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Details

Stereochemistry ABSOLUTE
Molecular Formula C60H74N12O10
Molecular Weight 1123.304
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VELDOREOTIDE

SMILES

[H][C@]3(CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC4=CNC5=C4C=CC=C5)NC(=O)[C@H](CC6=CC=CC=C6)NC(=O)CCCNC(=O)CCCN(CC(N)=O)C(=O)[C@H](CC7=CC=CC=C7)NC(=O)[C@@]([H])(NC(=O)[C@H](CCCCN)NC3=O)[C@@H](C)O

InChI

InChIKey=ABFNTRQPWNXUHA-VEVJRHMJSA-N
InChI=1S/C60H74N12O10/c1-37(73)54-59(81)70-50(31-39-18-6-3-7-19-39)60(82)72(36-51(62)74)29-15-26-52(75)63-28-14-25-53(76)66-47(30-38-16-4-2-5-17-38)56(78)68-49(33-41-35-65-45-23-11-9-21-43(41)45)58(80)69-48(32-40-34-64-44-22-10-8-20-42(40)44)57(79)67-46(55(77)71-54)24-12-13-27-61/h2-11,16-23,34-35,37,46-50,54,64-65,73H,12-15,24-33,36,61H2,1H3,(H2,62,74)(H,63,75)(H,66,76)(H,67,79)(H,68,78)(H,69,80)(H,70,81)(H,71,77)/t37-,46+,47+,48-,49+,50+,54+/m1/s1

HIDE SMILES / InChI

Description

Somatoprim (DG3173) is a heptapeptide somatostatin analog (SSA) that binds with high affinity to sstr2, sstr4 and sstr5 and shows a very low insulin suppression in contrast to other SSA. Initially developed by Ipsen, it is under active development by licensee Aspireo Pharmaceuticals, an Israeli company. In vitro as well as in vivo testing showed a dose-dependent GH lowering effect. Somatoprim has demonstrated a unique receptor binding and pharmacological profile which is differentiated from SSAs that are currently marketed or in clinical development. In particular, Somatoprim has shown an improved side effect profile with reduced adverse effects on the gastrointestinal tract and glucose metabolism. Furthermore, assessment of growth hormone secretion in cultured human somatotroph adenoma tissue treated with Somatoprim indicates that it has the potential to increase the response rate of acromegalic patients to SSA therapy. Somatoprim is currently in phase I/II of clinical development.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Acromegaly: octreotide and Somatoprim (DG3173). Eligible patients are to receive 300 ug octreotide as active comparator, followed by four ascending doses of 100 ug, 300 ug, 900 ug and 1800 ug DG3173. All treatments will be administered consecutively to all patients as single subcutaneous bolus injections.
Route of Administration: Other
In Vitro Use Guide
PTR-3173 suppressed GH release from both fetal pituitaries (maximal suppression of 54% with 10 nM) and cultures of GH-cell adenomas (35% suppression with 100 nM).