WordNet
- muscle relaxant (trade name Flexeril) used for muscle spasms or acute injury (同)Flexeril
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/06/03 19:25:35」(JST)
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| Systematic (IUPAC) name | |
|---|---|
| 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)- N,N-dimethyl-1-propanamine | |
| Clinical data | |
| Trade names | Amrix (former Flexeril) |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682514 |
| Pregnancy cat. | Category B |
| Legal status | ℞ Prescription only |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 33% to 55% [1][2] |
| Metabolism | hepatic |
| Half-life | 18 hours (range 8–37 hours; n=18) |
| Excretion | renal |
| Identifiers | |
| CAS number | 303-53-7 Y |
| ATC code | M03BX08 |
| PubChem | CID 2895 |
| DrugBank | DB00924 |
| ChemSpider | 2792 Y |
| UNII | 69O5WQQ5TI Y |
| KEGG | D07758 Y |
| ChEBI | CHEBI:3996 Y |
| ChEMBL | CHEMBL669 Y |
| Chemical data | |
| Formula | C20H21N |
| Mol. mass | 275.387 g/mol |
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Cyclobenzaprine, brand names Amrix, Flexeril and Fexmid, is a muscle relaxer medication used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions.[3] It is the best-studied drug for this application,[4] it has also been used off-label for fibromyalgia treatment.[5] A new bedtime formulation of cyclobenzaprine is under development for the management of fibromyalgia syndrome.[6]
Contents
- 1 Medical use
- 2 Side effects
- 2.1 Overdose
- 3 Interactions
- 4 Comparison to other medications
- 5 Chemistry
- 6 Formulations
- 7 See also
- 8 References
Medical use
After sustaining an injury, muscle spasms may occur to stabilize the affected body part and prevent further damage. They also generate pain. Cyclobenzaprine is FDA-approved to treat such muscle spasms associated with acute, painful musculoskeletal conditions.[3] It decreases pain in the first two weeks,[4][7] peaking in the first few days, but has no proven benefit after two weeks.[4][8] Since no benefit is proven beyond that, therapy should not be continued long-term.[9] It is not useful for spasticity due to neurologic conditions such as cerebral palsy.[9][10]
Cyclobenzaprine has also shown effectiveness in the treatment of fibromyalgia symptoms, with a report of 4.8 patients needing treatment for each (1) patient reporting pain reduction (but no change in fatigue or tender points).[11]
In elderly patients, cyclobenzaprine HCl may be started at a lower dose and titrated slowly upward. Cyclobenzaprine is recommended for use up to 3 weeks, but clinical efficacy has not been demonstrated beyond this point and long term use of cyclobenzaprine is not recommended.[12] Cyclobenzaprine, however, has not been documented to cause intense physical and psychological withdrawal symptoms following discontinuation such as those which occur with its benzodiazepine, barbiturate, and carbamate alternatives, although the potential for rebound plasticity is of clinical relevance.
Side effects
Meta-analysis studies have found significantly increased rates of drowsiness (38% of patients), dry mouth (24%), dizziness (10%), and adverse events of any kind in patients taking cyclobenzaprine versus placebo.[8] Drowsiness and dry mouth appear to intensify with increasing dose.[13]
The sedative effects of cyclobenzaprine are likely due to its antagonistic effect on histamine, serotonin, and muscarinic receptors. Agitation is a common side effect observed especially in the elderly. In general, the NCQA recommends avoiding the use of cyclobenzaprine in the elderly because of the potential for more severe side effects.[14] There is one case report of overdose causing rhabdomyolysis (muscle breakdown).[15] Treatment protocols and support should follow the same as for any structurally related tricyclic, such as tricyclic antidepressants.[15]
Overdose
The most common effects of overdose are drowsiness and tachycardia.[3] Rare but potentially critical complications are cardiac arrest, cardiac dysrhythmias, severe hypotension, seizures, and neuroleptic malignant syndrome.[3] Life-threatening overdose is rare,[3] however, as the median lethal dose is approximately 338 mg/kg in mice and 425 mg/kg in rats.[3] The potential harm is increased when central nervous system depressants and antidepressants are also used; deliberate overdose often includes alcohol among other drugs.[3]
Interactions
Cyclobenzaprine has major contraindications with monoamine oxidase inhibitors (MAOIs). At least one study also found increased risk of serotonin syndrome when cyclobenzaprine was taken with the serotonergic drugs duloxetine or phenelzine.[16]
The following substances may interact with cyclobenzaprine:
- Alcohol
- Central nervous system (CNS) depressants (eg. opioids, benzodiazepines, nonbenzodiazepines, phenothiazines, carbamates, barbiturates)
- Tricyclic antidepressants may increase the chance of side effects.
- Monoamine oxidase inhibitors taken within two weeks of cyclobenzaprine may result in serious, life-threatening side effects.[9]
If co-administered with opioids the dose of one or both medicines should be reduced accordingly. The patient should be monitored for excessive sedation.
Comparison to other medications
Cyclobenzaprine has been found to be non-inferior to tizanidine, orphenadrine, and carisoprodol in the treatment of acute lower back pain, although none have been proven to be effective for long term use (beyond two weeks of treatment). No differences in pain or spasm scores were noted among these agents, nor when compared to benzodiazepines.[17] However, nonbenzodiazepine (including cyclobenzaprine) treatment was found to have a lower risk of medication abuse and continuation of use against medical advice. Side effects such as sedation and ataxia are also less pronounced with nonbenzodiazepine antispasmodics.
In a study on the treatment of musculoskeletal pain treatment with cyclobenzaprine alone or in combination with ibuprofen no significant differences in pain scores were noted among the three treatment groups. Peak benefit was found to occur on day 7 of the treatment for all groups.[18]
Chemistry
Cyclobenzaprine, N,N-dimethyl-3-(dibenzo[a,d]cyclohepten-5-ylidene)propylamine, is synthesized by reacting 5H-dibenzo[a,d]cyclohepten-5-one with 3-dimethylaminopropylmagnesium chloride and subsequent dehydration of the resulting carbinol in acidic conditions into cyclobenzaprine.
- H.La Roche, GB 858187 (1961).
- F.J. Villani, C.A. Ellis, C. Teihman, C. Biges, J. Med. Pharm. Chem., 5, 373 (1962).
- Winthrop, S. O.; Davis, M. A.; Myers, G. S.; Gavin, J. G.; Thomas, R.; Barber, R. (1962). "New Psychotropic Agents. Derivatives of Dibenzo[a,d]-1,4-cycloheptadiene". The Journal of Organic Chemistry 27: 230. doi:10.1021/jo01048a057. edit
Formulations
Cyclobenzaprine 10mg
Orally, cyclobenzaprine is marketed as Apo-Cyclobenzaprin, Flexeril, Fexmid and Novo-Cycloprine. It is available in generic form. A once-a-day, extended-release formulation, Amrix, is available.[19] Cyclobenzaprine is also used by compounding pharmacies in topical creams.
Cyclobenzaprine is regulated in the U.S. for prescription use only. Though it does not fall within most governmental guidelines as a controlled substance, possession of it without a valid or current prescription may be illegal, depending upon various state and local laws.
See also
- Amitriptyline
- Cyproheptadine
References
- ^ Micromedex® 2010 - DRUGDEX® Evaluations (Cyclobenzaprine Hydrochloride)
- ^ Cyclobenzaprine HCl Oral tablets USP Revised, April 2005
- ^ a b c d e f g "Flexeril (Cyclobenzaprine HCl) Tablets" (pdf). U. S. Food and Drug Administration. 2003. Retrieved 26 July 2009
- ^ a b c Chou R, Peterson K, Helfand M (2004). "Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review". Journal of Pain Symptom Management 28 (2): 140–175. doi:10.1016/j.jpainsymman.2004.05.002. PMID 15276195.
- ^ "Cyclobenzaprine Hydrochloride" (subscription required). MicroMedex. 5 Feb 2010. Retrieved 16 Feb 2010.
- ^ http://clinicaltrials.gov/ct2/show/NCT01903265?term=bestfit&rank=1
- ^ van Tulder MW, Touray T, Furlan AD, Solway S, Bouter LM (2003). "Muscle relaxants for non-specific low back pain". In Van Tulder, Maurits W. Cochrane Database Systematic Reviews 2 (1–2): 91–9. doi:10.1002/14651858.CD004252. PMID 12804507.
- ^ a b Browning R, Jackson JL, O’Malley PG (2001). "Cyclobenzaprine and back pain: a meta-analysis". Archives of Internal Medicine 161 (13): 1613–1620. doi:10.1001/archinte.161.13.1613. PMID 11434793.
- ^ a b c "Cyclobenzaprine official FDA information, side effects, and uses". Drugs.com. October 2009. Retrieved 19 Feb 2010.
- ^ Ashby P, Burke D, Rao S, et al (1972). "Assessment of cyclobenzaprine in the treatment of spasticity". J Neurol Neurosurg Psychiatry 35 (5): 599–605. doi:10.1136/jnnp.35.5.599. PMC 494138. PMID 4563483.
- ^ Tofferi JK, Jackson JL, O'Malley PG (15 Feb 2004). "Treatment of fibromyalgia with cyclobenzaprine: A meta-analysis". Arthritis Rheum. 51 (1): 9–13. doi:10.1002/art.20076. PMID 14872449.
- ^ Cyclobenzaprine Information and Uses - RxWiki.com
- ^ "Flexeril: Side effects". RxList.com. Retrieved 22 Feb 2010.
- ^ "High risk medications" (pdf). National Committee for Quality Assurance. Retrieved 22 Feb 2010.
- ^ a b Chabria, Shiven B (17 July 2006). "Rhabdomyolysis: a manifestation of cyclobenzaprine toxicity". Journal of Occupational Medicine and Toxicology 1 (1): 16. doi:10.1186/1745-6673-1-16. PMC 1540431. PMID 16846511.
- ^ Keegan MT, Brown DR & Rabinstein AA (2006). "Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs". Anesthesia & Analgesia 103 (6): 1466–8. doi:10.1213/01.ane.0000247699.81580.eb. PMID 17122225.
- ^ http://www.medscape.com/viewarticle/572676_4. Missing or empty
|title=(help) - ^ http://www.annemergmed.com/article/S0196-0644(04)01009-1/abstract. Missing or empty
|title=(help) - ^ Amrix website
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UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
- 1. 成人における初期治療の効果がない線維筋痛症の治療 treatment of fibromyalgia in adults not responsive to initial therapies
- 2. 成人における線維筋痛症の初期治療 initial treatment of fibromyalgia in adults
- 3. 急性腰痛の治療 treatment of acute low back pain
- 4. 頚部痛の治療 treatment of neck pain
- 5. 筋骨格系の胸痛の治療 treatment of musculoskeletal chest pain
English Journal
- Drug-Drug Interactions Between the Anti-Hepatitis C Virus 3D Regimen of Ombitasvir, Paritaprevir/Ritonavir, and Dasabuvir and Eight Commonly Used Medications in Healthy Volunteers.
- Polepally AR1, King JR2, Ding B3, Shuster DL2, Dumas EO4, Khatri A2, Chiu YL3, Podsadecki TJ4, Menon RM2.
- Clinical pharmacokinetics.Clin Pharmacokinet.2016 Aug;55(8):1003-14. doi: 10.1007/s40262-016-0373-8.
- BACKGROUND AND AIMS: The three direct-acting antiviral regimen of ombitasvir/paritaprevir/ritonavir and dasabuvir (3D regimen) is approved for treatment of hepatitis C virus (HCV) genotype 1 infection. Drug-drug interaction (DDI) studies of the 3D regimen and commonly used medications were conduct
- PMID 26895022
- Two steps modification for improvement of cyclobenzaprine transdermal delivery: releasing from patch and penetrating through skin.
- Lv S1, Quan P1, Wang W1, Fang L1.
- Drug development and industrial pharmacy.Drug Dev Ind Pharm.2016 Jul 19:1-8. [Epub ahead of print]
- The aim of this study was to improve the transdermal delivery of cyclobenzaprine (CBZ) from drug-in-adhesive patch which showed less side effects and better compliance. CBZ base was prepared and then characterized using differential scanning calorimetry (DSC). The interaction between CBZ and pressur
- PMID 27436573
- Variations in enzymatic hydrolysis efficiencies for amitriptyline and cyclobenzaprine in urine.
- Mastrianni KR1, Lee LA2, Brewer WE1, Dongari N3, Barna M3, Morgan SL4.
- Journal of analytical toxicology.J Anal Toxicol.2016 Jul 11. [Epub ahead of print]
- A collaborative study was conducted to investigate discrepancies in recoveries of two commonly prescribed compounds, amitriptyline and cyclobenzaprine, in patient urine samples when hydrolyzed with different enzymes from different sources. A 2- to 10-fold increase in analyte recoveries was seen for
- PMID 27405366
Japanese Journal
- CAFC(連邦巡回控訴裁判所)最新判決ウォッチング(第153回)[EMC Corporation事件-Misc. Dkt. No. 100 (May 4, 2012), Bayer Schering Pharma AG対Lupin Ltd.事件-Nos. 2011-1143, -1228 (April 16, 2012), Cyclobenzaprine Hydrochloride Extended Release Capsule特許訴訟事件-Nos. 2011-1399, -1409 (April 16, 2012)]
- チャルセン クリストファー・E,キャノム ハンナ
- The Lawyers 9(7), 48-52, 2012-07
- NAID 40019381344
- Cyclobenzaprine and back pain : a meta-analysis
- BROWNING R
- Arch Intern Med 161, 1613-1620, 2001
- NAID 30005427021
- Quinone-Dependent Tertiary Amine N-Oxide Reduction in Rat Blood
- Kitamura Shigeyuki,Terada Akira,Inoue Naoko [他],KAMIO Hiroshi,OHTA Shigeru,TATSUMI Kiyoshi
- Biological & pharmaceutical bulletin 21(12), 1344-1347, 1998-12-15
- … Cyclobenzaprine N-oxide and brucine N-oxide are similarly transformed to the corresponding amines by the above reducing system in blood.These results suggest that blood plays an important role in the reduction of tertiary amine N-oxide to tertiary amines. …
- NAID 110003639296
Related Links
- Do not use cyclobenzaprine if you have taken an MAO inhibitor in the past 14 days. A dangerous drug interaction could occur. MAO inhibitors include isocarboxazid, linezolid, phenelzine, rasagiline, selegiline, and tranylcypromine.
- Flexeril (cyclobenzaprine) is a muscle relaxant. It works by blocking nerve impulses (or pain sensations) that are sent to your brain. Flexeril is used together with rest and physical therapy to treat skeletal muscle conditions such as ...
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★リンクテーブル★
| リンク元 | 「シクロベンザプリン」 |
| 拡張検索 | 「cyclobenzaprine hydrochloride」 |