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Cyclacillin

Cyclacillin structure

CAS No:
3485-14-1
Formula:
C15H23N3O4S
Chemical Name:
Cyclacillin
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-,[2S-(2α,5α,6β)]-;(2S,5R,6R)-6-[[(1-Aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-(1-Aminocyclohexanecarboxamido)penicillanic acid;Cyclacillin;Wy 4508;Aminocyclohexylpenicillin;Penicillin,(aminocyclohexyl)-;6-(1-Aminocyclohexylcarboxamido)penicillanic acid;Ciclacillum;Ciclacillin;(1-Aminocyclohexyl)penicillin;Ultracillin;Vastcillin;Wyvital;Cyclapen;Calthor;Citosarin;Vatracin;Syngacillin;Vipicil;NSC 88789;26718-31-0;33776-57-7;38237-98-8;59235-11-9
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Solid

Cyclacillin is a penicillin. It has a role as an antibacterial drug.|A cyclohexylamido analog of penicillanic acid.|Cyclacillin is a semi-synthetic beta-lactam aminocyclohexylpenicillin antibiotic. Cyclacillin is bactericidal and binds to specific penicillin-binding proteins, thereby inhibiting transpeptidation during peptidoglycan synthesis. This leads to an interruption of the bacterial cell wall, causing instability of bacterial cell wall and results in cell lysis. Cyclacillin is beta-lactamase susceptible.|A cyclohexylamido analog of PENICILLANIC ACID.

Cyclacillin Basic Attributes

Molecular Weight：

341.42582

Exact Mass：

341.43

EC Number：

222-470-8

UNII：

72ZJ154X86

NSC Number：

88789

DSSTox ID：

DTXSID9022861

NCI Thesaurus Code：

C47464

Characteristics

PSA：

138.03000

XLogP3：

1.30880

Appearance：

Solid

Density：

1.4g/cm3

Melting Point：

182-183 °C

Boiling Point：

649.6ºC at 760mmHg

Flash Point：

346.7ºC

Refractive Index：

1.631

Water Solubility：

32g/L(25 ºC)

Toxicity：

Oral-rat LD50: 5010 mg/kg; Abdominal cavity-mouse LD50: 3776 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Specific rotation：

D25 +268° (water)

Safety Information

Storage features：

Warehouse ventilated, low temperature and dry

Toxicity

Toxicity class：

moderately toxic

Toxicity Summary：

Symptoms of overdose include severe diarrhea, nausea and vomiting.

Drug Information

Drug Indication：

For the treatment of bacterial infections caused by susceptible organisms.

Pharmacology：

Cyclacillin, a penicillin, is a cyclohexylamido analog of penicillanic acid. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. Cyclacillin has been replaced by newer penicillin treatments.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Moderately absorbed.

Mechanism of Action：

The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.

MeSH Entry Terms：

Aminocyclohexylpenicillin

Cyclacillin 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:341.4
XLogP3:1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:341.14092740
Monoisotopic Mass:341.14092740
Topological Polar Surface Area:138
Heavy Atom Count:23
Complexity:559
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes