| Identification | More | [Name]
7-Ethyl-10-hydroxycamptothecin | [CAS]
86639-52-3 | [Synonyms]
4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
7-ETHYL-10-HYDROXYCAMPTOTHECIN
7-ETHYL-10-HYDROXYCAMPTOTHECINE
7-ETHYL-10-HYDROXY-CPT
CAMPTOTHECIN, 7-ETHYL-10-HYDROXY
SN38
10-dihydroxy-
4’:6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione,4,7-diethyl-1h-pyrano(3
7-ethyl-10-hydroxy-captotheci
7-Ethyl-10-hydroxycamptothecin(SN-38)
SN 38 Lactone
(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
7-ETHYL-10-HYDRO(20)S-CAMPTOTHECIN
7-Ethyl-10-Hydroxy Campothecin
7-Ethyl-10-hydroxycamptothecin (TECANS)
7-ethyl-10-hydrol-Camptothecin
7-ETHYL-10-HYDROXYCAMPTTHECIN(SN38)
7-10-hydroxycamptothecin
(4S)-4,9-Dihydroxy-4,11-diethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
(4S)-4,9-Dihydroxy-4α,11-diethyl-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione | [EINECS(EC#)]
643-093-9 | [Molecular Formula]
C22H20N2O5 | [MDL Number]
MFCD06762720 | [Molecular Weight]
392.4 | [MOL File]
86639-52-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Light-Yellow Solid | [Melting point ]
217 °C | [Boiling point ]
810.3±65.0 °C(Predicted) | [density ]
1.51±0.1 g/cm3(Predicted) | [refractive index ]
21.5 ° (C=0.2, THF) | [storage temp. ]
−20°C | [solubility ]
DMSO: soluble1mg/mL | [form ]
powder | [pka]
9.13±0.40(Predicted) | [color ]
Off-white | [Usage]
A metabolite of Irinotecan, a DNA topoisomerase inhibitor | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. | [InChI]
InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1 | [InChIKey]
FJHBVJOVLFPMQE-QFIPXVFZSA-N | [SMILES]
N1C2C(=CC(O)=CC=2)C(CC)=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O | [CAS DataBase Reference]
86639-52-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
2811 | [WGK Germany ]
3 | [RTECS ]
UQ0491000 | [HazardClass ]
6.1 | [PackingGroup ]
Ⅲ | [HS Code ]
29399900 |
| Hazard Information | Back Directory | [Description]
SN-38 (86639-52-3) is the active metabolite of CPT-11 that inhibits DNA topoisomerase I (IC50 values are 0.74 and 1.9 μM in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC50 values are 0.077 and 1.3 μM respectively) but does not affect protein synthesis. SN-38 displays potent antitumor activity against a range of human tumor cell lines (IC50 values are 3.3, 13, 19 and 22 nM for HCT-116, BEL-7402, HL60 and HeLa cells respectively). | [Chemical Properties]
Light-Yellow Solid | [Uses]
A metabolite of Irinotecan, a DNA topoisomerase inhibitor | [Definition]
ChEBI: A member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substitu
nts at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself. | [Biological Activity]
Active metabolite of CPT-11 that inhibits DNA topoisomerase I (IC 50 values are 0.74 and 1.9 μ M in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC 50 values are 0.077 and 1.3 μ M respectively) but does not affect protein synthesis. Displays potent antitumor activity against a range of human tumor cell lines (IC 50 values are 3.3, 13, 19 and 22 nM for HCT-116, BEL-7402, HL60 and HELA cells respectively). | [Cytotoxicity]
7-Ethyl-10-hydroxycamptothecin has been found to be 200–2000 times more cytotoxic than CPT-11, but has not been used as an anticancer drug due to its poor solubility in pharmaceutically acceptable solvents and low affinity to lipid membranes. SN-38 also undergoes a reversible conversion to an inactive open lactone ring structure at physiological pH. | [storage]
Store at +4°C | [structure and hydrogen bonding]
7-Ethyl-10-hydroxycamptothecin belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). | [References]
1) Koizumi et al. (2006), Novel SN-38-incorporating polymeric micelles, NKK012, eradicate vascular endothelial growth factor-secreting bulky tumors; Cancer Res., 66 10048
2) Gao et al. (2005), Synthesis and antitumor activity of the hexacyclic camptothecin derivatives; Bioorg. Med. Chem. Lett., 15 3233
3) Kawato et al. (1991), Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11; Cancer Res., 51 4187 |
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