Compound: cyclobenzaprine
SMILES: N(CCC=C1c2c(C=Cc3c1cccc3)cccc2)(C)C
InChIKey: JURKNVYFZMSNLP-UHFFFAOYSA-N
Synonyms: cyclobenzaprine, 303-53-7, Proheptatriene, Proheptatrien, Ciclobenzaprina, Proeptatriene, Lisseril, Fexmid, Cyclobenzaprinum, 10,11-Dehydroamitriptyline, 3-(5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine, 69O5WQQ5TI, MK-130, MK-130 (AS THE BASE), 5-(3-Dimetilaminopropiliden)-5H-dibenzo-(a,d)-ciclopentene, 1-Propanamine, 3-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, N,N-Dimethyl-5H-dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, CHEBI:3996, DTXSID0046933, N,N-Dimethyl-3-(dibenzo(a,d)cycloheptene-4-ylidene)propylamine, 1-Propanamine, 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, 5H-DIBENZO(a,d)CYCLOHEPTENE-delta(sup 5),gamma-PROPYLAMINE, N,N-DIMETHYL-, 3-(5H-DIBENZO(A,D)(7)ANNULEN-5-YLIDENE)-N,N-DIMETHYLPROPAN-1-AMINE, dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})amine, (3-Dibenzo(a,d)cyclohepten-5-ylidene-propyl)-dimethyl-amine, (3-Dibenzo[a,d]cyclohepten-5-ylidene-propyl)-dimethyl-amine, 3-(dibenzo(1,2-a:1',2'-e)(7)annulen-11-ylidene)-N,N-dimethylpropan-1-amine, 3-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)-N,N-dimethylpropan-1-amine, dimethyl((3-((2E)-tricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene)propyl))amine, RefChem:5714, DTXCID8026933, M03BX08, 206-145-8, Cyclobenzaprine [INN], MK 130, Ro 4-1577, 3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine, Cyclobenzaprine (INN), Flexeril hydrochloride, MK-130 HCl, N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)propan-1-amine, Proeptatriene [Italian], dimethyl(3-{tricyclo[9.4.0.0,3,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}propyl)amine, Cyclobenzaprinum [INN-Latin], Ciclobenzaprina [INN-Spanish], 5H-Dibenzo(a,d)cycloheptene-.delta.5,.gamma.-propylamine, N,N-dimethyl-, EINECS 206-145-8, CAS-6202-23-9, UNII-69O5WQQ5TI, cyclobenzaprin, 9715 R.P, 9715 R.P., 5-(3-Dimetilaminopropiliden)-5H-dibenzo-(a,d)-ciclopentene [Italian], NCI78206, Amrix (Salt/Mix), Flexeril (Salt/Mix), Cycloflex (Salt/Mix), Spectrum_001535, Prestwick0_000445, Prestwick1_000445, Prestwick2_000445, Prestwick3_000445, Spectrum2_001534, Spectrum3_001566, Spectrum4_000162, Spectrum5_001259, Lopac-C-4542, CHEMBL669, NCIStruc1_001572, NCIStruc2_001486, CYCLOBENZAPRINE [MI], BIDD:PXR0152, Lopac0_000303, Oprea1_534683, SCHEMBL38527, BSPBio_000490, BSPBio_003072, KBioGR_000643, KBioSS_002015, BIDD:GT0485, DivK1c_000047, SPBio_001348, SPBio_002429, CYCLOBENZAPRINE [VANDF], BPBio1_000540, GTPL7152, CYCLOBENZAPRINE [WHO-DD], SCHEMBL29520569, HSDB 8305, KBio1_000047, KBio2_002015, KBio2_004583, KBio2_007151, KBio3_002572, NINDS_000047, BDBM112774, MSK10273, 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine, BBL035415, CCG-36511, EBC-26404, N,N-dimethyl-5H-dibenzo(a,d)cycloheptene-Delta(5,gamma)-propylamine, NCGC00013841, STL416209, CYCLOBENZAPRINE [USP IMPURITY], AKOS025255657, DB00924, RP 9715, SDCCGSBI-0050291.P005, IDI1_000047, MRF-0000742, QTL1_000027, Cyclobenzaprine hydrochloride (Salt/Mix), NCGC00013841-02, NCGC00013841-03, NCGC00013841-04, NCGC00013841-05, NCGC00013841-06, NCGC00013841-08, NCGC00013841-19, NCGC00096951-01, NCGC00162122-01, NCI60_041725, SBI-0050291.P003, US8629135, SW-01, DB-047767, AB00514668, NS00003374, C06931, D07758, EN300-708806, AB00053651_07, L001021, Q5198674, BRD-K42348709-003-05-7, BRD-K42348709-003-08-1, BRD-K42348709-003-13-1, 5-(3-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene, 5H-Dibenzo[a,d]cycloheptane, 5-dimethylaminopropylidenyl-, AMITRIPTYLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY], NORTRIPTYLINE HYDROCHLORIDE IMPURITY E [EP IMPURITY], 5-(3-dimethylaminopropylidene)- 5H-dibenzo[a,d]cycloheptene, N,N-Dimethyl-5H-dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine #, 3-(dibenzo[[?],[?]][7]annulen-11-ylidene)-N,N-dimethyl-propan-1-amine, N,N-Dimethyl-5H-dibenzo(a,d)cycloheptene-.delta.5,.gamma.-propylamine, Cyclobenzaprine; Amitriptyline EP Impurity B; Nortriptyline Hydrochloride EP Impurity E, N,N-DIMETHYL-5H-DIBENZO(A,D)CYCLOHEPTENE-(SUP .DELTA.5,.GAMMA.)-PROPYLAMINE
Theoretical properties:
molecular_formula: C20H21N
molecular_weight: 275.4 g/mol
exact_mass: 275.167399674 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 3
heavy_atom_count: 21
topological_polar_surface_area: 3.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: BP: 175-180 °C at 1 atm
solubility: Freely Soluble
Descriptions:
pubchem: Cyclobenzaprine is 5-Methylidene-5H-dibenzo[a,d]cycloheptene in which one of the hydrogens of the methylidene group is substituted by a 2-(dimethylamino)ethyl group. A centrally acting skeletal muscle relaxant, it is used as its hydrochloride salt in the symptomatic treatment of painful muscle spasm. It has a role as an antidepressant, a tranquilizing drug and a muscle relaxant. It derives from a hydride of a dibenzo[a,d][7]annulene.
chebi: 5-Methylidene-5<em>H</em>-dibenzo[<em>a</em>,<em>d</em>]cycloheptene in which one of the hydrogens of the methylidene group is substituted by a 2-(dimethylamino)ethyl group. A centrally acting skeletal muscle relaxant, it is used as its hydrochloride salt in the symptomatic treatment of painful muscle spasm.
chembl: CYCLOBENZAPRINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Cyclobenzaprine, sold under several brand names including, historically, Flexeril, is a muscle relaxer used for muscle spasms from musculoskeletal conditions of sudden onset. It is not useful in cerebral palsy. It is taken by mouth.
Common side effects include headache, tiredness, dizziness, and dry mouth. Serious side effects may include an irregular heartbeat. There is no evidence of harm in pregnancy, but it has not been well studied in this population. It should not be used together with MAOIs. How it works is unclear. In any case, it is known to inhibit serotonin and norepinephrine reuptake and to block serotonin, adrenergic, histamine, and muscarinic acetylcholine receptors. Chemically, it is very similar to tricyclic antidepressants like amitriptyline.
Cyclobenzaprine was approved for medical use in the United States in 1977. It is available by prescription as a generic medication. In 2023, it was the 47th most commonly prescribed medication in the United States, with more than 13 million prescriptions. It was not available in the United Kingdom as of 2012.