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MedKoo Cat#: 318850 | Name: Terlipressin acetate
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Description:

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

Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of low blood pressure. It has been found to be effective when norepinephrine does not help. Indications for use include norepinephrine-resistant septic shock and hepatorenal syndrome. In addition, it is used to treat bleeding esophageal varices. Terlipressin is currently not available in the United States, or Canada, but it is available in New Zealand, Australia, much of Europe, India & UAE.

Chemical Structure

Terlipressin acetate
Terlipressin acetate
CAS#914453-96-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 318850

Name: Terlipressin acetate

CAS#: 914453-96-6 (acetate)

Chemical Formula: C54H78N16O17S2

Exact Mass: 0.0000

Molecular Weight: 1287.43

Elemental Analysis: C, 50.38; H, 6.11; N, 17.41; O, 21.13; S, 4.98

Price and Availability

Size Price Availability Quantity
50mg USD 500.00 2 Weeks
100mg USD 800.00 2 Weeks
200mg USD 1,400.00 2 Weeks
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Related CAS #
914453-96-6 (acetate) 14636-12-5 (acetate) 14636-12-5 (free base)
Synonym
TGLVP; triglycyl lysine vasopressin; Gly-Gly-Gly-8-Lys-vasopressin; Terlipressin; Terlipressin acetate; trade names Teripress, Glypressin.
IUPAC/Chemical 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 acetate
InChi Key
LHXRPSJDWCCZBX-LCGYVTRFSA-N
InChi Code
InChI=1S/C52H74N16O15S2.C2H4O2/c53-17-5-4-9-37(45(58)76)68(25-41(57)72)52(83)38-10-6-18-67(38)51(82)36-27-85-84-26-35(61-44(75)24-60-43(74)23-59-42(73)22-54)50(81)64-33(20-29-11-13-30(69)14-12-29)48(79)63-32(19-28-7-2-1-3-8-28)47(78)62-31(15-16-39(55)70)46(77)65-34(21-40(56)71)49(80)66-36;1-2(3)4/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)(H2,58,76)(H,59,73)(H,60,74)(H,61,75)(H,62,78)(H,63,79)(H,64,81)(H,65,77)(H,66,80);1H3,(H,3,4)/t31-,32-,33-,34-,35-,36-,37-,38-;/m0./s1
SMILES Code
NCCCC[C@@H](C(N)=O)N(C([C@H]1N(C([C@@H](NC([C@H](CC(N)=O)NC([C@H](CCC(N)=O)NC([C@H](CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)N4)=O)=O)=O)=O)CSSC[C@H](NC(CNC(CNC(CN)=O)=O)=O)C4=O)=O)CCC1)=O)CC(N)=O.CC(O)=O
Appearance
Solid powder
Purity
>98% (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, not in water
Shelf Life
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1,287.43 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.

Recalculate based on batch purity %
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: Huang Y, Wang M, Wang J. Hyponatraemia induced by terlipressin: a case report and literature review. J Clin Pharm Ther. 2015 Nov 17. doi: 10.1111/jcpt.12335. [Epub ahead of print] Review. PubMed PMID: 26573870. 2: Taşliyurt T, Kutlutürk F, Erdemır F, Yelken BM, Yilmaz A, Kisacik B, Aytan P, Köseoğlu RD. Ischemic skin necrosis following terlipressin therapy: report of two cases and review of the literature. Turk J Gastroenterol. 2012;23(6):788-91. Review. PubMed PMID: 23864457. 3: Solà E, Cárdenas A, Ginès P. Results of pretransplant treatment of hepatorenal syndrome with terlipressin. Curr Opin Organ Transplant. 2013 Jun;18(3):265-70. doi: 10.1097/MOT.0b013e3283614c7a. Review. PubMed PMID: 23652609. 4: Biban P, Gaffuri M. Vasopressin and terlipressin in neonates and children with refractory septic shock. Curr Drug Metab. 2013 Feb;14(2):186-92. Review. PubMed PMID: 23439212. 5: Piazza O, Scarpati G, Rispoli F, Iannuzzi M, Tufano R, De Robertis E. Terlipressin in brain-death donors. Clin Transplant. 2012 Nov-Dec;26(6):E571-5. doi: 10.1111/ctr.12038. Epub 2012 Nov 2. Review. PubMed PMID: 23121213. 6: Gluud LL, Christensen K, Christensen E, Krag A. Terlipressin for hepatorenal syndrome. Cochrane Database Syst Rev. 2012 Sep 12;9:CD005162. doi: 10.1002/14651858.CD005162.pub3. Review. PubMed PMID: 22972083. 7: Serpa Neto A, Nassar AP, Cardoso SO, Manetta JA, Pereira VG, Espósito DC, Damasceno MC, Russell JA. Vasopressin and terlipressin in adult vasodilatory shock: a systematic review and meta-analysis of nine randomized controlled trials. Crit Care. 2012 Aug 14;16(4):R154. doi: 10.1186/cc11469. Review. PubMed PMID: 22889256; PubMed Central PMCID: PMC3580743. 8: Mazur JE, Cooper TB, Dasta JF. Terlipressin in hepatorenal syndrome. Ann Pharmacother. 2011 Mar;45(3):380-7. doi: 10.1345/aph.1P195. Epub 2011 Mar 8. Review. PubMed PMID: 21386023. 9: Meyer S, McGuire W, Gottschling S, Mohammed Shamdeen G, Gortner L. The role of vasopressin and terlipressin in catecholamine-resistant shock and cardio-circulatory arrest in children: review of the literature. Wien Med Wochenschr. 2011 Apr;161(7-8):192-203. doi: 10.1007/s10354-010-0853-7. Epub 2011 Jan 25. Review. PubMed PMID: 21253815. 10: Rajekar H, Chawla Y. Terlipressin in hepatorenal syndrome: Evidence for present indications. J Gastroenterol Hepatol. 2011 Jan;26 Suppl 1:109-14. doi: 10.1111/j.1440-1746.2010.06583.x. Review. PubMed PMID: 21199521. 11: Magan AA, Khalil AA, Ahmed MH. Terlipressin and hepatorenal syndrome: what is important for nephrologists and hepatologists. World J Gastroenterol. 2010 Nov 7;16(41):5139-47. Review. PubMed PMID: 21049548; PubMed Central PMCID: PMC2975085. 12: Elzouki AN, El-Menyar A, Ahmed E, Elbadri ME, Imam YZ, Gurbanna BA. Terlipressin-induced severe left and right ventricular dysfunction in patient presented with upper gastrointestinal bleeding: case report and literature review. Am J Emerg Med. 2010 May;28(4):540.e1-6. doi: 10.1016/j.ajem.2009.08.012. Epub 2010 Mar 12. Review. PubMed PMID: 20466263. 13: Dobre M, Demirjian S, Sehgal AR, Navaneethan SD. Terlipressin in hepatorenal syndrome: a systematic review and meta-analysis. Int Urol Nephrol. 2011 Mar;43(1):175-84. doi: 10.1007/s11255-010-9725-8. Epub 2010 Mar 20. Review. PubMed PMID: 20306131; PubMed Central PMCID: PMC3881971. 14: Sagi SV, Mittal S, Kasturi KS, Sood GK. Terlipressin therapy for reversal of type 1 hepatorenal syndrome: a meta-analysis of randomized controlled trials. J Gastroenterol Hepatol. 2010 May;25(5):880-5. doi: 10.1111/j.1440-1746.2009.06132.x. Epub 2010 Jan 14. Review. PubMed PMID: 20074149. 15: Morelli A, Ertmer C, Pietropaoli P, Westphal M. Terlipressin: a promising vasoactive agent in hemodynamic support of septic shock. Expert Opin Pharmacother. 2009 Oct;10(15):2569-75. doi: 10.1517/14656560903257808. Review. PubMed PMID: 19735216. 16: Fabrizi F, Dixit V, Messa P, Martin P. Terlipressin for hepatorenal syndrome: A meta-analysis of randomized trials. Int J Artif Organs. 2009 Mar;32(3):133-40. Review. PubMed PMID: 19440988. 17: Saner FH, Canbay A, Gerken G, Broelsch CE. Pharmacology, clinical efficacy and safety of terlipressin in esophageal varices bleeding, septic shock and hepatorenal syndrome. Expert Rev Gastroenterol Hepatol. 2007 Dec;1(2):207-17. doi: 10.1586/17474124.1.2.207. Review. PubMed PMID: 19072411. 18: Krag A, Borup T, Møller S, Bendtsen F. Efficacy and safety of terlipressin in cirrhotic patients with variceal bleeding or hepatorenal syndrome. Adv Ther. 2008 Nov;25(11):1105-40. doi: 10.1007/s12325-008-0118-7. Review. PubMed PMID: 19018483. 19: Singer M. Arginine vasopressin vs. terlipressin in the treatment of shock states. Best Pract Res Clin Anaesthesiol. 2008 Jun;22(2):359-68. Review. PubMed PMID: 18683481. 20: Leone M, Martin C. Role of terlipressin in the treatment of infants and neonates with catecholamine-resistant septic shock. Best Pract Res Clin Anaesthesiol. 2008 Jun;22(2):323-33. Review. PubMed PMID: 18683478.

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