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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015060
Secondary Accession Numbers
  • HMDB15060
Metabolite Identification
Common NameCyclobenzaprine
DescriptionCyclobenzaprine 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
Data?1582753252
Synonyms
ValueSource
(3-Dibenzo[a,D]cyclohepten-5-ylidene-propyl)-dimethyl-amineChEBI
CiclobenzaprinaChEBI
CyclobenzaprinumChEBI
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-Delta(5,gamma)-propylamineChEBI
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-delta(5,g)-propylamineGenerator
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-δ(5,γ)-propylamineGenerator
N,N-Dimethyl-5H-dibenzo(a,D)cycloheptene-δ(5,g)-propylamineHMDB
Cyclobenzaprine HCLHMDB
FlexerilHMDB
LisserilHMDB
Cyclobenzaprine hydrochlorideHMDB
Chemical FormulaC20H21N
Average Molecular Weight275.3874
Monoisotopic Molecular Weight275.167399677
IUPAC Namedimethyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine
Traditional Namecyclobenzaprine
CAS Registry Number303-53-7
SMILES
CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12
InChI Identifier
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
InChI KeyJURKNVYFZMSNLP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point216 - 218 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.0069 g/LNot Available
LogP5.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM164.730932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP4.73ALOGPS
logP4.61ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.62 m³·mol⁻¹ChemAxon
Polarizability32.95 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.89531661259
DarkChem[M-H]-168.29831661259
DeepCCS[M-2H]-193.88430932474
DeepCCS[M+Na]+169.44930932474
AllCCS[M+H]+166.232859911
AllCCS[M+H-H2O]+162.632859911
AllCCS[M+NH4]+169.632859911
AllCCS[M+Na]+170.532859911
AllCCS[M-H]-174.932859911
AllCCS[M+Na-2H]-174.432859911
AllCCS[M+HCOO]-173.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclobenzaprineCN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C123146.1Standard polar33892256
CyclobenzaprineCN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C122265.1Standard non polar33892256
CyclobenzaprineCN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C122250.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobenzaprine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9040000000-6d92a6b3b68f574cfa962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobenzaprine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobenzaprine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Positive-QTOFsplash10-004i-0090000000-b82bb6864d1db95902382016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Positive-QTOFsplash10-003r-2190000000-d7ca012a9442c5c5159d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Positive-QTOFsplash10-0f6x-9860000000-d6cd399a2bc4bff340b62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Negative-QTOFsplash10-00di-0090000000-2ec20dd7f67cc51c9e312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Negative-QTOFsplash10-00di-1090000000-6688ebb97b5d79eca3122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Negative-QTOFsplash10-002f-7290000000-87d189310c604e77fbc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Positive-QTOFsplash10-004i-0090000000-93624eb06b890930f7012021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Positive-QTOFsplash10-004i-0090000000-204146569caae8c2b6be2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Positive-QTOFsplash10-0a4i-3090000000-443350b9631b31aaa21c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 10V, Negative-QTOFsplash10-00di-0090000000-639559d845843ccd499a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 20V, Negative-QTOFsplash10-00di-0090000000-96cd6df79ac93f81d7ae2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobenzaprine 40V, Negative-QTOFsplash10-014i-0090000000-e16ad7a8e7b878d6be952021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00924 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00924 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00924
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2792
KEGG Compound IDC06931
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclobenzaprine
METLIN IDNot Available
PubChem Compound2895
PDB IDNot Available
ChEBI ID3996
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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:8818577 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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:8818577 ]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [PubMed:12498911 ]
  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:8884233 ]