4582. Gusperimus

Nomenclature

CAS number: 104317-84-2
7-[(Aminoiminomethyl)amino]-N-[2-[[4-[(3-aminopropyl)amino]butyl]amino]-1-hydroxy-2-oxoethyl]heptanamide; (±)-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.
C17H37N7O3; mol wt 387.52.
C 52.69%, H 9.62%, N 25.30%, O 12.39%.

Description and 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).

Chemical structure

Derivative

Trihydrochloride.

Nomenclature

CAS number: 85468-01-5
BMS-181173; NKT-01; NSC-356894; Spanidin (Nippon Kayaku).
C17H37N7O3.3HCl; mol wt 496.90.
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).

Derivative

()-Form trihydrochloride.

Nomenclature

CAS number: 84937-45-1

Properties

Prepd as the dihydrate. Colorless syrup, no def mp. [α]D25 7.3° (c = 1 in H2O). LD50 in mice (mg/kg): 35-40 i.v. or i.p. (Iwasawa).

Therapeutic Category

Immunosuppressant.

Keywords

Immunosuppressant