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Desvenlafaxine succinate

Desvenlafaxine succinate Structure
Desvenlafaxine succinate
  • CAS No.386750-22-7
  • Chemical Name:Desvenlafaxine succinate
  • CBNumber:CB01459766
  • Molecular Formula:C20H31NO6
  • Formula Weight:381.47
  • MOL File:386750-22-7.mol
Desvenlafaxine succinate Property
  • storage temp. Store at +4°C
  • solubility DMSO:3.0(Max Conc. mg/mL);7.51(Max Conc. mM)
  • form Powder
  • color White to off-white
  • Stability Hygroscopic
  • InChI InChI=1S/C16H25NO2.C4H6O4/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16;5-3(6)1-2-4(7)8/h6-9,15,18-19H,3-5,10-12H2,1-2H3;1-2H2,(H,5,6)(H,7,8)
  • InChIKey ORUUBRMVQCKYHB-UHFFFAOYSA-N
  • SMILES C(C(=O)O)CC(=O)O.C(C1C=CC(O)=CC=1)(C1(CCCCC1)O)CN(C)C
  • FDA UNII ZB22ENF0XR
  • NCI Drug Dictionary desvenlafaxine succinate
  • UNSPSC Code 41116107
  • NACRES NA.24
Safety
  • HS Code  :2922504500
  • NFPA 704:
    0
    2 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H302-H315-H319-H335
  • Precautionary statements P261-P305+P351+P338

Desvenlafaxine succinate Chemical Properties,Usage,Production

  • Description Desvenlafaxine Succinate is a dual serotonin and norepinephrine reuptake inhibitor (SNRI) that was approved for the treatment of major depressive disorder (MDD) in the United States in 2008. In order to improve the efficacy and safety profile of venlafaxine, Wyeth discovered and developed one of the major metabolites of venlafaxine, namely the O-desmethyl metabolite (desvenlafaxine). Desvenlafaxine is also being developed for the treatment of moderate to severe vasomotor symptoms associated with menopause (i.e., hot flashes and night sweats) and is also in phase III clinical trials to study it’s effectiveness in treating fibromyalgia and neuropathic pain.
  • Chemical Properties Desvenlafaxine succinate (Pristiq SR) is an extended-release tablet for oral administration that contains desvenlafaxine succinate, a structurally novel SNRI for treating MDD. Desvenlafaxine succinate is a white to off-white powder that is soluble in water. The solubility of Desvenlafaxine succinate is pH-dependent. Its octanol: aqueous system (at pH 7.0) partition coefficient is 0.21. Desvenlafaxine succinate (Pristiq SR) is available as a 50 mg extended-release tablet for oral administration. The 50 mg tablet consists of light pink, square (pyramid, one-sided), film-coated tablets debossed “W” over “50” on the flat side.
  • Uses Antianxiety therapeutic
  • Synthesis Desvenlafaxine has been prepared via two different routes, and both are described in the scheme. The first route involved simple demethylation of venlafaxine (67) using L-selectride in dimethoxyethane giving desvenlafaxine 68 as its free base in 91% yield. Compound 68 was then recrystallized with succinic acid in acetone/ water to give desvenlafaxine succinate (VIII) in 86% yield. An alternative method to prepare desvenlafaxine is described in the bottom portion of the scheme. 4-Benzyloxyphenylacetic acid 69 was converted to its corresponding acid chloride upon treatment with thionyl chloride and catalytic DMF in refluxing methylene chloride. The crude reaction mixture was added to a solution of dimethylamine hydrochloride and triethyl amine in methylene chloride at 5 ??C to give dimethylacetamide 70 in 90% yield. Deprotonation of 70 with LHMDS in THF at -70 ??C followed by addition of cyclohexanone gave alcohol 71 in 82% yield. Reduction of the acetamide with borane THF complex in refluxing THF produced dimethyl amine 72 in 66% yield. Catalytic hydrogenation in the presence of 20% Pd/C effected debenzylation of 72 to give desvenlafaxine free base 68 in 87% yield.

    Synthesis_386750-22-7

  • in vivo

    Desvenlafaxine succinate hydrate (30 mg/kg, orally) significantly increases extracellular NE levels but had no effect on DA levels using microdialysis[1].

    Animal Model:Male rats[1].
    Dosage:30 mg/kg.
    Administration:Orally.
    Result:Significantly increased extracellular NE levels compared with baseline in the male rat hypothalamus but had no effect on DA levels using microdialysis.
Desvenlafaxine succinate Preparation Products And Raw materials
Raw materials
Preparation Products
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Desvenlafaxine succinate Spectrum
386750-22-7, Desvenlafaxine succinateRelated Search:
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  • 386750-22-7
  • Desvenlafaxine succinate hydrate, 10 mM in DMSO
  • Norvenlafaxine succinate
  • Desvenlafaxine Succinate (1-[2-(Dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol hydrogen butanedioate monohydrate) (1175773)
  • TIANFUCHEM-- Desvenlafaxine succinate
  • Desvenlafaxine succinateQ: What is Desvenlafaxine succinate Q: What is the CAS Number of Desvenlafaxine succinate Q: What is the storage condition of Desvenlafaxine succinate Q: What are the applications of Desvenlafaxine succinate
  • RAC-O-DESMETHYL VENLAFAXINE-D6 SUCCINATE HYDRATE
  • Desvenlafaxine succinate USP/EP/BP
  • [2H6]-rac-O-Desmethyl Venlafaxine Succinate Hydrate
  • Desvenlafaxine succinic acid monohydrate
  • PRISTIQ SUCCINATE HYDRATE;O-DESMETHYLVENLAFAXINE SUCCINATE HYDRATE
  • Pristiq succinate hydrate
  • O-Desmethylvenlafaxine succinate hydrate
  • Desvenla succinate
  • 2-(1-Hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]dimethylammonium3-carboxypropanoatemonohydrate
  • 4-(2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol succinate monohydrate
  • Butanedioic acid, compd. with 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol, hydrate (1:1:1)
  • Desvenlafaxine (O-DesMethyl Venlafaxine) Succinate Monohydrate
  • (1R)-2-(2-(diMethylaMino)-1-phenylethyl)cyclohexanol
  • WY 45233 succinate
  • 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenolsuccinate
  • C16H25NO2.HOOCCH2CH2COOH.H2O
  • Desvenlafaxine (succinate hydrate)
  • Unii-zb22enf0xr
  • Pristiq
  • Desvenlafaxine succinate monohydrate

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