA3350037

Chembl Id: CHEMBL3350037

PubChem CID: 13690207

Max Phase: Preclinical

Molecular Formula: C49H66N10O10S2

Molecular Weight: 1019.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H](CO)NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@H](N)Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H](Cc2c[nH]c3ccccc23)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1

Standard InChI:  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

Standard InChI Key:  DEQANNDTNATYII-JDBXKHNRSA-N

Alternative Forms

1. Parent:

   

   ALA3350037

   H-D-Phe-Cys(1)-Phe-D-Trp-Lys-Thr-Cys(1)-D-aThr-ol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1019.26

Molecular Weight (Monoisotopic): 1018.4405

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References

1. Albert R, Smith-Jones P, Stolz B, Simeon C, Knecht H, Bruns C, Pless J..  (1998)  Direct synthesis of [DOTA-DPhe1]-octreotide and [DOTA-DPhe1,Tyr3]-octreotide (SMT487): two conjugates for systemic delivery of radiotherapeutical nuclides to somatostatin receptor positive tumors in man.,  8  (10): [PMID:9871736] [10.1016/s0960-894x(98)00187-5]

2. Osapay G, Prokai L, Kim HS, Medzihradszky KF, Coy DH, Liapakis G, Reisine T, Melacini G, Zhu Q, Wang SH, Mattern RH, Goodman M..  (1997)  Lanthionine-somatostatin analogs: synthesis, characterization, biological activity, and enzymatic stability studies.,  40  (14): [PMID:9216843] [10.1021/jm960850i]

3. Lewis I, Bauer W, Albert R, Chandramouli N, Pless J, Weckbecker G, Bruns C..  (2003)  A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential.,  46  (12): [PMID:12773038] [10.1021/jm021093t]

4. Gademann K, Kimmerlin T, Hoyer D, Seebach D..  (2001)  Peptide folding induces high and selective affinity of a linear and small beta-peptide to the human somatostatin receptor 4.,  44  (15): [PMID:11448228] [10.1021/jm010816q]

5. Liu S, Tang C, Ho B, Ankersen M, Stidsen CE, Crider AM..  (1998)  Nonpeptide somatostatin agonists with sst4 selectivity: synthesis and structure-activity relationships of thioureas.,  41  (24): [PMID:9822540] [10.1021/jm980118e]

6. Moore SB, van der Hoek J, de Capua A, van Koetsveld PM, Hofland LJ, Lamberts SW, Goodman M..  (2005)  Discovery of iodinated somatostatin analogues selective for hsst2 and hsst5 with excellent inhibition of growth hormone and prolactin release from rat pituitary cells.,  48  (21): [PMID:16220980] [10.1021/jm050376t]

7. Cyr JE, Pearson DA, Wilson DM, Nelson CA, Guaraldi M, Azure MT, Lister-James J, Dinkelborg LM, Dean RT..  (2007)  Somatostatin receptor-binding peptides suitable for tumor radiotherapy with Re-188 or Re-186. Chemistry and initial biological studies.,  50  (6): [PMID:17315859] [10.1021/jm061290i]

8. Su JC, Tseng CL, Chang TG, Yu WJ, Wu SK..  (2008)  A synthetic method for peptide-PEG-lipid conjugates: application of octreotide-PEG-DSPE synthesis.,  18  (16): [PMID:18656351] [10.1016/j.bmcl.2008.07.027]

9. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

10. Iddon L, Leyton J, Indrevoll B, Glaser M, Robins EG, George AJ, Cuthbertson A, Luthra SK, Aboagye EO..  (2011)  Synthesis and in vitro evaluation of [18F]fluoroethyl triazole labelled [Tyr3]octreotate analogues using click chemistry.,  21  (10): [PMID:21458258] [10.1016/j.bmcl.2011.03.016]

11. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

12. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

13. Pasternak A, Feng Z, de Jesus R, Ye Z, He S, Dobbelaar P, Bradley SA, Chicchi GG, Tsao KL, Trusca D, Eiermann GJ, Li C, Feng Y, Wu M, Shao Q, Zhang BB, Nargund R, Mills SG, Howard AD, Yang L, Zhou YP..  (2012)  Stimulation of Glucose-Dependent Insulin Secretion by a Potent, Selective sst3 Antagonist.,  3  (4): [PMID:24900466] [10.1021/ml200272z]

14. Yamada T, Kato Y, Kusuhara H, Lemaire M, Sugiyama Y..  (1998)  Characterization of the transport of a cationic octapeptide, octreotide, in rat bile canalicular membrane: possible involvement of P-glycoprotein.,  21  (1): [PMID:9743261] [10.1248/bpb.21.874]

15. Martín-Gago P, Ramón R, Aragón E, Fernández-Carneado J, Martin-Malpartida P, Verdaguer X, López-Ruiz P, Colás B, Cortes MA, Ponsati B, Macias MJ, Riera A..  (2014)  A tetradecapeptide somatostatin dicarba-analog: Synthesis, structural impact and biological activity.,  24  (1): [PMID:24342240] [10.1016/j.bmcl.2013.11.065]

16. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

17. Caumes C, Hjelmgaard T, Roy O, Reynaud M, Servent D, Taillefumier C, Faure S.  (2012)  Synthesis and binding affinities for sst receptors of cyclic peptoid SRIF-mimetics,  3  (12): [10.1039/C2MD20265D]

18. Smith LJ, Rought Whitta G, Dolenc J, Wang D, van Gunsteren WF..  (2016)  A molecular dynamics simulation investigation of the relative stability of the cyclic peptide octreotide and its deprotonated and its (CF3)-Trp substituted analogs in different solvents.,  24  (20): [PMID:27543388] [10.1016/j.bmc.2016.08.001]

Source

Source(3):

• Scientific Literature
• DrugMatrix
• TP-search Transporter Database