Cyclobenzaprine hydrochlorideProduct ingredient for Cyclobenzaprine

Name
Cyclobenzaprine hydrochloride
Drug Entry
Cyclobenzaprine

Cyclobenzaprine, a centrally-acting muscle relaxant, was first synthesized in 196111 and has been available for human use since 1977.10 It was initially studied for use as antidepressant given its structural similarity to tricyclic antidepressants - it differs from Amitriptyline by only a single double bond.11,10 Since its approval, it has remained relatively popular as an adjunctive, short-term treatment for acute skeletal muscle spasms secondary to musculoskeletal injury.

Accession Number
DBSALT000479
Structure
Thumb
Synonyms
Cyclobenzaprine HCl
UNII
0VE05JYS2P
CAS Number
6202-23-9
Weight
Average: 311.848
Monoisotopic: 311.144077416
Chemical Formula
C20H22ClN
InChI Key
VXEAYBOGHINOKW-UHFFFAOYSA-N
InChI
InChI=1S/C20H21N.ClH/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;1H
IUPAC Name
dimethyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}propyl)amine hydrochloride
SMILES
Cl.CN(C)CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C12
PubChem Compound
22576
ChemSpider
21168
ChEBI
3997
ChEMBL
CHEMBL1200636
Wikipedia
Cyclobenzaprine
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
Polarizability32.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon