(2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-{2-[2-(2-aminoacetamido)acetamido]acetamido}-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide

• ChemBase ID: 2364
• Molecular Formular: C52H74N16O15S2
• Molecular Mass: 1227.37216
• Monoisotopic Mass: 1226.49609775
• SMILES: S1SC[C@H](NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N)C1)CC(=O)N)CCC(=O)N)Cc1ccccc1)Cc1ccc(O)cc1
• Canonical SMILES: NCCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](Cc2ccc(cc2)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)CCC(=O)N)Cc1ccccc1
• 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
• InChIKey: BENFXAYNYRLAIU-QSVFAHTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-{2-[2-(2-aminoacetamido)acetamido]acetamido}-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide
• IUPAC Traditional name: (2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-{2-[2-(2-aminoacetamido)acetamido]acetamido}-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide; terlipressin
• Brand Name: Lucassin; Glypressin
• Synonyms: Terlipressinum [INN-Latin]; Terlipressine [INN-French]; Terlipressina [INN-Spanish]; N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin; terlipressin; Terlipressin; 1-Triglycyl-8-lysine Vasopressin Diacetate Salt; 130: PN: WO2010033207 SEQID: 171 claimed protein Diacetate Salt; Glycylpressin Diacetate Salt; Glypressin Diacetate Salt; Nα-Gly-Gly-Gly-8-Lys-vasopressin Diacetate Salt; Nα-Glycyl-glycyl-glycyl-[8-lysine]-vasopressin Diacetate Salt; Nα-Glycyl-glycyl-glycyl-lysine-vasopressin Diacetate Salt; Nα-Glycylglycylglycyl-vasopressin Diacetate Salt; Remestyp Diacetate Salt; Triglycyl-8-lysine-vasopressin Diacetate Salt; [N-α-Triglycyl-8-lysine]-vasopressin Diacetate Salt; Terlipressin Diacetate Salt

Database IDs

• CAS Number: 14636-12-5
• PubChem SID: 46504626; 160965815
• PubChem CID: 72081
• ATC CODE: H01BA04
• Chemspider ID: 65067
• DrugBank ID: DB02638
• KEGG ID: D06672
• Unique Ingredient Identifier: 7Z5X49W53P
• Wikipedia Title: Terlipressin

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.428936
• H Acceptors: 17
• H Donor: 16
• LogD (pH = 5.5): -14.516897
• LogD (pH = 7.4): -12.287832
• Log P: -10.092697
• Molar Refractivity: 305.1829 cm^3
• Polarizability: 119.32392 Å^3
• Polar Surface Area: 512.85 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.62
• LOG S: -3.87
• Solubility (Water): 1.67e-01 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: IV
• Protein Bound: ~30%

DETAILS

DrugBank - DB02638

• Drug Groups: approved; investigational
• Description: Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. It has been found to be effective when norepinephrine does not help. [Wikipedia]
• Indication: Commonly used to stop bleeding of varices in the food pipe (oesophagus).
• Pharmacology: Terlipressin is a medicine similar to a naturally occurring hormone present in the body, known as antidiuretic hormone (ADH) or vasopressin. ADH has two main effects in the body. Firstly, it causes narrowing of blood vessels (vasoconstriction), thereby limiting blood flow to a particular area of the body. It also acts on receptors in the kidney to retain water in the body, which helps to prevent excessive loss of water in the urine.
• Affected Organisms: Humans and other mammals
• Protein Binding: Approximately 30%
• References: Pesaturo AB, Jennings HR, Voils SA: Terlipressin: vasopressin analog and novel drug for septic shock. Ann Pharmacother. 2006 Dec;40(12):2170-7. Epub 2006 Dec 5. [Pubmed] ; Klein M, Weksler N, Borer A, Koyfman L, Kesslin J, Gurman GM: Terlipressin facilitates transport of septic patients treated with norepinephrine. Isr Med Assoc J. 2006 Oct;8(10):691-3. [Pubmed] ; Leone M, Charvet A, Delmas A, Albanese J, Martin C, Boyle WA: Terlipressin: a new therapeutic for calcium-channel blockers overdose. J Crit Care. 2005 Mar;20(1):114-5. [Pubmed] ; Matok I, Vard A, Efrati O, Rubinshtein M, Vishne T, Leibovitch L, Adam M, Barzilay Z, Paret G: Terlipressin as rescue therapy for intractable hypotension due to septic shock in children. Shock. 2005 Apr;23(4):305-10. [Pubmed] ; Kam PC, Williams S, Yoong FF: Vasopressin and terlipressin: pharmacology and its clinical relevance. Anaesthesia. 2004 Oct;59(10):993-1001. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - T115800

Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. Terlipressin is used norepinephrine-resistant septic shock and hepatorenal syndrome. Terlipressin is also used in the treatment of acute variceal bleedi

REFERENCES

• Pesaturo AB, Jennings HR, Voils SA: Terlipressin: vasopressin analog and novel drug for septic shock. Ann Pharmacother. 2006 Dec;40(12):2170-7. Epub 2006 Dec 5. Pubmed
• Klein M, Weksler N, Borer A, Koyfman L, Kesslin J, Gurman GM: Terlipressin facilitates transport of septic patients treated with norepinephrine. Isr Med Assoc J. 2006 Oct;8(10):691-3. Pubmed
• Leone M, Charvet A, Delmas A, Albanese J, Martin C, Boyle WA: Terlipressin: a new therapeutic for calcium-channel blockers overdose. J Crit Care. 2005 Mar;20(1):114-5. Pubmed
• Matok I, Vard A, Efrati O, Rubinshtein M, Vishne T, Leibovitch L, Adam M, Barzilay Z, Paret G: Terlipressin as rescue therapy for intractable hypotension due to septic shock in children. Shock. 2005 Apr;23(4):305-10. Pubmed
• Kam PC, Williams S, Yoong FF: Vasopressin and terlipressin: pharmacology and its clinical relevance. Anaesthesia. 2004 Oct;59(10):993-1001. Pubmed
• Uriz, J. et al.: J. Heptol., 33, 43 (2000)
• O'Brien, A. et al.: Lancet, 359, 1209 (2000)
• Burroughs, A.K. et al.: Digestion, 59, 26 (2000)
• Villanueva, C. et al.: Am. J. Gastroenterol., 100, 624 (2000)