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MedKoo Cat#: 598018 | Name: Vapreotide diacetate

Description:

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

Vapreotide diacetate is a synthetic analog of somatostatin, has analgesic activity most likely mediated through the blockade of neurokinin-1 receptor (NK1R), the substance P (SP)-preferring receptor.

Chemical Structure

Vapreotide diacetate
Vapreotide diacetate
CAS#936560-75-7 (diacetate)

Theoretical Analysis

MedKoo Cat#: 598018

Name: Vapreotide diacetate

CAS#: 936560-75-7 (diacetate)

Chemical Formula: C61H78N12O13S2

Exact Mass: 1250.5253

Molecular Weight: 1251.48

Elemental Analysis: C, 58.54; H, 6.28; N, 13.43; O, 16.62; S, 5.12

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
936560-75-7 (diacetate) 849479-74-9 (acetate) 103222-11-3 (free)
Synonym
Vapreotide diacetate;
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 diacetate
InChi Key
NSSGLJZEFUPZRE-QJHAWANGSA-N
InChi Code
1S/C57H70N12O9S2.2C2H4O2/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;2*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);2*1H3,(H,3,4)/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.CC(O)=O.CC(O)=O
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,251.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.

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