Desvenlafaxine

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Desvenlafaxine
Desvenlafaxine.svg
Desvenlafaxine3Dan2.gif
Systematic (IUPAC) name
4-[2-dimethylamino-1-(1-hydroxycyclohexyl)
ethyl]phenol
Clinical data
Trade names Pristiq, Desfax
AHFS/Drugs.com monograph
MedlinePlus a608022
Licence data US FDA:link
Pregnancy
category
  • AU: B2
  • US: C (Risk not ruled out)
Legal status
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability 80%
Protein binding Low (30%)
Metabolism CYP3A4, (CYP2D6 is not involved)
Biological half-life 11 h
Excretion 45% excreted unchanged in urine
Identifiers
CAS Number 93413-62-8 YesY
ATC code N06AX23 (WHO)
PubChem CID: 125017
IUPHAR/BPS 7158
DrugBank DB06700 YesY
ChemSpider 111300 YesY
UNII NG99554ANW YesY
KEGG D07793 YesY
ChEBI CHEBI:83527 N
ChEMBL CHEMBL1118 YesY
Chemical data
Formula C16H25NO2
Molecular mass 263.38 g/mol
  • OC2(C(c1ccc(O)cc1)CN(C)C)CCCCC2
  • 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 YesY
  • Key:KYYIDSXMWOZKMP-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Desvenlafaxine (brand name: Pristiq, Desfax), also known as O-desmethylvenlafaxine, is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class developed and marketed by Wyeth (now part of Pfizer). Desvenlafaxine is a synthetic form of the major active metabolite of venlafaxine (sold under the brand names Effexor and Efexor). It is being targeted as the first non-hormonal based treatment for menopause.[1]

Medical uses

Desvenlafaxine's primary use in medicine is the treatment of major depressive disorder.[2]

Adverse effects

Adverse effect incidence[2][3][4]

Very common (>10% incidence) adverse effects include:

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  • Nausea
  • Headache
  • Dizziness
  • Dry mouth
  • Hyperhidrosis
  • Diarrhea
  • Insomnia
  • Constipation
  • Fatigue

Common (1-10% incidence) adverse effects include:

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  • Tremor
  • Blurred vision
  • Mydriasis
  • Decreased appetite
  • Sexual dysfunction
  • Insomnia
  • Anxiety
  • Elevated cholesterol and triglycerides
  • Proteinuria
  • Vertigo
  • Feeling jittery
  • Asthenia
  • Nervousness
  • Hot flush
  • Irritability
  • Abnormal dreams
  • Urinary hesitation
  • Yawning
  • Rash

Uncommon (0.1-1% incidence) adverse effects include:

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Rare (<0.1% incidence) adverse effects include:

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Unknown frequency adverse effects include:

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Pharmacology

Desvenlafaxine is a synthetic form of the isolated major active metabolite of venlafaxine, and is categorized as a serotonin-norepinephrine reuptake inhibitor (SNRI). When most normal metabolizers take venlafaxine, approximately 70% of the dose is metabolized into desvenlafaxine, so the effects of the two drugs are expected to be very similar.[5] It works by blocking the "reuptake" transporters for key neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse. The neurotransmitters affected are serotonin (5-hydroxytryptamine) and norepinephrine (noradrenaline). It is approximately 10 times more potent at inhibiting serotonin uptake than norepinephrine uptake.[6]

The molecule resembles hordenine with additions.

Transporter Ki[nM][7]
SERT 61.4
NET 2953

Approval status

United States

Pristiq 50 mg tablets (US)

Wyeth announced on 23 January 2007 that it received an "approvable" letter from the Food and Drug Administration for desvenlafaxine. Final approval to sell the drug was contingent on a number of things, including:

  • a satisfactory FDA inspection of Wyeth's Guayama, Puerto Rico facility, where the drug is to be manufactured;
  • several postmarketing surveillance commitments, and follow-up studies on low-dose use, relapse, and use in children;
  • clarity by Wyeth around the company's product education plan for physicians and patients;
  • approval of desvenlafaxine's proprietary name, Pristiq.[8]

The FDA approved the drug for antidepressant use in February 2008, and was to be available in US pharmacies in May 2008.[9]

Canada

On February 4, 2009, Health Canada approved use of desvenlafaxine for treatment of depression in Canada.[10] Pristiq is now available in Canadian pharmacies.

European Union

In 2008, Wyeth withdrew its application for Ellefore, the product under review for treatment of major depressive disorder in the European Union. In 2012, Pfizer received authorization in Spain to market Pristiq for the disorder in 50 mg and 100 mg tablets.[11][12][13]

Clinical efficacy

In clinical trials, desvenlafaxine demonstrated a significant superiority to placebo both in changes from baseline in the HAM-D17 score[14] and in measures of well being such as the Sheehan Disability Scale (SDS) and 5-item World Health Organization Well-Being Index (WHO-5).[15]

See also

References

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External links

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  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Health Canada Notice of Compliance - Pristiq. February 4, 2009, retrieved on March 9, 2009.
  11. ↑ http://www.aemps.gob.es/cima/especialidad.do?metodo=verPresentaciones&codigo=75561
  12. ↑ http://www.aemps.gob.es/cima/especialidad.do?metodo=verPresentaciones&codigo=75560
  13. ↑ https://www.pfizer.es/sobre_pfizer/medicamentos/pristiq.html
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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