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Safety Information

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)

Quality Level

100

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR3945V
SLBC2842V
088K1461

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Shunzhen Zheng et al.
PloS one, 6(6), e21064-e21064 (2011-06-23)
Hepatocellular carcinoma (HCC) is the third most common cause of cancer related mortality worldwide. 9-Nitrocamptothecin (9NC) is a potent topoisomerase-I inhibitor with strong anticancer effect. To increase the solubility and stability, we synthesized a novel 9NC loaded liposomes (9NC-LP) via
Alfonso Quintas-Cardama et al.
Cancer, 107(7), 1525-1529 (2006-09-07)
Topoisomerase I inhibitors, like topotecan, have activity in myelodysplastic syndrome (MDS) and chronic myelomonocytic leukemia (CMML). 9-Nitro-camptothecin (9-NC) is a new oral topoisomerase inhibitor with a good safety profile. The aims of the current study were to evaluate the activity
Katayoun Derakhshandeh et al.
International journal of nanomedicine, 5, 463-471 (2010-10-20)
The purpose in this study was to investigate poly(ethylene glycol)-modified poly (d,l-lactide-co-glycolide) nanoparticles (PLGA-PEG-NPs) loading 9-nitrocamptothecin (9-NC) as a potent anticancer drug. 9-NC is an analog of the natural plant alkaloid camptothecin that has shown high antitumor activity and is
Ye Jiang et al.
International journal of pharmaceutics, 397(1-2), 116-121 (2010-07-20)
The effect of a series of cyclodextrins (CDs), especially hydroxypropyl-beta-cyclodextrin (HP-beta-CD), on aqueous solubility and chemical stability of 9-nitro-camptothecin (9-NC), was investigated with an aim of preparing a stable and effective parenteral formulation. The 9-NC/HP-beta-CD complex was obtained in solid
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
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