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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR3945V
SLBC2842V
088K1461

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J Chen et al.
Drug development and industrial pharmacy, 32(6), 719-726 (2006-08-04)
9-Nitrocamptothecin (9-NC), a newly developed camptothecin derivative, had poor solubility in any pharmaceutically acceptable solvents. One way of improving the solubility is to formulate the drug into liposomes. However, 9-NC has low affinity to lipid membranes resulting in a very
Simin Dadashzadeh et al.
Anti-cancer drugs, 19(8), 805-811 (2008-08-12)
The objective of this study was to evaluate the cytotoxicity and pharmacokinetics of total and lactone forms of 9-nitrocamptothecin (9-NC), an effective antineoplastic drug, after intravenous injection of drug incorporated into poly (DL-lactic-glycolic acid) nanoparticles (NPs). Drug-loaded NPs (9-NC.NP) were
George R Simon et al.
Molecular cancer therapeutics, 5(8), 2130-2137 (2006-08-25)
Resistance to topoisomerase (topo) I inhibitors has been related to down-regulation of nuclear target enzyme, whereas sensitization to topo II inhibitors may result from induction of topo II by topo I inhibitors. Here, we evaluated a sequence-specific administration of a
William C Zamboni et al.
Cancer chemotherapy and pharmacology, 62(3), 417-426 (2007-10-25)
We evaluated the antitumor activity of two different schedules of docetaxel and 9-nitrocamptothecin (9NC) in mice bearing human SKOV-3 ovarian carcinoma xenografts and evaluated the plasma, tissue, and tumor disposition of each agent alone and in combination. The following treatment
Venita Gresham Watson et al.
PloS one, 6(5), e17561-e17561 (2011-05-17)
To date, the Centre d'Etude Polymorphism Humain (CEPH) cell line model has only been used as a pharmacogenomic tool to evaluate which genes are responsible for the disparity in response to a single drug. The purpose of this study was
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