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Fexofenadine hydrochloride Produkt Beschreibung

Fexofenadine hydrochloride  Struktur
153439-40-8
CAS-Nr.
153439-40-8
Englisch Name:
Fexofenadine hydrochloride
Synonyma:
Fexo;Allegra;Telfast;Alernex;Feksine;Fexofen;Fexadyne;Vivafeks;MDL 16455A;Telfast BD
CBNumber:
CB0256621
Summenformel:
C32H40ClNO4
Molgewicht:
538.13
MOL-Datei:
153439-40-8.mol

Fexofenadine hydrochloride Eigenschaften

Schmelzpunkt:
148-150oC
RTECS-Nr.
CY1633377
storage temp. 
2-8°C
Löslichkeit
Soluble in Dimethyl sulfoxide (50 mM), and methanol.
Aggregatzustand
powder
Farbe
white to beige
Merck 
14,4068
InChIKey
RRJFVPUCXDGFJB-UHFFFAOYSA-N
CAS Datenbank
153439-40-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher Xi
R-Sätze: 36/37/38
S-Sätze: 26-36
WGK Germany  3
HS Code  2933399090

Fexofenadine hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Chemische Eigenschaften

Off-White Crystalline Solid

Originator

Alernex,Dabur Pharmaceuticals Ltd.,India

Verwenden

A metabolite of of terfenadine, a H1-Histamine receptor antagonist

Verwenden

The active metabolite of Terfenadine (T114500), a H1-histamine receptor antagonist.

Verwenden

Antihistaminic;histamine H1-receptor antagonist

Verwenden

Fexofenadine is a non-sedating antihistamine that selectively antagonizes the histamine H1 receptor with a Ki value of 10 nM and exhibits anti-inflammatory effects. It is devoid of central nervous system effects in part because it is a good substrate for the P-glycoprotein efflux pump situated within the blood-brain barrier.[Cayman Chemical]

Manufacturing Process

Microbiological Preparation of Fexofenadine (Patent U.S. 6,558,931)
Ten 250 ml Erlenmeyer flasks containing 100 ml of medium D are seeded with A. corymbifera LCP 63-1800. 50 mg of Terfenadine in 1 ml of ethanol is added to each Erlenmeyer flask. The content of 10 Erlenmeyer flasks are filtered on gauze (the supernatant has a pH equal to 8.0), and saturation with sodium chloride is carried out for 2 hours (pH = 5-6), followed by extracting 3 times with ethyl acetate and drying over magnesium sulfate. After evaporation under reduced pressure, 409 mg of expected crude product is obtained (yield = 77%, approximately 90% pure product). This product is purified on a column of silica gel (230-400 mesh, 40 g of silica, diameter = 3 cm) eluting with a methylene chloride/methanol/ammonium hydroxide mixture (82.5:15:2.5). 312 mg of pure Fexofenadine is recovered (61.4%).
Synthesis of Fexofenadine (Patent U.S. No. 5,578,610
Aluminum chloride (44 g; 0.33 mol) was added in portions to a solution of freshly distilled 4-chlorobutyryl chloride (17 mL; 0.15 mol) in 460 mL of carbon disulfide at -10°C under a nitrogen atmosphere. The mixture was stirred for 15 min, then the cooling bath was removed and the mixture was allowed to warm to ambient temperature. The mixture was stirred then for 15 min more, then cooled again to -10°C and a solution of ethyl-α,α- dimethylphenyl acetate (26.6 g; 0.14 mol) in 70 mL of carbon disulfide was added dropwise. The mixture was stirred for 3 hours, then stirred overnight at room temperature. The reaction mixture was partitioned between water and CHCl3. The combined organic portions were dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 and filtered through a plug of SiO2, eluting with 10% EtOAc in hexane. Yield of ethyl 3- and 4-(4-chloro-1-oxobutyl)-α,α-dimethylphenylacetate 39.4 g (as a mixture of aromatic regioisomers).
To a solution of 39.4 g of ethyl 3- and 4-(4-chloro-1-oxobutyl)-α,α- dimethylphenylacetate dissolved in 800 mL of methanol and 200 mL of water was added 40 g of NaOH. The mixture was refluxed for one hour. The cooled mixture was then concentrated in vacuo. The concentrate was diluted with water and washed with 2 portions of EtOAc. The aqueous layer was acidified with concentrated HCl and extracted with 2 portions of EtOAc. The extracts were dried over MgSO4, filtered, and concentrated in vacuo to afford 30.3 g of crude product. The crude product was dissolved in 600 mL of EtOAc, 38 g of cinchonidine was added, and the mixture was stirred overnight. The resulting solids were filtered and washed with EtOAc and sucked dry under a rubber dam to afford 25 g of a solid 4-(cyclopropyl-oxo-methyl)-α,α- dimethylphenylacetic acid.
A solution of 10.5 g of 4-(cyclopropyl-oxo-methyl)-α,α-dimethylphenylacetic acid in 250 mL of CH2Cl2 was cooled in an ice-MeOH bath and 25 g of trimethylsilyliodide was then added via pipette. The mixture was stirred in the ice bath for one hour, warmed to ambient temperature, and stirred for one hour. A solution of aqueous sodium bisulfite was then added and the mixture was stirred well. The phases were partitioned and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated in vacuo to afford 12.6 g (77%) of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid.
To a solution of 12.6 g of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid in 100 mL of ether cooled in an ice bath, was added 40 mL of ethereal CH2N2. The mixture was stirred at 0°C for few minutes, then let stand for 2 hours. A few drops of AcOH were added to decompose excess CH2N2, then the mixture was filtered and stripped to afford 12.6 g (96%) of methyl 4-(4-iodo-1- oxobutyl)-α,α-dimethylphenylacetate.
A solution of 12.6 g of methyl 4-(4-iodo-1-oxobutyl)-α,α- dimethylphenylacetate in 500 mL of toluene in a one liter three neck flask was added 8.8

Therapeutic Function

Antihistaminic

Allgemeine Beschreibung

Fexofenadine hydrochloride, (±)-4-[1-hydroxy-4-[4-(hydroxyldiphenylmethyl)- 1-piperinyl]butyl-α,α-dimethylbenzeneacetic acid (Allegra), occurs as a white to off-white crystalline powder that is freely soluble in methanol and ethanol, slightly soluble in chloroform and water, and insoluble in hexane.
This compound is marketed as a racemate and exists as a zwitterion in aqueous media at physiological pH. Fexofenadine is a primary oxidative metabolite of terfenadine. Terfenadine was developed during a search for new butyrophenone antipsychotic drugs as evidenced by the presence of the N-phenylbutanol substituent. It also contains a diphenylmethyl-piperidine moiety analogous to that found in the piperazine antihistamines.

Biologische Aktivität

Selective histamine H 1 receptor antagonist (pK i = 8.1). Active metabolite of terfenadine that displays non-sedating antiallergic effects.牋.

Fexofenadine hydrochloride Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Fexofenadine hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 350)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20010 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21032 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Shanghai Time Chemicals CO., Ltd.
+8618017249410 +86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
02783214688 bruce@xrdchem.cn CHINA 567 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 3001 55
Shanxi Naipu Import and Export Co.,Ltd
+8613734021967
kaia@neputrading.com CHINA 1011 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29961 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58

153439-40-8()Verwandte Suche:


  • α,α-dimethyl-4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]benzeneacetic acid
  • Benzeneacetic acid, 4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-α,α-dimethyl-, hydrochloride
  • MDL 16455A
  • Telfast
  • Telfast BD
  • 2-[4-[1-Hydroxy-4-[4-(hydroxy-diphenyl-methyl)-1-piperidyl]-butyl]phenyl]-2-methyl-propanoic acid hydrochloride
  • Allegra
  • Fexofenadine hydrochloride
  • 2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]-1-piperidyl]butyl]phenyl]-2-methyl-propionic acid hydrochloride
  • FERULICACIDPIPERAZINE
  • (Carboxyterfenadine-D10,Terfenadinecarboxylate)
  • Fexofenidine hydrochloride, MDL 16455 hydrochloride, Terfenidine carboxylate hydrochloride
  • (138452-21-8) fexofenadine hydrochloride
  • 2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]phenyl]-2-methylpropanoic acid hydrochloride
  • 2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]phenyl]-2-methyl-propanoic acid hydrochloride
  • Fexofenadine(Hclform)
  • α,α-Dimethyl-4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-benzeneaceticacidhydrochloride
  • Fexofenadine hydrochloride,Fexofenidine hydrochloride, MDL 16455 hydrochloride, Terfenidine carboxylate hydrochloride
  • 2-{4-[(1R)-1-hydroxy-4-[4-(hydroxydiphenylMethyl)piperidin-1-yl]butyl]phenyl}-2-Methylpropanoic acid
  • 4-[1-Hydroxy-4-[4-(hydroxydiphenylMethyl)-1-piperidinyl]butyl]-α,α-diMethylbenzeneacetic Acid Hydrochloride
  • Alernex
  • Carboxyterfenadine Hydrochloride
  • Feksine
  • Fexadyne
  • Fexo
  • Fexofen
  • Terfenadinecarboxylate Hydrochloride
  • Vivafeks
  • (R)-2-(4-(1-hydroxy-4-(4-(hydroxydiphenylMethyl)piperidin-1-yl)butyl)phenyl)-2-Methylpropanoic acid hydrochloride
  • 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid h
  • Benzeneaceticacid, 4-[1-hydroxy-4-[4-(hydroxydiphenylMethyl)-1-piperidinyl]butyl]-a,a-diMethyl-,hydrochloride (1:1)
  • feofenadine hydrochloride
  • 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic aci
  • FEXOFENADINE-D10 HCL
  • Non - Determination of hydrochloride
  • FexofenadineHydrochloride>
  • Fexofenadine Hydrochloride RS
  • Fexofenadine hydrochloride CRS
  • Fexofenadine hydrochloride b
  • Fexofenadine hydrochloride Fexofenadine hcl
  • Fexofenadine hydrochloride USP/EP/BP
  • Fexofenadine hydrochloride salt
  • 153439-40-8
  • C32H29D10NO4HCl
  • C32H39NO4ClH
  • C32H39NO4xHCl
  • C32H40ClNO4
  • C32H39ClNO4
  • API
  • Aromatics
  • Heterocycles
  • Metabolites & Impurities
  • Intermediates & Fine Chemicals
  • Metabolites
  • Pharmaceuticals
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