Structural Formula Vector Image
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.

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