2-(2-hydroxybenzoyloxy)benzoic acid

• ChemBase编号: 1210
• 分子式: C14H10O5
• 平均质量: 258.2262
• 单一同位素质量: 258.05282342
• SMILES: O(c1c(cccc1)C(=O)O)C(=O)c1c(O)cccc1
• Canonical SMILES: Oc1ccccc1C(=O)Oc1ccccc1C(=O)O
• InChI: InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)
• InChIKey: WVYADZUPLLSGPU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2-hydroxybenzoyloxy)benzoic acid
• IUPAC传统名: salina; 2-(2-hydroxybenzoyloxy)benzoic acid
• 商标名: Disalcid
• 别名: 水杨基水杨酸; Sasapyrine; 2-(2-Hydroxybenzoyl)oxybenzoic acid; 2-Hydroxybenzoic acid 2-carboxyphenyl ester; disalicylic acid; salicyloxysalicylic acid; Salsalate; Sasapyrine; Salsalatum [inn-latin]; salicylsalicylic acid; Salsalate; Salicylic Acid Salicylate; Diacesal; Diplosal; Disalcid; Disalgesic; Disalyl; Mono-Gesic; NSC 49171; Nobacid; Salflex; Salical; Salicyl Salicylate; Salicyloylsalicylic Acid; Salina; Salsalate; Salysal; Sasapirin; Sasapyrinum; o-Salicylsalicylic Acid; Salicylsalicylic acid; 2-((2-Hydroxybenzoyl)oxy)benzoic acid

登记号

• CAS号: 552-94-3
• EC号: 209-027-4
• MDL号: MFCD00020252
• PubChem SID: 160964671; 46506882
• PubChem CID: 5161

理论计算性质

JChem

• Acid pKa: 3.4033105
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.5542619
• LogD (pH = 7.4): 0.23430523
• Log P: 3.6386988
• 摩尔折射率: 67.098 cm^3
• 极化性: 25.454422 Å^3
• 极化表面积: 83.83 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -3.02
• 溶解度: 2.46e-01 g/l

分子性质

理化性质

• 溶解度: DMSO: ≥15 mg/mL
• 外观: white to tan powder
• 熔点: 132-138°C

安全信息

• 保存注意事项: Moisture Sensitive
• RTECS编号: DH2080000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-50; 36/37/38
• 安全公开号: 26-37; 61
• TSCA收录: 是
• GHS危险品标识: GHS07; GHS09
• GHS警示词: Warning
• GHS危险声明: H302-H400; H315-H319-H335
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P273
• 保存温度: room temp

药理学性质

• 作用靶点: Others

产品相关信息

• 纯度: ≥98% (HPLC); 95+%; 98%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C14H10O5

详细说明

DrugBank - DB01399

• Drug Groups: approved
• Description: 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.
• Indication: For relief of the signs and symptoms of rheumatoid arthritis, osteoarthritis and related rheumatic disorders.
• Pharmacology: 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.
• 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
• Biotransformation: 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.
• 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.
• 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.
• 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.
• External Links: RxList; PDRhealth; Drugs.com

Sigma Aldrich - SML0070

Biochem/physiol Actions
Salsalate is a nonsteroidal anti-inflammatory drug (NSAID), a nonacetylated salicylate with no more problems of gastrointestinal bleeding than placebo. It inhibits synthesis and release of prostaglandins through the inactivation of cyclooxygenase-1 (COX-1) and COX-2. Salsalate is currently being investigated as a treatment for Type 2 diabetes with possible use to prevent the disease in people at risk. It reduces blood glucose concentrations in patients with type 2 diabetes, as well as in insulin-resistant patients without diabetes.

Toronto Research Chemicals - S095700

Nonacetylated aspirin analog. Analgesic, anti-inflammatory.

参考文献

• Harrison, L.L., et al.: J. Pharm. Sci., 69, 1268 (1980)
• Dromgoole, S.M., et al.: J. Pharm. Sci., 73, 1657 (1980)