7100. Penicillin V

Nomenclature

CAS number: 87-08-1
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-phenoxyacetamidopenicillanic acid; penicillin phenoxymethyl; phenoxymethylpenicillin; phenoxymethylpenicillinic acid; Fenospen (Pharmacia); Oracilline (Schwarz); V-Cillin (Lilly).
C16H18N2O5S; mol wt 350.39.
C 54.84%, H 5.18%, N 7.99%, O 22.83%, S 9.15%.

Description and 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).

Chemical structure

Properties

Crystals, dec 120-128°. Stable in air up to 37°; relatively stable to acid. uv max: 268, 274 nm (ε 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 liquid petrolatum.

Derivative

Potassium salt.

Nomenclature

CAS number: 132-98-9
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).
C16H17KN2O5S; mol wt 388.48.
C 49.47%, H 4.41%, K 10.06%, N 7.21%, O 20.59%, S 8.25%.

Properties

Soluble in water. [α]D25 +223° (c = 0.2). LD50 orally in rats: >1040 mg/kg (Goldenthal).

Derivative

Calcium salt.

Nomenclature

CAS number: 147-48-8
Arcasin (Meda); Calcipen (Leo Pharm); Isocillin (Aventis); Ispenoral (Rosen); Megacillin (Grünenthal).
C32H34CaN4O10S2; mol wt 738.84.
C 52.02%, H 4.64%, Ca 5.42%, N 7.58%, O 21.65%, S 8.68%.

Derivative

Compd with dibenzylethylenediamine.

Nomenclature

CAS number: 5928-84-7
Penicillin V benzathine; penicillin V DBED; benzathine penicillin V; phenoxymethylpenicillin benzathine; benzathine benzylpenicillin.
(C16H18N2O5S)2.C16H20N2; mol wt 941.12.
C 61.26%, H 6.00%, N 8.93%, O 17.00%, S 6.81%.

Description and 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.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins