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87-08-1

Basic Information
CAS No.: 87-08-1
Name: PENICILLIN V
Article Data: 34
Molecular Structure:
Molecular Structure of 87-08-1 (PENICILLIN V)
Formula: C16H18 N2 O5 S
Molecular Weight: 350.395
Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)- (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-, (2S,5R,6R)- (9CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-,[2S-(2a,5a,6b)]-;6-(Phenoxyacetamido)penicillanic acid; Acipen-V; Calcipen; Crystapen V;Distaquaine V; Eskacillin V; Fenacilin; Meropenin; Oracillin; Oracilline;Oratren; Orocillin; Ospen; Pen-Oral; Pen-Vee; Pen-vee-oral; Penicillin V;Penicillin, phenoxymethyl-; Phenocillin; Phenopenicillin; Phenospen;Phenoxymethylpenicillin; Phenoxymethylpenicillinic acid; Stabicillin; V-Cil;V-Cillin; V-Cylina; V-Cyline; V-Tablopen; Vebecillin
EINECS: 201-722-0
Density: 1.3121 (rough estimate)
Melting Point: 120 - 128 C
Boiling Point: 681.4±55.0 °C(Predicted)
Solubility: Soluble white to off-white crystalline powder
Hazard Symbols: Not regulated UN NO.
Risk Codes: 42/43
Safety: Poison by intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: impaired liver function, dermatitis, fever. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Transport Information: 25kgs
PSA: 121.24000
LogP: 1.02590
Synthetic route
551-16-6

6-Aminopenicillanic Acid

2065-23-8

methyl 2-phenoxyacetate

87-08-1

penicilin V

Conditions
ConditionsYield
With recombinant Streptomyces lavendulae penicillinacylase In dimethyl sulfoxide at 30℃; for 10.8h; pH=7; Catalytic behavior; Kinetics; Concentration; pH-value; Solvent; Time; Enzymatic reaction;94.5%
65538-78-5

Penicillin-V-2'-bromethylester

87-08-1

penicilin V

Conditions
ConditionsYield
With lithium cobalt(I)-phthalocyanine; phenol In acetone for 4h; Ambient temperature;81%

(R)-2-[(2R,3R)-2-[(2R,3R)-1-((R)-1-Carboxy-2-methyl-propyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-yldisulfanyl]-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-butyric acid

87-08-1

penicilin V

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; dihydrogen peroxide; iron(II) sulfate; ascorbic acid In water1.3%
123314-55-6

(R)-((2R)-4t-carboxy-5,5-dimethyl-thiazolidin-2r-yl)-(2-phenoxy-acetylamino)-acetic acid

87-08-1

penicilin V

Conditions
ConditionsYield
With 1,4-dioxane; sodium hydroxide; dicyclohexyl-carbodiimide
1025-55-4

6-aminopenicillanic acid trimethylsilyl ester

701-99-5

Phenoxyacetyl chloride

87-08-1

penicilin V

Conditions
ConditionsYield
(i) Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/; Multistep reaction;
1203-85-6

6-β-aminopenicillanic acid sodium salt

701-99-5

Phenoxyacetyl chloride

87-08-1

penicilin V

53059-76-0

6β-benzylideneamino-penicillanic acid; 1,1,3,3-tetramethyl-butylamine salt

701-99-5

Phenoxyacetyl chloride

87-08-1

penicilin V

Conditions
ConditionsYield
With sodium 2-ethylhexanoic acid In chloroform-d1
701-99-5

Phenoxyacetyl chloride

40124-92-3

6R(β)-tritylaminopenicillanic acid

87-08-1

penicilin V

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetone
1098-87-9

penicillin V sodium salt

87-08-1

penicilin V

Conditions
ConditionsYield
Yield given;

Phenoxyacetyl-L-cysteinyl-D-valine

87-08-1

penicilin V

Conditions
ConditionsYield
With ammonium bicarbonate; iron(II) sulfate; catalase; ascorbic acid; diothiothreitol isopenicillin N synthetase from Cephalosporium acremonium CO728;
With isopenicillin N synthetase from Cephalosporium acremonium CO728; oxygen; ammonium bicarbonate; iron(II) sulfate; catalase; ascorbic acid; diothiothreitol In water at 27℃; Michaelis constant, maximum velocity;
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Chemistry

Molecular Structure:

Molecular Formula: C16H18N2O5S
Molecular Weight: 350.3895
IUPAC Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms of Penicillin V (CAS NO.87-08-1): 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((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-(2alpha,5alpha,6beta))- ; Penicillanic acid, 6-phenoxyacetamido- ; Phenoxymethylpenicillin
CAS NO: 87-08-1
Classification Code: Anti-Bacterial Agents ; Anti-Infective Agents ; Antibacterial ; Drug / Therapeutic Agent ; Human Data ; Mutation data
Melting point: 120-128°C
Index of Refraction: 1.65
Density: 1.45 g/cm3
Flash Point: 365.9 °C
Enthalpy of Vaporization: 105 kJ/mol
Boiling Point: 681.4 °C at 760 mmHg
Vapour Pressure: 1.69E-19 mmHg at 25 °C
Melting point: 120-128 °C
Storage tempreture: -20 °C
Solubility: Insoluble in water
Appearance: Crystalline solid

Uses

 Penicillin V (CAS NO.87-08-1) has been used for antibacterial.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intramuscular 1096mg/kg (1096mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
guinea pig LD50 intraperitoneal 822mg/kg (822mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 intramuscular > 1775mg/kg (1775mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 intraperitoneal 1351mg/kg (1351mg/kg)   Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956.
mouse LD50 oral 6578mg/kg (6578mg/kg)   Antibiotiki. Vol. 3(4), Pg. 37, 1958.
mouse LD50 subcutaneous > 4gm/kg (4000mg/kg)   Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956.
rat LD50 intramuscular > 1600mg/kg (1600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 intravenous > 1775mg/kg (1775mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 oral > 2220mg/kg (2220mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
women TDLo oral 10mg/kg/2D (10mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Lancet. Vol. 2, Pg. 1297, 1976.

Safety Profile

Poison by intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: impaired liver function, dermatitis, fever. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Hazard Codes of Penicillin V (CAS NO.87-08-1): HarmfulXn
Risk Statements: 42/43 
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 22-36 
S22: Do not breathe dust. 
S36: Wear suitable protective clothing.

Specification

 It is incompatible with acids, oxidizing agents (especially in the presence of trace metals), heavy metal ions such as copper, zinc and mercury; sympathomimetic amines, thiomersal, cetostearyl alcohol, hard paraffins, cocoa butter and many ionic an nonionic surface-active agents.