Vismodegib

Product Name: Vismodegib
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
Formula Weight: 421.3
MOL File: 879085-55-9.mol

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Vismodegib Property

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

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Safety

HS Code: 29333990
Hazardous Substances Data: 879085-55-9(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H360May damage fertility or the unborn child

H373May cause damage to organs through prolonged or repeated exposure

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P314Get medical advice/attention if you feel unwell.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 13613
Product name: GDC-0449
Purity: ≥98%
Packaging: 5mg
Price: $75
Updated: 2021/12/16

Cayman Chemical

Product number: 13613
Product name: GDC-0449
Purity: ≥98%
Packaging: 10mg
Price: $135
Updated: 2021/12/16

Cayman Chemical

Product number: 13613
Product name: GDC-0449
Purity: ≥98%
Packaging: 25mg
Price: $244
Updated: 2021/12/16

Cayman Chemical

Product number: 13613
Product name: GDC-0449
Purity: ≥98%
Packaging: 50mg
Price: $338
Updated: 2021/12/16

TRC

Product number: V674700
Product name: Vismodegib
Packaging: 50mg
Price: $375
Updated: 2021/12/16

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Vismodegib Chemical Properties,Usage,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.

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

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Vismodegib Suppliers

Canada 1 China 209 India 5 The Netherlands 1 United Kingdom 3 United States 22 Global 241

AdooQ BioScience, LLC

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View Lastest Price from Vismodegib manufacturers

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.

Product: Vismodegib 879085-55-9
Price: US $0.00/g
Min. Order: 1g
Purity: More Than 99%
Supply Ability: 100kg/Month
Release date: 2024-07-24

Senova Technology Co. Ltd.

Product: vismodegib 879085-55-9
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 10KG
Release date: 2023-12-14

Qiuxian Baitai New Material Co., LTD

Product: GDC-0449 879085-55-9
Price: US $73.00/mg
Min. Order: 1KG
Purity: 98%
Supply Ability: 50ton/Month
Release date: 2021-12-21

879085-55-9, VismodegibRelated Search:

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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)-

Vismodegib

GDC-0449,Vismodegib

GDC-0449

101098

CS-1913

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

Vismodegib, 98%, a Hedgehog inhibitor

GDC04499(Vismodegib)

GDC-0449;GDC 0449;GDC0449

Erivedge

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)

2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-methanesulfonylbenzamide

Xanthophyll Impurity 3

Vimodji

879085-55-9

Inhibitors

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