Gusperimus

Title: Gusperimus
CAS Registry Number: 104317-84-2
CAS Name: 7-[(Aminoiminomethyl)amino]-N-[2-[[4-[(3-aminopropyl)amino]butyl]amino]-1-hydroxy-2-oxoethyl]heptanamide
Additional Names: (±)-N-[[[4-[(3-aminopropyl)amino]butyl]carbamoyl]hydroxymethyl]-7-guanidinoheptanamide; 1-amino-19-guanidino-11-hydroxy-4,9,12-triazanonadecane-10,13-dione; deoxyspergualin; (±)-15-deoxyspergualin
Molecular Formula: C17H37N7O3
Molecular Weight: 387.52
Percent Composition: C 52.69%, H 9.62%, N 25.30%, O 12.39%
Literature References: Synthetic derivative of the antitumor antibiotic spergualin. Prepn: BE 894651; H. Umezawa et al., US 4518532 (1983, 1985 both to Microbiochem. Res. Found.); Y. Umeda et al., J. Antibiot. 38, 886 (1985). Prepn of the active (-)-isomer: H. Iwasawa et al., ibid. 35, 1665 (1982); H. Umezawa et al., EP 94632; eidem, US 4525299 (1983, 1985 both to Microbiochem. Res. Found.). Synthesis and bioactivity of isomers: Y. Umeda et al., J. Antibiot. 40, 1316 (1987). Mechanism of action study: W. E. G. Müller et al., ibid. 1028. HPLC determn in plasma: R. Nakanuma et al., J. Chromatogr. 527, 208 (1990). Pharmacokinetics: J. F. Muindi et al., Cancer Res. 51, 3096 (1991). Preliminary evaluation in renal transplant rejection: H. Amemiya et al., Transplant. Proc. 25, 730 (1993). Series of articles on synthesis and immunomodulating activity: Ann. N.Y. Acad. Sci. 685, 123-206 (1993).
Derivative Type: Trihydrochloride
CAS Registry Number: 85468-01-5
Manufacturers' Codes: BMS-181173; NKT-01; NSC-356894
Trademarks: Spanidin (Nippon Kayaku)
Molecular Formula: C17H37N7O3.3HCl
Molecular Weight: 496.90
Percent Composition: C 41.09%, H 8.11%, N 19.73%, O 9.66%, Cl 21.40%
Properties: White powder, prepd as the sesquihydrate. Sol in water. pH of 50 mg/ml saline soln: ~4.9. LD50 in mice (mg/kg): 25-50 i.p. (Umezawa).
Toxicity data: LD50 in mice (mg/kg): 25-50 i.p. (Umezawa)
Derivative Type: (-)-Form trihydrochloride
CAS Registry Number: 84937-45-1
Properties: Prepd as the dihydrate. Colorless syrup, no def mp. [a]D25 -7.3° (c = 1 in H2O). LD50 in mice (mg/kg): 35-40 i.v. or i.p. (Iwasawa).
Optical Rotation: [a]D25 -7.3° (c = 1 in H2O)
Toxicity data: LD50 in mice (mg/kg): 35-40 i.v. or i.p. (Iwasawa)
Therap-Cat: Immunosuppressant.
Keywords: Immunosuppressant.
Guvacine Gymnemic Acid Gypsogenin H3? Hachimycin

Gusperimus
Skeletal formula of a gusperimus minor tautomer
Identifiers
CAS number 104317-84-2 N
PubChem 55362, 91272 S
ChemSpider 49995 YesY, 82420 S YesY
UNII UJ0ZJ76DO9 YesY
KEGG D08032 YesY
MeSH gusperimus
ChEMBL CHEMBL406117 YesY, CHEMBL1172736 YesY
ATC code L04AA19
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C17H37N7O3
Molar mass 387.52 g mol−1
log P −0.933
Acidity (pKa) 11.588
Basicity (pKb) 2.409
Pharmacology
Bioavailability 100%
Routes of
administration
  • Intravenous
  • Subcutaneous
Legal status


Prescription only

Related compounds
Related compounds
  • Dibutylhexamethylenediamine
  • Acetyl hexapeptide-3
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 (see quotation) 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.

There is little information about the pharmacokinetic properties of gusperimus.