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Compound Detail

CHEMBL669

CYCLOBENZAPRINE
💊 Approved Drug
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💊 Approved Drug
CN(C)CCC=C1c2ccccc2C=Cc2ccccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL669
Name CYCLOBENZAPRINE
Phase Approved
Structure Type MOL
InChI Key JURKNVYFZMSNLP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ciclobenzaprina Cyclobenzaprine MK-130 (AS THE BASE) TNX-102
2
Targets
3
Activities
1
Assay Types
3
PK Parameters
20
Publications
4
Known Names
5
Indications

Molecular Properties

275.4
MW (Da)
4.55
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.68
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1977

Extended Properties

Molecular Formula C20H21N
MW 275.40
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.07

Indications

Fibromyalgia Liver Cirrhosis Pain Stress Disorders, Post-Traumatic Depressive Disorder

ATC Classification

M03BX08
cyclobenzaprine
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: MUSCLE RELAXANTS

Activity Summary

IC50 3 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proto-oncogene tyrosine-protein kinase receptor Ret
CHEMBL2041
 IC50 6.52 6.52 300.0 1
Voltage-dependent N-type calcium channel subunit alpha-1B
CHEMBL4478
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.07 mL.min-1.g-1 Homo sapiens
Fu 0.0073 - Rattus norvegicus
Fu 0.01 - Sus scrofa

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proto-oncogene tyrosine-protein kinase receptor Ret IC50 = 300.0 nM 6.52 Kinase Assay: Approximately 5-20 μg of purified GST-RET proteins were incubated ... -
Voltage-dependent N-type calcium channel subunit alpha-1B IC50 = 10000.0 nM 5.0 Inhibition of endogenous human CaV2.2 in human SH-SY5Y cells in presence of nife... 35308021

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 58
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
- 10.6019/CHEMBL3301361 ADMET 3
19256501 10.1021/jm801441s No relevant target 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
7452678 10.1021/jm00185a024 Canis familiaris 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
22328583 10.1124/dmd.111.043505 Cytochrome P450 2J2 2
24088053 10.1021/jm400813y D(2) dopamine receptor 2
24249037 10.1007/s11095-013-1232-z No relevant target 2

Data from ChEMBL 36 via Core Engine