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药品详细

Salsalate(双水杨酯)

化学结构式图
中文名
双水杨酯
英文名
Salsalate
分子式
C14H10O5
化学名
2-[(2-hydroxyphenyl)carbonyloxy]benzoic acid
分子量
Average: 258.2262
Monoisotopic: 258.05282343
CAS号
552-94-3
ATC分类
N02B Other Analgesics and Antipyretics
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate’s mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo. Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body. The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.

生产厂家
    封装厂家
    参考
    Synthesis Reference Not Available
    General Reference Not Available
    剂型
    规格
    化合物类型
    Type small molecule
    Classes
    • Benzoates
    • Salicylates and Derivatives
    • Phenylacetates
    Substructures
    • Carboxylic Acids and Derivatives
    • Hydroxy Compounds
    • Benzyl Alcohols and Derivatives
    • Acetates
    • Benzoates
    • Salicylates and Derivatives
    • Phenols and Derivatives
    • Phenylacetates
    • Ethers
    • Benzene and Derivatives
    • Aromatic compounds
    • Anisoles
    • Benzoyl Derivatives
    • Phenyl Esters
    适应症
    药理
    Indication For relief of the signs and symptoms of rheumatoid arthritis, osteoarthritis and related rheumatic disorders.
    Pharmacodynamics Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo.
    Mechanism of action The mode of anti-inflammatory action of salsalate and other nonsteroidal anti-inflammatory drugs is not fully defined, but appears to be primarily associated with inhibition of prostaglandin synthesis. This inhibition of prostaglandin synthesis is done through the inactivation of cyclooxygenase-1 (COX-1) and COX-2, which are reponsible for catalyzing the formation of prostaglandins in the arachidonic acid pathway. Although salicylic acid (the primary metabolite of salsalate) is a weak inhibitor of prostaglandin synthesis in vitro, salsalate appears to selectively inhibit prostaglandin synthesis in vivo, providing anti-inflammatory activity equivalent to aspirin and indomethacin. Unlike aspirin, salsalate does not inhibit platelet aggregation.
    Absorption Salsalate is insoluble in acid gastric fluids (< 0.1 mg/ml at pH 1.0), but readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged. The amount of salicylic acid available from salsalate is about 15% less than from aspirin, when the two drugs are administered on a salicylic acid molar equivalent basis (3.6 g salsalate/5 g aspirin). Food slows the absorption of all salicylates including salsalate.
    Volume of distribution Not Available
    Protein binding Salicylate: 90-95% bound at plasma salicylate concentrations <100 mcg/mL; 70-85% bound at concentrations of 100-400 mcg/mL; 25-60% bound at concentrations >400 mcg/mL.
    Metabolism
    Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body.
    Route of elimination Not Available
    Half life The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.
    Clearance Not Available
    Toxicity Death has followed ingestion of 10 to 30 g of salicylates in adults, but much larger amounts have been ingested without fatal outcome.
    Affected organisms
    • Humans and other mammals
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 147 °C PhysProp
    Predicted Properties
    Property Value Source
    water solubility 2.46e-01 g/l ALOGPS
    logP 3.44 ALOGPS
    logP 3.64 ChemAxon
    logS -3 ALOGPS
    pKa (strongest acidic) 3.4 ChemAxon
    pKa (strongest basic) -4.3 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 4 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 83.83 ChemAxon
    rotatable bond count 4 ChemAxon
    refractivity 67.1 ChemAxon
    polarizability 24.92 ChemAxon
    药物相互作用
    Drug Interaction
    Betamethasone The corticosteroid, betamethasone, may decrease the effect of the salicylate, salsalate.
    Chlorpropamide The salicylate, salsalate, increases the effect of the sulfonylurea, chlorpropamide.
    Dexamethasone The corticosteroid, dexamethasone, may decrease the effect of the salicylate, salsalate.
    Fludrocortisone The corticosteroid, fludrocortisone, may decrease the effect of the salicylate, salsalate.
    Gliclazide The salicylate, salsalate, increases the effect of the sulfonylurea, gliclazide.
    Glyburide The salicylate, salsalate, increases the effect of the sulfonylurea, glibenclamide.
    Hydrocortisone The corticosteroid, hydrocortisone, may decrease the effect of the salicylate, salsalate.
    Methazolamide The salicylate, salsalate, at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
    Methotrexate The salicylate, salsalate, increases the effect and toxicity of methotrexate.
    Prednisolone The corticosteroid, prednisolone, may decrease the effect of the salicylate, salsalate.
    Prednisone The corticosteroid, prednisone, may decrease the effect of the salicylate, salsalate.
    Probenecid The salicylate, salsalate, decreases the uricosuric effect of probenecid.
    Sulindac Risk of additive toxicity (e.g. bleed risk). Salsalate may decrease the serum concentration of sulindac. Consider alternate therapy or monitor for changes in the therapeutic effects of sulindac and adverse effects of both agents if the interacting agent is initiated, discontinued or dose changed.
    Tiaprofenic acid Increased risk of gastrointestinal bleeding.
    Tolmetin Additive effects increase the risk of GI bleeding. Monitor for increased bleeding risk during concomitant therapy.
    Trandolapril The salicylate, Salsalate, may reduce the efficacy of Trandolapril. Monitor for changes in Trandolapril efficacy if Salsalate is initiated, discontinued or dose changed.
    Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the salicylate, Salsalate. Monitor for increased bleeding during concomitant thearpy.
    Triamcinolone The corticosteroid, triamcinolone, may decrease the effect of the salicylate, salsalate.
    食物相互作用
    Not Available

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