| Identification | Back Directory | [Name]
7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID | [CAS]
3511-16-8 | [Synonyms]
Versapen
Penplenum
Hetacilina
HETACILLIN
Hetacilline
Hetacillinum
phenazacillin
Hetacillin USP/EP/BP
6-(2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)penicillanic acid
6-[2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl] penicillanic acid
7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID
7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID
7-(2,2-DIMETHYL-5-OXO-4-PHENYL-IMIDAZOLIDIN-1-YL)-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID USP/EP/BP
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(4R)-2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- | [EINECS(EC#)]
222-512-5 | [Molecular Formula]
C19H23N3O4S | [MDL Number]
MFCD00056861 | [MOL File]
3511-16-8.mol | [Molecular Weight]
389.47 |
| Chemical Properties | Back Directory | [Melting point ]
189.2-191.0° | [alpha ]
D25 +366° (pyridine) | [Boiling point ]
648.4±55.0 °C(Predicted) | [density ]
1.43±0.1 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly) | [form ]
Solid | [pka]
2.45±0.50(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic, Unstable in Solution |
| Hazard Information | Back Directory | [Description]
Hetacillin was synthesized by Bristol-Myers
Laboratories in 1964. It shows activity as strong
as that of ampicillin against a variety of
gram-positive and gram-negative bacteria.
Hetacillin shows almost the same pharmacokinetic properties as ampicillin when administered
orally and a later serum peak when given by intramuscular administration. When administered
either orally or intramuscularly, it is hydrolyzed
in vivo into ampicillin. Therefore, the clinical
applications of hetacillin are the same as those
of ampicillin. | [Originator]
Natacillin,Bristol Banyu,Japan,1970 | [Uses]
Antibacterial. | [Uses]
Hetacillin is a β-lactam antibiotic. | [Definition]
ChEBI:Hetacillin is a penicillin. It has a role as an antibacterial drug. It is a conjugate acid of a hetacillin(1-). | [Manufacturing Process]
To 100 grams of α-aminobenzylpenicillin slurried in 2,500 ml of acetone is
added 200 ml of a 22% solution of potassium ethylhexanoate in dry n-butanol
and the mixture is warmed to 45°C whereupon the acid dissolves. After the
mixture is agitated for 1 hour at 40° to 45°C, the product begins to crystallize
out. Agitation is continued for 4 hours at 45°C after which the product, the
potassium salt of hetacillin, is collected by filtration, washed with 500 ml of
dry acetone, dried for 17 hours at 40°C and found to weigh 70.0 grams. | [Brand name]
Versapen-K (Bristol-Myers Squibb)
. | [Therapeutic Function]
Antibacterial | [storage]
Store at -20°C |
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