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Linaclotide information


Linaclotide
Linaclotide structure. A 2D line-angle schematic of linaclotide (sequence CCEYCCNPACTGCY).[1] The phenolic ring of terminal tyrosine (Y) is in the lower left corner. Exaggerated bond lengths emphasize 3 disulfide (-S—S-) bonds between 6 cysteines (C's).
Clinical data
Trade namesLinzess
AHFS/Drugs.comMonograph
MedlinePlusa613007
License data
  • US DailyMed: Linaclotide
Routes of
administration		By mouth
ATC code
  • A06AX04 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)[3]
  • US: WARNING[2]Rx-only[4]
  • EU: Rx-only[5]
Identifiers
IUPAC name
  • L-Cysteinyl-L-cysteinyl-L-glutamyl-L-tyrosyl-L-cysteinyl-L-cysteinyl-L-asparaginyl-L-prolyl-L-alanyl-L-cysteinyl-L-threonylglycyl-L-cysteinyl-L-tyrosine cyclo(1-6),(2-10),(5-13)-tris(disulfide)
CAS Number
  • 851199-59-2 checkY
PubChem CID
  • 16158208
IUPHAR/BPS
  • 5017
ChemSpider
  • 17314504 ☒N
UNII
  • N0TXR0XR5X
KEGG
  • D09355 checkY
CompTox Dashboard (EPA)
  • DTXSID90234256 Edit this at Wikidata
ECHA InfoCard100.243.239 Edit this at Wikidata
Chemical and physical data
FormulaC59H79N15O21S6
Molar mass1526.73 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(O)[C@@H](NC(=O)[C@H]4NC(=O)CNC(=O)[C@@H](NC(=O)[C@H]2NC(=O)[C@@H](NC(=O)[C@H]5N(C(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CSSC1)CSSC2)CCC(=O)O)Cc3ccc(O)cc3)CSSC4)CC(=O)N)CCC5)C)[C@H](O)C)Cc6ccc(O)cc6
InChI
  • 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 ☒N
  • Key:KXGCNMMJRFDFNR-WDRJZQOASA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Linaclotide, (sold under the brand name Linzess in the US and Mexico, and as Constella elsewhere)[6] is a drug used to treat irritable bowel syndrome with constipation and chronic constipation with no known cause.[4][3] It has a black box warning about the risk of serious dehydration in children in the US; the most common adverse effects in others include diarrhea.[4]

It is an oligopeptide agonist of guanylate cyclase 2C and remains in the GI tract after it is taken by mouth. It was approved in the US and the European Union in 2012.[7]

It is marketed by Abbvie (formerly Allergan) in the United states and by Astellas in Asia;[citation needed] Ironwood Pharmaceuticals was the originator.[8][failed verification] In 2021, it was the 246th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[9][10]

  1. ^ Oh SA (17 August 2011). "Macrocycle Milestone for Ironwood Pharma". The Haystack. Archived from the original on 27 November 2018. Retrieved 11 February 2017 – via CENBlog.org.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ a b "UK label: Linaclotide Summary of Product Characteristics". Electronic Medicines Compendium. September 2017. Archived from the original on 15 April 2018. Retrieved 15 April 2018.
  4. ^ a b c "Linzess- linaclotide capsule, gelatin coated". DailyMed. 31 August 2021. Archived from the original on 29 March 2021. Retrieved 12 June 2023.
  5. ^ "Constella EPAR". European Medicines Agency. 24 May 2023. Archived from the original on 22 June 2021. Retrieved 12 June 2023.
  6. ^ "Linaclotide - Ironwood Pharmaceuticals". AdisInsight. Archived from the original on 7 October 2017. Retrieved 15 April 2018.
  7. ^ Yu SW, Rao SS (September 2014). "Advances in the management of constipation-predominant irritable bowel syndrome: the role of linaclotide". Therapeutic Advances in Gastroenterology. 7 (5): 193–205. doi:10.1177/1756283X14537882. PMC 4107700. PMID 25177366.
  8. ^ Nocera J (9 January 2018). "How Allergan Continues to Make Drug Prices Insane". Bloomberg News. Archived from the original on 15 April 2018. Retrieved 15 April 2018.
  9. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  10. ^ "Linaclotide - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

and 13 Related for: Linaclotide information

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Linaclotide

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Linaclotide, (sold under the brand name Linzess in the US and Mexico, and as Constella elsewhere) is a drug used to treat irritable bowel syndrome with...

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Ironwood Pharmaceuticals

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nutritional business. Currie directed the efforts that led to the discovery of linaclotide, which was based on an enterotoxin produced by some strains of Escherichia...

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Plecanatide

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has shown to be at least equally as effective as its main competitor, linaclotide (brand name Linzess), but has been shown to have a lower rate of diarrhea...

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Prokinetic agent

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Prucalopride Renzapride Tegaserod Mitemcinal Levosulpiride Cinitapride Linaclotide Vincenzi M, Kremić A, Jouve A, Lattanzi R, Miele R, Benharouga M, Alfaidy...

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Allergan

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(cryolipolysis), Alphagan (brimonidine), Vraylar (cariprazine HCI), Linzess (linaclotide), and Ubrelvy (ubrogepant). Biotech and pharmaceutical companies in the...

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Enterotoxin

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such an effect, such as Staphylococcus aureus and E. coli. The drug linaclotide, used to treat some forms of constipation, is based on the mechanism...

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Functional constipation

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of functional constipation. Prosecretory drugs including plecanatide, linaclotide, and lubiprostone alter gut epithelial channels, encouraging intestinal...

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Forest Laboratories

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(levothyroxine) for hypothyroidism and pituitary TSH suppression Linzess (linaclotide) for constipation-predominant irritable bowel syndrome and functional...

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ATC code A06

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A06AX02 Carbon dioxide producing drugs A06AX03 Lubiprostone A06AX04 Linaclotide A06AX05 Prucalopride A06AX06 Tegaserod A06AX07 Plecanatide A06AX08 Tenapanor...

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Almirall

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specialist dermatology company, Aqua Pharmaceuticals. The company launched linaclotide in Europe (Constella) for irritable bowel syndrome with constipation...

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Satish SC Rao

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Rachael; Ayyala, Deepak; Sharma, Amol (2020). "Randomised clinical trial: linaclotide vs placebo—a study of bi-directional gut and brain axis". Alimentary...

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Guanylate cyclase 2C

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specificity of the GC-C receptor. Guanylate cyclase 2C is the target of linaclotide and plecanatide, oligopeptide agonists used for the treatment of chronic...

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Guanylate cyclase activator

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GUCA2B There are several therapeutic drugs that act as GUCAs, including linaclotide and plecanatide, which are guanylate cyclase-C receptor agonists. These...

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