Almecillin

Almecillin
Clinical data

Other names	[(Allylthio)methyl]penicillin
ATC code	None
Identifiers
CAS Number	87-09-2
PubChem CID	71365
ChemSpider	64462
UNII	6246WH0S1O
ChEBI	CHEBI:51207
ChEMBL	ChEMBL2105909
CompTox Dashboard (EPA)	DTXSID50236034
Chemical and physical data
Formula	C₁₃H₁₆N₂O₄S₂
Molar mass	328.40 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1(C)S[C@@H]2[C@H](NC(=O)CSCC=C)C(=O)N2[C@H]1C(=O)O
InChI InChI=1S/C13H18N2O4S2/c1-4-5-20-6-7(16)14-8-10(17)15-9(12(18)19)13(2,3)21-11(8)15/h4,8-9,11H,1,5-6H2,2-3H3,(H,14,16)(H,18,19)/t8-,9+,11-/m1/s1 Key:QULKGELYPOJSLP-WCABBAIRSA-N

Almecillin (INN),^[1] also known as penicillin O, is a penicillin that is similar in antibiotic action to penicillin G. It is obtained by isolation from Penicillium chrysogenum.^[2]^[3]

References

^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 40" (PDF). World Health Organization. p. 170.
^ "Penicillin O". ChEBI. EMBL-EBI. Retrieved 11 June 2015.
^ Levitov MM, Inozemtseva II, Gotovtseva VA, Komokina ZF, Iudina OD, Kleiner GI, Ioffe RI, Nagle AM (November 1961). "[Production and basic properties of almecillin (allylmercaptomethylpenicillin)]". Meditsinskaia Promyshlennost' SSSR (in Russian). 11: 12–19. PMID 14464705.

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

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^‡

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Combinations

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§

Intracellular