Cat. No.: HY-12486

FL118

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

2 Cited Publications

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Based on 2 publication(s) in Google Scholar

FL118 (10,11-(Methylenedioxy)-20(S)-camptothecin), a 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.

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Pureté: 99.22%
CAS No.: 135415-73-5
Formule: C₂₁H₁₆N₂O₆
Masse moléculaire:392.36

Stockage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

FL118 Chemical Structure

CAS No.: 135415-73-5

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Activité biologique
- Description
- Cellular Effect
- In Vitro
- In Vivo
- Essai clinique
Chemical Information
Publications (2)
Solvant et solubilité
- In Vitro
Pureté et documentation
Références
Help & FAQs
Classifications
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Activité biologique

Description

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Cellular Effect

Cell Line	Type	Value	Description	References
2008	IC₅₀	37.28 nM Compound: 4; FL118	Antiproliferative activity against human 2008 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human 2008 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
A549	EC₅₀	0.86 nM Compound: 11; FL118	Antiproliferative activity against human A549 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay Antiproliferative activity against human A549 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay	[PMID: 38421819]
A549	IC₅₀	0.009 μM Compound: 3; FL118	Antiproliferative activity against human A549 cells assessed as reduction in cell viability by MTT assay Antiproliferative activity against human A549 cells assessed as reduction in cell viability by MTT assay	[PMID: 38092421]
A549	IC₅₀	0.083 μM Compound: 24; FL118, Table 2, cpd 7	Cytotoxicity against human A549 cells incubated for 48 hrs by by SpectraMax M5 microplate reader analysis Cytotoxicity against human A549 cells incubated for 48 hrs by by SpectraMax M5 microplate reader analysis	[PMID: 34175539]
A549	IC₅₀	43 ng/mL Compound: 11; FL118	Cytotoxicity against human A549 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Cytotoxicity against human A549 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 38421819]
A549	IC₅₀	50.7 nM Compound: FL118	Growth inhibition of human A549 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis Growth inhibition of human A549 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis	[PMID: 38100041]
Bel-7402	IC₅₀	21.75 nM Compound: 4; FL118	Antiproliferative activity against human Bel-7402 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human Bel-7402 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
EKVX	IC₅₀	0.006 μM Compound: 3; FL118	Antiproliferative activity against human EKVX cells assessed as cell growth inhibition incubated for 72 hrs by MTT assay Antiproliferative activity against human EKVX cells assessed as cell growth inhibition incubated for 72 hrs by MTT assay	[PMID: 38092421]
H69AR	IC₅₀	6.29 nM Compound: 4; FL118	Antiproliferative activity against human NCI-H69AR cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human NCI-H69AR cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
HCT-116	EC₅₀	0.36 nM Compound: 11; FL118	Antiproliferative activity against human HCT-116 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay Antiproliferative activity against human HCT-116 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay	[PMID: 38421819]
HCT-116	IC₅₀	0.005 μM Compound: 3; FL118	Antiproliferative activity against human HCT-116 cells assessed as reduction in cell proliferation measured after 72 hrs by MTT assay Antiproliferative activity against human HCT-116 cells assessed as reduction in cell proliferation measured after 72 hrs by MTT assay	[PMID: 38092421]
HCT-116	IC₅₀	23.5 nM Compound: FL118	Growth inhibition of human HCT-116 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis Growth inhibition of human HCT-116 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis	[PMID: 38100041]
HCT-116	IC₅₀	50 ng/mL Compound: 11; FL118	Cytotoxicity against human HCT-116 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Cytotoxicity against human HCT-116 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 38421819]
HCT-8	IC₅₀	0.005 μM Compound: 3; FL118	Antiproliferative activity against human HCT-8 cells assessed as inhibition of cell growth Antiproliferative activity against human HCT-8 cells assessed as inhibition of cell growth	[PMID: 38092421]
HeLa	IC₅₀	32.4 nM Compound: FL118	Growth inhibition of human HeLa cells incubated for 48 hrs by MTT reagent based ELISA reader analysis Growth inhibition of human HeLa cells incubated for 48 hrs by MTT reagent based ELISA reader analysis	[PMID: 38100041]
HeLa	IC₅₀	40 ng/mL Compound: 11; FL118	Cytotoxicity against human HeLa cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Cytotoxicity against human HeLa cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 38421819]
HeLa	IC₅₀	9.6 nM Compound: Methylenedioxy Camptothecin (table 1)	Concentration required to inhibit growth of human cervical HeLa carcinoma cell line Concentration required to inhibit growth of human cervical HeLa carcinoma cell line	[PMID: 15454230]
HepG2	IC₅₀	10.64 nM Compound: 4; FL118	Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human HepG2 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
HepG2	IC₅₀	104 ng/mL Compound: 11; FL118	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 38421819]
HepG2	IC₅₀	39.5 nM Compound: FL118	Growth inhibition of human HepG2 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis Growth inhibition of human HepG2 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis	[PMID: 38100041]
HL-60	IC₅₀	0.027 μM Compound: 5z	Inhibition of Topoisomerase I by cleavage complex formation in human HL-60 cells Inhibition of Topoisomerase I by cleavage complex formation in human HL-60 cells	[PMID: 8410981]
MCF7	IC₅₀	32.2 nM Compound: FL118	Growth inhibition of human MCF7 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis Growth inhibition of human MCF7 cells incubated for 48 hrs by MTT reagent based ELISA reader analysis	[PMID: 38100041]
MCF7	IC₅₀	63.26 nM Compound: 4; FL118	Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
NCI-H446	IC₅₀	18.54 nM Compound: 4; FL118	Antiproliferative activity against Irinotecan-resistant human NCI-H446 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against Irinotecan-resistant human NCI-H446 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
NCI-H446	IC₅₀	6.61 nM Compound: 4; FL118	Antiproliferative activity against etoposide/cisplatin combination-resistant human NCI-H446 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against etoposide/cisplatin combination-resistant human NCI-H446 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
NCI-H446	IC₅₀	8.87 nM Compound: 4; FL118	Antiproliferative activity against human NCI-H446 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human NCI-H446 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
NCI-H460	IC₅₀	0.003 μM Compound: 3; FL118	Antiproliferative activity against human NCI-H460 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay Antiproliferative activity against human NCI-H460 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay	[PMID: 38092421]
NCI-H69	IC₅₀	15.81 nM Compound: 4; FL118	Antiproliferative activity against human NCI-H69 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human NCI-H69 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
NSCLC	EC₅₀	1 nM Compound: 24; FL118, Table 2, cpd 7	Cytotoxicity against human NSCLC cells Cytotoxicity against human NSCLC cells	[PMID: 34175539]
PC-3	IC₅₀	8.1 nM Compound: Methylenedioxy Camptothecin (table 1)	Concentration required to inhibit growth of human prostate PC-3 carcinoma cell line Concentration required to inhibit growth of human prostate PC-3 carcinoma cell line	[PMID: 15454230]
SH-SY5Y	IC₅₀	24.19 nM Compound: 4; FL118	Antiproliferative activity against human SH-SY5Y cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human SH-SY5Y cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
SW-620	IC₅₀	0.009 μM Compound: 3; FL118	Antiproliferative activity against human SW620 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Antiproliferative activity against human SW620 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 38092421]
SW-620	IC₅₀	0.93 nM Compound: 4; FL118	Antiproliferative activity against human SW-620 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human SW-620 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]
U-87MG ATCC	IC₅₀	108.57 nM Compound: 4; FL118	Antiproliferative activity against human U87 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay Antiproliferative activity against human U87 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay	[PMID: 35932565]

In Vitro

FL118 (0-200 nM; 24, 48 and 72 h ) inhibits the cell proliferation of ES-2 and SK-O-V₃ cells^[1].
FL118 (0-100 nM; 0 and 24 h) inhibits the migration of ES-2 and SK-O-V₃ cells^[1].
FL118 (0-100 nM; 48 h) affects the expression level of cytoglobin (CYGB)^[1].
FL118 (10 and 100 nM; 48 h) inhibits PI3K/AKT/mTOR signaling pathway, and affects the expression level of vimentin and E-cadherin in ovarian cancer cells^[1].
FL118 (0-100 nM; 6 and 24 h) dephosphorylates and degrades DDX5^[2].
FL118 (0-500 nM; 24, 48, 72 h) regulates survivin, McL-1, XIAP, cIAP2, c-MYc and mKras by regulating DDX5^[2].
FL118 (0-1 μM, 24 h) shows significant cytotoxic activity against the three tumor cell lines (A549, MDA-MB-231, and RM-1 cells)^[3].
FL118 (0-10 nM, 48 h) increases the production of PARP cleavage, and induces apoptosis in A549^[3].
FL118 (0-10 nM, 48 h) arrests A549 cells mainly at the G2/M phase^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[1]

Cell Line:

ES-2 and SK-O-V₃ cell lines
Concentration:

10 and 100 nM
Incubation Time:

48 h
Result:

Effectively inhibited the activation of PI3K/AKT/mTOR signaling pathway in ovarian cancer cells and also inhibited the migration of ES-2 and SK-O-V₃ cells.

Cell Migration Assay ^[1]

Cell Line:

ES-2 and SK-O-V₃ cell lines
Concentration:

0, 10 and 100 nM
Incubation Time:

0 and 24 h
Result:

Inhibited the migration of ES-2 and SK-O-V₃ cells dose-dependenly.

RT-PCR^[1]

Cell Line:

ES-2 and SK-O-V₃ cell lines
Concentration:

0, 10 and 100 nM
Incubation Time:

48 h
Result:

Promoted CYGB expression.

Cell Proliferation Assay^[1]

Cell Line:

ES-2 and SK-O-V₃ cell lines
Concentration:

0, 1, 10, 50, 100 and 200 nM
Incubation Time:

24, 48 and 72 h
Result:

Inhibited the cell proliferation of ES-2 and SK-O-V₃ cells time- and dose-dependently.

Western Blot Analysis^[2]

Cell Line:

SW620 and Mia Paca-2
Concentration:

0, 10 and 100 nM
Incubation Time:

6 and 24 h
Result:

Induced dephosphorylation of DDX5 through the ubiquitin-proteasome degradation pathway and degraded DDX5 time-dependently.

Western Blot Analysis^[2]

Cell Line:

PDAC Panc1, CRC HCT-8, SW620, Mia Paca-2, Panc-1, HCT-8 cell lines
Concentration:

0, 10, 100 and 500 nM
Incubation Time:

24, 48, 72 h
Result:

Controled the expression of survivin, Mcl-1, XIAP, cIAP2, c-Myc and mKras by regulated DDX5, as an upstream master regulator in cancer development and malignant networks.

Cell Cytotoxicity Assay^[3]

Cell Line:

A549, MDA-MB-231, RM-1
Concentration:

0-1 μM
Incubation Time:

24 h
Result:

Showed cytotoxicity in A-549 (human lung carcinoma), MDA-MB-231 (human breast carcinoma) and RM-1 (mouse prostate carcinoma), with IC₅₀ values of 8.94 ± 1.54 , 24.73 ± 13.82, and 69.19 ± 8.34 nM, respectively.

Apoptosis Analysis^[3]

Cell Line:

A549 cells
Concentration:

0, 2.5, 5, 10 nM
Incubation Time:

48 h
Result:

Resulted in the downregulation of survivin. Increased the production of PARP cleavage in a concentration-dependent manner, which is the hallmark of apoptosis. Induced apoptosis in A549.

Cell Cycle Analysis^[3]

Cell Line:

A549 cells
Concentration:

0, 2.5, 5, 10 nM
Incubation Time:

48 h
Result:

Increased G2/M cell population in a concentration-dependent manner, and arrested A549 cells mainly at the G2/M phase.

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

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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.

Essai clinique

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS No. 135415-73-5
Appearance Solid
Masse moléculaire 392.36
Formule C₂₁H₁₆N₂O₆
Color Light brown to brown
SMILES

O=C1[C@](O)(CC)C(C=C2C3=NC4=CC5=C(C=C4C=C3CN2C6=O)OCO5)=C6CO1
Synonyms

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

Room temperature in continental US; may vary elsewhere.

Stockage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (2)

All In Vivo Efficacy Study

Sort by:

Journal Impact Factor

Nature

2026 Jun 24. PMID: 42343133
Cell Signal

USP7-DDX5-FASN axis drives fatty acid metabolism and supports hepatocellular carcinoma progression. [Abstract]

2025 Oct:134:111947. PMID: 40553965

FL118 purchased from MedChemExpress. Usage Cited in: Cell Signal. 2025 Oct:134:111947. [Abstract]

Growth curves for xenografted HepG2 tumors treated with FL118 (5 mg/kg; p.o.; once weekly for 2 weeks). Tumors were resected and weighed at the end of the experiments. FL118 developed significantly smaller and lighter tumors.

Solvant et solubilité

In Vitro:

DMSO : 1 mg/mL (2.55 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

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Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.5487 mL

12.7434 mL

25.4868 mL

5 mM

---

10 mM

---

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Calculateur de molarité

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculateur de dilution

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

Pureté et documentation

Select Batch:

Pureté: 99.98%

Assay: 99.98%

ee.: 99.98%

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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
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Instruction de manipulation (2659 KB)

Références

[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. [Content Brief]

[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. [Content Brief]

[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. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.5487 mL	12.7434 mL	25.4868 mL	63.7170 mL

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FL118

Bioactive Compound Library Max

Bioactive Compound Library

Apoptosis Compound Library

Anti-Cancer Compound Library

Clinical Compound Library

Orally Active Compound Library

Anti-Prostate Cancer Compound Library

Heterocyclic Compound Library

Cell Death Library

Anti-Ovarian Cancer Compound Library

Multi-Target Compound Library

MCE Bioactive Compound Library

Clinical Compound Library Plus

Non-Alcoholic Fatty Liver Disease (NAFLD) Compound Library

High-Throughput Bioactive Compound Library

Publications Citing Use of MedChemExpress (MCE) FL118

Voir tous les produits spécifiques à Isoform IAP

Activité biologique

Chemical Information

Publications (2)

Solvant et solubilité

Pureté et documentation

Références

Help & FAQs

Complete Stock Solution Preparation Table

FL118

Bioactive Compound Library Max

Bioactive Compound Library

Apoptosis Compound Library

Anti-Cancer Compound Library

Clinical Compound Library

Orally Active Compound Library

Anti-Prostate Cancer Compound Library

Heterocyclic Compound Library

Cell Death Library

Anti-Ovarian Cancer Compound Library

Multi-Target Compound Library

MCE Bioactive Compound Library

Clinical Compound Library Plus

Non-Alcoholic Fatty Liver Disease (NAFLD) Compound Library

High-Throughput Bioactive Compound Library

Publications Citing Use of MedChemExpress (MCE) FL118

Voir tous les produits spécifiques à Isoform IAP

Activité biologique

Chemical Information

Publications (2)

Solvant et solubilité

Pureté et documentation

Références

Help & FAQs

Complete Stock Solution Preparation Table

FL118 Related Classifications

HY-12486 Related Classifications