Vapreotide acetate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318972

CAS#: 849479-74-9

Description: Vapreotide (Sanvar) is a synthetic somatostatin analog. It is used in the treatment of esophageal variceal bleeding in patients with cirrhotic liver disease and AIDS-related diarrhea. It is an 8 residue peptide with sequence H-D-Phe-Cys(1)-Tyr-D-Trp-Lys-Val-Cys(1)-Trp-NH2.


Price and Availability

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Price

1g
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Size
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2g
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Size
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5g
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Vapreotide acetate is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318972
Name: Vapreotide acetate
CAS#: 849479-74-9
Chemical Formula: C59H74N12O11S2
Exact Mass:
Molecular Weight: 1191.434
Elemental Analysis: C, 59.48; H, 6.26; N, 14.11; O, 14.77; S, 5.38


Related CAS #: 849479-74-9 (acetate)   103222-11-3 (free)  

Synonym: BMY-41606; BMY 41606; BMY41606; RC160; RC 160; RC-160; DP-05-094; Octastatin; Vapreotide acetate

IUPAC/Chemical Name: (4R,7S,10S,13S,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 acetate

InChi Key: KBIZSMHYSQUHDH-CYKDYWLUSA-N

InChi Code: InChI=1S/C57H70N12O9S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t40-,43+,44+,45+,46+,47+,48+,49+;/m1./s1

SMILES Code: CC(O)=O.O=C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N1)=O)C(C)C)=O)CCCCN)=O)CC2=CNC3=C2C=CC=C3)=O)CC4=CC=C(C=C4)O)=O)CSSC[C@H]1C(N[C@H](C(N)=O)CC5=CNC6=C5C=CC=C6)=O)[C@H](N)CC7=CC=CC=C7


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, not in water

Shelf Life:
>2 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:
293490


References

1: 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.

2: 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.

3: 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.

4: 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.

5: 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.

6: Trojan J, Braden B. [Early administration of vapreotide for variceal bleeding in patients with cirrhosis]. Z Gastroenterol. 2003 Jan;41(1):151-3. German. PubMed PMID: 16308925.

7: 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.

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

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

10: 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.

11: 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.

12: 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.

13: Patch D, Burroughs A. Vapreotide in variceal bleeding. J Hepatol. 2002 Jul;37(1):167-8. PubMed PMID: 12076882.

14: 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.

15: 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.

16: 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.

17: 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.

18: O'Byrne KJ, Dobbs N, Propper DJ, Braybrooke JP, Koukourakis MI, Mitchell K, Woodhull J, Talbot DC, Schally AV, Harris AL. Phase II study of RC-160 (vapreotide), an octapeptide analogue of somatostatin, in the treatment of metastatic breast cancer. Br J Cancer. 1999 Mar;79(9-10):1413-8. PubMed PMID: 10188884; PubMed Central PMCID: PMC2362707.

19: 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.

20: 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.