Linaclotide acetateProduct ingredient for Linaclotide

Name
Linaclotide acetate
Drug Entry
Linaclotide

Linaclotide is a synthetic 14-amino acid cyclic peptide 2 and first-in-class guanylate cyclase-C (G-CC) agonist.2,7 Linaclotide is structurally related to human guanylin and uroguanylin, paracrine peptide hormones that are endogenous activators of GC-C.3 It is also a homolog of a heat-stable enterotoxin derived from Escherichia coli, the first natural ligand that activates GC-C.5

Linaclotide is used for the treatment of various types of constipation, including irritable bowel syndrome with constipation. Linaclotide was first approved by the FDA on August 30, 2012.2 It gained EMA and Health Canada approval on November 26, 2012 8 and December 3, 2013,9 respectively. Linaclotide works to improve the symptoms of constipation and gastrointestinal symptoms of conditions involving constipation.5

Accession Number
DBSALT000108
Structure
Synonyms
Not Available
External IDs
MM-416775
UNII
NSF067KU1M
CAS Number
851199-60-5
Weight
Average: 1586.788
Monoisotopic: 1585.411048177
Chemical Formula
C61H83N15O23S6
InChI Key
KWFNVZFWXXEJKL-YZDVLOIKSA-N
InChI
InChI=1S/C59H79N15O21S6.C2H4O2/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29;1-2(3)4/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95);1H3,(H,3,4)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-;/m0./s1
IUPAC Name
(2S)-2-{[(1R,4S,7S,13S,16R,21R,24R,27S,30S,33R,38R,44S)-21-amino-13-(carbamoylmethyl)-27-(2-carboxyethyl)-44-[(1R)-1-hydroxyethyl]-30-[(4-hydroxyphenyl)methyl]-4-methyl-3,6,12,15,22,25,28,31,40,43,46,51-dodecaoxo-18,19,35,36,48,49-hexathia-2,5,11,14,23,26,29,32,39,42,45,52-dodecaazatetracyclo[22.22.4.2^{16,33}.0^{7,11}]dopentacontan-38-yl]formamido}-3-(4-hydroxyphenyl)propanoic acid; acetic acid
SMILES
CC(O)=O.[H][C@]1(CSSC[C@]2([H])NC(=O)[C@H](CC3=CC=C(O)C=C3)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]3CSSC[C@H](NC(=O)[C@H](C)NC(=O)[C@@H]4CCCN4C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CSSC[C@H](N)C(=O)N3)NC2=O)C(=O)N[C@@]([H])([C@@H](C)O)C(=O)NCC(=O)N1)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
PubChem Compound
16158207
ChemSpider
17314503
ChEMBL
CHEMBL3301676
Predicted Properties
PropertyValueSource
Water Solubility0.701 mg/mLALOGPS
logP-1.5ALOGPS
logP-11Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.06Chemaxon
pKa (Strongest Basic)7.65Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count22Chemaxon
Hydrogen Donor Count19Chemaxon
Polar Surface Area573.91 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity368 m3·mol-1Chemaxon
Polarizability145.88 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon