cyclobenzaprine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
751 303-53-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cyclobenzaprine
  • proheptatrien
  • proheptatriene
  • cyclobenzaprine hydrochloride
  • cyclobenzaprine HCl
structurally related to tricyclic antidepressants relieves skeletal muscle spasm of local origin without interfering with muscle function, it is ineffective in muscle spasm due to central nervous system disease
  • Molecular weight: 275.40
  • Formula: C20H21N
  • CLOGP: 5.10
  • LIPINSKI: 1
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -4.60
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 200 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.37 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 55 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Aug. 26, 1977 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 4490.12 70.96 904 1453 20130 2335598
Toxicity to various agents 2598.48 70.96 634 1723 32120 2323608
Drug abuse 1735.93 70.96 383 1974 11643 2344085
Respiratory arrest 890.26 70.96 198 2159 5980 2349748
Cardio-respiratory arrest 818.10 70.96 199 2158 8947 2346781
Cardiac arrest 815.56 70.96 219 2138 14711 2341017
Death 443.13 70.96 216 2141 81252 2274476
Intentional product misuse 431.23 70.96 121 2236 9368 2346360
Poisoning 407.64 70.96 91 2266 2729 2352999
Drug hypersensitivity 365.87 70.96 160 2197 46483 2309245
Overdose 323.86 70.96 116 2241 19791 2335937
Intentional overdose 229.94 70.96 78 2279 11243 2344485
Temperature regulation disorder 201.01 70.96 32 2325 129 2355599
Somnolence 171.44 70.96 77 2280 23408 2332320
Decorticate posture 165.64 70.96 23 2334 23 2355705
Food allergy 157.36 70.96 32 2325 599 2355129
Coeliac disease 154.20 70.96 33 2324 799 2354929
Hypotension 142.04 70.96 75 2282 32361 2323367
Immunodeficiency 140.34 70.96 32 2325 1044 2354684
Unresponsive to stimuli 136.88 70.96 43 2314 4833 2350895
Bursitis 136.71 70.96 35 2322 1873 2353855
Suicide attempt 132.61 70.96 52 2305 11230 2344498
Constipation 120.79 70.96 59 2298 21570 2334158
Coma 107.28 70.96 42 2315 9014 2346714
Myocardial depression 102.46 70.96 16 2341 55 2355673
Asthma 98.23 70.96 42 2315 11272 2344456
Urinary incontinence 92.94 70.96 31 2326 4202 2351526
Respiratory depression 90.53 70.96 26 2331 2144 2353584
Serotonin syndrome 90.13 70.96 29 2328 3511 2352217
Exposure via ingestion 89.76 70.96 21 2336 767 2354961
Electrocardiogram QRS complex prolonged 87.72 70.96 22 2335 1080 2354648
Rash erythematous 86.14 70.96 32 2325 5944 2349784
Drug interaction 85.64 70.96 52 2305 29111 2326617
Sedation 83.37 70.96 27 2330 3335 2352393
Fluid retention 81.02 70.96 32 2325 7014 2348714
Encephalopathy 79.09 70.96 28 2329 4533 2351195
Depressed level of consciousness 78.66 70.96 32 2325 7572 2348156
Seizure 75.35 70.96 45 2312 24421 2331307
Hepatic enzyme increased 74.02 70.96 33 2324 9769 2345959
Upper respiratory tract infection 73.97 70.96 32 2325 8819 2346909
Loss of consciousness 72.43 70.96 40 2317 18727 2337001
Drug screen positive 71.40 70.96 18 2339 902 2354826
Hyperhidrosis 71.09 70.96 37 2320 15385 2340343

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 1709.67 96.32 388 920 15924 1729549
Toxicity to various agents 1235.28 96.32 337 971 28804 1716669
Drug abuse 1014.98 96.32 249 1059 13440 1732033
Respiratory arrest 435.69 96.32 108 1200 5731 1739742
Cardio-respiratory arrest 358.45 96.32 102 1206 9191 1736282
Cardiac arrest 340.71 96.32 111 1197 15819 1729654
Intentional product misuse 257.29 96.32 75 1233 7283 1738190
Overdose 245.22 96.32 88 1220 16613 1728860
Death 230.44 96.32 139 1169 87304 1658169
Poisoning 120.70 96.32 33 1275 2499 1742974
Intentional overdose 114.10 96.32 41 1267 7629 1737844
Depressed level of consciousness 108.51 96.32 38 1270 6554 1738919
Coma 101.18 96.32 37 1271 7225 1738248

Pharmacologic Action:

SourceCodeDescription
ATC M03BX08 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
Other centrally acting agents
FDA PE N0000175730 Centrally-mediated Muscle Relaxation
CHEBI has role CHEBI:51371 muscle relaxant
CHEBI has role CHEBI:35473 tranquilizing drug
CHEBI has role CHEBI:35469 antidepressant
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009125 Muscle Relaxants, Central
MeSH PA D009465 Neuromuscular Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Spasticity indication 221360009
Fibromyalgia off-label use 203082005 DOID:631
Sinus tachycardia contraindication 11092001
Glaucoma contraindication 23986001 DOID:1686
Hyperthyroidism contraindication 34486009 DOID:7998
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Hepatic failure contraindication 59927004
Open-angle glaucoma contraindication 84494001 DOID:1067
Heart block contraindication 233916004
Retention of urine contraindication 267064002
Myocardial infarction in recovery phase contraindication 418044006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.66 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
15MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 7544372 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
15MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 7829121 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
15MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 8877245 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
15MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 9375410 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
15MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 9399025 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
30MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 7544372 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
30MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 7829121 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
30MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 8877245 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
30MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 9375410 Nov. 14, 2023 RELIEF OF MUSCLE SPASM
30MG AMRIX TEVA PHARMS INTL N021777 Feb. 1, 2007 RX CAPSULE, EXTENDED RELEASE ORAL 9399025 Nov. 14, 2023 RELIEF OF MUSCLE SPASM

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 7.54 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 7.24 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 5.51 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR IC50 6.95 WOMBAT-PK
Histamine H1 receptor GPCR Ki 8.83 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 6.82 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 6.84 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 6.81 WOMBAT-PK
Sodium-dependent noradrenaline transporter Transporter Ki 7.44 WOMBAT-PK
Sodium-dependent serotonin transporter Transporter Ki 6.97 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 4.73 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 7.22 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 8.22 PDSP
Proto-oncogene tyrosine-protein kinase receptor Ret Kinase IC50 6.52 CHEMBL

External reference:

IDSource
4019699 VUID
N0000147791 NUI
C0056732 UMLSCUI
D00772 KEGG_DRUG
0VE05JYS2P UNII
6202-23-9 SECONDARY_CAS_RN
791 INN_ID
80802008 SNOMEDCT_US
4019699 VANDF
d00963 MMSL
21949 RXNORM
373779004 SNOMEDCT_US
004680 NDDF
CHEBI:3996 CHEBI
CHEMBL669 ChEMBL_ID
DB00924 DRUGBANK_ID
CHEMBL1200636 ChEMBL_ID
7152 IUPHAR_LIGAND_ID
2895 PUBCHEM_CID
C004704 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1920 CAPSULE, EXTENDED RELEASE 15 mg ORAL NDA AUTHORIZED GENERIC 19 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1921 CAPSULE, EXTENDED RELEASE 30 mg ORAL NDA AUTHORIZED GENERIC 19 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0115-1436 CAPSULE, EXTENDED RELEASE 15 mg ORAL NDA AUTHORIZED GENERIC 19 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0115-1437 CAPSULE, EXTENDED RELEASE 30 mg ORAL NDA AUTHORIZED GENERIC 19 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-0751 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-0761 TABLET, FILM COATED 7.50 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-0771 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0440-1350 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0440-7350 TABLET, FILM COATED 10 mg ORAL ANDA 11 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-3256 TABLET, FILM COATED 5 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-3330 TABLET, FILM COATED 7.50 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-5658 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-3520 TABLET, FILM COATED 10 mg ORAL ANDA 14 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7528 TABLET, FILM COATED 5 mg ORAL ANDA 14 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-8084 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-8182 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7809 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-072 TABLET, FILM COATED 10 mg ORAL ANDA 12 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-159 TABLET 10 mg ORAL ANDA 14 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-200 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10702-006 TABLET, FILM COATED 5 mg ORAL ANDA 13 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10702-007 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 12634-528 TABLET 10 mg ORAL ANDA 12 sections
CYCLOBENZAPRINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-065 TABLET 10 mg ORAL ANDA 13 sections
CYCLOBENZAPRINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-544 TABLET 5 mg ORAL ANDA 12 sections
Amrix HUMAN PRESCRIPTION DRUG LABEL 1 16590-596 CAPSULE, EXTENDED RELEASE 15 mg ORAL NDA 13 sections
FEXMID HUMAN PRESCRIPTION DRUG LABEL 1 16590-699 TABLET, FILM COATED 7.50 mg ORAL ANDA 13 sections
Amrix HUMAN PRESCRIPTION DRUG LABEL 1 16590-810 CAPSULE, EXTENDED RELEASE 30 mg ORAL NDA 13 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-036 TABLET 5 mg ORAL ANDA 14 sections
Cyclobenzaprine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-037 TABLET 10 mg ORAL ANDA 14 sections