dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})amine

• ChemBase编号: 800
• 分子式: C20H21N
• 平均质量: 275.38744
• 单一同位素质量: 275.16739968
• SMILES: N(CC/C=C\1/c2c(C=Cc3c1cccc3)cccc2)(C)C
• Canonical SMILES: CN(CC/C=C/1\c2ccccc2C=Cc2c1cccc2)C
• InChI: InChI=1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3
• InChIKey: JURKNVYFZMSNLP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})amine; dimethyl(3-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}propyl)amine
• IUPAC传统名: dimethyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})amine; cyclobenzaprine
• 商标名: Cyclobenz; Flexeril; Flexiban; Proeptatriene; Proheptatriene
• 别名: Cyclobenzaprine HCL; Cyclobenzaprine

登记号

• CAS号: 303-53-7
• PubChem SID: 46508313; 160964263
• PubChem CID: 2895
• CHEBI ID: 3996
• ATC码: M03BX08
• CHEMBL: 669
• Chemspider ID: 2792
• DrugBank ID: DB00924
• KEGG ID: D07758
• 美国药典/FDA物质标识码: 69O5WQQ5TI
• 维基百科标题: Cyclobenzaprine
• Medline Plus: a682514

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.1812798
• LogD (pH = 7.4): 2.2807164
• Log P: 4.6130133
• 摩尔折射率: 102.6238 cm^3
• 极化性: 35.348446 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.73
• LOG S: -4.6
• 溶解度: 6.89e-03 g/l

分子性质

理化性质

• 溶解度: Freely Soluble
• 疏水性(logP): 5.2

药理学性质

• 给药途径: Oral
• 生物利用度: 33% to 55%
• 排泄: renal
• 半衰期: 18 hours (range 8–37 hours; n=18)
• 代谢: hepatic
• 法定药品分级: rx-only
• 妊娠期药物分类: Category B

详细说明

DrugBank - DB00924

• Drug Groups: approved
• Description: Cyclobenzaprine is a skeletal muscle relaxant and a central nervous system (CNS) depressant. Cyclobenzaprine acts on the locus coeruleus where it results in increased norepinephrine release, potentially through the gamma fibers which innervate and inhibit the alpha motor neurons in the ventral horn of the spinal cord. It is structurally similar to Amitriptyline, differing by only one double bond.
• Indication: For use as an adjunct to rest and physical therapy for relief of muscle spasm associated with acute, painful musculoskeletal conditions.
• Pharmacology: Cyclobenzaprine, closely related to the antidepressant amitriptyline, is used as a skeletal muscle relaxant to reduce pain and tenderness and improve mobility. Unlike dantrolene, cyclobenzaprine cannot be used to treat muscle spasm secondary to cerebral or spinal cord disease.
• Toxicity: Oral mouse and rat LD₅₀ are 338 mg/kg and 425 mg/kg respectively. Signs of overdose include agitation, coma, confusion, congestive heart failure, convulsions, dilated pupils, disturbed concentration, drowsiness, hallucinations, high or low temperature, increased heartbeats, irregular heart rhythms, muscle stiffness, overactive reflexes, severe low blood pressure, stupor, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Extensively metabolized (gastrointestinal and hepatic).
• Absorption: Slowly but well absorbed after oral administration
• Half Life: 18 hours (range 8-37 hours)
• Protein Binding: Very high (93%)
• Elimination: Cyclobenzaprine is extensively metabolized, and is excreted primarily as glucuronides via the kidney.
• Clearance: * 0.7 L/min
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com