2-amino-N-[10-(4-aminobutyl)-4-{[1-carbamoyl-2-(1H-indol-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-phenylpropanamide

• ChemBase编号: 4397
• 分子式: C57H70N12O9S2
• 平均质量: 1131.3707
• 单一同位素质量: 1130.48301388
• SMILES: c12ccccc1[nH]cc2CC1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(NC(=O)C(N)Cc2ccccc2)C(=O)NC(C(=O)N1)Cc1ccc(cc1)O)C(=O)NC(C(=O)N)Cc1[nH]c2c(c1)cccc2)C(C)C)CCCCN
• Canonical SMILES: NCCCCC1NC(=O)C(NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(CSSCC(NC(=O)C(NC1=O)C(C)C)C(=O)NC(C(=O)N)Cc1cc2c([nH]1)cccc2)NC(=O)C(Cc1ccccc1)N)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C57H70N12O9S2/c1-32(2)49-57(78)68-48(55(76)64-44(50(60)71)28-37-26-35-14-6-8-16-41(35)62-37)31-80-79-30-47(67-51(72)40(59)24-33-12-4-3-5-13-33)56(77)65-45(25-34-19-21-38(70)22-20-34)53(74)66-46(27-36-29-61-42-17-9-7-15-39(36)42)54(75)63-43(52(73)69-49)18-10-11-23-58/h3-9,12-17,19-22,26,29,32,40,43-49,61-62,70H,10-11,18,23-25,27-28,30-31,58-59H2,1-2H3,(H2,60,71)(H,63,75)(H,64,76)(H,65,77)(H,66,74)(H,67,72)(H,68,78)(H,69,73)
• InChIKey: GAWXLRUZZFSQON-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-N-[10-(4-aminobutyl)-4-{[1-carbamoyl-2-(1H-indol-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-phenylpropanamide
• IUPAC传统名: 2-amino-N-[10-(4-aminobutyl)-4-{[1-carbamoyl-2-(1H-indol-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-phenylpropanamide
• 商标名: Sanvar; Sanvar IR
• 别名: Vapreotide acetate; Vapreotida [INN-Spanish]; Vapreotidum [inn-latin]; RC-160; vapreotide; BMY 41606; Octastatin; Vapreotide

登记号

• CAS号: 103222-11-3
• PubChem SID: 46506923; 160967829
• PubChem CID: 23725064

理论计算性质

JChem

• Acid pKa: 9.427821
• 质子受体: 11
• 质子供体: 13
• LogD (pH = 5.5): -3.5604823
• LogD (pH = 7.4): -1.3510058
• Log P: 0.75737387
• 摩尔折射率: 306.2041 cm^3
• 极化性: 121.69426 Å^3
• 极化表面积: 350.64 Å^2
• 可自由旋转的化学键: 18
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 2.7
• LOG S: -5.45
• 溶解度: 3.99e-03 g/l

详细说明

DrugBank - DB04894

• Drug Groups: approved; investigational
• Description: Vapreotide is a synthetic octapeptide somatostatin analog. It was being studied for the treatment of cancer.
• Indication: For the treatment of esophageal variceal bleeding in patients with cirrhotic liver disease and has also shown efficacy in the treatment of patients with AIDS-related diarrhea.
• Pharmacology: Vapreotide is a somatostatin analog with a higher metabolic stability than the parent hormone. Vapreotide reduces splanchnic blood flow; inhibits growth hormone release, and inhibits the release of peptides and vasoactive compounds from neuroendocrine tumors.
• Toxicity: Safety data are limited, however, headache, fatigue, diarrhea, nausea, vomiting, and abdominal pain have been reported commonly with the use of vapreotide.
• Affected Organisms: Humans and other mammals
• Half Life: 30 minutes
• Elimination: Vapreotide is 76% eliminated in bile. The remainder is renally eliminated.
• References: Sarr MG: The potent somatostatin analogue vapreotide does not decrease pancreas-specific complications after elective pancreatectomy: a prospective, multicenter, double-blinded, randomized, placebo-controlled trial. J Am Coll Surg. 2003 Apr;196(4):556-64; discussion 564-5; author reply 565. [Pubmed] ; Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. [Pubmed] ; Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. [Pubmed] ; Betoin F, Ardid D, Herbet A, Aumaitre O, Kemeny JL, Duchene-Marullaz P, Lavarenne J, Eschalier A: Evidence for a central long-lasting antinociceptive effect of vapreotide, an analog of somatostatin, involving an opioidergic mechanism. J Pharmacol Exp Ther. 1994 Apr;269(1):7-14. [Pubmed] ; Girard PM, Goldschmidt E, Vittecoq D, Massip P, Gastiaburu J, Meyohas MC, Coulaud JP, Schally AV: Vapreotide, a somatostatin analogue, in cryptosporidiosis and other AIDS-related diarrhoeal diseases. AIDS. 1992 Jul;6(7):715-8. [Pubmed] ; Stiefel F, Morant R: Vapreotide, a new somatostatin analogue in the palliative management of obstructive ileus in advanced cancer. Support Care Cancer. 1993 Jan;1(1):57-8. [Pubmed] ; Betoin F, Eschalier A, Duchene-Marullaz P, Lavarenne J: Seven-day antinociceptive effect of a sustained release vapreotide formulation. Neuroreport. 1994 Jan 31;5(5):642-4. [Pubmed]

参考文献

• Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. Pubmed
• Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. Pubmed
• Sarr MG: The potent somatostatin analogue vapreotide does not decrease pancreas-specific complications after elective pancreatectomy: a prospective, multicenter, double-blinded, randomized, placebo-controlled trial. J Am Coll Surg. 2003 Apr;196(4):556-64; discussion 564-5; author reply 565. Pubmed
• Betoin F, Ardid D, Herbet A, Aumaitre O, Kemeny JL, Duchene-Marullaz P, Lavarenne J, Eschalier A: Evidence for a central long-lasting antinociceptive effect of vapreotide, an analog of somatostatin, involving an opioidergic mechanism. J Pharmacol Exp Ther. 1994 Apr;269(1):7-14. Pubmed
• Girard PM, Goldschmidt E, Vittecoq D, Massip P, Gastiaburu J, Meyohas MC, Coulaud JP, Schally AV: Vapreotide, a somatostatin analogue, in cryptosporidiosis and other AIDS-related diarrhoeal diseases. AIDS. 1992 Jul;6(7):715-8. Pubmed
• Stiefel F, Morant R: Vapreotide, a new somatostatin analogue in the palliative management of obstructive ileus in advanced cancer. Support Care Cancer. 1993 Jan;1(1):57-8. Pubmed
• Betoin F, Eschalier A, Duchene-Marullaz P, Lavarenne J: Seven-day antinociceptive effect of a sustained release vapreotide formulation. Neuroreport. 1994 Jan 31;5(5):642-4. Pubmed