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Vismodegib

Vismodegib Structure
Vismodegib structure
CAS No.
879085-55-9
Chemical Name:
Vismodegib
Synonyms
Vismodegib;GDC-0449;Erivedge;101098;CS-1913;RG 3616;Vimodji;VisModegib Base;Vismodegib 13C7;Vismodegib, >=99%
CBNumber:
CB52500590
Molecular Formula:
C19H14Cl2N2O3S
Molecular Weight:
421.3
MDL Number:
MFCD12407408
MOL File:
879085-55-9.mol
Last updated:2024-11-19 20:33:22
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Vismodegib Properties

Melting point 179-181°C
Boiling point 561.6±50.0 °C(Predicted)
Density 1.440
storage temp. -20°
solubility Soluble in DMSO (up to 200 mg/ml) or in Ethanol (up to 10 mg/ml with warming)
form White solid.
pka 10.72±0.70(Predicted)
color Off-white or beige
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChI 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)
InChIKey BPQMGSKTAYIVFO-UHFFFAOYSA-N
SMILES C(NC1=CC=C(Cl)C(C2=NC=CC=C2)=C1)(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl
NCI Dictionary of Cancer Terms GDC-0449; vismodegib
FDA UNII 25X868M3DS
NCI Drug Dictionary Erivedge
ATC code L01XJ01
Proposition 65 List Vismodegib

Pharmacokinetic data

Protein binding >99%
Excreted unchanged in urine 4.4%
Volume of distribution 16.4-26.6 Litres
Biological half-life 12 days (single dose), 4 days (continuous)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS09
Signal word  Danger
Hazard statements  H410-H360-H373-H400
Precautionary statements  P260-P314-P501-P273-P391-P501-P273-P391-P501
HS Code  29333990
Hazardous Substances Data 879085-55-9(Hazardous Substances Data)

Vismodegib price More Price(35)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 13613 GDC-0449 ≥98% 879085-55-9 5mg $75 2021-12-16 Buy
Cayman Chemical 13613 GDC-0449 ≥98% 879085-55-9 10mg $135 2021-12-16 Buy
Cayman Chemical 13613 GDC-0449 ≥98% 879085-55-9 50mg $338 2021-12-16 Buy
Cayman Chemical 13613 GDC-0449 ≥98% 879085-55-9 25mg $244 2021-12-16 Buy
TRC V674700 Vismodegib 879085-55-9 50mg $375 2021-12-16 Buy
Product number Packaging Price Buy
13613 5mg $75 Buy
13613 10mg $135 Buy
13613 50mg $338 Buy
13613 25mg $244 Buy
V674700 50mg $375 Buy

Vismodegib Chemical Properties,Uses,Production

Description

In January 2012, the US FDA approved vismodegib (also referred to as GDC-0449) for the treatment of adults with metastatic basal cell carcinoma (BCC), with locally advanced BCC that has recurred following surgery or who are not candidates for surgery or radiation. Vismodegib inhibits the Hh sig?naling pathway by functioning as an antagonist of SMO thereby inhibiting the activation of Hedgehog target genes, resulting in decreased downstream pro?duction of proliferation factors. The IC50 of vismodegib in a Hedgehog?responsive cell line derived from human embryonic palatal mesenchyme cells was 2.8 nM. In preclinical in vivostudies, vismodegib at 12.5 mg/kg (bid) caused complete regression of tumors in a Hh pathway dependent medulloblas?tomaallograft model generated from Ptch+/-mice. A synthesis of vismodegib starting from 2-chloro-5-nitro aniline and employing a Negishi coupling with 2-pyridyl zinc iodide as a key step has been reported.

Chemical Properties

White Solid

Originator

Curis/Genentech (United States)

Uses

Vismodegib targets the Hedgehog (Hh) pathway. Inhibition of the Hh signaling may be effective in the treatment and prevention of many types of human cancers. Potent Hedgehog inhibitor.

Uses

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.

Definition

ChEBI: A benzamide obtained by formal condensation between the carboxy group of 2-chloro-4-(methylsulfonyl)benzoic acid and the anilino group of 4-chloro-3-(pyridin-2-yl)aniline. Used for the treatment metastatic basal cell carcinoma.

brand name

Erivedge

Clinical Use

Antineoplastic agent:
Treatment of basal cell carcinoma which is inappropriate for surgery or radiotherapy

Synthesis

The synthesis began with selective iodination of commercial carboxylic acid 179, affording trisubstituted arene 180 in 73% yield. A Curtius reaction then converted 180 to carbamate 181 in 84% 52 yield, and this was followed by a palladium(0)-catalyzed borylation of 181 which furnished Suzuki coupling partner 182 in 91% yield. Pinacol borane 182 was exposed to commercial 2-bromopyridine under conventional cross-coupling conditions to furnish biaryl 183, which underwent Boc-deprotection in quantitative conversion to generate 184. Amide bond formation with acid chloride 185 (readily available from the corresponding commercial acid) produced vismodegib (XXVIII) in 99% yield.

Synthesis_879085-55-9

target

Hedgehog

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration possibly reduced by rifampicin - avoid.
Antidepressants: concentration possibly reduced by St John’s wort - avoid.
Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin and phenytoin - avoid.
Antipsychotics: avoid with clozapine, increased risk of agranulocytosis.

Metabolism

Vismodegib is hepatically metabolised by CYP2C9 and CYP3A4, however more than 98
% of total systemic vismodegib is not metabolised. Metabolic pathways of vismodegib include oxidation, glucuronidation, and pyridine ring cleavage. The two most abundant oxidative metabolites recovered in faeces are produced in vitro by recombinant CYP2C9 and CYP3A4/5.
Vismodegib is slowly eliminated by a combination of metabolism and excretion of parent drug, the majority is recovered in the faeces (82
%). Vismodegib and its metabolites are eliminated mainly by the hepatic route.

storage

Store at -20°C

References

1) Rominger et al. (2009), Evidence for allosteric interactions of antagonist binding to the smoothened receptor; J. Pharmacol. Exp. Therap., 329 995 2) Tian et al. (2012), The hedgehog pathway inhibitor GDC-0449 alters intracellular Ca2+ homeostasis and inhibits cell growth in cisplatin-resistant lung cancer cells; Anticancer Res., 32 89 3) Zhang et al. (2009), Hedgehog pathway inhibitor HhAntag691 is a potent inhibitor of ABCG2/BCRP and ABCB1/Pgp; Neoplasia, 11 96 4) Cirrone and Harris (2012), Vismodegib anf the hedgehog pathway: a new treatment for basal cell carcinoma; Clin. Ther., 34 2039 5) Wu et al. (2017), Smoothened antagonist GDC-0449 (Vismodegib) inhibits proliferation and triggers apoptosis in colon cancer cell lines; Exp. Ther. Med., 13 2529 6)Singh et al. (2011) Hedgehog signaling antagonist GDC-0449 (Vismodegib) inhibits pancreatic cancer stem cell characteristics: molecular mechanisms; PLoS One 6?e27306 7) Rudin et al. (2009) Treatment of medulloblastoma with hedgehog pathway inhibitor GDC-0449; N. Engl. J. Med., 361?1173 8) Von Hoff et al. (2009) Inhibition of the hedgehog pathway in advanced basal-cell carcinoma; N. Engl. J. Med., 361?1164

Vismodegib Preparation Products And Raw materials

Raw materials

Preparation Products

Vismodegib Suppliers

Global( 240)Suppliers
Supplier Tel Email Country ProdList Advantage
Shijiazhuang Dingmin Pharmaceutical Sciences Co., Ltd.
+86-0311-67591193 +8613931880626 sales02@dingminpharma.com China 252 58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
+86-18600796368 +86-18600796368 sales@sjar-tech.com China 456 58
Senova Technology Co. Ltd. 		+86-0755-86703119 +8618503098836 info@senovatech.com China 351 58
Capot Chemical Co.,Ltd. 		+86-（0）57185586718 +86-13336195806 sales@capot.com China 29791 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Nanjing ChemLin Chemical Industry Co., Ltd. 		025-83697070 product@chemlin.com.cn CHINA 3009 60
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32957 60
career henan chemical co 		+86-0371-86658258 +8613203830695 sales@coreychem.com China 29880 58
Biochempartner 		0086-13720134139 candy@biochempartner.com CHINA 965 58
Hubei xin bonus chemical co. LTD 		86-13657291602 linda@hubeijusheng.com CHINA 22963 58
Supplier Advantage
Shijiazhuang Dingmin Pharmaceutical Sciences Co., Ltd.
58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
58
Senova Technology Co. Ltd. 		58
Capot Chemical Co.,Ltd. 		60
Henan Tianfu Chemical Co.,Ltd. 		55
Nanjing ChemLin Chemical Industry Co., Ltd. 		60
ATK CHEMICAL COMPANY LIMITED 		60
career henan chemical co 		58
Biochempartner 		58
Hubei xin bonus chemical co. LTD 		58

Related articles

  • What is Vismodegib
  • Vismodegib (GDC-0449; Vismo) is a first-in-class, orally administered Hedgehog pathway inhibitor approved in 2012.
  • Aug 1，2024

View Lastest Price from Vismodegib manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Vismodegib pictures 2024-11-19 Vismodegib
879085-55-9
 US $38.00-67.00 / mg 99.99% 10g TargetMol Chemicals Inc.
Vismodegib pictures 2024-11-18 Vismodegib
879085-55-9
 US $0.00 / g 1g More Than 99% 100kg/Month BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
vismodegib pictures 2023-12-14 vismodegib
879085-55-9
 US $0.00-0.00 / g 1g 98% 10KG Senova Technology Co. Ltd.
  • Vismodegib pictures
  • Vismodegib
    879085-55-9
  • US $38.00-67.00 / mg
  • 99.99%
  • TargetMol Chemicals Inc.
  • Vismodegib pictures
  • Vismodegib
    879085-55-9
  • US $0.00 / g
  • More Than 99%
  • BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
  • vismodegib pictures
  • vismodegib
    879085-55-9
  • US $0.00-0.00 / g
  • 98%
  • Senova Technology Co. Ltd.

Vismodegib Spectrum

2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide(879085-55-9)1HNMR

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2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide VisModegib (GDC-0449) BenzaMide, 2-chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(Methylsulfonyl)- GDC-0449,Vismodegib 2-Chloro-N-(4-chloro-3-(pyridin-2-yl)-phenyl)-4-(methylsulfonyl)benzamide VisModegib Base 2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide Vismodegib(GDC0449) Vismodegib 2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide Vismodegib, >=99% VISMODEGIB (GDC-0449);GDC0449 101098 CS-1913 Vismodegib, 98%, a Hedgehog inhibitor GDC04499(Vismodegib) GDC-0449;GDC 0449;GDC0449 RG 3616 2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide USP/EP/BP 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-(methylsulfon... 2-Chloro-N-(4-chloro-3-(pyridine-2-yl)phenyl)-4-(methylsulfonyl)benzamide Vismodegib 13C7 TIANFU-CHEM Vismodegib (GDC-0449) Erivedge GDC-0449 Vismodegib 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-methanesulfonylbenzamide Xanthophyll Impurity 3 Vimodji 879085-55-9 Inhibitors Aromatics Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Inhibitor API