Cyclobenzaprine
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1977
- First approval year
- 1977
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Cyclobenzaprine
- Molecular weight
- 275.4
- Structure (SMILES)
- CN(C)CCC=C1c2ccccc2C=Cc2ccccc21
- AMITRIPTYLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
- amitriptyline hydrochloride impurity b ep impurity
- ciclobenzaprina
- Ciclobenzaprina
- cyclobenzaprine
- Cyclobenzaprine
- cyclobenzaprine [INN]
- CYCLOBENZAPRINE [MI]
- CYCLOBENZAPRINE [USP IMPURITY]
- CYCLOBENZAPRINE [VANDF]
- Cyclobenzaprine [WHO-DD]
- cyclobenzaprine inn
- cyclobenzaprine mi
- cyclobenzaprine usp impurity
- cyclobenzaprine vandf
- cyclobenzaprine who dd
- mk 130 as the base
- MK-130 (AS THE BASE)
- n n dimethyl 5h dibenzo a d cycloheptene sup delta 5 gamma propylamine
- N,N-DIMETHYL-5H-DIBENZO(A,D)CYCLOHEPTENE-(SUP .DELTA.5,.GAMMA.)-PROPYLAMINE
- NORTRIPTYLINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
- nortriptyline hydrochloride impurity e ep impurity
- tnx 102
- TNX-102
- ATC classification codes
- M03BX08
Sources for recorded values
- CAS registry numbers
- 303-53-7
- ChEMBL ID
- CHEMBL669
- InChIKey
- JURKNVYFZMSNLP-UHFFFAOYSA-N
- PubChem compound IDs
- 2895
- RxNorm IDs (RxCUI)
- 21949
- FDA ingredient codes (UNII)
- 69O5WQQ5TI
- Applicant
- TWI PHARMS INC
- Approval date
- 31 Jan 2013
- Application number
- ANDA091281
- Patents
- 0
- Designations
- 1
- First in class
- No
- Fast track
- No
- Breakthrough designation
- Yes
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Pharmacology name
- cyclobenzaprine
- Type
- Synthetic organic
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Mechanism
- Serotonin 2a (5-HT2a) receptor antagonist
- Action type
- Antagonist
- Target
- 5-hydroxytryptamine receptor 2A
- Mechanism
- Serotonin 2c (5-HT2c) receptor antagonist
- Action type
- Antagonist
- Target
- 5-hydroxytryptamine receptor 2C
- Action type
- Antagonist
- Gene symbol
- HTR2A
- Protein identifier
- P28223
- Organism
- Homo sapiens
- Target development level
- Clinical
- Action type
- Antagonist
- Gene symbol
- HTR2C
- Protein identifier
- P28335
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Stress Disorders, Post-Traumatic
- Highest recorded phase
- 3
- Condition identifier
- EFO:0001358
- Subject identifier
- D013313
- Condition
- Liver Cirrhosis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0001422
- Subject identifier
- D008103
- Condition
- Pain
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003843
- Subject identifier
- D010146
- Condition
- Fibromyalgia
- Highest recorded phase
- 3
- Condition identifier
- EFO:0005687
- Subject identifier
- D005356
- Condition
- Depressive Disorder
- Highest recorded phase
- 1
- Condition identifier
- MONDO:0002050
- Subject identifier
- D003866
- Condition identifier
- EFO_0001358
- Highest recorded phase
- 3
- Condition identifier
- EFO_0001422
- Highest recorded phase
- 3
- Condition identifier
- EFO_0005687
- Highest recorded phase
- 3
- Condition identifier
- EFO_0009846
- Highest recorded phase
- 3
- Condition identifier
- HP_0002360
- Highest recorded phase
- 2
- Condition identifier
- HP_0003419
- Highest recorded phase
- 3
- Condition identifier
- HP_0012378
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0002050
- Condition identifier
- MONDO_0002050
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0003763
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005146
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005546
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0100233
- Highest recorded phase
- 2
- Event
- acute respiratory distress syndrome
- Reports
- 33
- Reporting signal score
- 73.9919
- Event
- agitation
- Reports
- 35
- Reporting signal score
- 27.1052
- Event
- anticholinergic syndrome
- Reports
- 11
- Reporting signal score
- 33.1371
- Event
- aspiration
- Reports
- 16
- Reporting signal score
- 35.6938
- Event
- asthma
- Reports
- 119
- Reporting signal score
- 230.061
- Event
- back pain
- Reports
- 143
- Reporting signal score
- 187.49
- Event
- balance disorder
- Reports
- 222
- Reporting signal score
- 609.73
- Event
- blepharospasm
- Reports
- 15
- Reporting signal score
- 42.21
- Event
- blood calcium decreased
- Reports
- 175
- Reporting signal score
- 707.191
- Event
- bradycardia
- Reports
- 38
- Reporting signal score
- 28.547
- Event
- bursitis
- Reports
- 120
- Reporting signal score
- 472.479
- Event
- cardiac arrest
- Reports
- 27
- Reporting signal score
- 31.7341
- Event
- clonus
- Reports
- 11
- Reporting signal score
- 26.8885
- Event
- coeliac disease
- Reports
- 111
- Reporting signal score
- 486.449
- Event
- cognitive disorder
- Reports
- 231
- Reporting signal score
- 734.264
- Event
- coma
- Reports
- 29
- Reporting signal score
- 28.2034
- Event
- conduction disorder
- Reports
- 9
- Reporting signal score
- 24.2384
- Event
- confusional state
- Reports
- 43
- Reporting signal score
- 19.0465
- Event
- constipation
- Reports
- 351
- Reporting signal score
- 791.776
- Event
- creatinine renal clearance decreased
- Reports
- 175
- Reporting signal score
- 817.818
- Event
- decorticate posture
- Reports
- 27
- Reporting signal score
- 169.599
- Event
- delirium
- Reports
- 47
- Reporting signal score
- 71.4101
- Event
- depressed level of consciousness
- Reports
- 207
- Reporting signal score
- 593.642
- Event
- drug hypersensitivity
- Reports
- 316
- Reporting signal score
- 538.61
- Event
- drug interaction
- Reports
- 58
- Reporting signal score
- 23.7815
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- Dose
- 5mg, 10mg
- How often
- Three times a day
Conditions of use
- Less frequent dosing for hepatically impaired or elderly patients
- Hydrogen bond acceptors
- 1
- Hydrogen bond donors
- 0
- Polar surface area
- 3.24
- Calculated partition coefficient (ALogP)
- 4.55
- Calculated partition coefficient (XLogP)
- 5.2
- Prodrug
- No
- Chirality
- Achiral
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Molecular formula
- C20H21N
- Monoisotopic mass
- 275.167399674
- Natural product
- Yes
- Recorded assays
- 1,282
- Active assays
- 95
- Confirmatory
- Other
- Summary
- Antidepressive Agents, Tricyclic
- Muscle Relaxants, Central
- Tranquilizing Agents
Distribution coefficient (LogD)
- Median
- 2.92
- Mean
- 2.97333
- Minimum
- 2.9
- Maximum
- 3.1
- Unit
- unitless
- Assays
- 3
- Standard deviation
- 0.110151
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Related records
Trials (24)
- 12-Month Open-Label Long-term Safety Study of TNX-102 SL Tablets in Fibromyalgia Patients
- 12-Week Open-Label Extension Study of TNX-102 SL in PTSD Patients
- A 3-Month Open-Label Safety and Efficacy Study of TNX-102 SL Tablets in Fibromyalgia Patients
- A 40-week Study to Evaluate TNX-102 SL 5.6 mg Taken Daily at Bedtime in Patients With PTSD
- A Phase 1, Open-Label, Parallel-Group, Single-Dose Study To Compare The Pharmakokinetics Of TNX-102 SL (Cyclobenzaprine Hydrochloride Sublingual Tablet) In Non-Elderly Versus Elderly Participants
- A Phase 2 Study to Evaluate the Efficacy and Safety of TNX-102 SL in Patients With Multi-Site Pain Associated With Post-Acute Sequelae of SARS-CoV-2 Infection
- A Phase 3 Study to Evaluate the Efficacy and Safety of TNX-102 SL in Participants With PTSD
- A Phase 3 Study To Evaluate The Efficacy And Safety Of TNX-102 SL In Patients With Fibromyalgia
- A Phase 3 Study to Evaluate the Efficacy and Safety of TNX-102 SL Taken Daily in Patients With Fibromyalgia
- A Single-Dose, Randomized, Open-Label, 2-Way Crossover Study to Evaluate the Dose-Proportionality, Safety, and Tolerability of TNX-102 SL (Cyclobenzaprine HCl Sublingual Tablets) in Healthy Japanese and Chinese Subjects
- A Study to Evaluate eFFIcacy and Safety of Sublingual TNX-102 SL Tablet Taken at Bedtime in Patients With fibRoMyalgia
- A Study To Evaluate The Efficacy And Safety Of TNX-102 SL In Patients With Fibromyalgia
- A Study to Evaluate TNX-102 SL Monotherapy Versus Placebo in Participants With Major Depressive Disorder (MDD)
- BEdtime Sublingual TNX-102 SL as Fibromyalgia Intervention Therapy (BESTFIT)
- Comparative Bioavailability of Sublingual TNX-102, Oral and Intravenous Cyclobenzaprine in Healthy Adults
- Comparative Pharmacokinetics and Safety of 3 Different Formulations of TNX-102 2.8 mg SL Tablets and Cyclobenzaprine 5 mg Oral Tablet in Healthy Adults
- Comparative Pharmacokinetics and Safety of TNX-102 SL Tablets and Cyclobenzaprine Oral Tablet in Healthy Adults
- Dose-Proportionality and Food Effect Study of TNX-102 SL
- Open Label Extension Safety and Efficacy Study of TNX-102 SL Tablets in Military Related PTSD and Related Conditions
- Repeat of: A Study to Evaluate Efficacy and Safety of Sublingual TNX-102 SL Tablet Taken at Bedtime in Patients With Fibromyalgia
In development for (4)
- Cirrhosis of liver Phase 3
- Depressive disorder Phase 1
- Fibromyalgia Phase 3
- Post-traumatic stress disorder Phase 3