General
Preferred name
PLECANATIDE
Synonyms
Trulance ()
Plecanatide (acetate) ()
Guanilib ()
Plecanatida ()
SP-304 (SYNERGY) ()
SP-304 ()
P&D ID
PD053913
CAS
467426-54-6
1075732-84-1
Tags
available
drug
Approved by
FDA
First approval
2017
Drug indication
Crohn disease
Chronic idiopathic constipation
Irritable bowel syndrome
Drug Status
approved
investigational
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Plecanatide is a synthetic analogue of , which is an agonist of the guanylate cyclase C (GC-C) receptor (GUCY2C) . Activation of GC-C in mucosal epithelial cells of the gastrointestinal tract (GI) tract causes the secretion of fluid, facilitating bowel movements. Plecanatide has potential to help manage constipating GI disorders, such as chronic idiopathic constipation and constipation-predominant irritable bowel syndrome (IBS-C). Plecanatide is one of the peptides claimed in patent WO2014151206, where it is represented by SEQ ID NO: 1 and code SP-304, with residue 3 (Aad) being gultamic acid (E, Glu) .
The SMILES and structure image used in this entry are from Chemicalize.
HELM notation is PEPTIDE1{N.D.E.C.E.L.C.V.N.V.A.C.T.G.C.L}$PEPTIDE1,PEPTIDE1,12:R3-4:R3|PEPTIDE1,PEPTIDE1,15:R3-7:R3$$$
DESCRIPTION Plecanatide is a synthetic analogue of , which is an agonist of the guanylate cyclase C (GC-C) receptor (GUCY2C) . Activation of GC-C in mucosal epithelial cells of the gastrointestinal (GI) tract causes the secretion of fluid, facilitating bowel movements. Plecanatide has potential to help manage constipating GI disorders, such as chronic idiopathic constipation and constipation-predominant irritable bowel syndrome (IBS-C). Plecanatide is one of the peptides claimed in patent WO2014151206, where it is represented by SEQ ID NO: 1 and code SP-304, with residue 3 (Aad) being gultamic acid (E, Glu) .
The SMILES and structure image used in this entry are from Chemicalize.
HELM notation is PEPTIDE1{N.D.E.C.E.L.C.V.N.V.A.C.T.G.C.L}$PEPTIDE1,PEPTIDE1,12:R3-4:R3|PEPTIDE1,PEPTIDE1,15:R3-7:R3$$$.
was the first GC-C activator to reach the clinic, like plecanatide it is approved for the treatment of chronic constipation and IBS-C. (GtoPdb)
ABSORPTION Plecanatide is minimally absorbed with negligible systemic availability following oral administration.; Concentrations of plecanatide and its active metabolite in plasma are below the limit of quantitation after an oral dose of 3 mg. Therefore, standard pharmacokinetic parameters such as AUC, maximum concentration (Cmax), and half-life (t½) cannot be calculated.
MOA Guanylate cyclase C (GC-C) agonist; Plecanatide and its active metabolite bind to GC-C and act locally on the luminal surface of intestinal epithelial cells; GC-C activation leads to increased cyclic guanosine monophosphate (cGMP), which, in turn, stimulates secretion of chloride and bicarbonate into the intestinal lumen, mainly by activation of the cystic fibrosis transmembrane conductance regulator (CFTR) ion channel, resulting in increased intestinal fluid and accelerated transit.; In animal models, plecanatide has been shown to increase fluid secretion into the gastrointestinal (GI) tract, accelerate intestinal transit, and cause changes in stool consistency.; In an animal model of visceral pain, plecanatide reduced abdominal muscle contractions, a measure of intestinal pain. The mechanism has not been studied.
Compound Sets
13
Cayman Chemical Bioactives
33878
ChEMBL Approved Drugs
CHEMBL2103867
ChEMBL Drugs
CHEMBL2103867
DrugBank
DB13170
DrugBank Approved Drugs
DB13170
DrugCentral
5208
DrugCentral Approved Drugs
5208
DrugMAP
DMKEX7O
DrugMAP Approved Drugs
DMKEX7O
Guide to Pharmacology
9069
MedChem Express Bioactive Compound Library
HY-108741
HY-108741A
Natural product-based probes and drugs
TargetMol Bioactive Compound Library
T9080
External IDs
21
Properties
(calculated by RDKit )
Molecular Weight
1680.63
Hydrogen Bond Acceptors
27
Hydrogen Bond Donors
23
Rotatable Bonds
28
Ring Count
3
Aromatic Ring Count
0
cLogP
-8.15
TPSA
718.13
Fraction CSP3
0.68
Chiral centers
16.0
Largest ring
29.0
QED
0.03
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
GPCR/G protein
Target
guanylate cyclase-C
Guanylate Cyclase
Biosynthetic Origin
Peptide (Ribosomal)
Therapeutic Indication
Irritable Bowel Syndrome
Source data