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103222-11-3 molecular structure
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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 ID: 4397
Molecular Formular: C57H70N12O9S2
Molecular Mass: 1131.3707
Monoisotopic Mass: 1130.48301388
SMILES and InChIs

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

Cite this record

CBID:4397 http://www.chembase.cn/molecule-4397.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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 Traditional name
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
Brand Name
Sanvar
Sanvar IR
Synonyms
Vapreotide acetate
Vapreotida [INN-Spanish]
Vapreotidum [inn-latin]
RC-160
vapreotide
BMY 41606
Octastatin
Vapreotide
CAS Number
103222-11-3
PubChem SID
46506923
160967829
PubChem CID
23725064

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.427821  H Acceptors 11 
H Donor 13  LogD (pH = 5.5) -3.5604823 
LogD (pH = 7.4) -1.3510058  Log P 0.75737387 
Molar Refractivity 306.2041 cm3 Polarizability 121.69426 Å3
Polar Surface Area 350.64 Å2 Rotatable Bonds 18 
Lipinski's Rule of Five false 
Log P 2.7  LOG S -5.45 
Solubility (Water) 3.99e-03 g/l 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB04894 external link
Item Information
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]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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