Cyclobenzaprine

Summary

Cyclobenzaprine (CHEMBL669) is an approved small-molecule tranquilizing drug (ATC M03BX08); indicated across 5 conditions including cirrhosis of liver and post-traumatic stress disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: M03BX08
• Indications: 5 conditions
• Clinical trials: 18
• Chemistry: 275.4 Da · C20H21N

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL669
Name	Cyclobenzaprine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	2895
ChEBI	CHEBI:3996
ATC	M03BX08
Molecular formula	C20H21N
Molecular weight	275.4
InChIKey	JURKNVYFZMSNLP-UHFFFAOYSA-N

SMILES: CN(C)CCC=C1C2=CC=CC=C2C=CC3=CC=CC=C31

IUPAC name: N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)propan-1-amine

ChEBI definition: 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.

Pharmacological roles (ChEBI): muscle relaxant, tranquilizing drug, antidepressant.

Also known as: Ciclobenzaprina, Cyclobenzaprine, MK-130 (AS THE BASE), TNX-102, cyclobenzaprine, SID11110649, SID11110650, SID4253288, SID50108641, SID90340629, SID50111010, CYCLOBENZAPRINE

Parent form; salt/anhydrous children: CHEMBL1200636

Patent coverage: 3,073 distinct patent families (11,673 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 11,582 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 27 (assay-derived). Sample: Inositol monophosphatase 1, Thrombopoietin, 5-hydroxytryptamine receptor 2B, Alpha-2C adrenergic receptor, Thyrotropin receptor, Proto-oncogene tyrosine-protein kinase receptor Ret, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1, D(2) dopamine receptor.

Bioactivity

ChEMBL activities: 30 potent at pChembl ≥ 5 of 39 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
SLC6A4	8.15	AC50	7	nM	CHEMBL_ACT_25149826
HRH1	7.68	AC50	21	nM	CHEMBL_ACT_25211983
P08482	7.5	Potency	31.6	nM	CHEMBL_ACT_4807357
HTR2A	7.36	AC50	44.1	nM	CHEMBL_ACT_25173435
P08482	6.95	Potency	112.2	nM	CHEMBL_ACT_4853962
CHRM1	6.75	AC50	180	nM	CHEMBL_ACT_25134922
CHRM2	6.64	AC50	230.3	nM	CHEMBL_ACT_25195135
ADRA1A	6.58	AC50	261.5	nM	CHEMBL_ACT_25137623
RET	6.52	IC50	300	nM	CHEMBL_ACT_17622012
P97697	6.5	Potency	316.2	nM	CHEMBL_ACT_4405748
KCNH2	6.46	AC50	350	nM	CHEMBL_ACT_25117079
CHRM3	6.46	AC50	350	nM	CHEMBL_ACT_25136188
SLC6A2	6.42	AC50	377.7	nM	CHEMBL_ACT_25144490
ADRA1A	6.33	AC50	470	nM	CHEMBL_ACT_25217706
HTR2C	6.06	AC50	880	nM	CHEMBL_ACT_25131293
HTR2A	6.02	AC50	960	nM	CHEMBL_ACT_25224691
DRD3	5.96	AC50	1100	nM	CHEMBL_ACT_25193011
HTR2B	5.9	AC50	1247	nM	CHEMBL_ACT_25227031
OPRK1	5.57	AC50	2666	nM	CHEMBL_ACT_25128956
CHRM2	5.55	AC50	2800	nM	CHEMBL_ACT_25213240
DRD2	5.44	AC50	3600	nM	CHEMBL_ACT_25139809
ADRA2C	5.41	AC50	3900	nM	CHEMBL_ACT_25147348
CYP2D6	5.4	Potency	3981	nM	CHEMBL_ACT_4973952
CYP2D6	5.4	AC50	3981	nM	CHEMBL_ACT_5986655
HTR1A	5.31	AC50	4938	nM	CHEMBL_ACT_25164344
CYP2D6	5.2	Potency	6310	nM	CHEMBL_ACT_4990191
CYP2D6	5.2	AC50	6310	nM	CHEMBL_ACT_5986733
TSHR	5.1	Potency	7943	nM	CHEMBL_ACT_3915733
TSHR	5.1	Potency	7943	nM	CHEMBL_ACT_4751058
CACNA1B	5	IC50	10000	nM	CHEMBL_ACT_24688785

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

5 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
cirrhosis of liver	3	MONDO:0005155	EFO:0001422
post-traumatic stress disorder	3	MONDO:0005146	EFO:0001358
fibromyalgia	3	MONDO:0005546	EFO:0005687
depressive disorder	1	MONDO:0002050	MONDO:0002050

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 18.

Phase distribution

Phase	Trials
PHASE1	5
Not specified	5
PHASE3	4
PHASE2	2
PHASE4	1
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01587274	PHASE4	COMPLETED	A Randomized Study of Three Medication Regimens for Acute Low Back Pain
NCT07404397	PHASE2/PHASE3	RECRUITING	Comparing Adjuvant Treatments for High Tone Pelvic Floor Dysfunction
NCT02642861	PHASE3	UNKNOWN	Cyclobenzaprine in Muscle Cramps With Liver Cirrhosis
NCT03025113	PHASE3	COMPLETED	Efficacy and Safety of the Combination of Ketoprofen and Cyclobenzaprine in Osteomuscular Treatment
NCT03127592	PHASE3	TERMINATED	Phase III Efficacy and Tolerability Trial of the Fixed Dose Combination of Etodolac 400 mg and Cyclobenzaprine 10 mg Versus Isolated Active Substances in Pain Control After Impacted Third Molar Extraction
NCT05683574	PHASE3	WITHDRAWN	Fixed-dose Combination of Etoricoxib + Cyclobenzaprine for Pain Relief After Third Molar Extraction in Brazil
NCT00790270	PHASE2	COMPLETED	Comparison of Ibuprofen, Cyclobenzaprine, or Both for Acute Cervical Strain: A Randomized Clinical Trial
NCT01921296	PHASE2	TERMINATED	Pilot Study of Cyclobenzaprine for Treatment of Sleep Disturbance in Aromatase Inhibitor-treated Breast Cancer Patients
NCT00913419	PHASE1	COMPLETED	To Demonstrate the Relative Bioavailability of Cyclobenzaprine HCl Tablets
NCT01634412	PHASE1	COMPLETED	Comparative Bioavailability of Sublingual TNX-102, Oral and Intravenous Cyclobenzaprine in Healthy Adults
NCT01689259	PHASE1	COMPLETED	Comparative Pharmacokinetics and Safety of TNX-102 SL Tablets and Cyclobenzaprine Oral Tablet in Healthy Adults
NCT01889173	PHASE1	COMPLETED	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
NCT04407377	PHASE1	COMPLETED	Effects of Tolperisone on Measures of Drowsiness and Cognitive Function
NCT03511118	Not specified	RECRUITING	Pharmacokinetics and Safety of Commonly Used Drugs in Lactating Women and Breastfed Infants
NCT01028014	Not specified	COMPLETED	Medication Effects on Periurethral Sensation,Urethral Sphincter Activity and Pressure Flow Parameters
NCT01081990	Not specified	COMPLETED	Use of Cyclobenzaprine After Vaginal Surgery
NCT02403687	Not specified	COMPLETED	Prospective Analgesic Compound Efficacy (PACE) Study
NCT04771741	Not specified	COMPLETED	Opiate Free Multimodal Pain Pathway in Elective Foot and Ankle Surgery: A Prospective Study

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).