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R3655

Sigma-Aldrich

Rubitecan

powder, ≥98% (HPLC)

Synonym(s):

9-nitrocamptothecin

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About This Item

Empirical Formula (Hill Notation):
C20H15N3O6
CAS Number:
91421-42-0
Molecular Weight:
393.35
MDL number:
MFCD06656294
UNSPSC Code:
12352204
PubChem Substance ID:
329824025
NACRES:
NA.77

product name

Rubitecan,

biological source

synthetic (organic)

Assay

≥98% (HPLC)

form

powder

mp

182-186 °C

solubility

DMSO: 1 mg/mL

storage temp.

room temp

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Xue Han et al.
International journal of pharmaceutics, 372(1-2), 125-131 (2009-01-27)
In this study, folate-conjugated polymer micelles were synthesized by mixing folate-poly(ethylene glycol)-distearoylphosphatidylethanolamine (FA-PEG-DSPE) and methoxy-poly(ethylene glycol)-distearoylphosphatidylethanolamine (MPEG-DSPE) to encapsulate anticancer agent 9-nitro-camptothecin (9-NC). Formulations were characterized by critical micellization concentration (CMC) values of copolymers, micelle particle size, zeta-potential, encapsulation efficiency
K Derakhshandeh et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 66(1), 34-41 (2006-10-31)
This study was aimed at developing a polymeric drug delivery system for a new and potent antitumor drug, 9-nitrocamptothecin (9-NC), intended for both intravenous administration and improving the therapeutic index of the drug. To achieve these goals, 9-NC loaded poly(DL-lactide-co-glycolide)
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
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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