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87-08-1

87-08-1 structure
87-08-1 structure
  • Name: Penicillin-V
  • Chemical Name: phenoxymethylpenicillin
  • CAS Number: 87-08-1
  • Molecular Formula: C16H18N2O5S
  • Molecular Weight: 350.389
  • Catalog: Pharmaceutical intermediate Heterocyclic compound Pyridine compound Nitropyridine
  • Create Date: 2018-02-09 08:00:00
  • Modify Date: 2024-01-03 15:54:21
  • 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].
Name phenoxymethylpenicillin
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
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
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.
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
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).

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)
Hazard Codes Xn
Risk Phrases R42/43
Safety Phrases 22-36
RIDADR NONH for all modes of transport
RTECS RY4025000
HS Code 3003101300
HS Code 3003101300

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