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药品详细

Salicyclic acid(水杨酸)

化学结构式图
中文名
水杨酸
英文名
Salicyclic acid
分子式
C7H6O3
化学名
2-hydroxybenzoic acid
分子量
Average: 138.1207
Monoisotopic: 138.031694058
CAS号
69-72-7
ATC分类
D11A 未知;N02B Other Analgesics and Antipyretics
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics.

生产厂家
    封装厂家
    参考
    Synthesis Reference Not Available
    General Reference
    1. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. Pubmed
    2. Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6. Pubmed
    剂型
    规格
    化合物类型
    Type small molecule
    Classes
    • Benzoates
    • Salicylates and Derivatives
    Substructures
    • Hydroxy Compounds
    • Benzyl Alcohols and Derivatives
    • Acetates
    • Benzoates
    • Salicylates and Derivatives
    • Phenols and Derivatives
    • Benzene and Derivatives
    • Carboxylic Acids and Derivatives
    • Aromatic compounds
    • Benzoyl Derivatives
    • Phenyl Esters
    适应症
    药理
    Indication Key additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts.
    Pharmacodynamics Salicylic acid treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. This effect on skin cells also makes salicylic acid an active ingredient in several shampoos meant to treat dandruff. Use of straight salicylic solution may cause hyperpigmentation on unpretreated skin for those with darker skin types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock. Subsalicylate in combination with bismuth form the popular stomach relief aid known commonly as Pepto-Bismol. When combined the two key ingredients help control diarrhea, nausea, heartburn, and even gas. It is also very mildly anti-biotic.
    Mechanism of action Salicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.
    Absorption Not Available
    Volume of distribution Not Available
    Protein binding Not Available
    Metabolism
    Not Available
    Route of elimination Not Available
    Half life Not Available
    Clearance Not Available
    Toxicity Oral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. Investigated a mutagen and reproductive effector.
    Affected organisms
    • Humans and other mammals
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 158 °C PhysProp
    boiling point 211 °C at 2.00E+01 mm Hg PhysProp
    water solubility 2240 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
    logP 2.26 HANSCH,C ET AL. (1995)
    logS -1.82 ADME Research, USCD
    Caco2 permeability -4.79 ADME Research, USCD
    pKa 2.97 SERJEANT,EP & DEMPSEY,B (1979)
    Predicted Properties
    Property Value Source
    water solubility 1.13e+01 g/l ALOGPS
    logP 1.96 ALOGPS
    logP 1.98 ChemAxon
    logS -1.1 ALOGPS
    pKa (strongest acidic) 2.79 ChemAxon
    pKa (strongest basic) -6.3 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 3 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 57.53 ChemAxon
    rotatable bond count 1 ChemAxon
    refractivity 35.3 ChemAxon
    polarizability 12.81 ChemAxon
    药物相互作用
    食物相互作用
    Not Available

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