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Simmitecan

CAT: 0013-GTR19208245-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19208245-01Size:1 mg
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Description
Simmitecan
CAS Number
1247847-78-4
Product Name Alternative
EXP 3892, EXP-3892, Topo I, Simmitecan Hydrochloride
Field of Research
Metabolism Research, Molecular Biology
Purity
98.20% (May vary between batches)
Solubility
H2O:25 mg/mL (39.36 mM) ; DMSO:100 mg/mL (157.44 mM)
Smiles
O=C1N2C (C=3C (C2) =CC=4C (N3) =CC=C (OC (=O) N5CCC (CC5) N6CCCCC6) C4CC=C) =CC7=C1COC (=O) [C@@]7 (CC) O.Cl
Molecular Formula
C34H39ClN4O6
Molecular Weight
635.15
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Simmitecan

Simmitecan Hydrochloride is the hydrochloride salt form of simmitecan, an ester prodrug of chimmitecan, a 9-alkyl substituted camptothecin derivative with potential antineoplastc activity. Upon intravenous administration, simmitecan is hydrolyzed by carboxylesterase and the activated form, chimmitecan, is produced. Chimmitecan inhibits topoisomerase I, stabilizes covalent topoisomerase I-DNA complexes, and inhibits the religation of topoisomerase I-mediated single-strand DNA breaks. Futhermore, the covalent topoisomerase I-DNA complexes interfere and block the DNA replication machinery, resulting in the production of potentially lethal double-strand DNA breaks. This leads to an inhibition of DNA replication and the induction of apoptosis. The modification at position 9 yields improved cytotoxicity compared to some other camptothecin analogues.

CAS Number1247847-78-4
PubChem CID71587955
IUPAC Name[(19S)-19-ethyl-19-hydroxy-14,18-dioxo-8-prop-2-enyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate;hydrochloride
Molecular FormulaC34H39ClN4O6
Molecular Weight635.1
Topological Polar Surface Area113
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count6
Heavy Atom Count45
Formal Charge0
Complexity1250
SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CC=C)OC(=O)N6CCC(CC6)N7CCCCC7)N=C4C3=C2)O.Cl
InChI
InChI=1S/C34H38N4O6.ClH/c1-3-8-23-24-17-21-19-38-28(18-26-25(31(38)39)20-43-32(40)34(26,42)4-2)30(21)35-27(24)9-10-29(23)44-33(41)37-15-11-22(12-16-37)36-13-6-5-7-14-36;/h3,9-10,17-18,22,42H,1,4-8,11-16,19-20H2,2H3;1H/t34-;/m0./s1
InChIKey
UWNITDCAZZJJFF-GXUZKUJRSA-N
Chemical Structure
2D Structure
2D structure of Simmitecan
CAS: 1247847-78-4
CID: 71587955
Formula: C34H39ClN4O6
MW: 635.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight635.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count6
Exact Mass634.2558127
Monoisotopic Mass634.2558127
Topological Polar Surface Area113 Ų
Heavy Atom Count45
Formal Charge0
Complexity1250
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

Alternative Products

CatalogName
XZB84778Simmitecan
HY-107133-01Simmitecan (hydrochloride)
BUP02221-01Simmitecan hydrochloride
T202854-01Simmitecan free base

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