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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 2895作成日：2026年10月27日

シクロベンザプリン

5-[3-(ジメチルアミノ)プロピリデン]-5H-ジベンゾ[a,d]シクロヘプテン · 3-(5H-ジベンゾ[a,d]シクロヘプテン-5-イリデン)-N,N-ジメチル-1-プロパンアミン · プロヘプタトリエン · シクロベンザプリン · N,N-ジメチル-3-(5H-ジベンゾ[a,d]シクロヘプテン-5-イリデン)プロパン-1-アミン · ジメチル(3-{トリシクロ[9.4.0.03,8]ペンタデカ-1(15),3,5,7,9,11,13-ヘプタエン-2-イリデン}プロピル)アミン · CYCLOBENZAPRINE · mk130

https://huagongshe.com/ja/chemical/2895

シクロベンザプリン の分子構造式

識別子と物理属性

CAS No.303-53-7
分子式C20H21N
平均分子量275.4 g/mol
単同位体質量275.16739967 g/mol
SMILESCN(C)CCC=C1c2ccccc2C=Cc2ccccc21
InChIKeyJURKNVYFZMSNLP-UHFFFAOYSA-N
PubChem CID2895
ChEMBLCHEMBL669
ChEBICHEBI:3996
EC No.206-145-8
DTXSIDDTXSID0046933
現地名シクロベンザプリン

化学・物理的性質

XLogP5.2
極性表面積3.2
水素結合供与体数0
水素結合受容体数1
回転可能結合数3
重原子数21
形式電荷0
複雑度365
医薬品DEA NFLIS-Drug Category -> Depressants and TranquilizersPharmaceuticals -> Listed in ZINC15
LogP（分配係数）5.24.81
溶解度Freely Soluble6.89e-03 g/L
Human DrugsBreast FeedingLactationMilk, HumanMuscle Relaxants, CentralPharmaceuticals
沸点BP: 175-180 °C at 1 atmbp1 175-180°
DecompositionWhen headted to decomposistion it emits toxic fumes of /nitrogen oxides/
融点216 - 218 °C (hydrochloride salt)
Physical DescriptionSolid
Stability/Shelf LifeStable under recommended storage conditions. /Cyclobenzaprine hydrochloride/
Dissociation Constants9.698.2418.47pKa = 9.76 (tertiary amine)
Collision Cross Section157.25 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]164.7 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]
Other Experimental PropertiesWhite to off-white crystalline powder from isopropanol. MP: 216-218 °C. Solubility in water: >20 g/100 mL. Freely soluble in methanol, ethanolsparingly soluble in isopropanolslightly soluble in chloroform, methylene chloride. Practically insoluble in hydrocarbons. UV max: 226, 295 nm (epsilon = 52300, 12000 /Cyclobenzaprine hydrochloride/
密度0.9504 (rough estimate)
屈折率1.7500 (estimate)
pKa（酸解離定数）pKa 8.47 (Uncertain)
BCS Class1
NISTの化学物質情報Cyclobenzaprine(303-53-7)

安全性と法規制

GHS 分類Not ClassifiedDangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
その他の安全情報IMAP assessments - 1-Propanamine, 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-: Environment tier I assessment
FDA 要件The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including cyclobenzaprine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Cyclobenzaprine hydrochloride/
Special ReportsWestrol MS et alTher Hypothermia Temp Manag 5 (3): 171-6 (2015). A discussion of cyclobenzaprine toxicity, hypothermia, ILE, and accidental hypothermic cardiac arrest ... .
Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas /Cyclobenzaprine hydrochloride/
Hazard Classes and CategoriesNot Classified
消火手順Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. /Cyclobenzaprine hydrochloride/Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. /Cyclobenzaprine hydrochloride/
保管条件Store at 20 deg to 25 °C (68 deg to 77 °F).Keep container tightly closed in a dry and well-ventilated place. /Cyclobenzaprine hydrochloride/
清掃方法ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dustEnvironmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drainsMethods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. /Cyclobenzaprine hydrochloride/

用途

説明

Cyclobenzaprine is structurally similar to tricyclic antidepressants. It acts at the brain stem level.

使用

Relaxant (muscle).

処分方法SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubberContaminated packaging: Dispose of as unused product. /Cyclobenzaprine hydrochloride/
Preventive MeasuresPrecautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. /Cyclobenzaprine hydrochloride/Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product. /Cyclobenzaprine hydrochloride/Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. /Cyclobenzaprine hydrochloride/SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Personal Protective Equipment (PPE)Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). /Cyclobenzaprine hydrochloride/Skin protection: Handle with gloves. /Cyclobenzaprine hydrochloride/Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. /Cyclobenzaprine hydrochloride/Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). /Cyclobenzaprine hydrochloride/
相互作用Concomitant use of cyclobenzaprine with diflunisal or naproxen reportedly was well tolerated and did not appear to result in any unexpected adverse effects. However, concomitant use of cyclobenzaprine with naproxen has been associated with an increased incidence of drowsiness. Plasma concentrations of aspirin or cyclobenzaprine were unaffected when the drugs were administered concomitantly. It has not been established whether combined therapy with cyclobenzaprine and aspirin (or other analgesics) will result in enhanced clinical efficacy.Cyclobenzaprine and structurally similar tricyclic antidepressants may block the hypotensive effects of guanethidine (no longer commercially available in the US) and other similarly acting drugs.Cyclobenzaprine and structurally similar tricyclic antidepressants may enhance the risk of seizures in patients receiving tramadol.Cyclobenzaprine may be additive with or may potentiate the action of other CNS depressants (e.g., alcohol, barbiturates). Cyclobenzaprine, especially when used concomitantly with alcohol or other CNS depressants, may impair the patient's ability to perform activities requiring mental alertness or physical coordination (e.g., operating machinery, driving a motor vehicle).For more Interactions (Complete) data for Cyclobenzaprine (9 total), please visit the HSDB record page.
HepatotoxicityThe product insert for cyclobenzaprine mentions that abnormal liver function, hepatitis, jaundice, and cholestasis occur in
有害作用The most common adverse drug reactions of cyclobenzaprine are somnolence, dry mucous membranes, dizziness, and confusion. Like other cyclical antidepressants, cyclobenzaprine antagonizes the muscarinic receptors, which may produce undesired side effects such as xerostomia, ileus, tachycardia, mydriasis, confusion, urinary retention, and hallucinations. Additionally, cyclobenzaprine antagonizes the alpha1 adrenergic receptor, causing a vasodilatory effect, and may contribute further to reflex tachycardia. Chronic cyclobenzaprine use can cause minor ALT elevation, but no reports of severe hepatotoxicity are reported.
毒性の概要IDENTIFICATION AND USE: Cyclobenzaprine (used in the form of cyclobenzaprine hydrochloride tablets) is indicated as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions. HUMAN EXPOSURE AND TOXICITY: Manifestations of toxicity may develop rapidly after a cyclobenzaprine overdose, and rarely, death may occur. The most common toxic effects associated with cyclobenzaprine overdose are drowsiness and tachycardialess frequent manifestations include tremor, agitation, coma, ataxia, hypertension, slurred speech, confusion, dizziness, nausea, vomiting, and hallucinations. Rarely, potentially serious effects may include cardiac arrest, chest pain, cardiac dysrhythmias, severe hypotension, seizures, and neuroleptic malignant syndrome. Serotonin syndrome is another potential side effect. Blood concentration of > or = 0.8 mg/L cyclobenzaprine may be associated with a fatal outcome. In one case of accidental overdose, the victim developed severe hypothermia and then developed cardiac arrest during transport. ANIMAL STUDIES: Ptyalism, emesis, tremors, convulsions and increased respiratory rate developed and death occurred within 1 hour following single oral doses of 180 mg/kg or more by gavage in dogs. Acute exposure to the drug in rats resulted in ataxia, decreased respiratory rate, sedation, flaccid hind legs, loss of the ear flick reflex, loss of the righting reflex with swimming movements, intermittent clonic convulsions, weight loss, lethargy, and then death. The drug was more toxic to infant and weanling rats than to young adults. In rats treated with cyclobenzaprine hydrochloride for up to 67 weeks at doses of approximately 5 to 40 times the maximum recommended human dose, pale, sometimes enlarged, livers were noted and there was a dose-related hepatocyte vacuolation with lipidosis. No evidence of embryo lethality or teratogenicity was revealed following oral doses of 5, 10 or 20 mg/kg/day in studies in mice and rabbits. The reproductive performance and fertility of males and females, and the growth and survival of their offspring were not adversely affected by doses of 5 or 10 mg/kg/day in rats. Litter size, size and survival of the pups, and weight gain of the mothers were decreased by doses of 20 mg/kg/day. Cyclobenzaprine hydrochloride was determined to have no genotoxic effects in several assays, including mouse bone marrow micronucleus assaySalmonella-Escherichia coli mammalian microsome reverse mutation assay with confirmatory assayand in a CHO cells chromosomal aberration assay with and without metabolic activation.Cyclobenzaprine is structurally and pharmacologically related to tricyclic antidepressants. Among the most dreaded toxicities linked with cyclical antidepressants, overdoses affect fast-acting sodium channels in the cardiac conduction system. Cyclical antidepressants block the cardiac sodium channel and cause prolongation of cardiac depolarization, which manifests as QRS widening on electrocardiograms. There is also evidence that cyclical antidepressants may decrease the seizure threshold by interfering with chloride conductance on the GABA receptor.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Manifestations of toxicity may develop rapidly after a cyclobenzaprine overdose, and rarely, death may occur. The most common toxic effects associated with cyclobenzaprine overdose are drowsiness and tachycardialess frequent manifestations include tremor, agitation, coma, ataxia, hypertension, slurred speech, confusion, dizziness, nausea, vomiting, and hallucinations. Rarely, potentially serious effects may include cardiac arrest, chest pain, cardiac dysrhythmias, severe hypotension, seizures, and neuroleptic malignant syndrome./CASE REPORTS/ In this case report, a 22-year-old male developed severe hypothermia after an accidental overdose of cyclobenzaprine. During transport, the patient developed cardiac arrest. He received active rewarming measures, including pleural lavage, gastric lavage, an intravascular heat exchange catheter, and cardiopulmonary bypass. Intravenous lipid emulsion (ILE) was also administered. A discussion of cyclobenzaprine toxicity, hypothermia, ILE, and accidental hypothermic cardiac arrest follows./CASE REPORTS/ A full-term male infant presented shortly after birth with respiratory distress. An echocardiogram done within the first hour of life showed an elevated pulmonary artery pressure, an associated right ventricular hypertrophy without a patent ductus arteriosus. The patient was treated for persistent pulmonary hypertension with favorable response. Maternal history was unremarkable except for chronic low back pain treated with cyclobenzaprine. A proposed mechanism for cyclobenzaprine includes inhibition of norepinephrine and serotonin reuptake, factors known to inhibit prostaglandin and nitric oxide. These two factors are the leading causes of in-utero ductal closure. ... Cyclobenzaprine use during late pregnancy should be considered a potential cause of early ductal closure./CASE REPORTS/ ... We report two ... cases of fatal cyclobenzaprine overdose with postmortem values. Case 1: a 56-year-old female was found in full cardiopulmonary arrest after a verbal suicide threat to a friend. Postmortem blood concentrations were cyclobenzaprine 0.96 mg/L and diazepam 0.3 mg/L. Case 2: a 37-year-old male was found in full arrest by a family member after an intentional ingestion of cyclobenzaprine. Postmortem blood concentrations were cyclobenzaprine 0.8 mg/L and ethanol 0.174 gm/dL. The concentrations of diazepam and ethanol reported in these two patients were not found in quantities usually associated with a fatal outcome, suggesting that the cyclobenzaprine was the primary cause of the fatality. Additionally, the blood was drawn from a femoral site, so that postmortem redistribution is not a likely factor. Blood concentration of > or = 0.8 mg/L cyclobenzaprine may be associated with a fatal outcome.For more Human Toxicity Excerpts (Complete) data for Cyclobenzaprine (14 total), please visit the HSDB record page.
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)cyclobenzaprineDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ Ptyalism, emesis, tremors, convulsions and increased respiratory rate developed and death occurred within 1 hour following single oral doses of 180 mg/kg or more by gavage in dogs./LABORATORY ANIMALS: Acute Exposure/ Oral LD50 values were approximately 338 mg/kg in mice and 425 mg/kg in rats. Both species exhibited similar signs of drug effects including ataxia, decreased respiratory rate, sedation, flaccid hind legs, loss of the ear flick reflex, loss of the righting reflex with swimming movements and intermittent clonic convulsions. Weight loss and lethargy preceded death which occurred 30 minutes to 7 days following administration. The drug was more toxic to infant and weanling rats than to young adults./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In rats treated with Cyclobenzaprine Hydrochloride for up to 67 weeks at doses of approximately 5 to 40 times the maximum recommended human dose, pale, sometimes enlarged, livers were noted and there was a dose-related hepatocyte vacuolation with lipidosis. In the higher dose groups this microscopic change was seen after 26 weeks and even earlier in rats which died prior to 26 weeksat lower doses, the change was not seen until after 26 weeks./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Following oral doses of 2, 5 and 10 mg/kg/day to mice for 81 weeks or to rats for 105 weeks, the onset, incidence and distribution of neoplasms was not affected by cyclobenzaprine hydrochloride.For more Non-Human Toxicity Excerpts (Complete) data for Cyclobenzaprine (10 total), please visit the HSDB record page.
Populations at Special RiskBecause cyclobenzaprine has adverse anticholinergic effects, it should be used with caution in patients with a history of urinary retention, angle-closure glaucoma, or increased intraocular pressure ... .Cyclobenzaprine should be used with caution in patients with mild hepatic impairment, and its use is not recommended in patients with moderate or severe hepatic impairment. Plasma concentrations of cyclobenzaprine are increased in patients with hepatic impairment, and such patients generally are more susceptible to sedation caused by some drugs, including cyclobenzaprine.Cyclobenzaprine is contraindicated in patients with hyperthyroidism, congestive heart failure, arrhythmias, heart block or conduction disorders, known hypersensitivity to the drug or any ingredient in the formulation and in the acute recovery phase following myocardial infarction.The plasma concentration of cyclobenzaprine is increased in the elderly. The elderly may also be more at risk for CNS adverse events such as hallucinations and confusion, cardiac events resulting in falls or other sequelae, drug-drug and drug-disease interactions. For these reasons, in the elderly, cyclobenzaprine should be used only if clearly needed.
Antidote and Emergency Treatment/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/Emergency and supportive measures. 1. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat coma, seizures, hypotension, and noncardiogenic pulmonary edema if they occur. /Opiates and opioids/For more Antidote and Emergency Treatment (Complete) data for Cyclobenzaprine (12 total), please visit the HSDB record page.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Non-Human Toxicity ValuesLD50 Mouse iv 36 mg/kgLD50 Mouse ip 90 mg/kgLD50 Mouse oral 250 mg/kgLD50 Rat oral 425 mg/kgLD50 Mouse oral 338 mg/kg
毒性LD50 oral in mouse: 250mg/kg
有害物質データ303-53-7(Hazardous Substances Data)