Home > Name List By other > (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9, 11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydr...

CAS No 23214-92-8 , (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,
11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,
12-dione

  • Name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,
    11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,
    12-dione
  • Synonyms: Adriamycin; Adriablastin; Doxil; Doxorubicinum; Adriblastin; Doxorubicine; Adriblastina; Myocet;(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,
    11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,
    12-dione; Rubex;
  • CAS Registry Number:
  • Transport: DOX
  • Boiling Point: RELATIVE DENSITY
  • Density: 1.61 g/cm3
  • Refractive index: 1.709
  • Water Solubility: Soluble
  • Safety Statements: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal, subcutaneous, parenteral, and intravenous routes. Human systemic effects by intravenous route: cardiac myopathy including infarction, nausea or vomiting, and effects on the hair. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.
  • Hazard Symbols: UN NO.
  • EINECS: 245-495-6
  • Molecular Weight: 543.51926
  • InchiKey: AOJJSUZBOXZQNB-TZSSRYMLSA-N
  • InChI: InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,
    16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)
    25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,
    15-,17-,22+,27-/m0/s1
  • Molecular Formula: C27H29NO11
  • Molecular Structure:CAS No:23214-92-8 (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,<br />11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,<br />12-dione

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References of (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,
11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,
12-dione
Title: Doxorubicin
CAS Registry Number: 23214-92-8
CAS Name: (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
Synonyms: 14-hydroxydaunomycin
Manufacturers' Codes: NSC-123127; FI-106
Molecular Formula: C27H29NO11
Molecular Weight: 543.52
Percent Composition: C 59.66%, H 5.38%, N 2.58%, O 32.38%
Literature References: Anthracycline antibiotic; interferes with topoisomerase II function. Isoln from Streptomyces peucetius var caesius: F. Arcamone et al., ZA 6802378; eidem, US 3590028 (1968, 1971 both to Farmitalia); eidem, Biotechnol. Bioeng. 11, 1101 (1969). Structural studies: F. Arcamone et al., Tetrahedron Lett. 10, 1007 (1969). Synthesis from daunomycin, q.v.: eidem, Chim. Ind. (Milan) 51, 834 (1969). Biochemical comparison with daunomycin: Wang et al., Proc. Am. Assoc. Cancer Res. 12, No. 62, 77 (1971). In acid environment doxorubicin breaks up into adriamycinone and daunosamine: A. Di Marco et al., Cancer Chemother. Rep. Part 1 53, 33 (1969). Pharmacokinetic and chemotherapeutic studies: E. Arena et al., Arzneim.-Forsch. 21, 1258 (1971). LC/MS/MS determn of doxorubicin and metabolites: R. D. Arnold et al., J. Chromatogr. B 808, 141 (2004). Toxicity study: C. Bertazzoli et al., Experientia 26, 389 (1970). Comprehensive description: A. Vigevani, M. J. Williamson, Anal. Profiles Drug Subs. 9, 245-274 (1980). Book: Doxorubicin, F. Arcamone, Ed. (Academic Press, New York, 1981) 369 pp. Review of clinical development: R. H. Blum, S. K. Carter, Ann. Intern. Med. 80, 249-259 (1974); of efficacy in cancer therapy: H. L. Davis, T. E. Davis, Cancer Treat. Rep. 63, 809-815 (1979); of clinical pharmacokinetics: P. A. J. Speth et al., Clin. Pharmacokinet. 15, 15-31 (1988); of mechanism of cardiotoxicity: R. D. Olson, P. S. Mushlin, FASEB J. 4, 3076-3086 (1990); of mechanism of action: G. Aubel-Sadron, D. Londos-Gagliardi, Biochimie 66, 333-352 (1984); D. A. Gewirtz, Biochem. Pharmacol. 57, 727-741 (1999); of liposomal formulations: D. N. Waterhouse et al., Drug Saf. 24, 903-920 (2001).
 
Derivative Type: Hydrochloride
CAS Registry Number: 25316-40-9
Trademarks: Adriacin (Pfizer); Adriblastina (Pfizer); Adriamycin (Pfizer)
Molecular Formula: C27H29NO11.HCl
Molecular Weight: 579.98
Percent Composition: C 55.91%, H 5.21%, N 2.42%, O 30.34%, Cl 6.11%
Properties: Red crystalline solid, mp 205° (dec). [a]D20 +248±2° (c = 0.1 in methanol). Absorption max (methanol): 233, 253, 290, 477, 495, 530 nm (e 38150, 25500, 8400, 13050, 13000, 7200). Apparent partition coefficient (1-octanol/Tris buffer pH 7.0): 0.52. Readily sol in water, normal saline, methanol, acetonitrile, THF. Practically insol in acetone, benzene, chloroform, ethyl ether and petr ether. Aq solns are yellow-orange at acid pHs, orange-red at neutral pHs and violet-blue at pH >9. LD50 i.v. in mice: 21.1 mg/kg (Bertazzoli, 1970).
Melting point: mp 205° (dec)
Optical Rotation: [a]D20 +248±2° (c = 0.1 in methanol)
Log P: partition coefficient (1-octanol/Tris buffer pH 7.0): 0.52
Absorption maximum: Absorption max (methanol): 233, 253, 290, 477, 495, 530 nm (e 38150, 25500, 8400, 13050, 13000, 7200)
Toxicity data: LD50 i.v. in mice: 21.1 mg/kg (Bertazzoli, 1970)
 
Derivative Type: Liposomal complex of the citrate
CAS Registry Number: 111266-55-8 (doxorubicin citrate)
Trademarks: Myocet (Elan)
Literature References: Doxorubicin citrate encapsulated in liposome carriers composed of egg phosphatidylcholine and cholesterol. Review of development and clinical efficacy in breast cancer: G. Batist et al., Expert Opin. Pharmacother. 3, 1739-1751 (2002).
 
Derivative Type: Liposomal complex of the hydrochloride
Trademarks: Caelyx (Schering-Plough); Doxil (Ortho Biotech)
Literature References: Doxorubicin HCl encapsulated in liposome carriers composed of N-(carbonyl-methoxypolyethylene glycol 2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine sodium salt, fully hydrogenated soy phosphatidylcholine, and cholesterol. Review of pharmacology and toxicology: P. K. Working, A. D. Dayan, Hum. Exp. Toxicol. 15, 752-785 (1996); of clinical experience in solid and hematological malignancies and AIDS-related Kaposi's sarcoma: M. Sharpe et al., Drugs 62, 2089-2126 (2002); of pharmacokinetics: A. Gabizon et al., Clin. Pharmacokinet. 42, 419-436 (2003).
Properties: LD50 in mice: 38.3±7.2 mg/kg (Working, Dayan).
Toxicity data: LD50 in mice: 38.3±7.2 mg/kg (Working, Dayan)
 
CAUTION: Doxorubicin hydrochloride is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-8.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs; Anthracyclines; Topoisomerase II Inhibitor.