Gusperimus HCl | BMS181173 | CAS#85468-01-5

MedKoo Cat#: 205766 | Name: Gusperimus HCl

Description:

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

Gusperimus is a derivative of the antitumor antibiotic spergualin with immunosuppressant activity. Gusperimus inhibits the interleukin-2-stimulated maturation of T cells to the S and G2/M phases and the polarization of the T cells into IFN-gamma-secreting Th1 effector T cells, resulting in the inhibition of growth of activated naive CD4 T cells; this agent may suppress growth of certain T-cell leukemia cell lines. Check for active clinical trials or closed clinical trials using this agent.

Chemical Structure

Gusperimus HCl

CAS#85468-01-5 (3HCl)

Theoretical Analysis

MedKoo Cat#: 205766

Name: Gusperimus HCl

CAS#: 85468-01-5 (3HCl)

Chemical Formula: C17H40Cl3N7O3

Exact Mass: 387.2958

Molecular Weight: 496.90

Elemental Analysis: C, 41.09; H, 8.11; Cl, 21.40; N, 19.73; O, 9.66

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 #

85468-01-5 (3HCl) 98629-43-7 (free base) 104317-84-2 (deleted)

Synonym

deoxyspergualin; Deoxyspergualin Hydrochloride; Gusperimus Trihydrochloride; Foreign brand name: Spanidin. Abbreviation: DSG. Code names: BMS181173; BMY422151; NKT01.

IUPAC/Chemical Name

N-(2-((4-((3-aminopropyl)amino)butyl)amino)-1-hydroxy-2-oxoethyl)-7-guanidinoheptanamide trihydrochloride

InChi Key

AXSPHUWXYSZPBG-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H37N7O3.3ClH/c18-9-7-11-21-10-5-6-12-22-15(26)16(27)24-14(25)8-3-1-2-4-13-23-17(19)20;;;/h16,21,27H,1-13,18H2,(H,22,26)(H,24,25)(H4,19,20,23);3*1H

SMILES Code

O=C(NC(O)C(NCCCCNCCCN)=O)CCCCCCNC(N)=N.[H]Cl.[H]Cl.[H]Cl

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).

HS Tariff Code

2934.99.9001

More Info

Gusperimus is an immunosuppressive drug. It is a derivative of the antitumor antibiotic spergualin, and inhibits the interleukin-2-stimulated maturation of T cells to the S and G2/M phases and the polarization of the T cells into IFN-gamma-secreting Th1 effector T cells, resulting in the inhibition of growth of activated naive CD4 T cells. Gusperimus was developed by Bristol-Myers Squibb. Currently, it is manufactured and sponsored for use as an orphan drug and for clinical studies by the Japanese company Euro Nippon Kayaku. The patent claim is that gusperimus may be useful for a variety of hyperreactive inflammatory diseases such as autoimmune diseases. The drug is available in vials containing 100 mg each. (source: http://en.wikipedia.org/wiki/Gusperimus).

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 496.90 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.

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: Banerjee T, Singh RR, Gupta S, Surolia A, Surolia N. 15-Deoxyspergualin hinders physical interaction between basic residues of transit peptide in PfENR and Hsp70-1. IUBMB Life. 2012 Jan;64(1):99-107. doi: 10.1002/iub.583. PubMed PMID: 22223537. 2: Evans CG, Smith MC, Carolan JP, Gestwicki JE. Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction. Bioorg Med Chem Lett. 2011 May 1;21(9):2587-90. Epub 2011 Mar 1. PubMed PMID: 21420295; PubMed Central PMCID: PMC3088103. 3: Lorenz HM, Schmitt WH, Tesar V, MÃ¼ller-Ladner U, Tarner I, Hauser IA, Hiepe F, Alexander T, Woehling H, Nemoto K, Heinzel PA. Treatment of active lupus nephritis with the novel immunosuppressant 15-deoxyspergualin: an open-label dose escalation study. Arthritis Res Ther. 2011 Mar 1;13(2):R36. PubMed PMID: 21356124; PubMed Central PMCID: PMC3132014. 4: Tomizawa K, Nagao T, Kusunoki R, Saiga K, Oshima M, Kobayashi K, Nakayama T, Tanokura M, Suzuki K. Reduction of MPO-ANCA epitopes in SCG/Kj mice by 15-deoxyspergualin treatment restricted by IgG2b associated with crescentic glomerulonephritis. Rheumatology (Oxford). 2010 Jul;49(7):1245-56. Epub 2010 Apr 8. PubMed PMID: 20378710. 5: Flossmann O, Jayne DR. Long-term treatment of relapsing Wegener's granulomatosis with 15-deoxyspergualin. Rheumatology (Oxford). 2010 Mar;49(3):556-62. Epub 2009 Dec 23. PubMed PMID: 20032220. 6: Asiedu C, Andrades P, Ray PD, George JF, Thomas JM. IL-10 and IL-4 in skin allograft survival induced by T-cell depletion plus deoxyspergualin. Cell Transplant. 2008;17(6):713-20. PubMed PMID: 18819259. 7: Flossmann O, Baslund B, Bruchfeld A, Tervaert JW, Hall C, Heinzel P, Hellmich B, Luqmani RA, Nemoto K, Tesar V, Jayne DR. Deoxyspergualin in relapsing and refractory Wegener's granulomatosis. Ann Rheum Dis. 2009 Jul;68(7):1125-30. Epub 2008 Aug 19. PubMed PMID: 18713783. 8: Marchase RB. Retraction: Peritransplant tolerance induction in macaques: early events reflecting the unique synergy between immunotoxin and deoxyspergualin. Transplantation. 2008 Aug 15;86(3):482. PubMed PMID: 18698255. 9: Sugawara A, Torigoe T, Tamura Y, Kamiguchi K, Nemoto K, Oguro H, Sato N. Polyamine compound deoxyspergualin inhibits heat shock protein-induced activation of immature dendritic cells. Cell Stress Chaperones. 2009 Mar;14(2):133-9. Epub 2008 Aug 7. PubMed PMID: 18686015; PubMed Central PMCID: PMC2727995. 10: Metzler B, Gfeller P, Wieczorek G, Katopodis A. Differential promotion of hematopoietic chimerism and inhibition of alloreactive T cell proliferation by combinations of anti-CD40Ligand, anti-LFA-1, everolimus, and deoxyspergualin. Transpl Immunol. 2008 Nov;20(1-2):106-12. Epub 2008 Jul 31. PubMed PMID: 18675355. 11: Norez C, Pasetto M, Dechecchi MC, Barison E, Anselmi C, Tamanini A, Quiri F, Cattel L, Rizzotti P, Dosio F, Cabrini G, Colombatti M. Chemical conjugation of DeltaF508-CFTR corrector deoxyspergualin to transporter human serum albumin enhances its ability to rescue Cl- channel functions. Am J Physiol Lung Cell Mol Physiol. 2008 Aug;295(2):L336-47. Epub 2008 May 30. PubMed PMID: 18515409. 12: Ohsawa I, Uemoto S, Kobayashi E, Murakami T. Control of cyclosporine A-induced tumor progression using 15-deoxyspergualin for rat cardiac transplantation. Transplantation. 2007 Aug 15;84(3):424-8. PubMed PMID: 17700170. 13: Shi Y, Moriyama T, Namba Y, Yamanaka M, Hanafuse T, Imamura R, Ichimaru N, Oka K, Kyo M, Tian Y, Takahara S, Ichikawa S, Okuyama A. Association of treatment with 15-deoxyspergualin and BK virus nephropathy in kidney allograft recipients. Clin Transplant. 2007 Jul-Aug;21(4):502-9. PubMed PMID: 17645710. 14: Lee J, Kim MS, Kim EY, Park HJ, Chang CY, Jung DY, Kwon CH, Joh JW, Kim SJ. 15-deoxyspergualin prevents mucosal injury by inhibiting production of TNF-alpha and down-regulating expression of MD-1 in a murine model of TNBS-induced colitis. Int Immunopharmacol. 2007 Aug;7(8):1003-12. Epub 2007 Apr 4. PubMed PMID: 17570317. 15: Ramya TN, Karmodiya K, Surolia A, Surolia N. 15-deoxyspergualin primarily targets the trafficking of apicoplast proteins in Plasmodium falciparum. J Biol Chem. 2007 Mar 2;282(9):6388-97. Epub 2006 Dec 28. PubMed PMID: 17194705. 16: KÃ¤lsch AI, Schmitt WH, Breedijk A, Marinaki S, Weigerding S, Nebe TC, Nemoto K, van der Woude FJ, Yard BA, Birck R. In vivo effects of cyclic administration of 15-deoxyspergualin on leucocyte function in patients with Wegener's granulomatosis. Clin Exp Immunol. 2006 Dec;146(3):455-62. PubMed PMID: 17100765; PubMed Central PMCID: PMC1810421. 17: Ramya TN, Surolia N, Surolia A. 15-deoxyspergualin inhibits eukaryotic protein synthesis through eIF2alpha phosphorylation. Biochem J. 2007 Jan 15;401(2):411-20. PubMed PMID: 16952278; PubMed Central PMCID: PMC1820809. 18: Thomas JM, Eckhoff DE, Contreras JL, Thomas FT, Neville DM Jr, Lobashevsky A, Hubbard WJ, Cook WJ. Retraction: Durable donor-specific T and B cell tolerance in rhesus macaques induced with peritransplantation anti-CD3 immunotoxin and deoxyspergualin: absence of chronic allograft nephropathy. Transplantation. 2006 Aug 27;82(4):577. PubMed PMID: 16926605. 19: Ramya TN, Surolia N, Surolia A. 15-Deoxyspergualin modulates Plasmodium falciparum heat shock protein function. Biochem Biophys Res Commun. 2006 Sep 22;348(2):585-92. Epub 2006 Jul 28. PubMed PMID: 16884692. 20: Jung DY, Lee HJ, Lee EN, Lee J, Kim EY, Park HJ, Chang CY, Lee SK, Joh JW, Kwon GY, Kim SJ. Beneficial effects of simultaneous treatment with 15-deoxyspergualin and monoclonal antibodies to CD45RB and CD154 on murine islet transplantation recipients. Transplantation. 2006 Jul 27;82(2):188-95. PubMed PMID: 16858281. 21: Imai H, Hotta O, Yoshimura M, Konta T, Tsubakihara Y, Miyazaki M, Tomida C, Kobayashi M, Suzuki S, Shiiki H, Yamauchi A, Yokoyama H, Nose M. Deoxyspergualin, an immunosuppressant, in patients suffering from nephropathies with crescent formation: an open-label trial to evaluate safety and efficacy. Clin Exp Nephrol. 2006 Mar;10(1):40-54. PubMed PMID: 16544177. 22: Kawagishi N, Satoh K, Enomoto Y, Akamatsu Y, Sekiguchi S, Satomi S. Usage of deoxyspergualin on steroid-resistant acute rejection in living donor liver transplantation. Tohoku J Exp Med. 2006 Mar;208(3):225-33. PubMed PMID: 16498230. 23: Asiedu CK, Goodwin KJ, Balgansuren G, Jenkins SM, Le Bas-Bernardet S, Jargal U, Neville DM Jr, Thomas JM. Elevated T regulatory cells in long-term stable transplant tolerance in rhesus macaques induced by anti-CD3 immunotoxin and deoxyspergualin. J Immunol. 2005 Dec 15;175(12):8060-8. Retraction in: Asiedu CK, Goodwin KJ, Balgansuren G, Jenkins SM, Le Bas-Bernardet S, Jargal U, Thomas JM, Neville DM Jr. J Immunol. 2006 Aug 1;177(3):2023. PubMed PMID: 16339543. 24: Kirk AD, Mannon RB, Kleiner DE, Swanson JS, Kampen RL, Cendales LK, Elster EA, Wakefield T, Chamberlain C, Hoffmann SC, Hale DA. Results from a human renal allograft tolerance trial evaluating T-cell depletion with alemtuzumab combined with deoxyspergualin. Transplantation. 2005 Oct 27;80(8):1051-9. PubMed PMID: 16278585. 25: Lorenz HM, Grunke M, Wendler J, Heinzel PA, Kalden JR. Safety of 15-deoxyspergualin in the treatment of glomerulonephritis associated with active systemic lupus erythematosus. Ann Rheum Dis. 2005 Oct;64(10):1517-9. PubMed PMID: 16162907; PubMed Central PMCID: PMC1755225. 26: Birck R, Newman M, Braun C, Neumann I, Nemoto K, Yard B, Waldherr R, van der Woude FJ. 15-Deoxyspergualin and cyclophosphamide, but not mycophenolate mofetil, prolong survival and attenuate renal disease in a murine model of ANCA-associated crescentic nephritis. Nephrol Dial Transplant. 2006 Jan;21(1):58-63. Epub 2005 Sep 2. PubMed PMID: 16141461. 27: Nojima M, Yoshimoto T, Nakao A, Maruyama T, Takiuchi H, Izumi M, Hashimoto M, Kyo M, Shima H. Combined therapy of deoxyspergualin and plasmapheresis: a useful treatment for antibody-mediated acute rejection after kidney transplantation. Transplant Proc. 2005 Mar;37(2):930-3. PubMed PMID: 15848578. 28: Amada N, Okazaki H, Sato T, Ohashi Y, Kikuchi H. Deoxyspergualin prophylaxis with tacrolimus further improves long-term graft survival in living-related renal-transplant recipients transfused with donor-specific blood. Transplant Proc. 2005 Mar;37(2):927-9. PubMed PMID: 15848577. 29: Schmitt WH, Birck R, Heinzel PA, GÃ¶bel U, Choi M, Warnatz K, Peter HH, van der Woude FJ. Prolonged treatment of refractory Wegener's granulomatosis with 15-deoxyspergualin: an open study in seven patients. Nephrol Dial Transplant. 2005 Jun;20(6):1083-92. Epub 2005 Apr 12. PubMed PMID: 15827051. 30: Kubota T. [Long-term survival of a heterologously transplanted heart following daily administration of cyclosporin and short-term treatment with 15-deoxyspergualin]. Hokkaido Igaku Zasshi. 2004 Nov;79(6):711-7. Japanese. PubMed PMID: 15675301. 31: Shirasugi N, Aramaki O, Hatano M, Suda H, Tanaka K, Inoue F, Akiyoshi T, Shimazu M, Kitajima M, Niimi M. Syenergistic effect of 15-deoxyspergualin with costimulation blockade on alloimmune response. Transplant Proc. 2004 Oct;36(8):2446-7. PubMed PMID: 15561275. 32: Braun N, Wernet D, Schnaidt M, Bevan DJ, Viebahn R, Risler T. Successful treatment of accelerated vascular rejection in a highly immunised renal transplant recipient with immunoadsorption and 15-deoxyspergualin. Transpl Int. 2004 Aug;17(7):384-6. Epub 2004 Jul 22. PubMed PMID: 15278264. 33: Tahara H, Iwanami N, Tabata N, Matsumura H, Matsuura T, Kurita T, Miyazawa M. Both T and non-T cells with proliferating potentials are effective in inducing suppression of allograft responses by alloantigen-specific intravenous presensitization combined with suboptimal doses of 15-deoxyspergualin. Transpl Immunol. 2004 Jun-Jul;13(1):25-32. PubMed PMID: 15203125. 34: Kawada M, Ishizuka M. Inhibition of CTP: phosphocholine cytidylyltransferase activity by 15-deoxyspergualin. J Antibiot (Tokyo). 2003 Aug;56(8):725-6. PubMed PMID: 14563164. 35: Asiedu CK, Dong SS, Lobashevsky A, Jenkins SM, Thomas JM. Tolerance induced by anti-CD3 immunotoxin plus 15-deoxyspergualin associates with donor-specific indirect pathway unresponsiveness. Cell Immunol. 2003 Jun;223(2):103-12. PubMed PMID: 14527508. 36: Yang H, Chen G, Kanai N, Shum J, Garcia B, Huang X, Min W, Luo Y, Dutartre P, Zhong R. Monotherapy with LF 15-0195, an analogue of 15-deoxyspergualin, significantly prolongs renal allograft survival in monkeys. Transplantation. 2003 Apr 27;75(8):1166-71. PubMed PMID: 12717197. 37: Wu G, Korsgren O, Sun S, Van Rooijen N, Tibell A. Effect of plasma exchange in combination with deoxyspergualin on the survival of guinea-pig hearts in macrophage-depleted C6-deficient rats. Xenotransplantation. 2003 May;10(3):214-22. PubMed PMID: 12694541. 38: Amada N, Okazaki H, Sato T, Miura S, Ohashi Y. Prophylactic deoxyspergualin treatment in living-related renal-transplant recipients transfused with donor-specific blood. Transplantation. 2003 Jan 15;75(1):60-6. PubMed PMID: 12544872. 39: Birck R, Warnatz K, Lorenz HM, Choi M, Haubitz M, GrÃ¼nke M, Peter HH, Kalden JR, GÃ¶bel U, Drexler JM, Hotta O, Nowack R, Van Der Woude FJ. 15-Deoxyspergualin in patients with refractory ANCA-associated systemic vasculitis: a six-month open-label trial to evaluate safety and efficacy. J Am Soc Nephrol. 2003 Feb;14(2):440-7. PubMed PMID: 12538745. 40: Matsui Y, Asano T, Kenmochi T, Tokoro Y, Jingu K, Maruyama M, Akutsu N, Miyauchi H, Itoh T, Saito T, Ochiai T. Cytoprotective effect of hepatic cell pretreatment with 15-deoxyspergualin to prevent warm ischemic reperfusion injuries in rats. Transplant Proc. 2002 Nov;34(7):2674-6. PubMed PMID: 12431570. 41: Holcombe H, Mellman I, Janeway CA Jr, Bottomly K, Dittel BN. The immunosuppressive agent 15-deoxyspergualin functions by inhibiting cell cycle progression and cytokine production following naive T cell activation. J Immunol. 2002 Nov 1;169(9):4982-9. PubMed PMID: 12391212. 42: Ablake M, Itoh M, Kaneko T, Iimura A, Nakamura Y, Meroni P, Nicoletti F. Short-term prophylaxis with deoxyspergualin prevents testicular autoimmunity in mice. Eur J Pharmacol. 2002 Aug 23;450(2):209-12. PubMed PMID: 12206860. 43: Juang JH, Hsu BR, Kuo CH. 15-Deoxyspergualin protects the islet graft from macrophage-mediated injury. Transplant Proc. 2002 Aug;34(5):1458-9. PubMed PMID: 12176438. 44: Kawada M, Masuda T, Ishizuka M, Takeuchi T. 15-Deoxyspergualin inhibits Akt kinase activation and phosphatidylcholine synthesis. J Biol Chem. 2002 Aug 2;277(31):27765-71. Epub 2002 May 20. PubMed PMID: 12021268. 45: Nishimura K, Ohki Y, Fukuchi-Shimogori T, Sakata K, Saiga K, Beppu T, Shirahata A, Kashiwagi K, Igarashi K. Inhibition of cell growth through inactivation of eukaryotic translation initiation factor 5A (eIF5A) by deoxyspergualin. Biochem J. 2002 May 1;363(Pt 3):761-8. PubMed PMID: 11964177; PubMed Central PMCID: PMC1222529. 46: Kimura Y, Yagi T, Iwagaki H, Watanabe K, Kai K, Yamamura M, Inagaki M, Tanaka S, Tanaka N. Immunomodulation based on a two-way paradigm with deoxyspergualin alleviates graft-versus-host reaction in small-bowel transplantation in rats. J Int Med Res. 2001 May-Jun;29(3):214-21. PubMed PMID: 11471859. 47: Amada N, Okazaki H, Sato T, Miura S, Ohashi Y. Prophylactic use of deoxyspergualin improves long-term graft survival in living related renal transplant recipients transfused with donor-specific blood. Transplant Proc. 2001 May;33(3):2256-7. PubMed PMID: 11377520. 48: Wu J, He J, Sooudi S, Jiang XL, Ray P, Thomas F, Thomas JM. Pretreatment of HL60 cells with Deoxyspergualin enhances trail-induced apoptosis independent of caspase 3 activation. Transplant Proc. 2001 Feb-Mar;33(1-2):278. PubMed PMID: 11266818. 49: Hiragino T, Takai K, Fujikawa K, Konishi M, Aoki A, Suga A, Fujimoto M, Nakamura K, Naito K. The effect of deoxyspergualin on rat thymocytes and thymic epithelial cells. Transplant Proc. 2000 Nov;32(7):2524-8. PubMed PMID: 11120278. 50: Tanabe K, Tokumoto T, Ishikawa N, Shimizu T, Okuda H, Ito S, Shimmura H, Inui M, Harano M, Ohtsubo S, Manu M, Shiroyanagi Y, Yagisawa T, Fuchinoue S, Toma H. Effect of Deoxyspergualin on the long-term outcome of renal transplantation. Transplant Proc. 2000 Nov;32(7):1745-6. PubMed PMID: 11119916.