CAS 103222-11-3|Octastatin|Vapreotide acetate|Vapreotidum [inn-latin]|2-amino-N-[10-(4-aminobutyl)-4-{[1-carbamoyl-2-(1H-indol-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmet...

General Information

Structure

Molecular Formula

C₅₇H₇₀N₁₂O₉S₂

Molecular Mass

1131.3707

Exact Mass

1130.48301388

Charge

0

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

Calculated Properties

JChem

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

Polarizability

121.69426

Polar Surface Area

350.64

Rotatable Bonds

18

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

2.7

LOG S

-5.45

Solubility (Water)

3.99e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

OctastatinVapreotide acetateVapreotidum [inn-latin]vapreotideBMY 41606Vapreotida [INN-Spanish]VapreotideRC-160

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

SanvarSanvar IR

Names and Identifiers

Registration numbers

PubChem CID

23725064

CAS Number

103222-11-3

PubChem SID

46506923160967829

Registration numbers

Properties

No Data Available

Click here to submit data

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:4397