Terlipressin | CAS# 14636-12-5 | Lysipressin Prodrug

MedKoo Cat#: 574149 | Name: Terlipressin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Terlipressin is a prodrug form of lysipressin and a partial agonist of the vasopressin V1A receptor. It is also an agonist of vasopressin V1B and V2 receptors. Terlipressin in combination with norepinephrine improves vascular reactivity and mean arterial pressure (MAP) in a rat model of liver cirrhosis with portal hypertension, arterial hypotension, high cardiac output, and low systemic vascular resistance.

Chemical Structure

Terlipressin

CAS#14636-12-5

Theoretical Analysis

MedKoo Cat#: 574149

Name: Terlipressin

CAS#: 14636-12-5

Chemical Formula: C52H74N16O15S2

Exact Mass: 1226.4961

Molecular Weight: 1227.38

Elemental Analysis: C, 50.89; H, 6.08; N, 18.26; O, 19.55; S, 5.22

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 475.00
100mg	USD 700.00
250mg	USD 1,200.00

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Related CAS #

No Data

Synonym

Glycylpressin, Remestyp, Terlipressin

IUPAC/Chemical Name

(S)-N-((S)-6-amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan-2-yl)-1-((4R,7S,10S,13S,16S,19R)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-19-(2-(2-(2-aminoacetamido)acetamido)acetamido)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide

InChi Key

BENFXAYNYRLAIU-QSVFAHTRSA-N

InChi Code

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

SMILES Code

OC(C=C1)=CC=C1C[C@H](NC([C@@H](NC(CNC(CNC(CN)=O)=O)=O)CSSC[C@@H](C(N2CCC[C@H]2C(N[C@@H](CCCCN)C(NCC(N)=O)=O)=O)=O)NC([C@H](CC(N)=O)N3)=O)=O)C(N[C@@H](CC4=CC=CC=C4)C(N[C@@H](CCC(N)=O)C3=O)=O)=O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,227.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Mujtaba MA, Elsiesy H, Faiz S, Hussain SA, Gamilla-Crudo AKN, Karim A, Khan MI, Khattak MW, Zafar Z, Kueht M, Jamil K. Defining Renal Recovery in Patients With Hepatorenal Syndrome-Acute Kidney Injury: Experience From North American Studies. JGH Open. 2024 Dec 10;8(12):e70058. doi: 10.1002/jgh3.70058. PMID: 39664961; PMCID: PMC11631707. 2: Law JH, Kow AW. Prediction and Management of Small-for-Size Syndrome in Living Donor Liver Transplantation. Clin Mol Hepatol. 2024 Dec 10. doi: 10.3350/cmh.2024.0870. Epub ahead of print. PMID: 39657750. 3: Biswas S, Shalimar. Optimizing Acute Variceal Bleeding Management: Abbreviated Therapy With Terlipressin and Antibiotics. Am J Gastroenterol. 2024 Sep 1;119(9):1943. doi: 10.14309/ajg.0000000000002841. Epub 2024 May 21. PMID: 39626065. 4: Shen L, Ying J, Zhao J. The Application of Terlipressin in the Management of Ascites in Liver Cirrhosis: Current Status and Prospects. Br J Hosp Med (Lond). 2024 Nov 30;85(11):1-13. doi: 10.12968/hmed.2024.0606. Epub 2024 Nov 25. PMID: 39618221. 5: Maiwall R, Pasupuleti SSR, Rastogi A, Sharma F, Hidam AK, Thomas S, Sarin SK. AARC score and urine NGAL predict terlipressin non-response and mortality in patients with acute-on-chronic liver failure. Hepatol Int. 2024 Nov 28. doi: 10.1007/s12072-024-10749-4. Epub ahead of print. PMID: 39607651. 6: Singh S, Chandan S, Vinayek R, Aswath G, Facciorusso A, Maida M. Comprehensive approach to esophageal variceal bleeding: From prevention to treatment. World J Gastroenterol. 2024 Nov 21;30(43):4602-4608. doi: 10.3748/wjg.v30.i43.4602. PMID: 39575399; PMCID: PMC11572636. 7: Nadim MK, Forni LG, Ostermann M; ADQI 29/ICA panel. Terlipressin use in hepatorenal syndrome-acute kidney injury in cirrhosis. Author's reply. Intensive Care Med. 2024 Nov 21. doi: 10.1007/s00134-024-07720-0. Epub ahead of print. PMID: 39570402. 8: Nadim MK, Kellum JA, Durand F. Reply to: "Shortening the albumin challenge from 48 to 24 hours may lead to overdiagnosis of hepatorenal syndrome-acute kidney injury and overtreatment with terlipressin". J Hepatol. 2024 Oct 23:S0168-8278(24)02646-1. doi: 10.1016/j.jhep.2024.10.025. Epub ahead of print. PMID: 39454689. 9: Wong F, Pappas SC. Terlipressin use in hepatorenal syndrome-acute kidney injury in cirrhosis. Intensive Care Med. 2024 Oct 23. doi: 10.1007/s00134-024-07681-4. Epub ahead of print. PMID: 39441357. 10: Jindal A, Sarin SK. Early Terlipressin for HRS-AKI in ACLF. Dig Dis Sci. 2024 Nov;69(11):4313. doi: 10.1007/s10620-024-08662-9. Epub 2024 Oct 17. PMID: 39419939. 11: Ahmed AI, Kaleem MZ, Abbarh S, Barjas HH, Ismail A, Albuni MK, Sawaf B. Terlipressin-induced skin necrosis in cirrhotic patients-A case report and comprehensive literature review. Clin Case Rep. 2024 Sep 29;12(10):e9141. doi: 10.1002/ccr3.9141. PMID: 39350912; PMCID: PMC11439737. 12: Shang Y, Wang C, Lu H, Chai L, Xu W, Bernardi M, Qi X. Incidence and type of adverse events in patients with cirrhosis receiving terlipressin: A systematic review and meta-analysis. Hepatol Commun. 2024 Sep 18;8(10):e0526. doi: 10.1097/HC9.0000000000000526. PMID: 39298544; PMCID: PMC11412712. 13: Wan YM, Huang SQ, Wu HM, Li YH, Yin HJ, Xu Y. Terlipressin versus placebo or noradrenalin in the treatment of hepatorenal syndrome: a systematic review and meta-analysis. Front Pharmacol. 2024 Sep 4;15:1418826. doi: 10.3389/fphar.2024.1418826. PMID: 39295934; PMCID: PMC11408352. 14: Olayinka OT, Orelus J, Nisar MR, Kotha R, Saad-Omer SI, Singh S, Yu AK. Comparative Mortality Rates of Vasoconstrictor Agents in the Management of Hepatorenal Syndrome: A Systematic Review and Meta-Analysis. Cureus. 2024 Aug 16;16(8):e67034. doi: 10.7759/cureus.67034. PMID: 39286706; PMCID: PMC11402629. 15: Gowda M, Dilipbhai DM, Jalihal U, Kumar MP, Gowda S B, Jain A, Ganjoo N. Efficacy and Safety of Terlipressin Infusion in Hepatorenal Syndrome-Acute Kidney Injury (HRS-AKI): A Retrospective Observational Study. Cureus. 2024 Aug 10;16(8):e66581. doi: 10.7759/cureus.66581. PMID: 39252705; PMCID: PMC11382811. 16: Dhoop S, Ahmed Z, Lombardi C, Abu-Rumaileh M, Arif SF, Sayeh W, Patel R, Sherafati A, Lee-Smith W, Hassan M. The effect of shortening vasoactive drug durations alongside endoscopic therapy in esophageal variceal bleeding: an updated systematic review and meta-analysis. Ann Gastroenterol. 2024 Sep- Oct;37(5):567-578. doi: 10.20524/aog.2024.0906. Epub 2024 Aug 19. PMID: 39238793; PMCID: PMC11372535. 17: Tan K, Jahanabadi H, Pandey D, Sinclair M, Majumdar A, Trubiano JA, Kwong JC, Testro A, Smibert O. Letter: Association between terlipressin and multi- drug-resistant organism rectal colonisation. Aliment Pharmacol Ther. 2024 Oct;60(8):1134-1136. doi: 10.1111/apt.18200. Epub 2024 Sep 5. PMID: 39238203. 18: Mücke MM, Gu W, Fernandez J, Trebicka J. Letter: Association between terlipressin and multidrug-resistant organism rectal colonization: Authors' reply. Aliment Pharmacol Ther. 2024 Oct;60(8):1137-1138. doi: 10.1111/apt.18256. Epub 2024 Sep 5. PMID: 39238201. 19: Terbah R, Koshy AN, Majumdar A, Vaz K, Testro A, Sinclair M. Long-Term Continuous Terlipressin Infusion Improves Cardiac Reserve in Patients With Decompensated Cirrhosis. Clin Gastroenterol Hepatol. 2024 Aug 30:S1542-3565(24)00778-X. doi: 10.1016/j.cgh.2024.08.010. Epub ahead of print. PMID: 39209185. 20: AlKindi F, AlHaj O, Alhanaee A, Almazrouei R, Boobes Y. Severe Hyponatremia Associated With Terlipressin Use in Esophageal Variceal Bleeding. Cureus. 2024 Jul 15;16(7):e64576. doi: 10.7759/cureus.64576. PMID: 39144872; PMCID: PMC11323788.