(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编号: 2364
• 分子式: C52H74N16O15S2
• 平均质量: 1227.37216
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (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
• 商标名: Lucassin; Glypressin
• 别名: 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

登记号

• CAS号: 14636-12-5
• PubChem SID: 46504626; 160965815
• PubChem CID: 72081
• ATC码: H01BA04
• Chemspider ID: 65067
• DrugBank ID: DB02638
• KEGG ID: D06672
• 美国药典/FDA物质标识码: 7Z5X49W53P
• 维基百科标题: Terlipressin

理论计算性质

JChem

• Acid pKa: 9.428936
• 质子受体: 17
• 质子供体: 16
• LogD (pH = 5.5): -14.516897
• LogD (pH = 7.4): -12.287832
• Log P: -10.092697
• 摩尔折射率: 305.1829 cm^3
• 极化性: 119.32392 Å^3
• 极化表面积: 512.85 Å^2
• 可自由旋转的化学键: 25
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -1.62
• LOG S: -3.87
• 溶解度: 1.67e-01 g/l

分子性质

药理学性质

• 给药途径: IV
• 蛋白结合率: ~30%

详细说明

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

参考文献

• 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)