disodium (2S)-2-[12-ethyl-8-(hydroxymethyl)-2-oxido-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate

• ChemBase ID: 177798
• Molecular Formular: C22H20N2Na2O6
• Molecular Mass: 454.38354
• Monoisotopic Mass: 454.11167493
• SMILES: c1(ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c(c(c2)C(C(=O)[O-])(CC)O)CO)CC)[O-].[Na+].[Na+]
• Canonical SMILES: CCC(c1cc2c3nc4ccc(cc4c(c3Cn2c(=O)c1CO)CC)[O-])(C(=O)[O-])O.[Na+].[Na+]
• InChI: InChI=1S/C22H22N2O6.2Na/c1-3-12-13-7-11(26)5-6-17(13)23-19-14(12)9-24-18(19)8-16(15(10-25)20(24)27)22(30,4-2)21(28)29;;/h5-8,25-26,30H,3-4,9-10H2,1-2H3,(H,28,29);;/q;2*+1/p-2/t22-;;/m0../s1
• InChIKey: OPIACBXCNWXXGI-IKXQUJFKSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S)-2-[12-ethyl-8-(hydroxymethyl)-2-oxido-9-oxo-9H,11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate
• IUPAC Traditional name: disodium (2S)-2-[12-ethyl-8-(hydroxymethyl)-2-oxido-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate
• Synonyms: (αS)-α,12-Diethyl-9,11-dihydro-α,2-dihydroxy-8-(hydroxymethyl)-9-oxo-9-indolizino[1,2-b]quinoline-7-acetic Acid Disodium Salt; SN 38 Acid Sodium Salt; SN-38 Carboxylate Disodium Salt

Database IDs

• PubChem SID: 164233708
• PubChem CID: 57347736

CALCULATED PROPERTIES

• Acid pKa: 3.2911637
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.8660746
• LogD (pH = 7.4): -2.1891825
• Log P: 0.2749474
• Molar Refractivity: 130.9952 cm^3
• Polarizability: 42.13392 Å^3
• Polar Surface Area: 136.85 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Yellow Solid
• Melting Point: >220°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S589960

The active metabolite of Irinotecan (carboxylate form). SN-38 lactone and carboxylate may be considered pharmacokinetically distinct agents.

REFERENCES

• Billecke, S., et al.: Drug Metab. Dispos., 28, 1335 (2000)
• Teiber, J., et al.: Biochem. Pharmacol., 66, 887 (2000)
• Ashley, G., et al.: J. Antibiot., 57, 224 (2000)