5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

• ChemBase编号: 348
• 分子式: C15H13NO3
• 平均质量: 255.26862
• 单一同位素质量: 255.08954328
• SMILES: OC(=O)C1CCn2c1ccc2C(=O)c1ccccc1
• Canonical SMILES: OC(=O)C1CCn2c1ccc2C(=O)c1ccccc1
• InChI: InChI=1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)
• InChIKey: OZWKMVRBQXNZKK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
• IUPAC传统名: ketorolac
• 商标名: Acular; Acular LS; Acular Preservative Free; Toradol
• 别名: Ketorolaco [Spanish]; Ketorolacum [Latin]; Ketoralac; Ketorolac Tromethamine; Ketorolac

登记号

• CAS号: 66635-83-4
• PubChem SID: 160963811; 46507019
• PubChem CID: 3826

理论计算性质

JChem

• Acid pKa: 3.8351793
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.6151371
• LogD (pH = 7.4): -0.9625098
• Log P: 2.2833629
• 摩尔折射率: 70.1945 cm^3
• 极化性: 26.83597 Å^3
• 极化表面积: 59.3 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: 2.66
• LOG S: -2.7
• 溶解度: 5.13e-01 g/l

分子性质

理化性质

• 溶解度: 25 mg/mL (tromethamine salt)
• 疏水性(logP): 2.1

详细说明

DrugBank - DB00465

• Drug Groups: approved
• Description: A pyrrolizine carboxylic acid derivative structurally related to indomethacin. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed)
• Indication: For the short-term (~5 days) management of moderately severe acute pain that requires analgesia at the opioid level, usually in a postoperative setting.
• Pharmacology: Ketorolac, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain. It is a peripherally acting analgesic. The biological activity of ketorolac tromethamine is associated with the S-form. Ketorolac tromethamine possesses no sedative or anxiolytic properties.
• Toxicity: LD₅₀ = 189 mg/kg (rat, oral).
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. Less than 50% of a dose is metabolized. The major metabolites are a glucuronide conjugate, which may also be formed in the kidney, and p-hydroxy ketorolac. Neither metabolite has significant analgesic activity.
• Absorption: Rapidly and completely absorbed after oral administration
• Half Life: 2.5 hours for the S-enantiomer compared with 5 hours for the R-enantiomer
• Protein Binding: 99%
• Elimination: The principal route of elimination of ketorolac and its metabolites is renal. Approximately 6% of a dose is excreted in the feces.
• Distribution: * 0.26 ± 0.08 L/kg [children 4 to 8 years old]
• Clearance: * 0.042 +/- 0.01 L/hr/kg [Pediatric Patients]; * 0.02 L/h/kg [Normal Subjects IM]; * 0.03 L/h/kg [Normal Subjects oral]; * 0.02 L/h/kg [Healthy Elderly Subjects IM]; * 0.02 L/h/kg [Healthy Elderly Subjects oral]; * 0.03 L/h/kg [Patients with Hepatic Dysfunction IM]; * 0.03 L/h/kg [Patients with Hepatic Dysfunction oral]; * 0.02 L/h/kg [Patients with Renal Impairment IM]; * 0.02 L/h/kg [Patients with Renal Impairment oral]; * 0.02 L/h/kg [Renal Dialysis Patients IM]
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