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
- External Links
- PubChem Compound
- 16158207
- ChemSpider
- 17314503
- ChEMBL
- CHEMBL3301676
- Predicted Properties
Property Value Source Water Solubility 0.701 mg/mL ALOGPS logP -1.5 ALOGPS logP -11 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 3.06 Chemaxon pKa (Strongest Basic) 7.65 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 22 Chemaxon Hydrogen Donor Count 19 Chemaxon Polar Surface Area 573.91 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 368 m3·mol-1 Chemaxon Polarizability 145.88 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon