Propicillin

Propicillin
Systematic (IUPAC) name

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxybutanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	551-27-9^Y
ATC code	J01CE03 (WHO)
PubChem	CID 92879
ChemSpider	83843^N
UNII	8X1R260V33^N
KEGG	C13110^N
ChEBI	CHEBI:52429^N
ChEMBL	CHEMBL1477112^N
Chemical data
Formula	C₁₈H₂₂N₂O₅S
Molar mass	378.44268 g/mol
SMILES CCC(C(=O)N[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)O)OC3=CC=CC=C3
InChI InChI=1S/C18H22N2O5S/c1-4-11(25-10-8-6-5-7-9-10)14(21)19-12-15(22)20-13(17(23)24)18(2,3)26-16(12)20/h5-9,11-13,16H,4H2,1-3H3,(H,19,21)(H,23,24)/t11?,12-,13+,16-/m1/s1^N Key:HOCWPKXKMNXINF-XQERAMJGSA-N^N
^NY (what is this?) (verify)

Propicillin is a penicillin. Properties are similar to benzylpenicillin particularly used in streptococcal infections, not resistant to penicillinase. It is acid resistant and can be used orally as the potassium salt.

Antibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular

Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Glycopeptide

Inhibit PG chain elongation: Vancomycin^# (Oritavancin
Telavancin)
Teicoplanin (Dalbavancin)
Ramoplanin

β-lactams/
(Inhibit PBP
cross-links)

Penicillins
(Penams)

Narrow Spectrum

β-lactamase Sensitive (1st Generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡

β-lactamase Resistant (2nd Generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended Spectrum

Aminopenicillins (3rd Generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Metampicillin^‡ Talampicillin^‡) Epicillin^‡

Carboxypenicillins (4th Generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡

Ureidopenicillins (4th Generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡

Other	Mecillinam^‡ (Pivmecillinam^‡) Sulbenicillin^‡

Penems

Faropenem^‡

Carbapenems

Cephalosporins/Cephamycins
(Cephems)

1st Generation (P Ec K)	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin^‡ Cefatrizine^‡

2nd Generation (H E N)	Cefaclor Cefotetan Cephamycin (Cefoxitin Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefminox^‡ Cefonicid^‡ Ceforanide^‡ Cefotiam^‡ Cefbuperazone^‡ Cefuzonam^‡ Cefmetazole)^‡ Carbacephem^‡ (Loracarbef^‡)

3rd Generation	Cefixime^# Ceftriaxone^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefotaxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef^‡ Latamoxef^‡‡)

4th Generation (Pseudomonas)	Cefepime Cefozopran^‡ Cefpirome^‡ Cefquinome^‡

5th Generation	Ceftaroline fosamil Ceftolozane Ceftobiprole^‡

Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase Inhibitors

Combinations

Other

polymyxins/detergent
- Colistin
- Polymyxin B
depolarizing
- Daptomycin
Hydrolyze NAM-NAG
- lysozyme
Gramicidin
Isoniazid
Teixobactin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

This article is issued from Wikipedia - version of the Saturday, April 02, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.