| Identification | More | [Name]
Rubitecan | [CAS]
91421-42-0 | [Synonyms]
(4s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione
9-NITRO-20(S)-CAMPTOTHECIN
9-NITROCAMPTOTHECIN
9-NITRO-CPT
CAMPTOTHECIN, 9-NITRO-20(S)-
orathecin
RUBETICAN
RUBITECAN
Rubitecane
(4S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[346,7]indolizinol[1,2-b]quinoline-3, 14(4H,-12H)-dione
9-NC
Oratheci
9-Nitrocamptothecin | [Molecular Formula]
C20H15N3O6 | [MDL Number]
MFCD06656294 | [Molecular Weight]
393.35 | [MOL File]
91421-42-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Amorphous Powder | [Melting point ]
182-186°C | [alpha ]
D23 +27° (c = 0.2 in CH3OH-CHCl3, 1:4) | [Boiling point ]
816.3±65.0 °C(Predicted) | [density ]
1.63 | [Fp ]
106℃ | [storage temp. ]
Room temp | [solubility ]
DMSO, Chloroform, Methanol | [form ]
Solid | [pka]
11.16±0.20(Predicted) | [color ]
Yellow | [biological source]
synthetic (organic) | [Usage]
Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin. Antineoplastic | [Merck ]
14,8288 | [InChI]
InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1 | [InChIKey]
VHXNKPBCCMUMSW-FQEVSTJZSA-N | [SMILES]
N1C2C(=C([N+]([O-])=O)C=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O | [CAS DataBase Reference]
91421-42-0(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Description]
Rubitecan, marketed by Supergen as Orathecin, is a promising oral treatment for solid melanoma, prostate, breast, ovarian, and other cancers, as well as leukemia. It is a derivative of camptothecin, a topoisomerase inhibitor known from Chinese Traditional Medicine. It selectively targets the critical S-stage of cellular reproduction – particularly in acidic environments, as in many cancer cells – relaxing DNA supercoiling and generating lethal breaks in the DNA. Due to insolubility, its biological delivery mechanism is not yet effective, and it has not been approved for clinical use.
| [Reference]
https://www.sciencedirect.com/topics/medicine-and-dentistry/rubitecan
https://en.wikipedia.org/wiki/Rubitecan
https://en.wikipedia.org/wiki/Topoisomerase_inhibitor
https://en.wikipedia.org/wiki/Camptothecin#cite_note-Y.Pommier_2003-14
https://www.ncbi.nlm.nih.gov/pubmed/1995300
|
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Amorphous Powder | [Uses]
Semisynthetic camptothecin which inhibits DNA topoisomerase I. Prodrug of 9-aminocamptothecin. Antineoplastic | [Definition]
ChEBI: A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin. | [References]
[1] E RUBIN. Identification of a mutant human topoisomerase I with intact catalytic activity and resistance to 9-nitro-camptothecin.[J]. The Journal of Biological Chemistry, 1994, 269 4: 2433-2439.
[2] H R HINZ. Pharmacokinetics of the in vivo and in vitro conversion of 9-nitro-20(S)-camptothecin to 9-amino-20(S)-camptothecin in humans, dogs, and mice.[J]. Cancer research, 1994, 54 12: 3096-3100.
[3] R. BERNACKI. In Vitro Antitumor Activity of 9‐Nitro‐Camptothecin as a Single Agent and in Combination with other Antitumor Drugs[J]. Annals of the New York Academy of Sciences, 2000, 922 1. DOI: 10.1111/j.1749-6632.2000.tb07046.x
[4] P. PANTAZIS. 9-nitro-camptothecin delays growth of U-937 leukemia tumors in nude mice and is cytotoxic or cytostatic for human myelomonocytic leukemia lines in vitro[J]. European Journal of Haematology, 1993, 50 2: 81-89. DOI: 10.1111/j.1600-0609.1993.tb00146.x |
|
|