ChemicalBook CAS DataBase List 86639-52-3

86639-52-3

Name	7-Ethyl-10-hydroxycamptothecin
CAS	86639-52-3
EINECS(EC#)	643-093-9
Molecular Formula	C22H20N2O5
MDL Number	MFCD06762720
Molecular Weight	392.4
MOL File	86639-52-3.mol

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

Chemical Properties

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
Optical Rotation	Consistent with structure
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

Symbol(GHS)	GHS07,GHS08
Signal word	Danger
Hazard statements	H302-H360D-H372
Precautionary statements	P202-P260-P264-P270-P301+P312-P308+P313
Hazard Codes	T
Risk Statements	25 less more
Safety Statements	45 less more
RIDADR	2811
WGK Germany	3
RTECS	UQ0491000
HazardClass	6.1
PackingGroup	Ⅲ
HS Code	29399900
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 4 Oral Repr. 1B STOT RE 1

Raw materials And Preparation Products

Hazard Information

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

Spectrum Detail

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