Vismodegib | GDC-0449 | RG3616 | CAS#879085-55-9 | Hedgehog Antagonist

MedKoo Cat#: 203500 | Name: Vismodegib

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Vismodegib, also known as GDC-0449 or RG3616, is a hedgehog antagonist, is also a n orally bioavailable small molecule with potential antineoplastic activity. Hedgehog antagonist 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.

Chemical Structure

Vismodegib

CAS#879085-55-9

Theoretical Analysis

MedKoo Cat#: 203500

Name: Vismodegib

CAS#: 879085-55-9

Chemical Formula: C19H14Cl2N2O3S

Exact Mass: 420.0102

Molecular Weight: 421.30

Elemental Analysis: C, 54.17; H, 3.35; Cl, 16.83; N, 6.65; O, 11.39; S, 7.61

Price and Availability

Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 250.00	Ready to ship
500mg	USD 450.00	Ready to ship
1g	USD 750.00	Ready to ship
2g	USD 1,250.00	Ready to ship
5g	USD 2,650.00	Ready to ship

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Related CAS #

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Synonym

GDC0449, GDC 0449, GDC-0449, RG3616, RG 3616, RG-3616, Vismodegib, Erivedge

IUPAC/Chemical Name

2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide

InChi Key

BPQMGSKTAYIVFO-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)

SMILES Code

O=C(NC1=CC=C(Cl)C(C2=NC=CC=C2)=C1)C3=CC=C(S(=O)(C)=O)C=C3Cl

Appearance

White solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

The Hedgehog signaling pathway plays an important role in tissue growth and repair; aberrant constitutive activation of Hedgehog pathway signaling and uncontrolled cellular proliferation may be associated with mutations in the Hedgehog-ligand cell surface receptors PTCH and SMO.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C20R10B05

View CoA: current batch, Lot#TZC50806

QC Data

View QC data: current batch, Lot#TZC50806

View QC data: current batch, Lot#C20R10B05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Vismodegib (GDC-0449) is a hedgehog pathway inhibitor with an IC50 of 3 nM.

In vitro activity:

Cell proliferation, apoptosis and the expression of EMT (epithelial mesenchymal transition) related genes for three prostate cancer cell lines were evaluated; androgen-dependent LNCaP and independent C4-2B and PC-3 in the presence of vismodegib in vitro. Vismodegib significantly inhibited cell proliferation and induced cell apoptosis in all cell lines in vitro (p<0.05). The results indicate that vismodegib inhibited cell proliferation via apoptosis and also suppressed EMT. Reference: Anticancer Res. 2020 Sep;40(9):5107-5114. https://ar.iiarjournals.org/content/40/9/5107.long

In vivo activity:

The effects of the SMO (Smoothened) antagonist, vismodegib, were investigated in the rat MPM (malignant pleural mesothelioma) model to elaborate the role of Hh (Hedgehog) signaling. Vismodegib was administered and six days later, it was observed that tumor volume measured by MRI was significantly reduced in the treated group compared with control (3-fold difference, P = 0.03; Fig. 3B). Consistently, significant reduction in macroscopic tumor volume (P = 0.03) of the treated group was detected (Fig. 3D). Tumor growth monitored by BLI (bioluminescence) seems to be reduced in the treated group compared with control (see images in Fig. 3E). Reference: Mol Cancer Ther. 2016 May;15(5):1095-105. https://mct.aacrjournals.org/content/15/5/1095.long

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	118.68

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 421.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Meerang M, Bérard K, Felley-Bosco E, Lauk O, Vrugt B, Boss A, Kenkel D, Broggini-Tenzer A, Stahel RA, Arni S, Weder W, Opitz I. Antagonizing the Hedgehog Pathway with Vismodegib Impairs Malignant Pleural Mesothelioma Growth In Vivo by Affecting Stroma. Mol Cancer Ther. 2016 May;15(5):1095-105. doi: 10.1158/1535-7163.MCT-15-0583. Epub 2016 Feb 2. PMID: 26839306. 2. Ishii A, Shigemura K, Kitagawa K, Sung SY, Chen KC, Yi-Te C, Liu MC, Fujisawa M. Anti-tumor Effect of Hedgehog Signaling Inhibitor, Vismodegib, on Castration-resistant Prostate Cancer. Anticancer Res. 2020 Sep;40(9):5107-5114. doi: 10.21873/anticanres.14514. PMID: 32878799.

In vitro protocol:

1. Ishii A, Shigemura K, Kitagawa K, Sung SY, Chen KC, Yi-Te C, Liu MC, Fujisawa M. Anti-tumor Effect of Hedgehog Signaling Inhibitor, Vismodegib, on Castration-resistant Prostate Cancer. Anticancer Res. 2020 Sep;40(9):5107-5114. doi: 10.21873/anticanres.14514. PMID: 32878799.

In vivo protocol:

1: Poggi L, Kolesar JM. Vismodegib for the treatment of basal cell skin cancer. Am J Health Syst Pharm. 2013 Jun 15;70(12):1033-8. doi: 10.2146/ajhp120311. Review. PubMed PMID: 23719880. 2: Dubey AK, Dubey S, Handu SS, Qazi MA. Vismodegib: the first drug approved for advanced and metastatic basal cell carcinoma. J Postgrad Med. 2013 Jan-Mar;59(1):48-50. Review. PubMed PMID: 23525058. 3: Cirrone F, Harris CS. Vismodegib and the hedgehog pathway: a new treatment for basal cell carcinoma. Clin Ther. 2012 Oct;34(10):2039-50. doi: 10.1016/j.clinthera.2012.08.011. Epub 2012 Oct 1. Review. PubMed PMID: 23036338. 4: Amaria RN, Bowles DW, Lewis KD, Jimeno A. Vismodegib in basal cell carcinoma. Drugs Today (Barc). 2012 Jul;48(7):459-67. doi: 10.1358/dot.2012.48.7.1808490. Review. PubMed PMID: 22844657. 5: Keating GM. Vismodegib: in locally advanced or metastatic basal cell carcinoma. Drugs. 2012 Jul 30;72(11):1535-41. doi: 10.2165/11209590-000000000-00000. Review. PubMed PMID: 22788238. 6: De Smaele E, Ferretti E, Gulino A. Vismodegib, a small-molecule inhibitor of the hedgehog pathway for the treatment of advanced cancers. Curr Opin Investig Drugs. 2010 Jun;11(6):707-18. Review. PubMed PMID: 20496266.