> Trialight public data. Index of pages: https://trialight.com/llms.txt
> Web page: https://trialight.com/data/asset/cyclobenzaprine-b63a35b9-14ef-4262-8b87-59a3229076ce
> Record changed: 2026-10-13

# Cyclobenzaprine

Highest phase reached

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

Drug type

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

First approval year

1977

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

## Development status

**First approval year**

1977

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**Listing at source**

Listed

**Highest phase reached**

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

## Names and chemistry

**Drug type**

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**Drug name**

Cyclobenzaprine

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**Molecular weight**

275.4

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**Structure (SMILES)**

CN(C)CCC=C1c2ccccc2C=Cc2ccccc21

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

### Other names (24)

- 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

## Identifiers

**ATC classification codes**

- M03BX08

Sources for recorded values

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**CAS registry numbers**

- 303-53-7

**ChEMBL ID**

CHEMBL669

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**InChIKey**

JURKNVYFZMSNLP-UHFFFAOYSA-N

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL669)

**PubChem compound IDs**

- 2895

**RxNorm IDs (RxCUI)**

- 21949

**FDA ingredient codes (UNII)**

- 69O5WQQ5TI

## Regulatory information

### United States

**Applicant**

TWI PHARMS INC

**Approval date**

31 Jan 2013

**Application number**

ANDA091281

### Other regulatory facts

**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

### Drug classification

**Pharmacology name**

cyclobenzaprine

**Type**

Synthetic organic

**Approval recorded by Guide to Pharmacology**

Yes

#### Administration routes

- Oral

### Open Targets mechanisms (2)

- **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

### DrugCentral mechanisms (2)

- **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

### Investigated indications (5)

- **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

### Open Targets indications (13)

- **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

### Reported adverse events (83)

- **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

And 58 more, listed on the interactive page.

### Trial references (18)

- NCT00913419  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00913419)
- NCT01903265  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01903265)
- NCT02015234  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02015234)
- NCT02589275  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02589275)
- NCT04172831  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04172831)
- NCT04508621  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT04508621)
- NCT05273749  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT05273749)
- NCT02277704  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02277704)
- NCT02421679  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02421679)
- NCT03062540  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03062540)
- NCT03110575  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03110575)
- NCT03508700  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03508700)
- NCT03841773  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03841773)
- NCT05372887  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT05372887)
- NCT02642861  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02642861)
- NCT02862977  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02862977)
- NCT03025113  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03025113)
- NCT03127592  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03127592)

## Dosing

**Dose**

5mg, 10mg

**How often**

Three times a day

### Conditions of use

- Less frequent dosing for hepatically impaired or elderly patients

## Chemical properties

**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

## Evidence counts

**Recorded assays**

1,282

**Active assays**

95

### Active assay types (3)

- Confirmatory
- Other
- Summary

## Pharmacologic actions

- Antidepressive Agents, Tricyclic  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D000929.html)
- Muscle Relaxants, Central  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D009125.html)
- Tranquilizing Agents  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D014149.html)

## Biological measurements

### Observed measurements

#### 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)](https://trialight.com/data/trial/a-study-to-evaluate-tnx-102-sl-monotherapy-versus-placebo-in-75d7ecca-34fa-4150-9930-3e6bc646568d.md)
- 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](https://trialight.com/data/condition/cirrhosis-of-liver-d90e4a84-9e82-54fc-a553-1e42086e8382.md) Phase 3
- [Depressive disorder](https://trialight.com/data/condition/depressive-disorder-7618feda-3f90-5521-94e1-99f7100e8324.md) Phase 1
- Fibromyalgia Phase 3
- Post-traumatic stress disorder Phase 3

### Targets (2)

- [HTR2A](https://trialight.com/data/target/htr2a-af531933-b067-5dbc-aea0-3a6ff026d9f3.md) Serotonin 2a (5-HT2a) receptor antagonist
- [HTR2C](https://trialight.com/data/target/htr2c-9cedb114-3d17-55cd-8571-6b4398b0f46f.md) Serotonin 2c (5-HT2c) receptor antagonist

---

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