CAS 87-08-1|Penicillin-V
| Common Name | Penicillin-V | ||
|---|---|---|---|
| CAS Number | 87-08-1 | Molecular Weight | 350.389 |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 681.4±55.0 °C at 760 mmHg |
| Molecular Formula | C16H18N2O5S | Melting Point | 120 - 128ºC |
| MSDS | / | Flash Point | 365.9±31.5 °C |
Names
| Name | phenoxymethylpenicillin |
|---|---|
| Synonym | More Synonyms |
Penicillin-V BiologicalActivity
| Description | Penicillin V (Phenoxymethylpenicillin) is a potent and orally active antibiotic. Penicillin V shows antibacterial activity for Streptococci, Clostridium difficile and staphylococcus aureus. Penicillin V has the potential for the research of otitis, sinusitis, pharyngitis and tonsillitis[1][2][3][4]. |
|---|---|
| Related Catalog | Research Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial |
| In Vitro | Penicillin V (0.002-8.0 mg/L) inhibits the growth of Streptococci, with the minimum inhibitory concentrations (MICs) of 0.004-0.008 mg/L[2]. Penicillin V (0.002-8.0 mg/L) shows antibacterial activity for Clostridium difficile with an MIC50 value of 4.0 mg/L and an MIC90 value of 8.0 mg/L[3]. Penicillin V (0.004-0.063 mg/L; 18 h) inhibits the growth of Staphylococcus aureus, with an MIC value of 0.016 mg/L[4]. |
| In Vivo | Penicillin V (0.063-0.25 mg/kg; s.c.) inhibits the outgrowth of S. aureus in mice thigh muscle[4]. Penicillin V (2 mg/kg; s.c.) exhibits the plasma half-life (61 min) and mean AUC (0.47 mg/L·h)[4]. Penicillin V (100 mg/kg; p.o. once daily for 5 d) avoids the fulminant infection of acute purulent otitis media (AOM) in rats[5]. Animal Model: Specific pathogen free (SPF) male Swiss mice (20-25 g) are inoculated S. aureus[4] Dosage: 0.063, 0.13, 0.25 mg/kg Administration: S.c. Result: Decreased the number of CFU (1.34×107 counts/mL) compared to controls (3.5×107 counts/mL) at the dose of 0.25 mg/kg. |
| References | [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. |
Chemical & Physical Properties
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 681.4±55.0 °C at 760 mmHg |
| Melting Point | 120 - 128ºC |
| Molecular Formula | C16H18N2O5S |
| Molecular Weight | 350.389 |
| Flash Point | 365.9±31.5 °C |
| Exact Mass | 350.093628 |
| PSA | 121.24000 |
| LogP | 1.88 |
| Vapour Pressure | 0.0±2.2 mmHg at 25°C |
| Index of Refraction | 1.651 |
| InChIKey | BPLBGHOLXOTWMN-MBNYWOFBSA-N |
| SMILES | CC1(C)SC2C(NC(=O)COc3ccccc3)C(=O)N2C1C(=O)O |
| Storage condition | −20°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Water Solubility | Very slightly soluble in water, soluble in ethanol (96 per cent). |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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)
Safety Information
| Hazard Codes | Xn |
|---|---|
| Risk Phrases | R42/43 |
| Safety Phrases | 22-36 |
| RIDADR | NONH for all modes of transport |
| RTECS | RY4025000 |
| HS Code | 3003101300 |
Customs
| HS Code | 3003101300 |
|---|
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Synonyms
| 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 |
