Cyclobenzaprine

• CAT Number: I006334
• CAS Number: 303-53-7
• Molecular Formula: C20H21N
• Molecular Weight: 275.395
• Purity: ≥95%
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term ,or -20 °C for long term
• IUPAC Name: 3-(dibenzo[1,2-a:1/',2/'-e][7]annulen-11-ylidene)-N,N-dimethylpropan-1-amine
• InChI: InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3
• InChIKey: JURKNVYFZMSNLP-UHFFFAOYSA-N
• SMILES: CN(C)CCC=C1C2=CC=CC=C2C=CC3=CC=CC=C31

Cyclobenzaprine, brand names Flexeril among others, is a muscle relaxer medication used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions. It is the best-studied drug for this application. It has also been used off-label for fibromyalgia treatment. A new sublingual formulation of cyclobenzaprine is under development for the chronic management of fibromyalgia syndrome. The exact mechanism of action of cyclobenzaprine has not been fully determined, but this drug seems to primarily act at the brain stem to reduce tonic somatic motor activity, influencing both gamma and alpha motor neurons leading to a reduction in muscle spasms.

Reference

1:Cyclobenzaprine Raises ROS Levels in Leishmania infantum and Reduces Parasite Burden in Infected Mice. Cunha-Júnior EF, Andrade-Neto VV, Lima ML, da Costa-Silva TA, Galisteo Junior AJ, Abengózar MA, Barbas C, Rivas L, Almeida-Amaral EE, Tempone AG, Torres-Santos EC.PLoS Negl Trop Dis. 2017 Jan 3;11(1):e0005281. doi: 10.1371/journal.pntd.0005281. eCollection 2017 Jan. PMID: 28045892 Free PMC Article2:Comparison of naproxen with cyclobenzaprine, oxycodone-acetaminophen, and placebo for the treatment of acute low back pain. Gottlieb M, Njie A.CJEM. 2016 Nov;18(6):491-494. Epub 2016 Sep 19. PMID: 27640607 3:Second-Order Peer Reviews of Clinically Relevant Articles for the Physiatrist: Naproxen with Cyclobenzaprine, Oxycodone/Acetaminophen, or Placebo to Treating Acute Low Back Pain: A Randomized Clinical Trial. Schneider BJ, Kennedy DJ, Kumbhare D.Am J Phys Med Rehabil. 2017 Jun;96(6):e119-e122. doi: 10.1097/PHM.0000000000000614. No abstract available. PMID: 27610552 4:Exudative Erythema Multiforme Due to Cyclobenzaprine. Gómez Torrijos E, García Arpa M, García Rodríguez C, Mendez Díaz Y, Borja Segade J, Galindo Bonilla PA, Feo Brito JF, García Rodríguez R.J Investig Allergol Clin Immunol. 2016;26(4):265-6. doi: 10.18176/jiaci.0064. No abstract available. PMID: 27470645 Free Article5:Two steps modification for improvement of cyclobenzaprine transdermal delivery: releasing from patch and penetrating through skin. Lv S, Quan P, Wang W, Fang L.Drug Dev Ind Pharm. 2016 Dec;42(12):2070-2077. Epub 2016 Jul 19. PMID: 27436573 6:Variations in enzymatic hydrolysis efficiencies for amitriptyline and cyclobenzaprine in urine. Mastrianni KR, Lee LA, Brewer WE, Dongari N, Barna M, Morgan SL.J Anal Toxicol. 2016 Nov;40(9):732-737. Epub 2016 Jul 11. PMID: 27405366 7:Determination of Degradation Products of Cyclobenzaprine Hydrochloride, Lidocaine and Piroxicam in a Semi-Topical Formulation: MS-MS Confirmation of Unknown Impurities. Cioroiu BI, Grigoriu IC, Cioroiu ME, Niculaua M, Lupuleasa R, Lazar MI.J Chromatogr Sci. 2016 Jul;54(6):902-11. doi: 10.1093/chromsci/bmw009. Epub 2016 Apr 7. PMID: 27056018 8:Cyclobenzaprine in the Treatment of Low Back Pain. Chaffee DM.Am Fam Physician. 2016 Feb 1;93(3):Online. Review. No abstract available. PMID: 26926618 Free Article9:ACP Journal Club. In acute low back pain, adding oxycodone/acetaminophen or cyclobenzaprine to naproxen did not improve pain or function. Carpenter CR.Ann Intern Med. 2016 Feb 16;164(4):JC19. doi: 10.7326/ACPJC-2016-164-4-019. No abstract available. PMID: 26882304 10:Painful Ejaculation with Cyclobenzaprine: A Case Report and Literature Review. Kraus MB, Wie CS, Gorlin AW, Wisenbaugh ES, Rosenfeld DM.Sex Med. 2015 Oct 19;3(4):343-5. doi: 10.1002/sm2.93. eCollection 2015 Dec. PMID: 26797071 Free PMC Article