Plecanatide Chemical Properties

Boiling point:

2120.0±65.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

pka

3.61±0.21(Predicted)

form 

Solid

color 

White to off-white

Sequence

Asn-Asp-Glu-Cys-Glu-Leu-Cys-Val-Asn-Val-Ala-Cys-Thr-Gly-Cys-Leu (Disulfide bridge: Cys4-Cys12; Cys7-Cys15)

InChI

InChI=1S/C65H104N18O26S4/c1-25(2)15-34-55(98)80-41-24-113-110-21-38(58(101)77-37(65(108)109)16-26(3)4)71-44(87)20-69-62(105)50(30(10)84)83-61(104)40(78-51(94)29(9)70-63(106)48(27(5)6)81-57(100)35(18-43(68)86)76-64(107)49(28(7)8)82-60(41)103)23-112-111-22-39(59(102)73-32(53(96)75-34)11-13-45(88)89)79-54(97)33(12-14-46(90)91)72-56(99)36(19-47(92)93)74-52(95)31(66)17-42(67)85/h25-41,48-50,84H,11-24,66H2,1-10H3,(H2,67,85)(H2,68,86)(H,69,105)(H,70,106)(H,71,87)(H,72,99)(H,73,102)(H,74,95)(H,75,96)(H,76,107)(H,77,101)(H,78,94)(H,79,97)(H,80,98)(H,81,100)(H,82,103)(H,83,104)(H,88,89)(H,90,91)(H,92,93)(H,108,109)/t29-,30+,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,48-,49-,50-/m0/s1

InChIKey

NSPHQWLKCGGCQR-DLJDZFDSSA-N

SMILES

S1C([H])([H])[C@@]2([H])C(N([H])[C@]([H])(C(N([H])[C@@]([H])(C([H])([H])C(N([H])[H])=O)C(N([H])[C@]([H])(C(N([H])[C@@]([H])(C([H])([H])[H])C(N([H])[C@]([H])(C(N([H])[C@]([H])(C(N([H])C([H])([H])C(N([H])[C@]([H])(C(N([H])[C@]([H])(C(=O)O[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)C([H])([H])S1)=O)=O)[C@@]([H])(C([H])([H])[H])O[H])=O)C([H])([H])SSC([H])([H])[C@@]([H])(C(N([H])[C@@]([H])(C([H])([H])C([H])([H])C(=O)O[H])C(N([H])[C@]([H])(C(N2[H])=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)=O)N([H])C([C@]([H])(C([H])([H])C([H])([H])C(=O)O[H])N([H])C([C@]([H])(C([H])([H])C(=O)O[H])N([H])C([C@]([H])(C([H])([H])C(N([H])[H])=O)N([H])[H])=O)=O)=O)=O)=O)C([H])(C([H])([H])[H])C([H])([H])[H])=O)=O)C([H])(C([H])([H])[H])C([H])([H])[H])=O

Safety Information

Hazardous Substances Data

467426-54-6(Hazardous Substances Data)

Plecanatide Usage And Synthesis

Uses

Plecanatide is used in the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation. It works as a laxative by drawing water in to the gastrointestinal tract thereby softening stool and encouraging its natural passage.

brand name

Trulance

General Description

Plecanatide is an oral guanylate cyclase-C agonist that is being developed by Synergy Pharmaceuticals for the treatment of gastrointestinal disorders, such as chronic idiopathic constipation (CIC) and irritable bowel syndrome with constipation (IBS-C). It is a synthetic analogue of human uroguanylin, a 16 amino acid peptide that regulates ion and fluid transport in the gastrointestinal tract. In January 2017, plecanatide received its first global approval in the USA for the treatment of adult patients with CIC. Plecanatide is undergoing phase III investigation in IBS-C.

Enzyme inhibitor

This uroguanylin analogue (FW = 1681.90 g/mol; CAS 467426-54-6), also known by the codename SP-304, binds to and activates guanylate cyclase-C (GC-C) receptors (EC50 ≈ 0.3 μM) expressed on the epithelial cells lining turn sequentially activates protein kinase G-II and the chloride channel known as the Cystic Fibrosis Transmembrane-conductance Regulator (CFTR) to regulate ion and fluid transport, to promote epithelial cell homeostasis, and to maintain barrier function in the GI mucosa. Plecanatide is a hexadecapeptide that is structurally identical to uroguanylin, except for an glutamate substitution at position-3. Oral treatment with plecanatide at a dose range between 0.05-2.5 mg/kg per day is as effective as once-daily treatment with 5-amino salicylic acid (100 mg/kg) or sulfasalazine (80 mg/kg). Amelioration of colitis by the treatment with plecanatide or dolcanatide was not dose-dependent, most likely due to saturation of available GC-C receptors.

in vivo

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