sodium (2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-[4-(piperidin-1-yl)piperidine-1-carbonyloxy]-9H,11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate

• ChemBase ID: 171745
• Molecular Formular: C33H39N4NaO7
• Molecular Mass: 626.67513
• Monoisotopic Mass: 626.27164389
• SMILES: C1CCCN(C1)C1CCN(CC1)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c(c(c2)C(C(=O)[O-])(O)CC)CO)CC.[Na+]
• Canonical SMILES: CCC(c1cc2c3nc4ccc(cc4c(c3Cn2c(=O)c1CO)CC)OC(=O)N1CCC(CC1)N1CCCCC1)(C(=O)[O-])O.[Na+]
• InChI: InChI=1S/C33H40N4O7.Na/c1-3-22-23-16-21(44-32(42)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26(25(19-38)30(37)39)33(43,4-2)31(40)41;/h8-9,16-17,20,38,43H,3-7,10-15,18-19H2,1-2H3,(H,40,41);/q;+1/p-1/t33-;/m0./s1
• InChIKey: DKZQEGIYKWOXLC-WAQYZQTGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-[4-(piperidin-1-yl)piperidine-1-carbonyloxy]-9H,11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate
• IUPAC Traditional name: sodium cpt-11 carboxylate form
• Synonyms: (αS)-2-[([1,4'-Bipiperidin]-1'-ylcarbonyl)oxy]-α,12-diethyl-9,11-dihydro-α-hydroxy-8-(hydroxymethyl)-9-oxo-indolizino[1,2-b]quinoline-7-acetic Acid Sodium Salt; CPT 11 Carboxylic Acid Sodium Salt; Irinotecan Carboxylate Sodium Salt

Database IDs

• PubChem SID: 164227655
• PubChem CID: 46781988

CALCULATED PROPERTIES

• Acid pKa: 2.9976683
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.6287106
• LogD (pH = 7.4): -0.6219612
• Log P: -0.6203045
• Molar Refractivity: 175.6596 cm^3
• Polarizability: 64.00215 Å^3
• Polar Surface Area: 146.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 177-183°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I767510

Carboxylate form of Irinotecan, a DNA topoisomerase inhibitor.

REFERENCES

• Kunimoto, T., et al.: Cancer Res., 47, 5944 (1987)
• Shimada, Y., et al.: J. Clin. Oncol., 11, 909 (1987)
• Chen, A., et al.: Annu. Rev. Pharmacol. Toxicol., 34, 191 (1987)