Vapreotide
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MedKoo CAT#: 598013

CAS#: 103222-11-3 (free)

Description: Vapreotide is used in therapy of experimental pancreatic neoplasms in hamsters.


Price and Availability

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Price

1mg
USD 340
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Price

Size
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Vapreotide purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598013
Name: Vapreotide
CAS#: 103222-11-3 (free)
Chemical Formula: C57H70N12O9S2
Exact Mass: 1130.483
Molecular Weight: 1131.38
Elemental Analysis: C, 60.51; H, 6.24; N, 14.86; O, 12.73; S, 5.67


Related CAS #: 936560-75-7 (diacetate)   849479-74-9 (acetate)   103222-11-3 (free)    

Synonym: Vapreotide; Sanvar IR; Vapreotidum; RC 160; RC-160; RC160;

IUPAC/Chemical Name: (4R,7S,10S,13R,16S,19R)-13-((1H-indol-3-yl)methyl)-N-((S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-19-((R)-2-amino-3-phenylpropanamido)-10-(4-aminobutyl)-16-(4-hydroxybenzyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide

InChi Key: SWXOGPJRIDTIRL-DOUNNPEJSA-N

InChi Code: 1S/C57H70N12O9S2/c1-32(2)49-57(78)68-48(55(76)64-44(50(60)71)26-35-28-61-41-16-8-6-14-38(35)41)31-80-79-30-47(67-51(72)40(59)24-33-12-4-3-5-13-33)56(77)65-45(25-34-19-21-37(70)22-20-34)53(74)66-46(27-36-29-62-42-17-9-7-15-39(36)42)54(75)63-43(52(73)69-49)18-10-11-23-58/h3-9,12-17,19-22,28-29,32,40,43-49,61-62,70H,10-11,18,23-27,30-31,58-59H2,1-2H3,(H2,60,71)(H,63,75)(H,64,76)(H,65,77)(H,66,74)(H,67,72)(H,68,78)(H,69,73)/t40-,43+,44+,45+,46-,47+,48+,49+/m1/s1

SMILES Code: CC([C@@H]1NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](Cc2ccccc2)N)=O)CSSC[C@@H](C(N[C@H](C(N)=O)Cc(c[nH]3)c4c3cccc4)=O)NC1=O)=O)Cc5ccc(O)cc5)=O)Cc(c[nH]6)c7c6cccc7)=O)CCCCN)=O)C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


References

1: Spitsin S, Tuluc F, Meshki J, Ping Lai J, Tustin Iii R, Douglas SD. Analog of somatostatin vapreotide exhibits biological effects in vitro via interaction with neurokinin-1 receptor. Neuroimmunomodulation. 2013;20(5):247-55. doi: 10.1159/000350468. Epub 2013 Jul 5. PubMed PMID: 23921645; PubMed Central PMCID: PMC3839635.

2: Feng Q, Yu MZ, Wang JC, Hou WJ, Gao LY, Ma XF, Pei XW, Niu YJ, Liu XY, Qiu C, Pang WH, Du LL, Zhang Q. Synergistic inhibition of breast cancer by co-delivery of VEGF siRNA and paclitaxel via vapreotide-modified core-shell nanoparticles. Biomaterials. 2014 Jun;35(18):5028-38. doi: 10.1016/j.biomaterials.2014.03.012. Epub 2014 Mar 27. PubMed PMID: 24680191.

3: Banerjee S, Wiggins WJ, Geoghegan JL, Anthony CT, Woltering EA, Masterson DS. Novel synthesis of various orthogonally protected Cα-methyllysine analogues and biological evaluation of a vapreotide analogue containing (S)-α-methyllysine. Org Biomol Chem. 2013 Oct 7;11(37):6307-19. doi: 10.1039/c3ob41282b. PubMed PMID: 23942875.

4: Calès P, Masliah C, Bernard B, Garnier PP, Silvain C, Szostak-Talbodec N, Bronowicki JP, Ribard D, Botta-Fridlund D, Hillon P, Besseghir K, Lebrec D; French Club for the Study of Portal Hypertension. Early administration of vapreotide for variceal bleeding in patients with cirrhosis. N Engl J Med. 2001 Jan 4;344(1):23-8. PubMed PMID: 11136956.

5: Fortune BE, Jackson J, Leonard J, Trotter JF. Vapreotide: a somatostatin analog for the treatment of acute variceal bleeding. Expert Opin Pharmacother. 2009 Oct;10(14):2337-42. doi: 10.1517/14656560903207019. Review. PubMed PMID: 19708854.

6: Ritz MA, Drewe J, Ziel A, Hildebrand P, Schneider P, Lahlou N, Beglinger C. The effects of vapreotide, a somatostatin analogue, on gastric acidity, gallbladder emptying and hormone release after 1 week of continuous subcutaneous infusion in normal subjects. Br J Clin Pharmacol. 1999 Feb;47(2):195-201. PubMed PMID: 10190655; PubMed Central PMCID: PMC2014164.

7: Veal N, Moal F, Oberti F, Vuillemin E, Calés P. Hemodynamic effects of acute and chronic administration of vapreotide in rats with cirrhosis. Dig Dis Sci. 2003 Jan;48(1):154-61. PubMed PMID: 12645803.

8: Vapreotide: BMY 41606, RC 160, Sanvar. Drugs R D. 2003;4(5):326-30. Review. PubMed PMID: 12952505.

9: Sarr MG; Pancreatic Surgery Group. 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 PMID: 12691930.

10: 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 PMID: 7909563.

11: Schuetz YB, Naik A, Guy RH, Vuaridel E, Kalia YN. Transdermal iontophoretic delivery of vapreotide acetate across porcine skin in vitro. Pharm Res. 2005 Aug;22(8):1305-12. Epub 2005 Aug 3. PubMed PMID: 16078140.

12: Calès P. Vapreotide acetate for the treatment of esophageal variceal bleeding. Expert Rev Gastroenterol Hepatol. 2008 Apr;2(2):185-92. doi: 10.1586/17474124.2.2.185. Review. PubMed PMID: 19072353.

13: Berger V, Alloui A, Kemeny JL, Dubray C, Eschalier A, Lavarenne J. Evidence for a role for bulbospinal pathways in the spinal antinociceptive effect of systemically administered vapreotide in normal rats. Fundam Clin Pharmacol. 1998;12(2):200-4. PubMed PMID: 9565775.

14: González-Barcena D, Schally AV, Vadillo-Buenfil M, Cortez-Morales A, Hernández L V, Cardenas-Cornejo I, Comaru-Schally AM. Response of patients with advanced prostatic cancer to administration of somatostatin analog RC-160 (vapreotide) at the time of relapse. Prostate. 2003 Aug 1;56(3):183-91. PubMed PMID: 12772187.

15: Norman P. Vapreotide (Debipharm). IDrugs. 2000 Nov;3(11):1358-72. PubMed PMID: 16047258.

16: Eloubeidi MA, Arguedas MR. Early administration of vapreotide for variceal bleeding in patients with cirrhosis. Gastrointest Endosc. 2002 Jan;55(1):135-7. PubMed PMID: 11789479.

17: Rothen-Weinhold A, Besseghir K, De Zelicourt Y, Gurny R. Development and evaluation in vivo of a long-term delivery system for vapreotide, a somatostatin analogue. J Control Release. 1998 Mar 2;52(1-2):205-13. PubMed PMID: 9685950.

18: Deghenghi R, Papotti M, Ghigo E, Muccioli G, Locatelli V. Somatostatin octapeptides (lanreotide, octreotide, vapreotide, and their analogs) share the growth hormone-releasing peptide receptor in the human pituitary gland. Endocrine. 2001 Feb;14(1):29-33. PubMed PMID: 11322499.

19: Bétoin F, Advenier C, Fardin V, Wilcox G, Lavarenne J, Eschalier A. In vitro and in vivo evidence for a tachykinin NK1 receptor antagonist effect of vapreotide, an analgesic cyclic analog of somatostatin. Eur J Pharmacol. 1995 Jun 12;279(2-3):241-9. PubMed PMID: 7556407.

20: 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 PMID: 7511473.