化合物信息

ID:4397

基本信息

化学结构

分子式

C₅₇H₇₀N₁₂O₉S₂

分子量

1131.3707

精确质量

1130.48301388

电荷

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

Canonic 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

Isomeric 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

计算属性

JChem

Acid pKa

9.427821

质子受体

质子供体

LogD (pH = 5.5)

-3.5604823

LogD (pH = 7.4)

-1.3510058

Log P

0.75737387

摩尔折射率

306.2041

极化性

121.69426

极化表面积

350.64

可自由旋转的化学键

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

数据来源

学术数据

数据来源

名称和标识

别名

BMY 41606vapreotideVapreotide acetateVapreotidum [inn-latin]Vapreotida [INN-Spanish]OctastatinVapreotideRC-160

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 IRSanvar

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

名称和标识

数据登录号

CAS号

103222-11-3

PubChem CID

23725064

PubChem SID

46506923160967829

数据登录号

化合物性质

暂无数据

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分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

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描述信息

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]

描述信息

参考文献

PubChem文献

数据源提供

• Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. 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

• 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

• Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

• ALOGPS 2.1

数据来源

• 学术数据

名称和标识

• 别名

• IUPAC传统名

• 商标名

• IUPAC标准名

数据登录号

• CAS号

• PubChem CID

• PubChem SID

• DrugBank

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

别名

BMY 41606vapreotideVapreotide acetateVapreotidum [inn-latin]Vapreotida [INN-Spanish]OctastatinVapreotideRC-160

IUPAC传统名

商标名

Sanvar IRSanvar

IUPAC标准名

PubChem CID

23725064

PubChem SID

46506923160967829

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

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

• 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]

• 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]

数据源提供

• Norman P: Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. 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

• 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

• Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. Pubmed