GUSPERIMUS TRIHYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H37N7O3.3ClH
Molecular Weight	496.904
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of GUSPERIMUS TRIHYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=AXSPHUWXYSZPBG-UHFFFAOYSA-N

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

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	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 1064
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 1064
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 1064

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 8429	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
Coexpression of CD4 and CD8alpha on rat T-cells in whole blood: a sensitive marker for monitoring T-cell immunosuppressive drugs.	2001 Aug 1	11406149
Pretreatment of HL60 cells with Deoxyspergualin enhances trail-induced apoptosis independent of caspase 3 activation.	2001 Feb-Mar	11266818
Identification of an inhibitor of hsc70-mediated protein translocation and ATP hydrolysis.	2001 Jan 12	11036084
Immunosuppression in ANCA-associated vasculitis.	2001 May	11377509
STEALTH in transplantation tolerance.	2002	12403353
Isolation of mouse-to-rat cardiac xenograft-infiltrating cells by ex vivo propagation.	2002 May	11983019
Effect of heat stress on lipopolysaccharide-induced vascular permeability change in mice.	2002 Nov	12388648
Inhibition of CTP: phosphocholine cytidylyltransferase activity by 15-deoxyspergualin.	2003 Aug	14563164
15-Deoxyspergualin in patients with refractory ANCA-associated systemic vasculitis: a six-month open-label trial to evaluate safety and efficacy.	2003 Feb	12538745
Prophylactic deoxyspergualin treatment in living-related renal-transplant recipients transfused with donor-specific blood.	2003 Jan 15	12544872
Effect of plasma exchange in combination with deoxyspergualin on the survival of guinea-pig hearts in macrophage-depleted C6-deficient rats.	2003 May	12694541
Safety of 15-deoxyspergualin in the treatment of glomerulonephritis associated with active systemic lupus erythematosus.	2005 Oct	16162907
15-Deoxyspergualin and cyclophosphamide, but not mycophenolate mofetil, prolong survival and attenuate renal disease in a murine model of ANCA-associated crescentic nephritis.	2006 Jan	16141461
15-Deoxyspergualin modulates Plasmodium falciparum heat shock protein function.	2006 Sep 22	16884692
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 Aug	17570317
Chemical conjugation of DeltaF508-CFTR corrector deoxyspergualin to transporter human serum albumin enhances its ability to rescue Cl- channel functions.	2008 Aug	18515409
Cooperation of salivary protein histatin 3 with heat shock cognate protein 70 relative to the G1/S transition in human gingival fibroblasts.	2009 May 22	19321452
Plasmodial heat shock proteins: targets for chemotherapy.	2010 Feb	20041948

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 `Fri Dec 15 16:46:56 GMT 2023` Edited by `admin` on `Fri Dec 15 16:46:56 GMT 2023`
Record UNII	QZS4144IO0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GUSPERIMUS TRIHYDROCHLORIDE

Official Name

English

NKT-01

Code

English

BMS-181173

Code

English

SPANIDIN

Brand Name

English

GUSPERIMUS HYDROCHLORIDE [JAN]

Common Name

English

GUSPERIMUS HYDROCHLORIDE

Common Name

English

BMY-42215-1

Code

English

Gusperimus hydrochloride [WHO-DD]

Common Name

English

GUSPERIMUS HYDROCHLORIDE [MART.]

Common Name

English

GUSPERIMUS TRIHYDROCHLORIDE [MI]

Common Name

English

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

Common Name

English

NSC-356894

Code

English

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

Systematic Name

English

GUSPERIMUS TRIHYDROCHLORIDE [USAN]

Common Name

English

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

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

342711