Avacopan

Product Name: Avacopan
CAS No.: 112093-28-4
Chemical Name: Avacopan
Synonyms: Avacopan;Endoxifen;Endoxifen(Z);(Z)-Endoxifen;Endoxifen (Z-isomer);salt CAS1032008-74-4;Tamoxifen Impurity 15;Tamoxifen Citrate Impurity 15;Endoxifen HCl Endoxifen Z-isomer;(Z)-4-Hydroxy-N-desmethyl Tamoxifen
CBNumber: CB31872472
Molecular Formula: C25H27NO2
Formula Weight: 373.49
MOL File: 112093-28-4.mol

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Avacopan Property

Melting point:: 127-129°C
Boiling point:: 519.3±50.0 °C(Predicted)
Density: 1.099±0.06 g/cm3(Predicted)
storage temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
solubility: DMSO : 50 mg/mL (133.87 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
form: Powder
pka: 10.36±0.15(Predicted)
color: White to off-white
Stability:: Light Sensitive, Temperature Sensitive
InChI: InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24-
InChIKey: MHJBZVSGOZTKRH-IZHYLOQSSA-N
SMILES: C1(O)=CC=C(/C(/C2=CC=C(OCCNC)C=C2)=C(/C2=CC=CC=C2)\CC)C=C1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H361Suspected of damaging fertility or the unborn child

H372Causes damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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N-Bromosuccinimide Price

Tocris

Product number: 3705
Product name: Endoxifen
Purity: ≥98%(HPLC)
Packaging: 10
Price: $221
Updated: 2021/12/16

Tocris

Product number: 3705
Product name: Endoxifen
Purity: ≥98%(HPLC)
Packaging: 50
Price: $909
Updated: 2021/12/16

TRC

Product number: H938500
Product name: (Z)-4-Hydroxy-N-desmethylTamoxifen(containsupto10%Eisomer)
Packaging: 0.5mg
Price: $180
Updated: 2021/12/16

Usbiological

Product number: 255247
Product name: Endoxifen
Packaging: 10mg
Price: $480
Updated: 2021/12/16

ApexBio Technology

Product number: B7481
Product name: Endoxifen
Packaging: 10mg
Price: $75
Updated: 2021/12/16

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Avacopan Chemical Properties,Usage,Production

Chemical Properties

Off-White to Pink Solid

Uses

A novel active metabolite of the anti-cancer drug Tamoxifen. It showed potent ER binding property, blocked estrogen stimulated growth of breast cancer cell and half maximal inhibition of estrogen responsive gene expression in ER pos. human breast ca

Uses

A novel active metabolite of the anti-cancer drug Tamoxifen (T006000). It showed potent ER binding property, blocked estrogen stimulated growth of breast cancer cell and half maximal inhibition of estrogen responsive gene expression in ER pos. human breast cancer cell line.

Definition

ChEBI: 4-Hydroxy-N-desmethyltamoxifen is a stilbenoid.

Indications

Avacopan is approved for the treatment of granulomatosis with polyangiitis (GPA) and microscopic polyangiitis (MPA). These two diseases are the two most common forms of non-neutrophil cytoplasmic antibody (ANCA)-associated vasculitis, a systemic autoimmune disease.

brand name

Tavneos

Biological Activity

(Z)-Endoxifen (endoxifen) is an active tamoxifen metabolite generated via actions of cytochrome P450 (CYP) enzymes CYP3A4/5 and CYP2D6. Endoxifen is more potent than tamoxifen as a selective estrogen receptor modulator (SERM) both in vitro and in vivo with good pharmacokinetics and oral availability (∼80% MCF-7 tumor growth inhibition with 4-8 mg/kg/day endoxifen or 20 mg/kg/day tamoxifen in mice via p.o.). Endoxifen also exhibits 4-fold higher PKC inhibitory potency than tamoxifen and can overcome tamoxifen resistance due to cytochrome CYP2D6 polymorphism.

Synthesis

The synthetic route for Avacopan is shown below: first, ethyl 3-(4-nitrophenyl)-3-oxopropanoate 18.1 was reacted with acrolein diethyl acetal in the presence of (R)-(-)-2-phenylglycidinol 18.2 to give tetrahydropyridine 18.3. Next, stereoselective olefinic reduction was carried out by palladium-catalysed hydrogenation ( possibly due to the stereoisomerism introduced by 18.2), along with nitro reduction and removal of the bis-epoxazole fragment to form piperidine. The crude amino ester was obtained as 78% ee by reductive amination with cyclopentanone. Subsequently, the 1:2 amine:salt adduct 18.4 was obtained in 70% yield from 18.3 by forming a salt with (-)-O,O′-di-p-tolyl-L-tartaric acid with an ee value >99:1. Saltolysis and an acylation reaction with 2-fluoro-6-methylbenzoyl chloride 18.5 yielded the amide 18.6. Finally, the amide 18.6 was formed via a Lewis acid-mediated amidation reaction with 4-methyl-5-trifluoromethylaniline 18.7, Avacopan (18) was obtained in 80% yield with de and ee >99.8%.

in vivo

Z-Endoxifen (Z-isomer) (5 mg/kg/day, s.c., gradual drug release every 30 days, pellets replaced every 90 days) effectively prevents breast cancer in the C3(1)-TAg mouse model^[3]. Z-Endoxifen (50 mg/kg, p.o., 5 times a week for 4 weeks) shows better antitumor efficacy in the MCF7LR resistant mouse model^[4]. Z-Endoxifen (75 mg/kg, p.o., once daily for 4 weeks) shows strong antitumor activity in the MCF7AC1 mouse breast cancer model^[4].

Animal Model:	C3(1)-TAg mouse mammary tumorigenesis model, developed by breeding FVB/NJ females with FVB/C3(1)-TAg males (8 weeks), resulting in SV40 T-antigen expression in mammary gland cells and tamoxifen resistance^[3]
Dosage:	5 mg/kg/day
Administration:	Subcutaneously implanted pellets, replaced every 90 days, with each pellet designed to release the drug gradually over 30 days.
Result:	Significantly increased tumor latency and reduced tumor growth.

Animal Model:	MCF7LR mouse breast cancer model, simulating endocrine-resistant breast cancer, developed by prolonged exposure to Letrozole^[4]
Dosage:	Z-Endoxifen: 50 mg/kg (Tamoxifen (HY-13757A): 500 μg/day, Exemestane (HY-13632): 250 μg/day，Everolimus (HY-10218): 2.5 mg/day)
Administration:	Z-Endoxifen: oral gavage (p.o.), the others administered subcutaneously, 5 times a week for 4 weeks
Result:	Significantly reduced tumor volume in the MCF7LR resistant model compared to Tamoxifen and Exemestane.

Avacopan Preparation Products And Raw materials

Raw materials

Preparation Products

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Avacopan Suppliers

Canada 1 China 101 India 3 United Kingdom 3 United States 12 Global 120

Shanghai Boyle Chemical Co., Ltd.

Tel
Fax: 86-21-57758967
Email: sales@boylechem.com
Country: China
ProdList: 2922
Advantage: 55

J & K SCIENTIFIC LTD.

Tel: 18210857532; 18210857532
Fax: 86-10-82849933
Email: jkinfo@jkchemical.com
Country: China
ProdList: 96815
Advantage: 76

Nanjing Chemlin Chemical Co., Ltd

Tel: 025-83697070
Fax: +86-25-83453306
Email: info@chemlin.com.cn
Country: China
ProdList: 15883
Advantage: 64

Chemsky（shanghai）International Co.,Ltd.

Tel: 021-50135380
Email: shchemsky@sina.com
Country: China
ProdList: 32321
Advantage: 50

BOC Sciences

Tel: 1-631-485-4226; 16314854226
Email: info@bocsci.com
Country: United States
ProdList: 12952
Advantage: 65

MedChemexpress LLC

Tel: 021-58955995
Fax: 609-228-5909
Email: sales@medchemexpress.cn
Country: United States
ProdList: 4861
Advantage: 58

AdooQ BioScience, LLC

Tel: +1 (866) 930-6790
Fax: +1 (866) 333-9607
Email: info@adooq.com
Country: United States
ProdList: 2782
Advantage: 58

Shanghai TaoSu Biochemical Technology Co., Ltd.

Tel: 021-33632979
Fax: 021-34692979
Email: info@tsbiochem.com
Country: China
ProdList: 8065
Advantage: 58

ChemStrong Scientific Co.,Ltd

Tel: 0755-0755-66853366 13670046396
Fax: 0755-28363542
Email: sales@chem-strong.com
Country: China
ProdList: 18333
Advantage: 56

Finetech Industry Limited

Tel: 027-87465837 19945049750
Fax: 027-8777-2287
Email: sales@finetechnology-ind.com
Country: China
ProdList: 9637
Advantage: 58

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View Lastest Price from Avacopan manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: Avacopan 112093-28-4
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98
Supply Ability: 10000KGS
Release date: 2025-11-24

Shaanxi Dideu Medichem Co. Ltd

Product: Endoxifen 112093-28-4
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 1000KG
Release date: 2024-07-16

Career Henan Chemical Co

Product: Endoxifen 112093-28-4
Price: US $3.00/KG
Min. Order: 1KG
Purity: 90%-99.9%
Supply Ability: 10kg
Release date: 2019-07-04

112093-28-4, AvacopanRelated Search:

Endoxifen HCl Tamoxifen Impurity 3 4-Benzyloxy β-Hydroxy TaMoxifen TaMoxifen DiMer 1-(4-(2-Dimethylamino)-2-ethoxyphenyl butanone N-Desmethyl-4-hydroxy Tamoxifen β-D-Glucuronide (E/Z Mixture) 4Hydroxy Tamoxifen Tamoxifen EP Impurity D (E)-4-Alloxycarboxyl Tamoxifen desdimethyltamoxifen TAMOXIFEN-N-OXIDE Droloxifene (E)-4-Acetoxy Tamoxifen N-Desmethyl Tamoxifen Methanethiosulfonate 2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol (E)-4-Hydroxy-N-desmethyl Tamoxifen 4-HYDROXYTAMOXIFEN

(Z)-4-Hydroxy-N-desmethyl Tamoxifen

4-[(1Z)-1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol

Endoxifen

Phenol, 4-[(1Z)-1-[4-[2-(MethylaMino)ethoxy]phenyl]-2-phenyl-1-butenyl]-

(Z)-4-Hydroxy-N-desmethyl Tamoxifen (contains up to 10% E isomer) see D292043

(Z)-4-Hydroxy-N-desmethyl Tamoxifen (contains up to 10% E isomer)

(Z)-4-Hydroxy-N-DesMethyl TaMoxifen (Endoxifen)

(Z)-Endoxifen

Endoxifen (Z-isomer)

Avacopan

4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

(Z)-4-Hydroxy-N-desmethyl Tamoxifen (contains 3% E isomer)

Endoxifen(Z)

salt CAS1032008-74-4

(Z)-4-Hydroxy-N-desmethyl Tamoxifen (mixture of isomers)

4-[(Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

(E/Z)-4-[1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol

(Z)-4-(1-(4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

Endoxifen Z-isomer (contains 3% E isomer))

Phenol, 4-[(1Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-

Tamoxifen Citrate Impurity 17((Z)-4-Hydroxy-N-Desmethyl Tamoxifen)

Endoxifen HCl Endoxifen Z-isomer

Tamoxifen Impurity 15

Potassium Channel,Endoxifen (Z-isomer),Endoxifen (Zisomer),Endoxifen (Z isomer),Inhibitor,KcsA,inhibit,Estrogen Receptor/ERR

Endoxifen (Z-isomer), 10 mM in DMSO

Tamoxifen Citrate Impurity 15

112093-28-4

Inhibitors

Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals

Aromatics

Intermediates & Fine Chemicals

Metabolites & Impurities

Pharmaceuticals