nefazodone
American Heritage Dictionary:
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ne·fa·zo·done
(nə-fā'zə-dōn', -făz'ə-) 
n.
An oral antidepressant with a chemical structure unrelated to SSRIs, tricyclics, or monoamine oxidase inhibitors, thought to inhibit neuronal uptake of serotonin and norepinephrine in the central nervous system.
n.
An oral antidepressant with a chemical structure unrelated to SSRIs, tricyclics, or monoamine oxidase inhibitors, thought to inhibit neuronal uptake of serotonin and norepinephrine in the central nervous system.
[nef- (alteration of PHEN(YL)) + (TR)AZODONE.]
Drug Info:
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Nefazodone
Brand names: Serzone®
Chemical formula:
- Drug Forms:
- Nefazodone Hydrochloride Oral tablet (below)
- Nefazodone tablets
Nefazodone Hydrochloride Oral tablet
What is this medicine?
NEFAZODONE (nef AY zoe done) is used to treat depression.
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
•attempted suicide or thinking about it
•bipolar disorder or mania
•heart disease, previous heart attack or stroke
•liver disease or a history of liver disease
•seizures
•an unusual or allergic reaction to nefazodone, other medicines, food, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding
How should I use this medicine?
Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. You may take this medicine with or without food. Take your medicine at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your doctor's advice.
A special MedGuide will be given to you by the pharmacist with each prescription and refill. Be sure to read this information carefully each time.
Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.
What may interact with this medicine?
Do not take this medicine with any of the following medications:
•carbamazepine
•cisapride
•duloxetine
•eplerenone
•ergot alkaloids like dihydroergotamine, ergotamine, methysergide
•linezolid
•lovastatin
•medicines called MAO Inhibitors like Nardil, Parnate, Marplan, Eldepryl
•methylene blue
•pimozide
•ranolazine
•simvastatin
•SSRIs like citalopram, escitalopram, fluoxetine, fluvoxamine, paroxetine, and sertraline
•trazodone
•triazolam
•venlafaxine
•red yeast rice
This medicine may also interact with the following medications:
•atorvastatin
•buspirone
•cyclosporine
•desipramine
•digoxin
•erythromycin
•general anesthetics
•haloperidol
•ketoconazole
•lithium
•medicines for anxiety or sleeping problems, such as alprazolam, diazepam, or clonazepam
•phenytoin
•tacrolimus
•warfarin
This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.
What should I watch for while using this medicine?
Visit your doctor or health care professional for regular checks on your progress. Continue to take your medicine even if you do not immediately feel better. It can take several weeks before you feel the full effect of this medicine.
Patients and their families should watch out for depression or thoughts of suicide that get worse. Also watch out for sudden or severe changes in feelings such as feeling anxious, agitated, panicky, irritable, hostile, aggressive, impulsive, severely restless, overly excited and hyperactive, or not being able to sleep. If this happens, especially at the beginning of treatment or after a change in dose, call your doctor.
You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how this medicine affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells. Alcohol can make you more drowsy and dizzy. Avoid alcoholic drinks.
Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water will help.
What side effects may I notice from receiving this medicine?
Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•changes in vision
•dark urine
•feeling faint or lightheaded, falls
•flu-like symptoms like fever, chills, cough, muscle or joint aches and pains
•irregular heartbeat
•loss of appetite for several days
•prolonged or painful erection
•redness, blistering, peeling or loosening of the skin, including inside the mouth
•seizures
•suicidal thoughts or other mood changes
•trouble passing urine or change in the amount of urine
•unusually tired or weak
•yellowing of the eyes or skin
Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•constipation
•nausea or stomach upset
This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.
Where should I keep my medicine?
Keep out of the reach of children.
Store at room temperature below 40 degrees C (104 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.
Last updated: 10/25/2004 10:24:00 AM
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
Wikipedia on Answers.com:
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Nefazodone
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|---|---|
| Systematic (IUPAC) name | |
| 1-(3-[4-(3-chlorophenyl)piperazin-1-yl]propyl)-3-ethyl-4-(2-phenoxyethyl)-1H-1,2,4-triazol-5(4H)-one | |
| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a695005 |
| Pregnancy cat. | C |
| Legal status | ℞ Prescription only |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 20% (variable) |
| Protein binding | >99% |
| Metabolism | Hepatic (active metabolites, including mCPP)[1] |
| Half-life | 2–4 hours |
| Excretion | Urine (55%), Feces (20–30%) |
| Identifiers | |
| CAS number | 83366-66-9  |
| ATC code | N06AX06 |
| PubChem | CID 4449 |
| DrugBank | DB01149 |
| ChemSpider | 4294 |
| UNII | 59H4FCV1TF |
| KEGG | D08257 |
| ChEBI | CHEBI:7494 |
| ChEMBL | CHEMBL623 |
| Chemical data | |
| Formula | C25H32ClN5O2 |
| Mol. mass | 470.01 g/mol |
| SMILES | eMolecules & PubChem |
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Nefazodone (Serzone, Nefadar) is an antidepressant marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries due to the rare incidence of hepatotoxicity (liver damage), which could lead to the need for a liver transplant, or even death. The incidence of severe liver damage is approximately 1 in every 250,000 to 300,000 patient-years.[2] On June 14, 2004, Bristol-Myers Squibb discontinued the sale of Serzone in the United States and Canada. Several generic formulations of nefazodone are still available.[3][4]
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Pharmacology
Nefazodone acts primarily as a potent antagonist at the 5-HT2A receptors (Kd 26 nM).[5] It also has moderate affinity for the α1-adrenergic receptor (Kd 48 nM) and 5-HT1A receptor (Kd 80 nM), and very low affinity for the α2-adrenergic receptor (Kd 640 nM) and D2 receptor (Kd 910 nM).[5] It acts as an antagonist at all of these sites.[5][6] Nefazodone has low affinity for the serotonin (200 nM), norepinephrine (360 nM), and dopamine (360 nM) transporters as well, and therefore acts as a weak serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).[7] It has negligible affinity for the H1 receptor (24,000 nM) or muscarinic acetylcholine receptors (11,000 nM), and accordingly lacks any antihistamine or anticholinergic side effects.[7]
Dosing
Nefazodone doses for adults typically start at 100 mg twice daily (200 mg/day) to a maximum of 600 mg/day (300 mg twice daily), according to Food and Drug Administration (FDA) regulations. Some patients with severe depression were treated with more than 600 mg/day. Most patients were treated with 300 mg–600 mg daily.
Side effects
Common and mild side effects of nefazodone reported in clinical trials more often than placebo include dry mouth (25%), sedation/somnolence (25%), nausea (22%), dizziness (17%), blurred/abnormal vision (16%), weakness (11%), lightheadedness (10%), confusion (7%), and orthostatic hypotension (5%).[8] Rare and serious adverse reactions may include allergic reaction, fainting, priapism (painful/prolonged erection), and jaundice.[9]
Unlike most serotonin reuptake inhibitors, nefazodone has a low incidence of negative effects on libido or sexual function, and is occasionally used as treatment for to SSRI or SNRI-induced impotence and anorgasmia in men.[10] Additionally, unlike mirtazapine, nefazodone is not especially associated with increased appetite and weight gain either.[11]
Interactions
Nefazodone is a potent inhibitor of CYP3A4, an isozyme of the cytochrome P450 system, and may therefore interact adversely with many commonly-used medications that are metabolized by CYP3A4.[1][12]
Advantages
Nefazodone's claimed advantages over other antidepressants include reduced possibility of disturbed sleep or sexual dysfunction, and ability to treat some patients who did not respond to other antidepressant drugs.
Nefazodone, though an antidepressant, may also be beneficial in the prophylaxis of migraines due to its antagonistic effects on the 5-HT2A[13] and 5-HT2C receptors.[14][15] It has a more favorable side effect profile than amitriptyline, a tricyclic antidepressant commonly used for migraine prophylaxis.
See also
Chemistry
Nefazadone is a piperazine compound incorporating a 1,2,4-triazol-3-one ring. Rxn of the starting propionamide with phosgene leads to the corresponding imino chloride. This intermediate is condensed with hydrazine methylurethane to afford the corresponding guanidine from the displacement of chlorine by basic hydrazine nitrogen. Rxn with sodium methoxide leads first to the ionization of the amine on the side chain; this then cyclizes to a triazolone by displacing the carbamate methoxyl. Alkylation of the anion from rxn of the triazolone with a strong base with chloride affords nefazodone.
References
- ^ a b Lexi-Comp (September 2008). "Nefazodone". The Merck Manual Professional. http://www.merck.com/mmpe/lexicomp/nefazodone.html. Retrieved on November 29, 2008.
- ^ Rxlist.com: "Nefazodone Prescribing Information", accessed 8 January 2007.]
- ^ FDA Orange Book, accessed 15 January 2006.
- ^ About.com: "Serzone Pulled from U.S. Market", accessed 15 January 2006.
- ^ a b c Cusack B, Nelson A, Richelson E. (1994). "Binding of Antidepressants to Human Brain Receptors: Focus on Newer Generation Compounds.". Psychopharmacology (Berl). 114 (4): 559–565. doi:10.1007/BF02244985. PMID 7855217.
- ^ Sanchez, C; J. Hyttel (1999). "Comparison of the Effects of Antidepressants and Their Metabolites on Reuptake of Biogenic Amines and on Receptor Binding". Celular and Molecular Neurobiology 19 (4): 467–89. doi:10.1023/A:1006986824213. PMID 10379421.
- ^ a b Tatsumi M, Groshan K, Blakely RD, Richelson E. (1997). "Pharmacological Profile of Antidepressants and Related Compounds at Human Monoamine Transporters.". Eur J Pharmacol. 340 (2–3): 249–258. doi:10.1016/S0014-2999(97)01393-9. PMID 9537821.
- ^ "Nefazodone (Serzone) FAQ". http://www.dr-bob.org/tips/nefazodone.html#side-effects.
- ^ http://www.drugs.com/serzone.html
- ^ http://sulcus.berkeley.edu/mcb/165_001/papers/manuscripts/_684.html
- ^ Sussman N, Ginsberg DL, Bikoff J (April 2001). "Effects of nefazodone on body weight: a pooled analysis of selective serotonin reuptake inhibitor- and imipramine-controlled trials". The Journal of Clinical Psychiatry 62 (4): 256–60. doi:10.4088/JCP.v62n0407. PMID 11379839.
- ^ Spina E, Santoro V, D'Arrigo C (July 2008). "Clinically relevant pharmacokinetic drug interactions with second-generation antidepressants: an update". Clin Ther 30 (7): 1206–27. doi:10.1016/S0149-2918(08)80047-1. PMID 18691982. http://linkinghub.elsevier.com/retrieve/pii/S0149-2918(08)80047-1.
- ^ Saper JR, Lake AE, Tepper SJ (May 2001). "Nefazodone for chronic daily headache prophylaxis: an open-label study". Headache 41 (5): 465–74. doi:10.1046/j.1526-4610.2001.01084.x. PMID 11380644. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0017-8748&date=2001&volume=41&issue=5&spage=465.
- ^ Mylecharane EJ (1991). "5-HT2 receptor antagonists and migraine therapy". J. Neurol. 238 (Suppl 1): S45–52. doi:10.1007/BF01642906. PMID 2045831.
- ^ Millan MJ (2005). "Serotonin 5-HT2C receptors as a target for the treatment of depressive and anxious states: focus on novel therapeutic strategies". Therapie 60 (5): 441–60. doi:10.2515/therapie:2005065. PMID 16433010.
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American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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