Penicillin V
Title: Penicillin V
CAS Registry Number: 87-08-1
CAS Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: 6-phenoxyacetamidopenicillanic acid; penicillin phenoxymethyl; phenoxymethylpenicillin; phenoxymethylpenicillinic acid
Trademarks: Fenospen (Pharmacia); Oracilline (Schwarz); V-Cillin (Lilly)
Molecular Formula: C16H18N2O5S
Molecular Weight: 350.39
Percent Composition: C 54.84%, H 5.18%, N 7.99%, O 22.83%, S 9.15%
Literature References: Obtained by adding 2-phenoxyethanol to the Penicillium culture using yeast autolyzate as source of nitrogen: Brandl et al., Wien. Med. Wochenschr. 1953, 602; Brandl, Margreiter, Oesterr. Chem.-Ztg. 55, 11-21 (1954), C.A. 48, 10296 (1954). Purification: Parker et al., J. Pharm. Pharmacol. 7, 683 (1953). Total synthesis: Sheehan, Henery-Logan, J. Am. Chem. Soc. 79, 1262 (1957); 81, 3089 (1959); 84, 2983 (1962). Prepn from 6-aminopenicillanic acid: Glambitza, Ann. 673, 166 (1964). Soly data: Weiss et al., Antibiot. Chemother. 7, 374 (1957). The biologically active form is the dextrorotatory D-form; the DL-form is half as active. L-Penicillin V has little, if any, antibiotic activity. Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description of the potassium salt: J. M. Dunham in Anal. Profiles Drug Subs. 1, 249-300 (1972); D. H. Sieh, ibid. 17, 677-748 (1988).
Properties: Crystals, dec 120-128°. Stable in air up to 37°; relatively stable to acid. uv max: 268, 274 nm (e 1330, 1100). Soly in water at pH 1.8 (acidified with HCl) = 25 mg/100 ml. Sol in polar organic solvents. Practically insol in vegetable oils and in liq petrolatum.
Absorption maximum: uv max: 268, 274 nm (e 1330, 1100)
 
Derivative Type: Potassium salt
CAS Registry Number: 132-98-9
Trademarks: Antibiocin (Orion); Calciopen (AstraZeneca); Cliacil (Aventis); Fenoxypen (Novo); Milcopen (Leiras); Ospen (Biochemie); Pen-Vee K (Biochemie); Primcillin (AstraZeneca); Veetids (BMS); Vepicombin (Nycomed); V-Pen (Orion); V-Tablopen (Viatris)
Molecular Formula: C16H17KN2O5S
Molecular Weight: 388.48
Percent Composition: C 49.47%, H 4.41%, K 10.06%, N 7.21%, O 20.59%, S 8.25%
Properties: Soluble in water. [a]D25 +223° (c = 0.2). LD50 orally in rats: >1040 mg/kg (Goldenthal).
Optical Rotation: [a]D25 +223° (c = 0.2)
Toxicity data: LD50 orally in rats: >1040 mg/kg (Goldenthal)
 
Derivative Type: Calcium salt
CAS Registry Number: 147-48-8
Trademarks: Arcasin (Meda); Calcipen (Leo Pharm); Isocillin (Aventis); Ispenoral (Rosen); Megacillin (Grñenthal)
Molecular Formula: C32H34CaN4O10S2
Molecular Weight: 738.84
Percent Composition: C 52.02%, H 4.64%, Ca 5.42%, N 7.58%, O 21.65%, S 8.68%
 
Derivative Type: Compd with dibenzylethylenediamine
CAS Registry Number: 5928-84-7
Additional Names: Penicillin V benzathine; penicillin V DBED; benzathine penicillin V; phenoxymethylpenicillin benzathine; benzathine benzylpenicillin
Molecular Formula: (C16H18N2O5S)2.C16H20N2
Molecular Weight: 941.12
Percent Composition: C 61.26%, H 6.00%, N 8.93%, O 17.00%, S 6.81%
Literature References: Prepn: R. Brunner et al., US 2820789 (1958 to American Home Products).
Properties: Practically white powder having a characteristic odor, mp 105-109°. Soly at ~28° (mg/ml): water 0.321; ethanol 14.6.
Melting point: mp 105-109°
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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