Structural Formula Vector Image
Title: Hetacillin
CAS Registry Number: 3511-16-8
CAS Name: (2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanic acid; phenazacillin
Manufacturers' Codes: BRL-804
Trademarks: Versapen (BMS)
Molecular Formula: C19H23N3O4S
Molecular Weight: 389.47
Percent Composition: C 58.59%, H 5.95%, N 10.79%, O 16.43%, S 8.23%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn and structure: Hardcastle et al., J. Org. Chem. 31, 897 (1966); Johnson, Panetta, US 3198804 (1965 to Bristol-Myers). Pharmacology: Kirby, Kind, Ann. N.Y. Acad. Sci. 145, 291 (1967); Ueda et al., J. Antibiot. 20B, 206 (1967), C.A. 69, 95016w (1968). Stability studies: Saccani, Pansera, Boll. Chim. Farm. 107, 640 (1968). Epimerization at C-6 to epihetacillin: Johnson et al., Tetrahedron Lett. 1968, 1903.
Properties: Rectangular plates from water + methyl isobutyl ketone, dec 182.8-183.9°; also reported as mp 189.2-191.0°. [a]D25 +366° (pyridine). Practically insol in most organic solvents and water; sol in dil aq NaOH soln (pH 7-8), DMF, DMSO, pyridine, methanol (with dec).
Melting point: mp 189.2-191.0°
Optical Rotation: [a]D25 +366° (pyridine)
Derivative Type: Potassium salt
CAS Registry Number: 5321-32-4
Trademarks: Hetacin-K (Fort Dodge); Natacillin (Banyu); Versatrex (BMS)
Molecular Formula: C19H22KN3O4S
Molecular Weight: 427.56
Percent Composition: C 53.37%, H 5.19%, K 9.14%, N 9.83%, O 14.97%, S 7.50%
Derivative Type: Methyl ester
Molecular Formula: C20H25N3O4S
Molecular Weight: 403.50
Percent Composition: C 59.53%, H 6.24%, N 10.41%, O 15.86%, S 7.95%
Properties: Crystals from carbon tetrachloride, mp 101.5-102°. Sol in most organic solvents.
Melting point: mp 101.5-102°
Derivative Type: Epihetacillin
Properties: Crystals, mp 164-165°. [a]D23 +232° (pyridine).
Melting point: mp 164-165°
Optical Rotation: [a]D23 +232° (pyridine)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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