Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00366)
Name
Linaclotide
Synonyms    Click to Show/Hide the Synonyms of This API
Linaclotide; Linzess; 851199-59-2; CHEBI:68551; MD-1100; Cys Cys Glu Tyr Cys Cys Asn Pro Ala Cys Thr Gly Cys Tyr (disulfide bridge: 1-6; 2-10; 5-13); Linaclotide [USAN:INN]; HSDB 8224; ASP0456; Constella (TN); ASP 0456; ASP-0456; Linzess (TN); Linaclotide (JAN/USAN); CHEMBL3301675; SCHEMBL13114620; DTXSID90234256; DB08890; NCGC00389841-01; L-Tyrosine, L-cysteinyl-L-cysteinyl-L-alpha-glutamyl-L-tyrosyl-L-cysteinyl-L-cysteinyl-L-asparaginyl-L-prolyl-L-alanyl-L-cysteinyl-L-threonylglycyl-L-cysteinyl-, cyclic (1->6),(2->10),(5->13)-tris(disulfide); D09355; Q3832559; L-cysteinyl-L-cysteinyl-L-alpha-glutamyl-L-tyrosyl-L-cysteinyl-L-cysteinyl-L-asparaginyl-L-prolyl-L-alanyl-L-cysteinyl-L-threonylglycyl-L-cysteinyl-L-tyrosine cyclic (1->6),(2->10),(5->13)-tris(disulfide)
Clinical Status
Approved
Disease Indication Irritable bowel syndrome ICD-11: DD91 [1]
PubChem CID
16158208
Formula
C59H79N15O21S6
Canonical SMILES
C[C@H]1C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)[C@@H](C)O)C(=O)N[C@@H](CC4=CC=C(C=C4)O)C(=O)O)C(=O)N[C@@H](CSSC[C@@H](C(=O)N3)N)C(=O)N[C@H](C(=O)N5CCC[C@H]5C(=O)N1)CC(=O)N)CC6=CC=C(C=C6)O)CCC(=O)O
InChI
1S/C59H79N15O21S6/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/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)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-/m0/s1
InChIKey
KXGCNMMJRFDFNR-WDRJZQOASA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=16158208"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 1526.8 Topological Polar Surface Area 726
XlogP -6.8 Complexity 3030
Heavy Atom Count 101 Rotatable Bond Count 13
Hydrogen Bond Donor Count 19 Hydrogen Bond Acceptor Count 28
Full List of Drug Formulations (DFMs) Containing This API
          Linaclotide 0.072 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Histidine; Talc; Titanium dioxide; Calcium chloride; Cellulose, microcrystalline; Gelatin; Polyvinyl alcohol, unspecified; Powdered cellulose
                   Dosage Form Oral Capsule
                   Company Allergan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Histidine DIG Info Integral membrane E16 (IC50 = 20000 nM) [2]
          Linaclotide 0.145 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Leucine; Titanium dioxide; Calcium chloride; Cellulose, microcrystalline; Gelatin; Hypromelloses
                   Dosage Form Oral Capsule
                   Company Allergan; Avera McKennan Hospital; Lake Eire Medical & Surgical Supply DBA Quality Care Products
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Leucine DIG Info Integral membrane E16 (IC50 = 85000 nM) [2]
          Linaclotide 0.29 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Leucine; Titanium dioxide; Calcium chloride; Cellulose, microcrystalline; Gelatin; Hypromelloses
                   Dosage Form Oral Capsule
                   Company Allergan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Leucine DIG Info Integral membrane E16 (IC50 = 85000 nM) [2]
References
1 FDA label for approved linaclotide from the official website of the U.S. Food and Drug Administration.
2 Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1). J Med Chem. 2018 Aug 23; 61(16):7358-7373.

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