87-08-1

• 常用中文名：青霉素V
• 常用英文名：Penicillin-V
• CAS号：87-08-1
• 分子式：C₁₆H₁₈N₂O₅S
• 分子量：350.389
• 相关类别： 医药中间体 杂环化合物 吡啶类化合物 硝基吡啶
• 发布时间：2018-02-09 08:00:00
• 更新时间：2024-01-03 15:54:21
• 青霉素V(苯氧甲基青霉素)是一种有效的口服抗生素。青霉素V对链球菌、艰难梭菌和金黄色葡萄球菌具有抗菌活性。青霉素V具有研究中耳炎、鼻窦炎、咽炎和扁桃体炎的潜力[1][2][3][4]。

名称

• 中文名: 青霉素V
• 英文名: phenoxymethylpenicillin
• 中文别名: 苯氧甲基青霉素; 青黴素V
• 英文别名: penicillin-V; Oracillin; Pen-vee-oral; Fenospen; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Penicillin phenoxymethyl; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; PenicillinV; Phenocillin; Beromycin; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(phenyloxy)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Phenopenicillin; Acipen-V; Phenomycilline; Phenospen; V-Cillin; [2S-(2a,5a,6b)]-3,3-Dimethyl-7-oxo-6-[(phenoxy acetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; Orocillin; penicillin V; 6-phenoxyacetamidopenicillanic acid; dowpen v-k; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-, (2S,5R,6R)-; 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-, (2S,5R,6R)-; penicillin VK; Phenoxymethylpenicillin

物化性质

• 密度: 1.5±0.1 g/cm3
• 沸点: 681.4±55.0 °C at 760 mmHg
• 熔点: 120 - 128ºC
• 分子式: C₁₆H₁₈N₂O₅S
• 分子量: 350.389
• 闪点: 365.9±31.5 °C
• 精确质量: 350.093628
• PSA: 121.24000
• LogP: 1.88
• 外观性状: 白色至灰白色结晶粉末
• 蒸汽压: 0.0±2.2 mmHg at 25°C
• 折射率: 1.651
• 储存条件: −20°C
• 稳定性: Stable. Combustible. Incompatible with strong oxidizing agents.
• 水溶解性: Very slightly soluble in water, soluble in ethanol (96 per cent).

生物活性

• 描述: 青霉素V(苯氧甲基青霉素)是一种有效的口服抗生素。青霉素V对链球菌、艰难梭菌和金黄色葡萄球菌具有抗菌活性。青霉素V具有研究中耳炎、鼻窦炎、咽炎和扁桃体炎的潜力[1][2][3][4]。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 体外研究: 青霉素V(0.002-8.0mg/L)抑制链球菌的生长,最低抑制浓度(MIC)为0.004-0.008mg/L[2]。青霉素V(0.002-8.0 mg/L)对艰难梭菌具有抗菌活性,MIC50值为4.0 mg/L,MIC90值为8.0 g/L[3]。青霉素V(0.004-0.063 mg/L；18 h)抑制金黄色葡萄球菌的生长,MIC值为0.016 mg/L[4]。
• 体内研究: 青霉素V(0.063-0.25mg/kg；s.c.)抑制小鼠大腿肌肉中金黄色葡萄球菌的生长[4]。青霉素V(2 mg/kg；s.c.)的血浆半衰期(61 min)和平均AUC(0.47 mg/L·h)[4]。青霉素V(100mg/kg；每天一次,持续5天)可避免大鼠急性化脓性中耳炎(AOM)的暴发性感染[5]。动物模型：无特异性病原体(SPF)雄性瑞士小鼠(20-25 g)接种金黄色葡萄球菌[4]剂量：0.063、0.13、0.25 mg/kg给药：S.c.结果：与对照组(3.5×107计数/mL)相比,0.25 g/kg剂量下的CFU数量(1.34×107计数/mL)减少。
• 参考文献:

  [1]. Sabath LD. Et, al. Phenoxymethylpenicillin (penicillin V) and phenethicillin. Med Clin North Am. 1970 Sep;54(5):1101-11.

  [2]. Kamme C, et, al. In vitro effect on group A streptococci of loracarbef versus cefadroxil, cefaclor and penicillin V. Scand J Infect Dis. 1993;25(1):37-42.

  [3]. Norén T, et, al. In vitro susceptibility to 17 antimicrobials of clinical Clostridium difficile isolates collected in 1993-2007 in Sweden. Clin Microbiol Infect. 2010 Aug;16(8):1104-10.

  [4]. Overbosch D, et, al. Comparative pharmacodynamics and clinical pharmacokinetics of phenoxymethylpenicillin and pheneticillin. Br J Clin Pharmacol. 1985 May;19(5):657-68.

  [5]. Hermansson A, et, al. Prevention of experimental acute otitis media with penicillin V. Acta Otolaryngol. Jan-Feb 1990;109(1-2):119-23.

  [6]. Timm A, et al. Photolysis of four β‑lactam antibiotics under simulated environmental conditions: Degradation, transformation products and antibacterial activity. Sci Total Environ. 2019 Feb 15;651(Pt 1):1605-1612.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : RY4025000 CHEMICAL NAME : Penicillanic acid, 6-phenoxyacetamido- CAS REGISTRY NUMBER : 87-08-1 BEILSTEIN REFERENCE NO. : 0096259 LAST UPDATED : 199612 DATA ITEMS CITED : 15 MOLECULAR FORMULA : C16-H18-N2-O5-S MOLECULAR WEIGHT : 350.42 WISWESSER LINE NOTATION : T45 ANV ESTJ CMV1OR& F1 F1 GVQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 10 mg/kg/2D TOXIC EFFECTS : Liver - liver function tests impaired Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - body temperature increase TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2220 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1775 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1600 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 6578 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1351 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >4 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >1775 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 822 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 1096 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes MUTATION DATA TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Rodent - mouse Ascites tumor DOSE/DURATION : 200 ug/L REFERENCE : NEOLA4 Neoplasma. (Karger-Libri, P.O. Box, CH-4009 Basel, Switzerland) V.4- 1957- Volume(issue)/page/year: 22,105,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83957 No. of Facilities: 61 (estimated) No. of Industries: 2 No. of Occupations: 6 No. of Employees: 2874 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83957 No. of Facilities: 114 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 1964 (estimated) No. of Female Employees: 959 (estimated)

安全

• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R42/43
• 安全声明 (欧洲): 22-36
• 危险品运输编码: NONH for all modes of transport
• RTECS号: RY4025000
• 海关编码: 3003101300

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