Pentostatin
Title: Pentostatin
CAS Registry Number: 53910-25-1
CAS Name: (8R)-3-(2-Deoxy-b-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
Additional Names: 2¢-deoxycoformycin; DCF; 2¢-dCF
Manufacturers' Codes: CL-67310465; NSC-218321; CI-825
Trademarks: Nipent (SuperGen)
Molecular Formula: C11H16N4O4
Molecular Weight: 268.27
Percent Composition: C 49.25%, H 6.01%, N 20.88%, O 23.86%
Literature References: Adenosine deaminase inhibitor. Isoln from Streptomyces antibioticus and structure determn: P. W. K. Woo et al., J. Heterocycl. Chem. 11, 641 (1974). Isoln and purification: A. Ryder et al., DE 2517596; eidem, US 3923785 (both 1975 to Parke-Davis). Total synthesis: E. Chan et al., J. Org. Chem. 47, 3457 (1982). Preliminary biosynthetic study: J. C. Hanvey et al., Biochemistry 27, 5790 (1988). Inhibition of deaminases in vitro: T. Rogler-Brown et al., Biochem. Pharmacol. 27, 2289 (1978); C. Frieden et al., Biochem. Biophys. Res. Commun. 91, 278 (1979); in vivo: W. Plunkett et al., Biochem. Pharmacol. 28, 201 (1979). Toxicology study: J. F. Smyth et al., Cancer Chemother. Pharmacol. 1, 49 (1978). Clinical pharmacology: J. F. Smyth et al., ibid. 5, 93 (1980); P. P. Major et al., Blood 58, 91 (1981); F. J. Cummings et al., Clin. Pharmacol. Ther. 44, 501 (1988). Enzymatic determn in biological fluids: M. M. Chassin et al., Biochem. Pharmacol. 28, 1849 (1979); A. E. Staubus et al., ibid. 33, 1633 (1984). Clinical evaluation in hairy cell leukemia: J. B. Johnston et al., J. Natl. Cancer Inst. 80, 765 (1988). Brief review: P. O'Dwyer et al., Ann. Intern. Med. 108, 733 (1988). Review of clinical pharmacology and immunosuppressive effects: M. Higman et al., Expert Opin. Pharmacother. 5, 2605-2613 (2004).
Properties: White crystals from methanol/water, mp 220-225° (Woo), also reported as 204-209.5° with darkening at >150° (Chan). uv max (water, pH 7): 282 nm (e 8000); (pH 11): 283 nm (e 7970); (pH 2): 273 nm (e 7570 initially, 3143 after 6.5 hrs). [a]D25 +76.4° (c = 1 in water); [a]D23 +73.0° (c = 1, pH 7 buffer). pKa 5.2 in water. Freely sol in distilled water.
Melting point: mp 220-225° (Woo), also reported as 204-209.5° with darkening at >150° (Chan)
pKa: pKa 5.2 in water
Optical Rotation: [a]D25 +76.4° (c = 1 in water); [a]D23 +73.0° (c = 1, pH 7 buffer)
Absorption maximum: uv max (water, pH 7): 282 nm (e 8000); (pH 11): 283 nm (e 7970); (pH 2): 273 nm (e 7570 initially, 3143 after 6.5 hrs)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic.

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