386750-22-7 Usage
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. It is a major metabolite of venlafaxine, developed by Wyeth to improve the efficacy and safety profile of the original drug. Desvenlafaxine is also being explored for its potential in treating moderate to severe vasomotor symptoms associated with menopause, as well as fibromyalgia and neuropathic pain.
Uses
Used in Antidepressant Applications:
Desvenlafaxine succinate is used as an antidepressant for the treatment of major depressive disorder (MDD). It works by inhibiting the reuptake of serotonin and norepinephrine, thereby increasing their levels in the brain and improving mood and reducing depressive symptoms.
Used in Antianxiety Applications:
Desvenlafaxine succinate is used as an antianxiety therapeutic for managing anxiety symptoms that may accompany major depressive disorder or other anxiety-related conditions. By modulating the levels of serotonin and norepinephrine, it can help alleviate anxiety and promote a sense of calm.
Used in Menopause Treatment:
Desvenlafaxine succinate is used as a treatment for moderate to severe vasomotor symptoms associated with menopause, such as hot flashes and night sweats. Its dual action on serotonin and norepinephrine reuptake can help alleviate these uncomfortable symptoms and improve the quality of life for menopausal women.
Used in Pain Management:
Desvenlafaxine succinate is being studied for its potential use in treating fibromyalgia and neuropathic pain. As an SNRI, it may help alleviate chronic pain by modulating the levels of serotonin and norepinephrine in the brain, which are neurotransmitters involved in pain perception and modulation.
Used in Clinical Trials:
Desvenlafaxine succinate is currently in phase III clinical trials to further evaluate its effectiveness in treating fibromyalgia and neuropathic pain. These trials aim to provide more evidence-based data on the drug's efficacy and safety profile for these specific conditions.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 386750-22-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,8,6,7,5 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 386750-22:
(8*3)+(7*8)+(6*6)+(5*7)+(4*5)+(3*0)+(2*2)+(1*2)=177
177 % 10 = 7
So 386750-22-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H25NO2.C4H6O4.H2O/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);1H2
386750-22-7Relevant articles and documents
A succinic acid to a venlafaxine monohydrate new crystal and preparation method (by machine translation)
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Paragraph 0059; 0060, (2017/06/20)
The invention relates to a venlafaxine succinate monohydrate of the new crystalline form VI, the crystalline form VI of the X - ray powder diffraction pattern includes the following 2 θ angle peaks represented in: 5.14 °, 10 . 26°, 13 . 16°, 14 . 28°, 16 . 67°, 19 . 14°, 20 . 60°, 23 . 30° and 25.86 °. The invention also relates to a method for preparing said form VI. The invention VI crystalline form is easy to prepare, has good stability and preparation moldability, and compared with the yu Jingxing I, II and M, crystalline form VI production yield optimum, the prepared tablet release curve closer to the commercial preparation. (by machine translation)
NOVEL HYDRATE FORM OF O-DESMETHYL VENLAFAXINE SUCCINATE
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Page/Page column 10, (2008/06/13)
The present invention relates to a novel hydrate form of O-desmethyl venlafaxine succinate. The present invention further relates to processes for the preparation of the novel hydrate form, pharmaceutical compositions comprising it, second medical uses of the novel hydrate form, and methods using it for treating diseases such as generalised anxiety disorder, anxiety, depressive disorder, depression and panic disorder.
