Desvenlafaxine

Các tên gọi khác (4 ) :

Desvenlafaxine
O-desmethylvenlafaxine
ODV
Pristiq

serotonin uptake inhibitors, neurotransmitter uptake inhibitors, antidepressive agents

Thuốc Gốc

Small Molecule

CAS: 93413-62-8

CTHH: C₁₆H₂₅NO₂

PTK: 263.3752

Desvenlafaxine (O-desmethylvenlafaxine) the major active metabolite of venlafaxine, is an antidepressant from the serotonin-norepinephrine reuptake inhibitor (SNRI class). Desvenlafaxine may be used to treat major depressive disorder and is being studied for use in the management of vasomotor symptoms in postmenopausal women. It is formulated as an extended release tablet. FDA approved in 2008.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₆H₂₅NO₂

Phân tử khối

263.3752

Monoisotopic mass

263.188529049

InChI

InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3

InChI Key

InChIKey=KYYIDSXMWOZKMP-UHFFFAOYSA-N

IUPAC Name

4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol

Traditional IUPAC Name

desvenlafaxine

SMILES

CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1

Độ hòa tan

Soluble

logP

0.21

logS

-2.3

pKa (strongest acidic)

10.11

pKa (Strongest Basic)

8.87

PSA

43.7 Å²

Refractivity

78.54 m³·mol^-1

Polarizability

30.29 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : Desvenlafaxine is a selective serotonin and norepinephrine reuptake inhibitor. It lacks significant activity on muscarinic-cholinergic, H₁-histaminergic, or α₁-adrenergic receptors in vitro. Desvenlafaxine does not appear to exert activity against calcium, chloride, potassium and sodium ion channels and also lacks monoamine oxidase (MAO) inhibitory activity. It was also shown to lack significant activity again the cardiac potassium channel, hERG, in vitro. Compared to other SNRIs, desvenlafaxine undergoes simple metabolism, has a low risk of drug-drug interactions and does not have to be extensively titrated to reach a therapeutic dose. Some of the limitations of desvenlafaxine include moderate efficacy in the treatment of major depressive disorder, similar safety and tolerability profile to other SNRIs and possible transient discontinuation symptoms upon cessation of therapy.

Cơ Chế Tác Dụng : Desvenlafaxine (O-desmethylvenlafaxine) the major active metabolite of venlafaxine, is an antidepressant from the serotonin-norepinephrine reuptake inhibitor (SNRI class). Desvenlafaxine may be used to treat major depressive disorder and is being studied for use in the management of vasomotor symptoms in postmenopausal women. It is formulated as an extended release tablet. FDA approved in 2008. Desvenlafaxine, the major active metabolite of venlafaxine, is a selective serotonin and norepinephrine reuptake inhibitor. The clinical effect of desvenlafaxine is thought to occur via potentiation of serotonin and norepinephrine in the central nervous system. Unlike venlafaxine, desvenlafaxine is thought to have a differential serotonergic and noradrenergic activity profile.

Dược Động Học :

▧ Absorption :
Absolute bioavailability is approximately 80% and is unaffected by food. Peak plasma concentration is reached in 7.5 hours.
▧ Volume of Distribution :
3.4 L/kg, distribution into nonvascular compartments
▧ Protein binding :
~ 30%, protein binding is independent of drug concentration.
▧ Metabolism :
The primary route of metabolism is via conjugation mediated by UGT isoforms. Desvenlafaxine also undergoes oxidative N-demethylation via cytochrome P450 3A4 to a minor extent. CYP2D6 is not involved with the metabolism of desvenlafaxine.
▧ Route of Elimination :
Excreted in the urine. Approximately 45% of the total oral dose is excreted unchanged in urine. Approximately 19% of the total oral dose is excreted as the glucuronide metabolite and < 5% is excreted as the oxidative metabolite, N,O-didesmethylvenlafaxine. Excreted in human milk.
▧ Half Life :
The mean terminal half life is 11.1 hours and may be prolonged in patients with renal and/or moderate to severe hepatic impairment.

Độc Tính : The safety and tolerability of desvenlafaxine is similar to other SNRIs. Common side effects upon initiation or dose increase include increased blood pressure and heart rate, agitation, tremor, sweating, nausea, headache, and sleep disturbances. May cause sexual dysfunction and weight loss in some patients. May cause increases in fasting serum total cholesterol, LDL cholesterol, and triglycerides. Withdrawal effects may occur and thus, the dose of desvenlafaxine should be titrated down prior to discontinuation.

Chỉ Định : Desvenlafaxine is indicated for the treatment of major depressive disorder in adults.

Tương Tác Thuốc :

Almotriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Amitriptyline Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Amoxapine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Bromocriptine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Buspirone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Citalopram Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Clomipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Desipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dextromethorphan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dihydroergotamine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dipivefrin Desvenlafaxine may increase the tachycardic and vasopressor effects of dipivefrin. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Doxepin Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Duloxetine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Eletriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Ephedrine Desvenlafaxine may increase the tachycardic and vasopressor effects of ephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Epinephrine Desvenlafaxine may increase the tachycardic and vasopressor effects of epinephrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Ergoloid mesylate Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Ergonovine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Ergotamine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Escitalopram Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Fluoxetine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Fluvoxamine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Frovatriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Imipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Isocarboxazid Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Isometheptene Desvenlafaxine may increase the tachycardic and vasopressor effects of isometheptene. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
L-Tryptophan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Levonordefrin Desvenlafaxine may increase the tachycardic and vasopressor effects of levonordefrin. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Linezolid Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Lithium Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Maprotiline Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Methylergometrine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Milnacipran Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Mirtazapine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Moclobemide Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Naratriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Nefazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Norepinephrine Desvenlafaxine may increase the tachycardic and vasopressor effects of norepinephrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Nortriptyline Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Paroxetine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Pethidine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Phenelzine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Procarbazine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Promethazine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Protriptyline Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Pseudoephedrine Desvenlafaxine may increase the tachycardic and vasopressor effects of pseudoephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Rasagiline Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Rizatriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
S-Adenosylmethionine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Selegiline Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Sertraline Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Sibutramine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
St. John's Wort Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Sumatriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tapentadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tranylcypromine Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Zolmitriptan Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.

Liều Lượng & Cách Dùng : Tablet, film coated, extended release - Oral - 100 mg
Tablet, film coated, extended release - Oral - 50 mg

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Pristiq 50 mg extended-release tablet

Giá bán buôn : USD >4.31

Đơn vị tính : tablet
Biệt dược thương mại : Pristiq 100 mg extended-release tablet

Giá bán buôn : USD >4.46

Đơn vị tính : tablet

Nhà Sản Xuất

Công ty : Wyeth

Sản phẩm biệt dược : Pristiq
Công ty :

Sản phẩm biệt dược : Zyven-OD

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB06700

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=125017

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=99443254

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D02570

ChemSpider

http://www.chemspider.com/Chemical-Structure.111300.html

BindingDB

http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50010875

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0008-1211-14

PharmGKB

http://www.pharmgkb.org/drug/PA165958374

Wikipedia

http://en.wikipedia.org/wiki/Desvenlafaxine

RxList

http://www.rxlist.com/pristiq-drug.htm

PDRhealth

http://www.pdrhealth.com/drugs/rx/rx-mono.aspx?contentFileName=pri2009.html&contentName=Pristiq&contentId=611

Drugs.com

http://www.drugs.com/ppa/desvenlafaxine-succinate.html

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