R3655
Rubitecan
powder, ≥98% (HPLC)
Synonym(s):
9-nitrocamptothecin
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About This Item
Empirical Formula (Hill Notation):
C20H15N3O6
CAS Number:
Molecular Weight:
393.35
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Rubitecan,
SMILES string
CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5c(cccc5nc34)[N+]([O-])=O)C2=O
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
InChI key
VHXNKPBCCMUMSW-FQEVSTJZSA-N
biological source
synthetic (organic)
assay
≥98% (HPLC)
form
powder
mp
182-186 °C
solubility
DMSO: 1 mg/mL
storage temp.
room temp
Quality Level
Biochem/physiol Actions
Topoisomerase I inhibitor. Rubitecan induces protein- linked DNA single strand breaks, blocking DNA and RNA synthesis in dividing cells. This mode of action makes rubitecan a potential chemotherapeutic agent, and it has been used with some success against refractory pancreatic cancer.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Howard A Burris et al.
The oncologist, 10(3), 183-190 (2005-03-29)
Additional systemic treatments for locally advanced or metastatic pancreatic cancer are needed, as current treatment options produce only modest survival benefits. Rubitecan (Orathecin; Supergen Inc., Dublin, CA, http://www.supergen.com) is an orally active camptothecin derivative with demonstrated responses in patients with
Jun Chen et al.
International journal of pharmaceutics, 340(1-2), 29-33 (2007-04-21)
Pharmacokinetics and lactone/carboxylate equilibrium of 9-Nitrocamptothecin (9-NC) were compared after intravenous (i.v.) and intramuscular (i.m.) injection at a dose of 1.5mg/kg 9-NC solution. The concentrations of three different forms of 9-NC, namely lactone, carboxylate and total 9-NC, were measured by
Zhisong Cao et al.
Anti-cancer agents in medicinal chemistry, 12(7), 818-828 (2012-05-16)
All chemotherapeutic agents currently in use have a narrow window of therapeutic index of 1 to 1.2. Camptothecin ester compounds are reported to have a wider therapeutic index when being used to treat human xenografts in nude mice. As a
Jieming Gao et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 34(2-3), 85-93 (2008-04-18)
9-Nitro-20(S)-camptothecin (9-NC) has achieved remarkable curative effect in anticancer research. However, the clinical application of 9-NC is largely hampered by its poor solubility and stability. In this paper, novel amphiphilic block copolymers derived from d,l-lactide, trimethylene carbonate, and methylated poly(ethylene
Li-Jun Zhang et al.
Pulmonary pharmacology & therapeutics, 21(1), 239-246 (2007-06-15)
This study was designed to investigate in vitro release, in vivo tissue distribution and the damage to the lungs of 9-nitrocamptothecin (9-NC) liposomes. In vitro release of 9-NC from liposomes was carried out in phosphate buffer saline solution (PBS) pH
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