(19S)-8-[(dimethylamino)methyl]-19-(2H5)ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

• ChemBase ID: 178746
• Molecular Formular: C23H23N3O5
• Molecular Mass: 421.44582
• Monoisotopic Mass: 421.16377085
• SMILES: O1C(=O)[C@@](c2c(C1)c(=O)n1c(c2)c2c(C1)cc1c(n2)ccc(c1CN(C)C)O)(CC)O
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
• InChI: InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
• InChIKey: UCFGDBYHRUNTLO-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-8-[(dimethylamino)methyl]-19-(^2H₅)ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• IUPAC Traditional name: (19S)-8-[(dimethylamino)methyl]-19-(^2H₅)ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• Synonyms: (4S)-10-[(Dimethylamino)methyl]-4-(ethyl-d5)-4,9-dihydroxy-1H-pyrano[3’,4’,6-7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; NSC-609669-d5; SKF-104864A-d5; Hycamtin-d5; Topotecan-d5

Database IDs

• CAS Number: 1133355-98-2
• PubChem SID: 164234656
• PubChem CID: 25241308

CALCULATED PROPERTIES

• Acid pKa: 7.999574
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.4005558
• LogD (pH = 7.4): -0.9559677
• Log P: -0.35709506
• Molar Refractivity: 115.0161 cm^3
• Polarizability: 44.844234 Å^3
• Polar Surface Area: 103.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T542503

Labelled Topotecan (T542500). A DNA topoisomerase I inhibitor; semisynthetic analog of Camptothecin. Antineoplastic.

REFERENCES

• Beijnen, J.H., et al.: J. Pharm. Biomed. Anal., 8, 789 (1990)
• BeiKingsburg, W.D., et al.: J. Med. Chem., 34, 98 (1990)
• Rowinsky, E.K., et al.: J. Clin. Oncol., 10, 647 (1990)