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Identification
NameCyclobenzaprine
Accession NumberDB00924  (APRD00213)
TypeSmall Molecule
GroupsApproved
Description

Cyclobenzaprine is a skeletal muscle relaxant and a central nervous system (CNS) depressant. Cyclobenzaprine acts on the locus coeruleus where it results in increased norepinephrine release, potentially through the gamma fibers which innervate and inhibit the alpha motor neurons in the ventral horn of the spinal cord. It is structurally similar to Amitriptyline, differing by only one double bond.

Structure
Thumb
Synonyms
SynonymLanguageCode
(3-Dibenzo[a,d]cyclohepten-5-ylidene-propyl)-dimethyl-amineNot AvailableNot Available
CiclobenzaprinaNot AvailableNot Available
CyclobenzaprineNot AvailableNot Available
CyclobenzaprinumNot AvailableNot Available
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-delta(5,gamma)-propylamineNot AvailableNot Available
N,N-dimethyl-5H-dibenzo(a,d)cycloheptene-Δ5,γ-propylamineNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amrixcapsule, extended release15 mgoralSTAT Rx USA LLC2007-10-01Not AvailableUs
Amrixcapsule, extended release30 mgoralSTAT Rx USA LLC2007-10-01Not AvailableUs
Amrixcapsule, extended release15 mgoralRebel Distributors Corp.2007-10-01Not AvailableUs
Amrixcapsule, extended release30 mgoralRebel Distributors Corp2007-10-01Not AvailableUs
Amrixcapsule, extended release15 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-01-03Not AvailableUs
Amrixcapsule, extended release30 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-10-01Not AvailableUs
Amrixcapsule, extended release15 mgoralPhysicians Total Care, Inc.2009-04-16Not AvailableUs
Cyclobenzaprine Hydrochloridecapsule, extended release15 mgoralCIMA LABS INC2007-10-022015-02-28Us
Cyclobenzaprine Hydrochloridecapsule, extended release30 mgoralCIMA LABS INC2007-11-012015-02-28Us
Amrixcapsule, extended release15 mgoralCephalon, Inc.2007-10-01Not AvailableUs
Amrixcapsule, extended release30 mgoralCephalon, Inc.2007-10-01Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cyclobenzaprine Hydrochloridetablet10 mgoralKAISER FOUNDATION HOSPITALS2010-03-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralMylan Pharmaceuticals Inc.1991-05-30Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated7.5 mgoralMylan Pharmaceuticals Inc.2013-04-24Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralMylan Pharmaceuticals Inc.2006-02-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralLiberty Pharmaceuticals, Inc.1989-05-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralWatson Laboratories, Inc.2006-02-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated7.5 mgoralWatson Laboratories, Inc.2006-02-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralWatson Laboratories, Inc.1989-05-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralQualitest Pharmaceuticals2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralQualitest Pharmaceuticals2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralMajor Pharmaceuticals1988-02-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralBlenheim Pharmacal, Inc.2012-03-30Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralBlenheim Pharmacal, Inc.2010-01-25Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralKvk Tech, Inc.2014-07-31Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralKvk Tech, Inc.2014-07-31Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralSTAT Rx USA LLC2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralSTAT Rx USA LLC2010-04-29Not AvailableUs
Fexmidtablet, film coated7.5 mgoralSTAT Rx USA LLC2008-11-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralRebel Distributors2006-04-19Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralRebel Distributors2010-02-18Not AvailableUs
Fexmidtablet, film coated7.5 mgoralRebel Distributors Corp2008-11-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralREMEDYREPACK INC.2013-12-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralREMEDYREPACK INC.2014-12-16Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralREMEDYREPACK INC.2013-03-13Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralCamber Pharmaceuticals2012-04-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralCamber Pharmaceuticals2012-04-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralAidarex Pharmaceuticals LLC2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet7.5 mgoralAidarex Pharmaceuticals LLC2011-08-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralRx Change Co.2014-11-06Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-04-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralLake Erie Medical DBA Quality Care Products LLC2010-04-23Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralLake Erie Medical DBA Quality Care Products LLC2006-04-04Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralSTAT Rx USA LLC2010-04-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralSTAT Rx USA LLC2010-04-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralPd Rx Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralPd Rx Pharmaceuticals, Inc.2006-12-06Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralPd Rx Pharmaceuticals, Inc.2012-03-14Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralPd Rx Pharmaceuticals, Inc.2012-03-14Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralPharmaceutica North America, Inc.2013-08-07Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralREMEDYREPACK INC.2011-04-26Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2014-02-20Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2012-03-05Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2013-05-24Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2013-06-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2013-06-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralLake Erie Medical DBA Quality Care Product LLC2010-07-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-02-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralPliva Inc.1995-09-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralAv Pak2014-06-10Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralUnit Dose Services2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralUnit Dose Services2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralMylan Institutional Inc.1997-08-25Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mg/301oralNorthwind Pharmaceuticals2014-05-16Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralNorthwind Pharmaceuticals, LLC2014-11-24Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralBreckenridge Pharmaceutical, Inc.2006-12-06Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2013-02-25Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralREMEDYREPACK INC.2013-03-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralREMEDYREPACK INC.2013-06-09Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralREMEDYREPACK INC.2013-05-22Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralREMEDYREPACK INC.2014-02-06Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2014-11-06Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2014-08-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralMutual Pharmaceutical1995-05-23Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralMutual Pharmaceutical1995-05-23Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralState of Florida DOH Central Pharmacy2014-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralPhysicians Total Care, Inc.1997-03-17Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralPhysicians Total Care, Inc.2006-05-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralCardinal Health2011-07-15Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralPd Rx Pharmaceuticals, Inc.2010-05-24Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralPd Rx Pharmaceuticals, Inc.2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralLake Erie Medical DBA Quality Care Products LLC2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralClinical Solutions Wholesale2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralClinical Solutions Wholesale2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralNew Horizon Rx Group, LLC2013-08-25Not AvailableUs
Fexmidtablet, film coated7.5 mgoralShionogi Inc.2011-10-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralJUBILANT CADISTA PHARMACEUTICALS, INC.2006-04-06Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralJUBILANT CADISTA PHARMACEUTICALS, INC.2006-04-04Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralGolden State Medical Supply, Inc.2006-02-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2014-10-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2015-01-12Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralREMEDYREPACK INC.2014-11-12Not AvailableUs
Cyclobenzaprine Hydrochloridetablet7.5 mgoralDIRECT RX2014-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralDIRECT RX2014-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralProficient Rx LP1989-05-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralProficient Rx LP2012-03-14Not AvailableUs
Cyclobenzaprine Hydrochloridetablet7.5 mgoralProficient Rx LP2011-08-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralProficient Rx LP2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralRanbaxy Pharmaceuticals Inc2008-05-12Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated7.5 mgoralRanbaxy Pharmaceuticals Inc2008-05-12Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralRanbaxy Pharmaceuticals Inc2008-05-12Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralbryant ranch prepack2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralbryant ranch prepack2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralMc Kesson Packaging Services Business Unit Of Mc Kesson Corporation2007-06-14Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralReady Meds2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralAmneal Pharmaceuticals2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralAurobindo Pharma Limited2008-09-26Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralAurobindo Pharma Limited2008-09-26Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralMed Vantx, Inc.1995-09-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralDispensing Solutions, Inc.1989-05-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralContract Pharmacy Services Pa2010-04-23Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralRed Pharm Drug Inc.2007-01-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralRed Pharm Drug Inc.2010-07-12Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralRed Pharm Drug Inc.2010-02-18Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralAphena Pharma Solutions Tennessee, Llc1989-05-03Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralAmerican Health Packaging2009-10-14Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralAmerican Health Packaging2014-05-30Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralDispensing Solutions, Inc.2007-02-28Not AvailableUs
Cyclobenzaprine Hydrochloridetablet7.5 mgoralDispensing Solutions, Inc.2011-08-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralKeltman Pharmaceuticals Inc.2006-08-24Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralKeltman Pharmaceuticals Inc.2010-06-10Not AvailableUs
Fexmidtablet, film coated7.5 mgoralVictory Pharma, Inc.2008-11-01Not AvailableUs
Cyclobenzaprine Hydrochloridetablet5 mgoralLegacy Pharmaceutical Packaging2012-04-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet10 mgoralLegacy Pharmaceutical Packaging2012-04-02Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralPreferred Pharmaceuticals, Inc.2011-07-07Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated5 mgoralPreferred Pharmaceuticals, Inc.2014-02-26Not AvailableUs
Cyclobenzaprine Hydrochloridetablet7.5 mgoralPreferred Pharmaceuticals, Inc.2012-05-08Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated7.5 mgoralKLE 2, Inc.2011-08-29Not AvailableUs
Cyclobenzaprine Hydrochloridetablet, film coated10 mgoralMc Kesson Contract Packaging2011-09-29Not AvailableUs
Cyclobenzaprinetablet10 mgoralSanis Health IncNot AvailableNot AvailableCanada
Cyclobenzaprinetablet10 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
FlexerilJanssen
FlexibanSIT
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cyclobenzaprine Hydrochloride
6202-23-9
Thumb
  • InChI Key: VXEAYBOGHINOKW-UHFFFAOYSA-N
  • Monoisotopic Mass: 311.144077416
  • Average Mass: 311.848
DBSALT000479
Categories
CAS number303-53-7
WeightAverage: 275.3874
Monoisotopic: 275.167399677
Chemical FormulaC20H21N
InChI KeyJURKNVYFZMSNLP-UHFFFAOYSA-N
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
IUPAC Name
dimethyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine
SMILES
CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions.
PharmacodynamicsCyclobenzaprine, closely related to the antidepressant amitriptyline, is used as a skeletal muscle relaxant to reduce pain and tenderness and improve mobility. Unlike dantrolene, cyclobenzaprine cannot be used to treat muscle spasm secondary to cerebral or spinal cord disease.
Mechanism of actionLike other tricyclic antidepressants, cyclobenzaprine exhibits anticholinergic activity, potentiation of norepinephrine, and antagonism of reserpine. Cyclobenzaprine does not directly act on the neuromuscular junction or the muscle but relieves muscle spasms through a central action, possibly at the brain stem level. Cyclobenzaprine binds to the serotonin receptor and is considered a 5-HT2 receptor antagonist that reduces muscle tone by decreasing the activity of descending serotonergic neurons.
AbsorptionSlowly but well absorbed after oral administration
Volume of distributionNot Available
Protein bindingVery high (93%)
Metabolism

Extensively metabolized (gastrointestinal and hepatic).

SubstrateEnzymesProduct
Cyclobenzaprine
desmethylcyclobenzaprineDetails
Route of eliminationCyclobenzaprine is extensively metabolized, and is excreted primarily as glucuronides via the kidney.
Half life18 hours (range 8-37 hours)
Clearance
  • 0.7 L/min
ToxicityOral mouse and rat LD50 are 338 mg/kg and 425 mg/kg respectively. Signs of overdose include agitation, coma, confusion, congestive heart failure, convulsions, dilated pupils, disturbed concentration, drowsiness, hallucinations, high or low temperature, increased heartbeats, irregular heart rhythms, muscle stiffness, overactive reflexes, severe low blood pressure, stupor, and vomiting.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.9512
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7567
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.6447
Renal organic cation transporterInhibitor0.7955
CYP450 2C9 substrateNon-substrate0.7826
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7501
CYP450 1A2 substrateInhibitor0.7324
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8933
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.9158
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6955
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8127
BiodegradationNot ready biodegradable0.8727
Rat acute toxicity2.9697 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7531
hERG inhibition (predictor II)Inhibitor0.6767
Pharmacoeconomics
Manufacturers
  • Anesta ag
  • Actavis totowa llc
  • Aurobindo pharma ltd
  • Cadista pharmaceuticals inc
  • Invagen pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Orit laboratories llc
  • Pliva inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • Mcneil pediatrics
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseoral15 mg
Capsule, extended releaseoral30 mg
Tabletoral10 mg
Tabletoral5 mg
Tabletoral7.5 mg
Tablet, film coatedoral10 mg
Tablet, film coatedoral10 mg/301
Tablet, film coatedoral5 mg
Tablet, film coatedoral7.5 mg
Prices
Unit descriptionCostUnit
Cyclobenzaprine hcl crystal273.88USD g
Cyclobenzaprine hcl powder35.84USD g
Fexmid 7.5 mg tablet4.18USD tablet
Flexeril 5 mg tablet2.04USD tablet
Flexeril 10 mg tablet1.74USD tablet
Cyclobenzaprine HCl 5 mg tablet1.71USD tablet
Cyclobenzaprine 5 mg tablet1.64USD tablet
Cyclobenzaprine HCl 10 mg tablet0.47USD tablet
Cyclobenzaprine 10 mg tablet0.41USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States73877932005-02-262025-02-26
United States75443722003-11-142023-11-14
Properties
StateSolid
Experimental Properties
PropertyValueSource
boiling point173-177Not Available
water solubilityFreely SolubleNot Available
logP5.2Not Available
pKa8.47Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00689 mg/mLALOGPS
logP4.73ALOGPS
logP4.61ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.62 m3·mol-1ChemAxon
Polarizability32.95 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Villani, F.J.; US. Patent 3,409,640; November 5,1968; assigned to Schering Corporation.

General ReferenceNot Available
External Links
ATC CodesM03BX08
AHFS Codes
  • 12:20.00
PDB EntriesNot Available
FDA labelDownload (230 KB)
MSDSDownload (73.1 KB)
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
IndacaterolConcomitant therapy with monoamine oxidase inhibitors, tricyclic antidepressants, or other drugs that prolong the QTc interval should be monitored closely. These drugs may potentiate the effect of adrenergic agonist on the cardiovascular system.
RasagilineIncreased risk of toxicity with this association
RivastigminePossible antagonism of action
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Cyclobenzaprine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
ThiabendazoleThe strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Cyclobenzaprine by decreasing Cyclobenzaprine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Cyclobenzaprine if Thiabendazole is initiated, discontinued or dose changed.
TramadolIncreases risk of seizure.
TranylcypromineIncreased risk of serotonin syndrome. Concomitant use should be avoided. These agents should not be administered within 14 days of each other.
TriprolidineTriprolidine and Cyclobenzaprine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
TrospiumTrospium and Cyclobenzaprine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

Targets

1. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

References:

  1. Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. Pubmed
  2. Kobayashi H, Hasegawa Y, Ono H: Cyclobenzaprine, a centrally acting muscle relaxant, acts on descending serotonergic systems. Eur J Pharmacol. 1996 Sep 5;311(1):29-35. Pubmed

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Wang RW, Liu L, Cheng H: Identification of human liver cytochrome P450 isoforms involved in the in vitro metabolism of cyclobenzaprine. Drug Metab Dispos. 1996 Jul;24(7):786-91. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Wang RW, Liu L, Cheng H: Identification of human liver cytochrome P450 isoforms involved in the in vitro metabolism of cyclobenzaprine. Drug Metab Dispos. 1996 Jul;24(7):786-91. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 10, 2014 09:39