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

• ChemBase ID: 800
• Molecular Formular: C20H21N
• Molecular Mass: 275.38744
• Monoisotopic Mass: 275.16739968
• SMILES: N(CC/C=C\1/c2c(C=Cc3c1cccc3)cccc2)(C)C
• Canonical SMILES: CN(CC/C=C/1\c2ccccc2C=Cc2c1cccc2)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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; dimethyl(3-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}propyl)amine
• IUPAC Traditional name: 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; cyclobenzaprine
• Brand Name: Cyclobenz; Flexeril; Flexiban; Proeptatriene; Proheptatriene
• Synonyms: Cyclobenzaprine HCL; Cyclobenzaprine

Database IDs

• CAS Number: 303-53-7
• PubChem SID: 160964263; 46508313
• PubChem CID: 2895
• CHEBI ID: 3996
• ATC CODE: M03BX08
• CHEMBL: 669
• Chemspider ID: 2792
• DrugBank ID: DB00924
• KEGG ID: D07758
• Unique Ingredient Identifier: 69O5WQQ5TI
• Wikipedia Title: Cyclobenzaprine
• Medline Plus: a682514

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.1812798
• LogD (pH = 7.4): 2.2807164
• Log P: 4.6130133
• Molar Refractivity: 102.6238 cm^3
• Polarizability: 35.348446 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.73
• LOG S: -4.6
• Solubility (Water): 6.89e-03 g/l

PROPERTIES

Physical Property

• Solubility: Freely Soluble
• Hydrophobicity(logP): 5.2

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 33% to 55%
• Excretion: renal
• Half Life: 18 hours (range 8–37 hours; n=18)
• Metabolism: hepatic
• Legal Status: rx-only
• Pregnancy Category: Category B

DETAILS

DrugBank - DB00924

• Drug Groups: approved
• 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.
• Indication: For use as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions.
• Pharmacology: Cyclobenzaprine, 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.
• Toxicity: Oral 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
• Biotransformation: Extensively metabolized (gastrointestinal and hepatic).
• Absorption: Slowly but well absorbed after oral administration
• Half Life: 18 hours (range 8-37 hours)
• Protein Binding: Very high (93%)
• Elimination: Cyclobenzaprine is extensively metabolized, and is excreted primarily as glucuronides via the kidney.
• Clearance: * 0.7 L/min
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com