Gusperimus
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Other names
N-[2-[4-(3-Aminopropylamino)butylamino]-1-hydroxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide[1]
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Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
KEGG | |
MeSH | gusperimus |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C17H37N7O3 | |
Molar mass | 387.529 g·mol−1 |
log P | −0.933 |
Acidity (pKa) | 11.588 |
Basicity (pKb) | 2.409 |
Pharmacology | |
L04AA19 (WHO) | |
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Pharmacokinetics: | |
100% | |
Legal status |
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Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gusperimus is an
Gusperimus was developed by
There is little information about the
Overview
The European Commission assigned orphan drug status to Gusperimus in 2001 for the treatment of granulomatosis with polyangiitis, a serious form of vasculitis frequently associated with permanent disability and/or fatal outcome. There have been many cases of patients resistant to all forms of usual treatment responding very well to Gusperimus.
It has been proposed that gusperimus may benefit patients with the neurological disease
There have also been positive and negative anecdotal reports in patients with multiple sclerosis. As with ALS, there are no sufficient studies in MS patients.
Gusperimus may possibly be of use in more common diseases and conditions such as rheumatoid arthritis, Crohn's disease, lupus erythematosus, and the prevention and therapy of transplant rejection or graft-versus-host disease.
Adverse effects
Currently, only provisional and preliminary data about side-effects is available. The following side-effects have been noticed so far:
- Dysgeusia (abnormal or bad taste)
- Drug induced leukopenia (very common)[quantify]
- Significant infections related to therapy.
It is not known if therapy with gusperimus may increase the risk of malignant diseases (lymphoma, leukemia, solid tumors), as is the case with other highly potent immunosuppressant agents such as ciclosporin or tacrolimus.
Interactions
There has been little experience about clinically relevant interactions. These might be:
- Other immunosuppressant drugs : Risk of infections increased.
- Myelotoxic drugs like 6-Mercaptopurin : Risk of serious bone marrow damage increased.
- Certain NSAIDs: Increased risk of hepatotoxic reactions.
Dosage
Gusperimus is used in therapeutic cycles. The daily dose and the length of each cycle as well as the length of the treatment free interval depend on the degree of leukopenia/neutropenia caused by gusperimus. It is recommended to obtain complete WBC (White Blood Cell) counts during and after each cycle frequently.
Synonyms
2Common references are:
- (+−)-15-Deoxyspergualin,
- 1-Amino-19-guanidino-11-hydroxy-4,9,12-triazanonadecane-10,13-dione,
- 15-Deoxyspergualin,
- 15-Deoxyspergualin Hydrochloride,
- 7-{(Aminoiminomethyl)amino]-N-[2-[[4-[(3-aminopropyl)amino]butyl]amino]]-
1-hydroxy-2-oxoethyl]heptanamide, - Gusperimus (Trihydrochloride),
- N-[[[4-[(3-Aminopropyl)amino]-butyl]carbamoyl]hydroxymethyl]]-
7-guanidinoheptanamide, - Spanidin
Synthesis
- The BOC derivative of 4-aminobutanol is oxidized with Collins reagent to afford the aldehyde.
- Condensation with the lithium hexamethyldisilazaneleads to the chain extended acid.
- The carboxylic acid is then activated by conversion to its N-hydroxysuccinimide ester; That group is displaced by ammonia to give the corresponding amide and the BOC group is removed by acid to give the intermediate.
- Treatment of the aminoamide with 1-amidino-3,5-dimethylpyrazole leads to an exchange of the amidine function and formation of the corresponding guanidine.
- The saturated guanidino-amide is obtained by aminals.
- Reaction with the carbinolamine, gusperimus.
References
- ^ "gusperimus - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 4 July 2012.
- .
This article includes a list of general references, but it lacks sufficient corresponding inline citations. (February 2008) |
- https://web.archive.org/web/20120204123305/http://www.bizbozos.com/nci_Gusperimus
- http://ec.europa.eu/enterprise/pharmaceuticals/register/o034.htm
- https://web.archive.org/web/20060109201017/http://www.als.net/research/treatments/treatmentDetail.asp?treatmentID=858
- "Gusperimus: Leucopenia, infection, dysgeusia: 3 case reports". Reactions Weekly. 1 (1080): 13. 2005.