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Hetacillin

Hetacillin structure

CAS No:
3511-16-8
Formula:
C19H23N3O4S
Chemical Name:
Hetacillin
Synonyms:
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)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-,D-(-)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-,[2S-[2α,5α,6β(S*)]]-;(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;BRL 804;BL-P 804;Hetacillin;Phenazacillin;Versapen;Vimocilin;Penplenum;Etacillin;Versatrex;14537-96-3
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself, but quickly splits of acetone in the human body to form ampicillin, which is active against a variety of bacteria.

Solid

Hetacillin is a penicillin. It has a role as an antibacterial drug. It is a conjugate acid of a hetacillin(1-).|Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). Hetacillin has been withdrawn from the market since it has been discovered that it has no therapeutic advantage compared to non-ester derivatives like ampicillin.|Hetacillin is a semi-synthetic penicillin compound with bactericidal properties. Hetacillin is a prodrug that is converted to ampicillin via esterases. Ampicillin binds to inactivated penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs, including transpeptidases, carboxypeptidases, and endopeptidases, participate in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. This results in the weakening of the bacterial cell wall and eventually causes cell lysis. (NCI05)

Hetacillin Basic Attributes

Molecular Weight：

389.47

Exact Mass：

389.47

EC Number：

222-512-5

UNII：

TN4JSC48CV

DSSTox ID：

DTXSID4023121

NCI Thesaurus Code：

C47555

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

115.25000

XLogP3：

1.61570

Appearance：

Solid

Density：

1.43g/cm3

Melting Point：

190 °C

Boiling Point：

648.4ºC at 760mmHg

Flash Point：

345.9ºC

Refractive Index：

1.672

Water Solubility：

5.12e-01 g/L

Specific rotation：

D25 +366° (pyridine)

Safety Information

Precautionary statement(s)：

P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501

Hazard Statements：

H317

GHS Classification：

|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.

Pharmacology：

Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs).

Metabolism/Metabolites：

Hydrolyzed to active ampicillin via esterases

Mechanism of Action：

Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. _In vitro_ studies have shown that hetacillin is resistant to beta lactamase activity. However, this effect is transient, as the hydrolysis product, ampicillin, is readily inactivated by beta lactamase. Hetacillin locks up the offending amino group and prevents the decomposition of Hetacillin. Once hydrolyzed to ampicillin (and acetone), ampicillin binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

MeSH Entry Terms：

hetacillin

Hetacillin Use and Manufacturing

Uses

Antibacterial.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:389.5
XLogP3:-0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:389.14092740
Monoisotopic Mass:389.14092740
Topological Polar Surface Area:115
Heavy Atom Count:27
Complexity:688
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes