Vismodegib (GDC-0449)

Catalog No.S1082

Vismodegib (GDC-0449) Chemical Structure

Molecular Weight(MW): 421.3

Vismodegib (GDC-0449) is a potent, novel and specific hedgehog inhibitor with IC50 of 3 nM and also inhibits P-gp with IC50 of 3.0 μM in a cell-free assay.

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Cited by 39 Publications

Purity & Quality Control

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Biological Activity

Description Vismodegib (GDC-0449) is a potent, novel and specific hedgehog inhibitor with IC50 of 3 nM and also inhibits P-gp with IC50 of 3.0 μM in a cell-free assay.
Targets
Hedgehog [1]
(Cell-free assay)
3 nM
In vitro

GDC-0449 targets the Hedgehog signaling pathway, blocking the activities of the Hedgehog-ligand cell surface receptors PTCH and/or SMO and suppressing Hedgehog signaling. GDC-0449 prevents multiple ATP-binding cassette (ABC) transporters. GDC-0449 also blocks ABCG2, Pgp, and MRP1-important ABC transporters associated with MDR. GDC-0449 is a potent inhibitor of ABC transporters, ABCG2/BCRP and ABCB1/Pgp, and is a mild inhibitor of ABCC1/MRP1. In ABCG2-overexpressing HEK293 cells, GDC-0449 increases retention of the fluorescent ABCG2 substrate BODIPY-prazosin and resensitizes these cells to mitoxantrone. In Madin-Darby canine kidney II cells engineered to overexpress Pgp or MRP1, GDC-0449 increases the retention of calcein-AM and resensitizes them to colchicine. GDC-0449 also resensitizes human non-small cell lung carcinoma cells NCI-H460/par and NCI-H460/MX20, which overexpress ABCG2 in response to mitoxantrone, to mitoxantrone, and to topotecan or SN-38. The IC50 values of GDC-0449 for prevention of ABCG2 and Pgp are about 1.4 μM and 3.0 μM, respectively. [2] GDC-0449 alters intracellular Ca2+ homeostasis and inhibits cell growth in cisplatin-resistant lung cancer cells. [3]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
IGROV-1 NWrTS2VNT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M1fsbWlEPTB;MD6wO|I1QCEQvF2= NYjrO2JNW0GQR1XS
HCE-T NVrFclBoT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MYrJR|UxRTFwM{KyOFch|ryP MljTV2FPT0WU
D-542MG M1e0TWdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MljaTWM2OD1zLki2O|M4KM7:TR?= NEfWW3FUSU6JRWK=
23132-87 NWXlPWFwT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NXnmTHMzUUN3ME20MlQxOTR5IN88US=> NWTrfIRkW0GQR1XS
HDLM-2 NYPwbFNiT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M3XReGlEPTB;OD6wOFc3PiEQvF2= NYLvS2l[W0GQR1XS
ACN M3jGWGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NWnpZoNGUUN3ME24MlUxOTB7IN88US=> MoHQV2FPT0WU
HuO-3N1 MYjHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NUDW[ZNYUUN3ME25MlYxOTB6IN88US=> NGjyWXRUSU6JRWK=
BHT-101 M2TZTmdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MU\JR|UxRTFzLkO4JO69VQ>? NGPQdHhUSU6JRWK=
KYSE-150 NWj3UG83T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M3i3RWlEPTB;MUGuOVg1OSEQvF2= MULTRW5ITVJ?
MC-IXC NWOwNpRDT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NXixXmNCUUN3ME2xNk4zOjl{IN88US=> NVjn[4N{W0GQR1XS
D-423MG MUfHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NXjrWmp4UUN3ME2xNk44PjV5IN88US=> NHLVZWdUSU6JRWK=
NY MYTHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MW\JR|UxRTF2Lki5NFMh|ryP NYHw[GlEW0GQR1XS
HOS NWf5bIVHT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M3LRRWlEPTB;MUWuOlcyQSEQvF2= NHjvfHFUSU6JRWK=
NB7 NFniZoVIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MWXJR|UxRTF3Lki5NUDPxE1? MU\TRW5ITVJ?
DMS-273 MlLxS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NX7TSYJzUUN3ME2xOk43PzF|IN88US=> NFHYXI5USU6JRWK=
MDA-MB-361 NVLQcHQ5T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M3[2cmlEPTB;MUeuNlcyOSEQvF2= NHHLZXRUSU6JRWK=
DU-145 NFTVemZIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MkHSTWM2OD1zOD6zNkDPxE1? NWnuZ21ZW0GQR1XS
NCI-H82 NXXsNIRYT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NGXFUpJKSzVyPUG5Mlg{QDZizszN NHjZVFBUSU6JRWK=
NCI-SNU-1 NWD0V2hmT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M3H2R2lEPTB;MkCuNFE6PiEQvF2= NEe1dIlUSU6JRWK=
GCT NVH1RoxyT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MnXETWM2OD1{MD64PFI1KM7:TR?= NXnsRYdjW0GQR1XS
C2BBe1 MYjHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MlP6TWM2OD1{MT6xNFU5KM7:TR?= M{XLfnNCVkeHUh?=
LB2241-RCC MYjHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MmTSTWM2OD1{MT64OFQyKM7:TR?= NX3MRoFzW0GQR1XS
COLO-829 M3r6SWdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MkjTTWM2OD1{Mj6xPFcyKM7:TR?= Mmj6V2FPT0WU
EW-11 NH7FZ25Iem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NGPMeIVKSzVyPUKyMlgxOjJizszN MWfTRW5ITVJ?
NCI-H526 NFW5SHJIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NU[yW5ExUUN3ME2yN{41PzF5IN88US=> MXPTRW5ITVJ?
SF295 M{noPGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MXjJR|UxRTJ2LkCyOVIh|ryP MX;TRW5ITVJ?
D-566MG MmjxS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NHjrXmdKSzVyPUK1MlI6PDNizszN NHO4fJpUSU6JRWK=
8505C NXjCOVd2T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NELJNWlKSzVyPUK1MlY{OzFizszN M4jtNHNCVkeHUh?=
HT-29 M1jLeWdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 M33lOmlEPTB;Mk[uNFQ{OSEQvF2= NGjPWHhUSU6JRWK=
NBsusSR MnXES5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? MVXJR|UxRTJ4LkiwNFYh|ryP M2fjZXNCVkeHUh?=
BV-173 Ml\xS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NWr5b49SUUN3ME2yPE4{OTh{IN88US=> MljzV2FPT0WU
CTB-1 Mo[1S5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NV3acFduUUN3ME2zNE4yODNzIN88US=> MlLsV2FPT0WU
JAR M{Prdmdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MXvJR|UxRTN{LkWzO|Eh|ryP M{KzcnNCVkeHUh?=
CAMA-1 MnnDS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? Mlj5TWM2OD1|Mz60OlE2KM7:TR?= MX\TRW5ITVJ?
CAL-51 NEXXWXRIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= M{HFeGlEPTB;M{SuO|E4PiEQvF2= NFfpN2RUSU6JRWK=
A172 NVzidoNNT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NH7VRnFKSzVyPUO3MlQ6OjFizszN MmrDV2FPT0WU
QIMR-WIL MoLjS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? M1;1NWlEPTB;M{iuNFcxQCEQvF2= MnjMV2FPT0WU
AsPC-1 NUW0TXpCT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MYHJR|UxRTN6LkS2OVEh|ryP NIfvR5dUSU6JRWK=
MKN7 NHTlWpNIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NWjHO25wUUN3ME2zPU4xODd7IN88US=> MnzWV2FPT0WU
ONS-76 M37kfWdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 M{HlN2lEPTB;NEOuN|A2PyEQvF2= NIjZc4JUSU6JRWK=
RS4-11 MYnHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NIPWR3BKSzVyPUS0MlA4PTJizszN MVHTRW5ITVJ?
NOS-1 M3;XUGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NUHSb4tGUUN3ME20OE43ODNzIN88US=> NHS3[45USU6JRWK=
A101D NYLzNVQ3T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NU[wc3ptUUN3ME20OE45ODJ|IN88US=> MVTTRW5ITVJ?
HCC1806 MVnHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NHP0OY1KSzVyPUS2MlEyPDhizszN M2XxNnNCVkeHUh?=
CAL-27 MYXHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NXPWN3ZWUUN3ME20O{44OjR4IN88US=> M4fmUHNCVkeHUh?=
BT-549 NEOzUJdIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MWPJR|UxRTR6LkWzNVUh|ryP MWDTRW5ITVJ?
LCLC-97TM1 Mn7OS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? M2LlUGlEPTB;NEmuNlQyOyEQvF2= NV[xb25VW0GQR1XS
A4-Fuk NVHoWW1KT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M1PiVGlEPTB;NEmuPFQ6KM7:TR?= MUDTRW5ITVJ?
OVCAR-4 NXXWSHU6T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NWjWTYplUUN3ME21NE4xPjBzIN88US=> NXjKNWtSW0GQR1XS
HD-MY-Z NFzKRXBIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NYHZTno1UUN3ME21NE44PzZ2IN88US=> NVvkPVY{W0GQR1XS
NCI-H292 MV3Hdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? M1PvPWlEPTB;NUCuPFc2QCEQvF2= MkKyV2FPT0WU
Sk-ChA-1  MmTQS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? MX2wMlI26oDVNUCg{txO NYDWWFJYPzJiaB?= MYHJR|UxRTd2LkW0xtEzNjV6zszN NXfLNGVOOjV5NEK0PFI>
Mz-ChA-1 NET2cZlIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NUHOcWVzOC5{NfMAl|UxKM7:TR?= MXm3NkBp MYnJR|UxRTV2Lkm3xtE{NjR3zszN Mmn0NlU4PDJ2OEK=
Smo-WT MnyxS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? Mn7vTWM2OMLib3[gNVTDqG6P M2faZlI1OjlzMUC0
Smo-D473H  NF3XdpJIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NVL4d4hmUUN3MNMgc4YhPy5zwrFOwG0> M1PESVI1OjlzMUC0
K562 MWrGeY5kfGmxbjDBd5NigQ>? NHHQR2IyOCEQvF2= NIDj[FY4OiCq M3uxOJJm\HWlZYOgeIhmKGW6cILld5Nqd25ib3[gS4xqOcLi NVvoPVhPOjN|MUm4NlQ>
T315I BCR-ABL BaF3 M1zxRWZ2dmO2aX;uJGF{e2G7 M{X0O|ExKM7:TR?= NI\2RYk4OiCq MmTydoVlfWOnczD0bIUh\XiycnXzd4lwdiCxZjDHcIkyyqB? M3XvZVI{OzF7OEK0
TF-1 BCR-ABL NWrKd5FxTnWwY4Tpc44hSXO|YYm= M2LWXlExKM7:TR?= NXzRZXhwPzJiaB?= MlO1doVlfWOnczD0bIUh\XiycnXzd4lwdiCxZjDHcIkyyqB? M{n1XlI{OzF7OEK0

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
Fas / DR4 / DR5 / Cleaved PARP / Bcl-2 / Cleaved caspase-3 / PDGFRα; 

PubMed: 22087285     


Pancreatic CSCs were treated with GDC-0449 (0, 1, 5 and 10 µM) for 48 h. The expression of Fas, DR4/TRAIL-R1, DR5/TRAIL-R2, PARP cleavage, Bcl-2, and Caspase-3 by the Western blot analysis. β-Actin was used as a loading control.

p-GSK3β / GSK3β / p-Akt / Akt / Gli1; 

PubMed: 27143997     


Cells were pretreated with or without 30 μM GDC-0449 for 2 h before TMT treatment. After incubation with 3.75 μM TMT for another 24 h, the expression levels of proteins were determined through Western blot analysis.

Gli1 / SOX2 / OCT4; 

PubMed: 26418365     


The activation of Hedgehog pathways and CSC markers were tested by immunoblotting analysis in Hs578T and BT549 cells. β‐Actin was used as a loading control.

p53 / Cyclin D1 / p21; 

PubMed: 28195165     


GDC-0449 treatment affected the expression levels of cell cycle-related protein levels. U251 cells were treated with 0.1% DMSO or GDC-0449 at the indicated concentrations for 24 h. Cells were then harvested and examined using Western blot analysis with the indicated antibodies.

Bcl-2 / Bax; 

PubMed: 28195165     


GDC-0449 treatment affected the expression levels of cell cycle-related protein levels. U251 cells were treated with 0.1% DMSO or GDC-0449 at the indicated concentrations for 24 h. Cells were then harvested and examined using Western blot analysis with the indicated antibodies.

22087285 27143997 26418365 28195165
Immunofluorescence
Gli1 / Gli2; 

PubMed: 22087285     


GDC-0449 inhibits expression of Gli1 and Gli2 in human pancreatic CSCs. The cells were seeded on fibronectin-coated coverslips and treated with GDC-0449 (10 µM) for 48 h. Subsequently, cells were fixed with 4% paraformaldehyde, blocked in 10% normal goat serum and stained with Gli1 and Gli2 primary antibodies (1∶100) for 16 h at 4°C and washed with PBS. Afterwards, cells were incubated with fluorescently labeled secondary antibody (1∶200) along with DAPI (1 mg/ml) for 1 h at room temperature and cells were mounted and visualized under a fluorescent microscope. For better visuality, the color of DAPI was changed from blue to red.

22087285
Growth inhibition assay
Cell viability; 

PubMed: 29042665     


GDC-0449 improves the anti-proliferation activity in NIH-3T3 cells but not in BxPC-3, Panc-1, MIAPaca-2 and SW1990 cells when cultured alone. The cytotoxicities of GDC-0449, Dox or Dox with GDC-0449 (5 μM or 10 μM) were measured by performing a 48-h MTT assay in BxPC-3 (A), Panc-1 (B), MIAPaca-2 (C), SW1990 (D) and NIH-3T3 (E) cells. Apoptosis rate was detected by flow cytometry (Annexin V staining) analysis after treatment with Dox (200 nM) with or without GDC-0449 for 24 h (F). Data are presented as the mean ± SD. *P < 0.05, **P < 0.01.

29042665
In vivo GDC-0449 has been used to treat medulloblastoma in animal models. [2] GDC-0449 prevents the growth of primary pancreatic xenografts without non-specifically inhibiting pancreatic cell proliferation. Oral dosing of GDC-0449 causes tumor regressions in the Ptch(+/-) allograft model of medulloblastoma at doses ≥25 mg/kg and tumor growth inhibition at doses up to 92 mg/kg dosed twice daily in two ligand-dependent colorectal cancer models, D5123, and 1040830. Analysis of Hh pathway activity and PK/PD modeling reveals that GDC-0449 inhibits Gli1 with a similar IC50 in both the medulloblastoma and D5123 models (0.165 μM and 0.267 μM, respectively). Pathway modulation is linked to efficacy using an integrated PK/PD model revealing a steep relationship where > 50% of the activity of GDC-0449 is associated with >80% repression of the Hh pathway. [4]

Protocol

Cell Research:[2]
+ Expand
  • Cell lines: MDCKII cells
  • Concentrations: 20 μM
  • Incubation Time: 2 hours
  • Method: MDCKII cells are seeded into 24-well plates at a density of 3 × 105 cells per well and are allowed to attach. Medium is then changed to that containing different drugs (50 μM VP, 50 μM indomethacin, or 20 μM GDC-0449 in DMSO or DMSO alone as control, and nonfluorescent calcein-AM is added to a final concentration of 1.0 μM and incubated at 37 °C for 2 hours. Cells are then washed twice with Ca2+, Mg2+-containing Hank's balanced salt solution buffer and lysed by shaking in 0.01% Triton X-100 in PBS buffer for 1 hour at room temperature or overnight at 4 °C. The lysate is then transferred into 96-well plates, and the fluorescence signal caused by the cell-derived calcein is quantified spectrophotometrically with a SpectraMax M5 Multi-Detection Readerusing an excitation wavelength of 495 nm and an emission wavelength of 515 nm. All manipulations are performed in the dark. All readings are expressed as mean ?SEM normalized to the control.
    (Only for Reference)
Animal Research:[4]
+ Expand
  • Animal Models: Ptch(+/-) allograft model, D5123 and 1040830
  • Formulation: In 0.5% methyl-cellulose, 0.2% tween-80
  • Dosages: ~ 100 mg/kg
  • Administration: Orally
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 84 mg/mL (199.38 mM)
Water Insoluble
Ethanol Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
2% DMSO+30% PEG 300+5% Tween 80+ddH2O
For best results, use promptly after mixing.
10mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 421.3
Formula

C19H14Cl2N2O3S

CAS No. 879085-55-9
Storage powder
in solvent
Synonyms N/A

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Clinical Trial Information

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT03767439 Not yet recruiting Basal Cell Nevus Syndrome Columbia University February 2019 Phase 2
NCT03767439 Not yet recruiting Basal Cell Nevus Syndrome Columbia University February 2019 Phase 2
NCT03610022 Recruiting Metastatic Basal Cell Carcinoma|Locally Advanced Basal Cell Carcinoma University Hospital Bordeaux September 3 2018 Phase 4
NCT03610022 Recruiting Metastatic Basal Cell Carcinoma|Locally Advanced Basal Cell Carcinoma University Hospital Bordeaux September 3 2018 Phase 4
NCT03498521 Recruiting Cancer of Unknown Primary Site Hoffmann-La Roche|Foundation Medicine Inc. July 10 2018 Phase 2
NCT03498521 Recruiting Cancer of Unknown Primary Site Hoffmann-La Roche|Foundation Medicine Inc. July 10 2018 Phase 2

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID