GUSPERIMUS

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H37N7O3
Molecular Weight	387.5208
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCCNCCCCNC(=O)C(O)NC(=O)CCCCCCNC(N)=N

InChI

InChIKey=IDINUJSAMVOPCM-UHFFFAOYSA-N

InChI=1S/C17H37N7O3/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)

HIDE SMILES / InChI

Molecular Formula	C17H37N7O3
Molecular Weight	387.5208
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500065437.pdf
Curator's Comment: description was created based on several sources, including, www.ncbi.nlm.nih.gov/pubmed/24501242

Gusperimus is an antibiotic, isolated from cultures of the soil commensal Bacillus laterosporus. It possess immunosuppressive properties and exerts its effect through binding to heat shock proteins Hsp90 and Hsc70. Although initially, the drug was being investigated for the treatment of cancer, it recieved orphan designation for the treatment of refractory Wegener’s granulomatosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Heat shock protein HSP90 35 Target ID: CHEMBL2095165 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11964177	Binding Agent 1076
Heat shock 70 kDa protein 1A 4 Target ID: P0DMV8 Gene ID: 3303\|\|\|3304 Gene Symbol: HSPA1A Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/11964177	Binding Agent 1076
Heat shock 70 kDa protein 1B 3 Target ID: P0DMV9 Gene ID: 3303\|\|\|3304 Gene Symbol: HSPA1B Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/11964177	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Wegener’s granulomatosis 5 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500065437.pdf	Primary		Approved 8583	SPANIDIN Approved Use Spanidin (0.5 mg/kg body weight (BW)) is indicated as therapy for induction of remission in adult patients suffering from refractory Wegener’s granulomatosis, unresolved by standard treatment with cyclophosphamide and glucocorticoids according to EULAR recommendations. Launch Date 2001

PubMed

Title	Date	PubMed
Clinicopathological analysis of acute vascular rejection cases after renal transplantation.	2010-07	20590689
Reduction of MPO-ANCA epitopes in SCG/Kj mice by 15-deoxyspergualin treatment restricted by IgG2b associated with crescentic glomerulonephritis.	2010-07	20378710
Long-term treatment of relapsing Wegener's granulomatosis with 15-deoxyspergualin.	2010-03	20032220
Plasmodial heat shock proteins: targets for chemotherapy.	2010-02	20041948
Deoxyspergualin in relapsing and refractory Wegener's granulomatosis.	2009-07	18713783
Cooperation of salivary protein histatin 3 with heat shock cognate protein 70 relative to the G1/S transition in human gingival fibroblasts.	2009-05-22	19321452
Polyamine compound deoxyspergualin inhibits heat shock protein-induced activation of immature dendritic cells.	2009-03	18686015
Induction of T regulatory cells attenuates idiopathic nephrotic syndrome.	2009-01	19020006
Differential promotion of hematopoietic chimerism and inhibition of alloreactive T cell proliferation by combinations of anti-CD40Ligand, anti-LFA-1, everolimus, and deoxyspergualin.	2008-11	18675355
Maintaining remission in a patient with vasculitis.	2008-09	18648340
Evaluation of the ameliorative effects of immunosuppressants on crescentic glomerulonephritis in SCG/Kj mice.	2008-09	18602063
Chemical conjugation of DeltaF508-CFTR corrector deoxyspergualin to transporter human serum albumin enhances its ability to rescue Cl- channel functions.	2008-08	18515409
IL-10 and IL-4 in skin allograft survival induced by T-cell depletion plus deoxyspergualin.	2008	18819259
Control of cyclosporine A-induced tumor progression using 15-deoxyspergualin for rat cardiac transplantation.	2007-08-15	17700170
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.	2007-08	17570317
Association of treatment with 15-deoxyspergualin and BK virus nephropathy in kidney allograft recipients.	2007-07-25	17645710
15-deoxyspergualin primarily targets the trafficking of apicoplast proteins in Plasmodium falciparum.	2007-03-02	17194705
Steroid-resistant late acute rejection after a living donor liver transplantation: case report and review of the literature.	2007-02	17287604
15-deoxyspergualin inhibits eukaryotic protein synthesis through eIF2alpha phosphorylation.	2007-01-15	16952278
In vivo effects of cyclic administration of 15-deoxyspergualin on leucocyte function in patients with Wegener's granulomatosis.	2006-12	17100765
15-Deoxyspergualin modulates Plasmodium falciparum heat shock protein function.	2006-09-22	16884692
Beneficial effects of simultaneous treatment with 15-deoxyspergualin and monoclonal antibodies to CD45RB and CD154 on murine islet transplantation recipients.	2006-07-27	16858281
Vasculitis treatment - new therapeutic approaches.	2006-06	16525829
Deoxyspergualin, an immunosuppressant, in patients suffering from nephropathies with crescent formation: an open-label trial to evaluate safety and efficacy.	2006-03	16544177
Usage of deoxyspergualin on steroid-resistant acute rejection in living donor liver transplantation.	2006-03	16498230
15-Deoxyspergualin and cyclophosphamide, but not mycophenolate mofetil, prolong survival and attenuate renal disease in a murine model of ANCA-associated crescentic nephritis.	2006-01	16141461
Induction of tolerance to composite tissue allograft in a rat model.	2006	17091475
The molecular chaperone hsp70 interacts with the cytosolic II-III loop of the Cav2.3 E-type voltage-gated Ca2+ channel.	2006	16543726
Elevated T regulatory cells in long-term stable transplant tolerance in rhesus macaques induced by anti-CD3 immunotoxin and deoxyspergualin.	2005-12-15	16339543
Results from a human renal allograft tolerance trial evaluating T-cell depletion with alemtuzumab combined with deoxyspergualin.	2005-10-27	16278585
Safety of 15-deoxyspergualin in the treatment of glomerulonephritis associated with active systemic lupus erythematosus.	2005-10	16162907
Prolonged treatment of refractory Wegener's granulomatosis with 15-deoxyspergualin: an open study in seven patients.	2005-06	15827051
Combined therapy of deoxyspergualin and plasmapheresis: a useful treatment for antibody-mediated acute rejection after kidney transplantation.	2005-03	15848578
Deoxyspergualin prophylaxis with tacrolimus further improves long-term graft survival in living-related renal-transplant recipients transfused with donor-specific blood.	2005-03	15848577
A case of acute humoral rejection with various depositions of C4d, IgG, IgM, and C3c in peritubular capillaries and/or glomerular capillaries.	2005	15955172
Small molecule modulators of endogenous and co-chaperone-stimulated Hsp70 ATPase activity.	2004-12-03	15448148
Novel immunosuppressants.	2004-12	15598332
[Long-term survival of a heterologously transplanted heart following daily administration of cyclosporin and short-term treatment with 15-deoxyspergualin].	2004-11	15675301
Adenovirus-mediated CTLA4 immunoglobulin G gene therapy in cardiac xenotransplantation.	2004-10	15561287
Syenergistic effect of 15-deoxyspergualin with costimulation blockade on alloimmune response.	2004-10	15561275
Results of kidney transplantation in patients receiving MMF- or MMF and basiliximab-containing immunosuppression.	2004-09	15518755
Successful treatment of accelerated vascular rejection in a highly immunised renal transplant recipient with immunoadsorption and 15-deoxyspergualin.	2004-08	15278264
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.	2003-09-10	15203125
Inhibition of CTP: phosphocholine cytidylyltransferase activity by 15-deoxyspergualin.	2003-08	14563164
Tolerance induced by anti-CD3 immunotoxin plus 15-deoxyspergualin associates with donor-specific indirect pathway unresponsiveness.	2003-06	14527508
Heterologous immunity provides a potent barrier to transplantation tolerance.	2003-06	12813024
Effect of plasma exchange in combination with deoxyspergualin on the survival of guinea-pig hearts in macrophage-depleted C6-deficient rats.	2003-05	12694541
Pretransplant xenogeneic blood transfusions reduce the humoral response in a mouse-to-rat heart transplantation model.	2003-03	12641653
Stable alpha- and beta-islet cell function after tolerance induction to pancreatic islet allografts in diabetic primates.	2003-02	12603208
Prophylactic deoxyspergualin treatment in living-related renal-transplant recipients transfused with donor-specific blood.	2003-01-15	12544872

Patents

Sample Use Guides

In Vivo Use Guide

0.5 mg/kg body weight (BW)

Route of Administration: Intravascular

In Vitro Use Guide

To test whether Gusperimus influences the proloferative response of human B-cells, the cells were cultured on CDw32L with 1 ug/ml anti-CD40 mAb with or without IL-10 (100 ng/ml), IL-2 (500 U/ml) or IL-4 (500 U/ml) for 7 days. The drug was added at concentration of 0.2-200 ug/ml. The drug inhibited the prolifirative response of anti-CD40 stimulated B lymphocytes. The inhibition varied among cultures from 48% to 85% at 200 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:46:06 GMT 2025` Edited by `admin` on `Mon Mar 31 18:46:06 GMT 2025`
Record UNII	UJ0ZJ76DO9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-15-DEOXYSPERGUALIN

Preferred Name

English

GUSPERIMUS

Official Name

English

Gusperimus [WHO-DD]

Common Name

English

(±)-N-(((4-((3-AMINOPROPYL)AMINO)BUTYL)CARBAMOYL)HYDROXYMETHYL)-7-GUANIDINOHEPTANAMIDE

Systematic Name

English

HEPTANAMIDE, 7-((AMINOIMINOMETHYL)AMINO)-N-(2-((4-((3-AMINOPROPYL)AMINO)BUTYL)AMINO)-1-HYDROXY-2-OXOETHYL)-

Systematic Name

English

GUSPERIMUS [MI]

Common Name

English

gusperimus [INN]

Common Name

English

(±)-DEOXYSPERGUALIN

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

96896