Ciclesonide

ChemicalBook > CAS DataBase List > Ciclesonide

Product Name: Ciclesonide
CAS No.: 126544-47-6
Chemical Name: Ciclesonide
Synonyms: Zetonna;Ciclesonide;Cyclosonide;Ciclesonide CRS;Alvesco, Ciclesonide;C11666300 Ciclesonide;Ciclesonide(RPR251526);Ciclesonide, 10 mM in DMSO;Ciclesonide containing impurity A CRS;(11β,16α)-16,17-[[(R)-CyclohexylMethylene]bis(oxy)]-11-hydroxy-21-(2-Methyl-1-oxopropoxy)-pregna-1,4-diene-3,20-dione
CBNumber: CB3717420
Molecular Formula: C32H44O7
Formula Weight: 540.69
MOL File: 126544-47-6.mol

Less

Ciclesonide Property

Melting point:: 202-209?C
Boiling point:: 665.0±55.0 °C(Predicted)
Density: 1.23±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,2-8°C
solubility: Chlorofrom (Slightly), Methanol (Slightly)
form: Solid
pka: 14.25±0.70(Predicted)
color: White to Off-White
biological source: synthetic
Water Solubility: water: <0.1g/L
acetone: soluble
ethanol: soluble
InChIKey: LUKZNWIVRBCLON-GXOBDPJESA-N
SMILES: [C@@]12(C(=O)COC(=O)C(C)C)O[C@H](C3CCCCC3)O[C@@H]1C[C@@]1([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]21C |&1:0,11,19,21,23,33,35,37,40,r|

Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

Less

N-Bromosuccinimide Price

Sigma-Aldrich

Product number: Y0001553
Product name: Ciclesonide
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: y0001553
Price: $220
Updated: 2024/03/01

Cayman Chemical

Product number: 18227
Product name: Ciclesonide
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 18227
Product name: Ciclesonide
Purity: ≥98%
Packaging: 5mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 18227
Product name: Ciclesonide
Purity: ≥98%
Packaging: 10mg
Price: $184
Updated: 2024/03/01

Cayman Chemical

Product number: 18227
Product name: Ciclesonide
Purity: ≥98%
Packaging: 50mg
Price: $759
Updated: 2024/03/01

Less

Ciclesonide Chemical Properties,Usage,Production

Description

Ciclesonide, a new inhaled corticosteroid (ICS), is indicated for the prophylactic treatment of persistent asthma. ICS treatment is a widely accepted standard of care for maintenance therapy of chronic asthma, and the currently available agents include fluticasone propionate, budesonide, triamcinolone acetonide, flunisolide, and beclomethasone dipropionate. These agents exert their potent anti-inflammatory effects via modulation of the glucocorticoid receptor (GR). Although ICS drugs are generally safe and well tolerated compared with oral corticosteroids, many have measurable systemic exposures, and concerns over potential side effects resulting from it severely limit the dose at which they can be administered for long-term therapy. Systemic adverse effects associated with corticosteroids include HPA axis suppression, osteoporosis, abnormal glucose metabolism, cataracts, and glaucoma, some of which could potentially occur with the long-term use of high dose ICS. The key differentiators for ciclesonide relative to other ICS drugs are its longer duration of action and lower systemic exposure. Ciclesonide is an isobutyryl ester prodrug. It is cleaved by the endogenous esterases in the lung to des-isobutyryl ciclesonide (des- CIC), which is a potent GR agonist. The binding affinity of des-CIC for human GR (K_i=0.31 nM) is similar to other ICS such as budesonide (K_i=0.44nM) and fluticasone propionate (K_i=0.24nM), while ciclesonide itself has about 100-fold lower affinity (K_i=37nM). In lung tissue, des-CIC undergoes reversible lipid conjugation to form oleate and palmitate ester conjugates, which act as a slow-release pool for the drug and increase the pulmonary residence time. This, in turn, contributes to the enhanced local effects and the long duration of action.
Inhaled ciclesonide was generally well tolerated in these clinical studies. Ciclesonide did not suppress biochemical markers of adrenal function in 52-week studies; however, the long-term (＞52 weeks) systemic effects remain unknown. Ciclesonide is chemically produced via a semi-synthesis starting from 16-α-hydroxyprednisolone by first converting to a triisobutyryl ester intermediate with isobutyric anhydride, and subsequent reaction of the triester with cyclohexane carboxaldehyde and hydrochloric acid in dioxane. The latter step produces the cyclic ketal as a mixture of diastereomers, which is subjected to HPLC and fractional crystallization to produce ciclesonide.

Chemical Properties

White Solid

Originator

Recordati Espana (Spain)

Uses

A glucocorticoid microemulsion nasal preparation allergy inhibitor rhinitis.

Definition

ChEBI: Ciclesonide is an organic molecular entity.

brand name

Alvesco (Dynamit Nobel GmbH).

General Description

Ciclesonide (Omnaris) is a prodrug that requireshydrolysis of the isobutyrate ester at C21 to form theactive corticosteroid (des-ciclesonide). It has minimal oralbioavailability due to extensive metabolism, mainly byCYP3A4. The metabolites of ciclesonide have not beenfully characterized.

Synthesis

Two separate approaches to the syntheses of the chiral ciclesonide have been described in the patent literature. The first route involves a chiral resolution step and the second approach highlights a stereoselective trans acetalization approach. The first synthesis of ciclesonide started by reacting (11|?,16|á)-11, 16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione (1) with isobutyric anhydride to make the tri-isobutyl ester in 87% yield. Reaction of the tri-ester with cyclohexane carboxaldehyde in the presence of HCl and 70% perchloric acid gave the cyclohexane acetal 3, which was then separated into the desired isomer ciclesonide (I) by HPLC or recrystallization.

storage

Store at +4°C

Ciclesonide Preparation Products And Raw materials

Raw materials

Preparation Products

Less

Ciclesonide Suppliers

Americas 1 Canada 1 China 188 Europe 3 Germany 1 India 9 Japan 1 The Netherlands 1 United Kingdom 9 United States 24 Global 238

Nanjing LuoDa Chemical Co., Ltd

Tel: 025-66016961 13382082786
Fax: 025-52204547
Country: China
ProdList: 287
Advantage: 55

Jiangxi ravel Biotechnology Co.,Ltd

Tel: 18502762009
Email: 721846333@qq.com
Country: China
ProdList: 2449
Advantage: 58

Shanghai Boyle Chemical Co., Ltd.

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

Chembest Research Laboratories Limited

Tel: +86-21-20908456
Fax: 021-58180499
Email: sales@BioChemBest.com
Country: China
ProdList: 6005
Advantage: 61

Shanghai Hanhong Scientific Co.,Ltd.

Tel: 021-54306202 13764082696
Email: info@hanhongsci.com
Country: China
ProdList: 42958
Advantage: 64

Chemsky（shanghai）International Co.,Ltd.

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

China DongFan Chemical Co.,LTD

Tel: 86-0571-85151182
Fax: 86-0571-85151182
Country: China
ProdList: 5691
Advantage: 66

XiaoGan ShenYuan ChemPharm co,ltd

Tel: 15527768850
Email: 1791901229@qq.com
Country: China
ProdList: 8835
Advantage: 52

Hangzhou Yuhao Chemical Technology Co., Ltd

Tel: 0571-82693216
Fax: +86-571-82880190
Email: info@yuhaochemical.com
Country: China
ProdList: 9387
Advantage: 52

Shanghai Sphchem Co., Ltd.

Tel: 021-56491756 13512199871
Fax: 021-5649-1756
Email: 2819742715@qq.com
Country: China
ProdList: 4001
Advantage: 55

Chengdu Ai Keda Chemical Technology Co., Ltd.

Tel: 4008-755-333 18080918076
Fax: 028-86757656
Email: 800078821@qq.com
Country: China
ProdList: 9718
Advantage: 55

Shanghai SynFarm Pharmaceutical Technology Co., Ltd.

Tel: 021-50793966 18917198199
Fax: +86-21-50793967
Email: info@synfarm.com
Country: China
ProdList: 280
Advantage: 58

S.Z. PhyStandard Bio-Tech. Co., Ltd.

Tel: 0755-83725681-603
Fax: +86 755 28094224
Country: China
ProdList: 4496
Advantage: 50

Beijing HuaMeiHuLiBiological Chemical

Tel: 010-56205725
Fax: 010-65763397
Email: waley188@sohu.com
Country: China
ProdList: 12335
Advantage: 58

NCE Biomedical Co.,Ltd.

Tel: 4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
Fax: +86-27-87599188
Country: China
ProdList: 1493
Advantage: 55

Shanghai T&W Pharmaceutical Co., Ltd.

Tel: +86 21 61551611
Fax: +86 21 50676805
Country: China
ProdList: 9891
Advantage: 58

Haoyuan Chemexpress Co., Ltd.

Tel: 021-58950125
Fax: (86) 21-58955996
Email: info@chemexpress.com
Country: China
ProdList: 7552
Advantage: 61

UHN Shanghai Research & Development Co., Ltd.

Tel: 021-58958002 18930822973
Fax: +86 (21) 5895-8628
Email: sales@uhnshanghai.com
Country: China
ProdList: 997
Advantage: 58

China Nobel Chem Co., Limited

Tel: +86(0)21 60484900
Fax: +86(0)21 60484900
Country: China
ProdList: 764
Advantage: 50

Guangzhou Isun Pharmaceutical Co., Ltd

Tel: 020-39119399 18927568969
Fax: 020-39119999
Email: isunpharm@qq.com
Country: China
ProdList: 4674
Advantage: 55

Nanjing Sunlida Biological Technology Co., Ltd.

Tel: 025-57798810
Fax: 025-57019371
Email: sales@sunlidabio.com
Country: China
ProdList: 3239
Advantage: 55

TargetMol Chemicals Inc.

Tel: 021-021-33632979 15002134094
Fax: 021-33632979
Email: marketing@targetmol.com
Country: China
ProdList: 7783
Advantage: 58

Vientiane Tianjin Hengyuan Technology Co., Ltd.

Tel: 15722085254
Fax: 022-26358246
Email: phytochemical@126.com
Country: China
ProdList: 813
Advantage: 55

ChemStrong Scientific Co.,Ltd

Tel: 0755-0755-66853366 13670046396
Fax: 0755-28363542
Email: sales@chem-strong.com
Country: China
ProdList: 18097
Advantage: 56

Chengdu HuaXia Chemical Reagent Co. Ltd

Tel: 400-1166-196 13458535857
Fax: QQ：800101999
Email: cdhxsj@163.com
Country: China
ProdList: 13350
Advantage: 58

Suzhou yacoo science co.,Ltd

Tel: 0512-87182056 18013166090
Fax: 0512-87182056
Email: lingling.qi@yacoo.com.cn
Country: China
ProdList: 7295
Advantage: 60

Wuhan Dahua Pharmaceutical Co., Ltd.

Tel: 027-59262863 13277907145 3091977954
Fax: 027-59420980
Country: China
ProdList: 4943
Advantage: 58

Credit Asia Chemical Co., Ltd.

Tel: +86 (21) 61124340
Fax: +86 (21) 6129-4103
Country: China
ProdList: 9756
Advantage: 58

LETOPHARM LIMITED

Tel: +86-21-5821 5861
Fax: +86-21-5106 2861
Email: sales@letopharm.com
Country: China
ProdList: 2384
Advantage: 58

Guangzhou Ciming Biological Technology Co., Ltd.

Tel: 020-38082199,29065168,38082986,29878298,29866629,4000192398
Fax: +86 (20)38082986
Country: China
ProdList: 830
Advantage: 60

Shanghai Lollane Biological Technology Co.,Ltd.

Tel: 021-52996696，15000506266 15000506266
Fax: +86-21-52996696
Country: China
ProdList: 4569
Advantage: 55

Watson Biotechnology Co.,Ltd

Tel: 027-59207879 1972026995 18140587686
Fax: QQ：1972026995
Email: sales@3600chem.com
Country: China
ProdList: 4657
Advantage: 55

Jinan Putubio Tech Co., Ltd.

Tel: +86 (531) 8099-2215
Fax: +86 (531) 8099-2215
Email: putubio@outlook.com
Country: China
ProdList: 1261
Advantage: 55

Pharmacodia (Beijing) Co.,Ltd

Tel: +86-400-851-9921
Fax: +86-10-82826195
Email: sales@pharmacodia.com
Country: China
ProdList: 2317
Advantage: 55

Guangzhou QiYun Biotechnology Co., Ltd.

Tel: 020-61288194 61288195
Fax: 020-61288700
Email: 505721671@qq.com
Country: China
ProdList: 3866
Advantage: 58

Shanghai YuanYe Biotechnology Co., Ltd.

Tel: 021-61312847; 18021002903
Fax: QQ:3008007432
Email: 3008007409@qq.com
Country: China
ProdList: 27313
Advantage: 60

parabiochem

Tel: 025-83453382-8005
Fax: 025-83453382
Email: sale@parabiochem.com
Country: China
ProdList: 9595
Advantage: 55

Raw material medicin reagent co.,Ltd

Tel
Email: sales@njromanme.com
Country: China
ProdList: 4529
Advantage: 58

Shanghai Rechem science Co., Ltd.

Tel: 21-31433387 15618786686
Fax: QQ:1369748377
Email: sales@rechemscience.com
Country: China
ProdList: 2948
Advantage: 58

Beijing Solarbio Science & Tecnology Co., Ltd.

Tel: 010-50973130 4009686088
Email: 3193328036@qq.com
Country: China
ProdList: 29764
Advantage: 68

Hubei widely chemical technology Co., Ltd.

Tel: 027-83991130 18627774460
Fax: 027-83991130
Email: 1718093273@QQ.COM
Country: China
ProdList: 1879
Advantage: 58

Anhui Shixing Chemical Co., Ltd.

Tel: 0551-65361219 17756579152
Fax: 0551-65361219
Email: hfchuandi@163.com
Country: China
ProdList: 112
Advantage: 58

Amadis Chemical Company Limited

Tel: 571-89925085
Fax: 0086-571-89925065
Email: sales@amadischem.com
Country: China
ProdList: 131957
Advantage: 58

Guangzhou Kafen Biotech Co.,Ltd

Tel: 18029243487 2355327168
Fax: 020-31121510
Email: gy@yccreate.com
Country: China
ProdList: 4749
Advantage: 55

Lynnchem

Tel: 86-(0)29-85992781 17792393971
Email: info@lynnchem.com
Country: China
ProdList: 4587
Advantage: 58

Wuhan Runzeweiye Technology Co., Ltd.

Tel: 15172337137 15172337137
Fax: 027-50779735
Email: 940329747@qq.com
Country: China
ProdList: 632
Advantage: 55

Wuhai Shuou Technology Co., Ltd.

Tel: 17792809151
Fax: 18872220797
Email: 2355916837@ycphar.com
Country: China
ProdList: 6133
Advantage: 55

Nanjing Klender Bio-Technology Co., Ltd.

Tel: 025-52343882 18112933882
Fax: 025-52343882
Email: sales@kldbio.com
Country: China
ProdList: 2019
Advantage: 55

Wellman Pharmaceutical Group Limited

Tel: 027-83778875 15807197853
Fax: 027-83991220
Email: 15807197853@163.com
Country: China
ProdList: 4032
Advantage: 58

Wuhan Zonvsicom chemicals Co.,Ltd.

Tel: 15623071665
Fax: 027-59257948
Email: sales@zvsicom.com
Country: China
ProdList: 299
Advantage: 58

Less

View Lastest Price from Ciclesonide manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Ciclesonide 126544-47-6
Price: US $0.00/g
Min. Order: 10g
Purity: 97.0-103.0%
Supply Ability: 50kg/month
Release date: 2021-06-19

Henan Bao Enluo International TradeCo.，LTD

Product: Ciclesonide 126544-47-6
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000tons
Release date: 2023-07-26

Jiangsu Monade Biological Technology Co., Ltd.

Product: Ciclesonide 126544-47-6
Price: US $0.00/g
Min. Order: 100g
Purity: 99.99%
Supply Ability: 10000
Release date: 2021-09-06

126544-47-6, CiclesonideRelated Search:

(r)-budesonide Halcinonide Desonide Desisobutyryl Ciclesonide Cyclohexanecarboxaldehyde Ciclesonide Prednisolone 16alpha-Hydroxyprednisonlone acetate Prednisolone-21-acetate 11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Budesonide Ciclesonide

(r)-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde 21-isobutyrate

Ciclesonide

(11β,16α)-16,17-[[(R)-CyclohexylMethylene]bis(oxy)]-11-hydroxy-21-(2-Methyl-1-oxopropoxy)-pregna-1,4-diene-3,20-dione

Ciclesonide(RPR251526)

Ciclesonide containing impurity A CRS

Ciclesonide CRS

Zetonna

Pregna-1,4-diene-3,20-dione, 16,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11β,16α)-

2-[(6aR,6bS,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-Cyclohexyl-7-hydroxy-6a,8a-dimethyl-4-oxo-1,2,4,6a,6b,7,8,8a,11a,12,12a,12b-dodecahydro-8bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl]-2-oxoethyl Isobutyrate

Alvesco, Ciclesonide

Pregna-1,4-diene-3,20-dione,16,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-,(11b,16a)-

(2′R)-2′-c yc loh e xyl-11β-h yd roxy-3,20-d i oxo-16βh -[1,3]d i oxolo[4′,5′:16,17]pre g na -1,4-d i e n-21-yl 2-me th ylpropa noa te

Cyclosonide

C11666300 Ciclesonide

Ciclesonide, 10 mM in DMSO

126544-47-6

C33H46O7

C32H44O7

Other APIs

Inhibitors

Intermediates & Fine Chemicals

Pharmaceuticals

Steroids