User:Mr. Ibrahem/Linaclotide

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Mr. Ibrahem/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, Constella
AHFS/Drugs.comMonograph
MedlinePlusa613007
License data
Routes of
administration		By mouth
Drug classGuanylate cyclase-C (GC-C) agonist[2]
Legal status
Legal status
Identifiers
  • 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)
Chemical and physical data
FormulaC59H79N15O21S6
Molar mass1526.73 g·mol−1
3D model (JSmol)
  • 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=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 and Constella, is a medication used to treat irritable bowel syndrome with constipation and chronic constipation of unknown cause.[2] It is taken by mouth.[2]

Common side effects include diarrhea, abdominal pain, and intestinal gas.[3][4] Rarely this may lead to dehydration, low potassium, and low blood pressure with standing.[3] It works by attaching to guanylate cyclase C receptors in the intestines which results in greater fluid release.[3]

Linaclotide was approved for medical use in the United States and Europe in 2012.[3][2] In 2017, it was the 257th most commonly prescribed medication in the United States, with more than one million prescriptions.[5][6] In the United Kingdom 4 weeks of medication costs the NHS about £38 as of 2021.[7] This amount in the United States costs about 430 USD.[8]

References[edit]

  1. ^ Oh, See Arr (August 17, 2011). "Macrocycle Milestone for Ironwood Pharma". The Haystack. Archived from the original on 5 June 2019. Retrieved 11 February 2017 – via CENBlog.org.
  2. ^ a b c d e "Linaclotide Monograph for Professionals". Drugs.com. Archived from the original on 19 October 2021. Retrieved 23 November 2021.
  3. ^ a b c d e "Constella". Archived from the original on 22 June 2021. Retrieved 23 November 2021.
  4. ^ a b c "DailyMed - LINZESS- linaclotide capsule, gelatin coated". dailymed.nlm.nih.gov. Archived from the original on 29 March 2021. Retrieved 23 November 2021.
  5. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  6. ^ "Linaclotide - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 11 April 2020.
  7. ^ BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 52. ISBN 978-0857114105.
  8. ^ "Linaclotide Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 23 November 2021.
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