Terlipressin

Terlipressin
Names
Trade namesTeripress, Glypressin, Terlivaz, others
Other namesTerlipressin acetate, triglycyl lysine vasopressin
IUPAC name
  • 1-{[(4R,7S,10S,13S,16S,19R)-19-{[({[(aminoacetyl)amino]acetyl}amino)acetyl]amino}-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-N-(2-amino-2-oxoethyl)-L-lysinamide
Clinical data
Drug classVasopressin analog[1]
Main usesEsophageal varices, hepatorenal syndrome[2][3]
Side effectsAbdominal pain, nausea, respiratory failure, diarrhea[3]
Routes of
use		IV
External links
AHFS/Drugs.comMonograph
Pharmacokinetics
Protein binding~30%
Chemical and physical data
FormulaC52H74N16O15S2
Molar mass1227.38 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N)CNC(=O)[C@@H](NC(=O)[C@H]4N(C(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)CN)CSSC1)Cc2ccc(O)cc2)Cc3ccccc3)CCC(=O)N)CC(=O)N)CCC4)CCCCN
InChI
  • InChI=1S/C52H74N16O15S2/c53-17-5-4-9-31(45(76)60-23-41(57)72)63-51(82)38-10-6-18-68(38)52(83)37-27-85-84-26-36(61-44(75)25-59-43(74)24-58-42(73)22-54)50(81)65-34(20-29-11-13-30(69)14-12-29)48(79)64-33(19-28-7-2-1-3-8-28)47(78)62-32(15-16-39(55)70)46(77)66-35(21-40(56)71)49(80)67-37/h1-3,7-8,11-14,31-38,69H,4-6,9-10,15-27,53-54H2,(H2,55,70)(H2,56,71)(H2,57,72)(H,58,73)(H,59,74)(H,60,76)(H,61,75)(H,62,78)(H,63,82)(H,64,79)(H,65,81)(H,66,77)(H,67,80)/t31-,32-,33-,34-,35-,36-,37-,38-/m0/s1 checkY
  • Key:BENFXAYNYRLAIU-QSVFAHTRSA-N checkY

Terlipressin, sold under the brand names Teripress among others, is a medication used to treat bleeding esophageal varices and kidney problems in hepatorenal syndrome.[2][3] In these conditions it decreases the risk of death.[4] It is given by injection into a vein.[3]

Common side effects include abdominal pain, nausea, respiratory failure, and diarrhea.[3] Other side effects may include mesenteric ischemia and heart ischemia.[3] Use during pregnancy may harm the baby.[3] It is a vasopressin receptor activator.[3]

Terlipressin has been in medical use in various parts of the world since 1975.[4] It was approved for medical use in the United States in 2022.[3] In the United Kingdom it costs the NHS about £18 for 1 mg vial as of 2021.[2]

Medical use

Indications for use include hepatorenal syndrome,[5] and to treat bleeding esophageal varices.[6]

It has been studied for norepinephrine-resistant septic shock.[7][4] And it may also helps prevent urination.[8] Though is believed to have less of these two effects than vasopressin.[2]

Dosage

For esophageal varices it is used at a dose of 1 to 2 mg initially.[2] This may be repeated every 4 to 6 hours for 48 to 72 hours depending on the formulation.[2]

Side effects

Ischemic bowel necrosis due to terlipressin

Other possible side effects of this medication, though rare, are:[9]

  • Difficulty breathing
  • Chest pain (angina)
  • Irregular heart beats
  • Necrosis

Pregnancy

Terlipressin should not be used during pregnancy.

Society and culture

Availability

Terlipressin is not available in Canada,[10] but it is available in New Zealand,[11] Australia, much of Europe,[12] India, Pakistan & UAE.

See also

References

  1. ↑ Srivastava, Ved (22 June 2017). Peptide-based Drug Discovery: Challenges and New Therapeutics. Royal Society of Chemistry. p. 187. ISBN 978-1-78801-171-6. Archived from the original on 14 December 2022. Retrieved 14 December 2022.
  2. 1 2 3 4 5 6 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 98. ISBN 978-0857114105.
  3. 1 2 3 4 5 6 7 8 9 "DailyMed - TERLIVAZ- terlipressin injection, powder, lyophilized, for solution". dailymed.nlm.nih.gov. Archived from the original on 28 September 2022. Retrieved 12 December 2022.
  4. 1 2 3 Kulkarni, Anand V.; Arab, Juan Pablo; Premkumar, Madhumita; Benítez, Carlos; Tirumalige Ravikumar, Sowmya; Kumar, Pramod; Sharma, Mithun; Reddy, Duvvuru Nageshwar; Simonetto, Douglas A.; Rao, Padaki Nagaraja (December 2020). "Terlipressin has stood the test of time: Clinical overview in 2020 and future perspectives". Liver International. 40 (12): 2888–2905. doi:10.1111/liv.14703.
  5. ↑ Uriz J, Ginès P, Cárdenas A, Sort P, Jiménez W, Salmerón J, Bataller R, Mas A, Navasa M, Arroyo V, Rodés J (2000). "Terlipressin plus albumin infusion: an effective and safe therapy of hepatorenal syndrome". J Hepatol. 33 (1): 43–8. doi:10.1016/S0168-8278(00)80158-0. PMID 10905585.
  6. ↑ Ioannou G, Doust J, Rockey D (2003). Ioannou GN (ed.). "Terlipressin for acute esophageal variceal hemorrhage". Cochrane Database Syst Rev (1): CD002147. doi:10.1002/14651858.CD002147. PMC 7017851. PMID 12535432.
  7. ↑ O'Brien A, Clapp L, Singer M (2002). "Terlipressin for norepinephrine-resistant septic shock". Lancet. 359 (9313): 1209–10. doi:10.1016/S0140-6736(02)08225-9. PMID 11955542. S2CID 38463837.
  8. ↑ Kam, P. C. A.; Williams, S.; Yoong, F. F. Y. (2004). "Vasopressin and terlipressin: pharmacology and its clinical relevance". Anaesthesia. 59 (10): 993–1001. doi:10.1111/j.1365-2044.2004.03877.x. ISSN 1365-2044. PMID 15488059. S2CID 26849892.
  9. ↑ "TERLIPRESSIN ACETATE 1 MG SOLUTION FOR INJECTION". Drugs.com. Archived from the original on 26 June 2019. Retrieved 16 December 2021.
  10. ↑ "Drug Product Search". Archived from the original on 2008-07-14.
  11. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 2021-12-20. Retrieved 2021-12-02.{{cite web}}: CS1 maint: archived copy as title (link)
  12. ↑ "Terlipressin". Archived from the original on 2019-06-26. Retrieved 2021-12-02.
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