10,11-methylenedioxycamptothecin

Product Name: 10,11-methylenedioxycamptothecin
CAS No.: 135415-73-5
Chemical Name: 10,11-methylenedioxycamptothecin
Synonyms: CAS:135415-73-5;RPFYDENHBPRCTN-NRFANRHFSA-N;10,11-methylenedioxycamptothecin;(20RS)-10,11-Methylenedioxycamptothecin;10,11-(Methylenedioxy)-20(S)-camptothecin;10,11-(Methylenedioxy)camptothecin(FL118);(4S)-4-Ethyl-4-hydroxy-8,9-methylenedioxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(S)-7-Ethyl-7-hydroxy-7H-[1,3]dioxolo[4,5-g]pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-8,11(10H,13H)-dione;(S)-7-Ethyl-7-hydroxy-7H-[1,3]dioxolo[4,5-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-8,11(10H,13H)-dione;(4S)-4-Hydroxy-4-ethyl-8,9-(methylenedioxy)-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
CBNumber: CB21318999
Molecular Formula: C21H16N2O6
Formula Weight: 392.36
MOL File: 135415-73-5.mol

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10,11-methylenedioxycamptothecin Property

Boiling point:: 812.1±65.0 °C(Predicted)
Density: 1?+-.0.1 g/cm3(Predicted)
pka: 11.18±0.20(Predicted)
form: Solid
color: Light brown to brown
InChI: InChI=1S/C21H16N2O6/c1-2-21(26)13-5-15-18-11(7-23(15)19(24)12(13)8-27-20(21)25)3-10-4-16-17(29-9-28-16)6-14(10)22-18/h3-6,26H,2,7-9H2,1H3/t21-/m0/s1
InChIKey: RPFYDENHBPRCTN-NRFANRHFSA-N
SMILES: N1C2C(=CC3OCOC=3C=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O

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Hazard and Precautionary Statements (GHS)

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10,11-methylenedioxycamptothecin Chemical Properties,Usage,Production

Uses

FL118 (10,11-(Methylenedioxy)-20(S)-camptothecin), a Camptothecin.html" class="link-product" target="_blank">Camptothecin (HY-16560) analogue, is a potent and orally active survivin inhibitor. FL118 binds to oncoprotein DDX5 (p68) to dephosphorylates and degrades DDX5. FL118 can be used for the research of cancer[1][2].

in vivo

FL118 (5 and 10 mg/kg; p.o. once a week for 20 days) inhibits antitumor activity^[1].
FL118 (0-1.5 mg/kg, i.p. once every other day for five times) effectively eliminates human colon and head-and-neck tumors that acquire irinotecan or topotecan resistance^[4].
FL118 (1.5 mg/kg, i.v. once) exhibits favorable pharmacokinetics profiles^[4].
Pharmacokinetic Parameters of FL118 in female SCID mice^[4].

Sample	FaDu	SW620	Plasma
T_1/2 (hr)	6.852	12.75	1.788
T_max (hr)	0.167	0.167	0.167
C_max (ng/g, mL)	115	158	43
AUC (hr*ng/g)	413	842	82
AUC_∞ (hr*ng/g)	448	897	104
AUC% Extrap (%)	7.74	6.17	21.7
Vz (g/kg) (ml/kg)	33052	30742	36849
Cl (g/hr/kg) (ml/hr/kg)	3343	1671	14287

Animal Model:	Fmale BALB/c nude mice^[1]
Dosage:	5 and 10 mg/kg
Administration:	Oral gavage; 5 mg/kg for once a week; 10 mg/kg for once a week; for 20 days
Result:	Showed better antitumor activity than topotecan and dose-dependenly suppressed the growth of ES-2 tumors by upregulating the expression level of CYGB.

Animal Model:	SCID (severe combined immunodeficiency) mice bearing human SW620 (colon) and FaDu (head-and-neck) xenograft tumors (ten-week-old, female, 20-25 g, 5 mice per cage)^[4]
Dosage:	0, 0.75, 1, 1.5 mg/kg
Administration:	IP, once every other day for five times as one cycle (If tumors relapse, mice were treated with FL118 for second or third cycles)
Result:	Eliminated human xenograft tumors that acquired irinotecan or topotecan resistance, and was also effective after multiple cycles of treatment without the generation of FL118 resistance.

Animal Model:	SCID (severe combined immunodeficiency) mice bearing human SW620 (colon) and FaDu SCID mice bearing human SW620 (colon) and FaDu (head-and-neck) xenograft tumors (ten-week-old, female, 20-25 g, 5 mice per cage)^[4]
Dosage:	1.5 mg/kg
Administration:	IV, once
Result:	Exhibited favorable pharmacokinetics profiles.

References

[1] Zhao H, et al. FL118, a novel anticancer compound, inhibits proliferation and migration of ovarian cancer cells via up-regulation of cytoglobin in vivo and in vitro[J]. Translational Cancer Research, 2017, 6(6):1294-1304.
[2] Ling X, et al. FL118, acting as a 'molecular glue degrader', binds to dephosphorylates and degrades the oncoprotein DDX5 (p68) to control c-Myc, survivin and mutant Kras against colorectal and pancreatic cancer with high efficacy. Clin Transl Med. 2022 May;12(5):e881. DOI:10.1002/ctm2.881
[3] Wu G, et al. Synthesis of novel 10,11-methylenedioxy-camptothecin glycoside derivatives and investigation of their anti-tumor effects in vivo. RSC Adv. 2019 Apr 9;9(20):11142-11150. DOI:10.1039/c9ra00315k
[4] Ling X, et, al. FL118, a novel camptothecin analogue, overcomes irinotecan and topotecan resistance in human tumor xenograft models. Am J Transl Res. 2015 Oct 15;7(10):1765-81. PMID:26692923

10,11-methylenedioxycamptothecin Preparation Products And Raw materials

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10,11-methylenedioxycamptothecin Suppliers

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135415-73-5, 10,11-methylenedioxycamptothecinRelated Search:

10,11-methylenedioxycamptothecin

(20RS)-10,11-Methylenedioxycamptothecin

(4S)-4-Ethyl-4-hydroxy-8,9-methylenedioxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

(4S)-4-Ethyl-4β-hydroxy-8,9-(methylenedioxy)-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

(4S)-4-Hydroxy-4-ethyl-8,9-(methylenedioxy)-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

(4S)-4α-Ethyl-4-hydroxy-4,12-dihydro-8,9-methylenedioxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

(4S)-4α-Ethyl-4-hydroxy-8,9-(methylenedioxy)-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

10,11-(Methylenedioxy)-20(S)-camptothecin

10H-1,3-Dioxolo(4,5-G)pyrano(3',4':6,7)indolizino(1,2-B)quinoline-8,11(7H,13H)-dione, 7-ethyl-7-hydroxy-, (7S)-

RPFYDENHBPRCTN-NRFANRHFSA-N

10,11-(Methylenedioxy)camptothecin(FL118)

(S)-7-Ethyl-7-hydroxy-7H-[1,3]dioxolo[4,5-g]pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-8,11(10H,13H)-dione

(S)-7-Ethyl-7-hydroxy-7H-[1,3]dioxolo[4,5-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-8,11(10H,13H)-dione

CAS:135415-73-5

135415-73-5