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CAS No 72496-41-4 , Pirarubicin

  • Name: Pirarubicin
  • Synonyms: Pirarubicin;Pirarubicin;(2''R)-4'-O-Tetrahydropyranyldoxorubicin; Therarubicin;Pinorubicin; (2''R)-4'-O-Tetrahydropyranyladriamycin; 4'-O-Tetrahydropyranyladriamycin; 5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,(8S,10S)- (9CI);5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,[8S-[8a,10a(S*)]]-; THP-Adriamycin;
  • CAS Registry Number:
  • Flash Point: 834.7 ºC at 760 mmHg
  • Boiling Point: 834.7 ºC at 760 mmHg
  • Density: 1.51 g/cm3
  • Refractive index: 1.67
  • Water Solubility: slightly soluble in water
  • Safety Statements: S26;S37/39;
  • Hazard Symbols: Xi
  • Flash Point: 834.7 ºC at 760 mmHg
  • Molecular Weight: 627.64
  • InChI: InChI=1/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19?,21+,22-,31+,32-/m0/s1
  • Risk Statements: 36/37/38
  • Molecular Formula: C32H37NO12
  • Molecular Structure:CAS No:72496-41-4 Pirarubicin

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References of Pirarubicin
Title: Pirarubicin
CAS Registry Number: 72496-41-4
CAS Name: (8S,10S)-10-[[3-Amino-2,3,6-trideoxy-4-O-[(2S)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
Synonyms: 4￠-O-tetrahydropyranyl doxorubicin; (2￠￠R)-4￠-O-tetrahydropyranyladriamycin; tepirubicin; THP; THP-ADM; THP-adriamycin
Manufacturers' Codes: 1609-RB
Trademarks: Theprubicin (Aventis)
Molecular Formula: C32H37NO12
Molecular Weight: 627.64
Percent Composition: C 61.24%, H 5.94%, N 2.23%, O 30.59%
Literature References: Structural analog of doxorubicin, q.v. Prepn of (2￠￠R) and (2￠￠S)-diastereomers: H. Umezawa et al., J. Antibiot. 32, 1082 (1979); idem et al., EP 14853; eidem, US 4303785 (1980, 1981 both to Microbiochem. Res. Found. Japan). Absolute configuration: idem et al., J. Antibiot. 37, 1094 (1984). HPLC determn in biological fluids: Y. Matsushita et al., ibid. 36, 880 (1983). Cellular uptake and inhibition of DNA synthesis: S. Kunimoto et al., ibid. 312 (1983). Mechanism of action study: K.-I. Kiyomiya et al., Int. J. Oncol. 21, 1081 (2002). Clinical pharmacokinetics and toxicity: A. A. Miller, C. G. Schmidt, Cancer Res. 47, 1461 (1987). Overview of clinical experience: H. Majima, K. Ohta, Biomed. Pharmacother. 41, 237-243 (1987). Clinical evaluation in metastatic colon cancer: D. Fallik et al., Ann. Oncol. 14, 856 (2003)
Properties: Red solid, mp 188-192° (dec). [a]D25 +175 ±25° (c = 0.2 in CHCl3). uv and visible max (methanol): 234, 252, 290, 498, 531.5, 580 nm (E1%1cm 480, 350, 110, 140, 100, 45). Sol in ethyl acetate, chloroform, and ethanol; slightly sol in water, n-hexane, petr ether. Ethanolic and acidic solutions are red in color; give a positive ninhydrin reaction and do not reduce Fehling's solution. LD50 i.v. in mice: 27.8 mg/kg (Umezawa, 1979).
Melting point: mp 188-192° (dec)
Optical Rotation: [a]D25 +175 ±25° (c = 0.2 in CHCl3)
Absorption maximum: uv and visible max (methanol): 234, 252, 290, 498, 531.5, 580 nm (E1%1cm 480, 350, 110, 140, 100, 45)
Toxicity data: LD50 i.v. in mice: 27.8 mg/kg (Umezawa, 1979)
 
Derivative Type: Hydrochloride
CAS Registry Number: 95343-20-7
Trademarks: Pinorubin (Nippon Kayaku); Therarubicin (Meiji Seika)
Molecular Formula: C32H37NO12.HCl
Molecular Weight: 664.10
Percent Composition: C 57.87%, H 5.77%, N 2.11%, O 28.91%, Cl 5.34%
Properties: Red crystalline solid. Sol in water and methanol.
 
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Anthracyclines; Topoisomerase II Inhibitor.