Ácido 6-aminopenicilánico

El ácido 6-aminopenicilánico (6-APA) es un compuesto químico que forma el núcleo fundamental de la molécula de los antibióticos del grupo de las penicilinas y usado en la fabricacion de penicilinas sintéticas.1 2 La estructura comprende un anillo betalactámico unido a un anillo tiazolidínico. La adición de diferentes moléculas sobre el 6-aminopenicilánico determina la farmacología esencial y las propiedades antibacterianas de los compuestos así formados.3

Ácido 6-aminopenicilánico

Aviso médico

Nombre (IUPAC) sistemáticoÁcido (2S,5R,6R)-6-amino-3,3-dimetil-7-oxo-4-tia-1-azabiciclo[3.2.0]heptano-2-

carboxílico

IdentificadoresNúmero CAS 1203-85-6Código ATC  ?PubChem 592657ChEBI  ?Datos químicosFórmula C8H12N2O3S 

Peso mol. 216.2575 gr/molSMILES CC1(C(N2C(S1)C(C2=O)N)C(=O)O)CSinónimos Penicina o peninaDatos físicosP. fusión 198 °C (388 °F)Punto de ebullición 209 °C (408 °F)

FarmacocinéticaBiodisponibilidad  ?Metabolismo  ?Vida media  ?Excreción  ?

Consideraciones terapéuticasCat. embarazo ?Estado legal

Vías adm. Intramuscular y oral

6-AMINOPENICILLANIC ACIDPRODUCT IDENTIFICATIONCAS NO. 551-16-6EINECS NO. 208-993-4FORMULA C8H12N2O3SMOL WT. 216.25H.S. CODE 2941.10TOXICITY  SYNONYMS 6-APA; (+)-6-Aminopenicillanic acid; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7- oxo-, [2S-(2alpha,5alpha,6beta)]-; (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid; Acido 6-aminopenicillanico (Italian); 6-Amino-3,3-dimethyl-7-oxo-4-thia-1 -azabicyclo [3.2.0]heptane-2- carboxylic acid; PRICECLASSIFICATION  PHYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE white powderMELTING POINT 198 - 200 CBOILING POINT > 200 C(Decomposes)SPECIFIC GRAVITY  SOLUBILITY IN WATER  pH  VAPOR DENSITY  AUTOIGNITION > 250 CNFPA RATINGS Health: 1; Flammability: 0; Reactivity: 0REFRACTIVE INDEX  FLASH POINT  STABILITY Stable under ordinary conditionsAPPLICATIONS6-Aminopenicillanic acid is the active core body of all penicillins substituted at the 6-amino position resulting in a variety of antibacterial and pharmacologic characteristics. It is a non-hygroscopic crystal that decompose at 209 C; SALES SPECIFICATIONAPPEARANCE white to off white free flowing crystalline powderIDENTIFICATION CompliesOPTICAL ROTATION +260° ~ +280°ASSAY 98.0 - 101.0 %PENICILLIN G 0.6 % maxPHENYLACETIC ACID 0.6 % maxSULPHATED ASH 0.5% maxWATER 0.3% max

pH 3.5 - 5.5N,N-DIMETHYLANILINE AbsentTRANSPORTATIONPACKING 25kgs in Bag HAZARD CLASS Not regulatedUN NO.  OTHER INFORMATIONHazard Symbols: n/a, Risk Phrases: n/a, Safety Phrases: 24/25GENERAL DESCRIPTION OF PENICILLIN· Penicillin: Any of a large group of broad-spectrum antibiotic drugs derived directly or indirectly from molds of the genus Penicillium and other soil-inhabiting fungi grown on special culture media, which exert a bacteriocidal as well as a bacteriostatic effect on susceptible bacteria during their growth stage by the inhibition of biosynthesis of their cell wall mucopeptide. Penicillin, beta-lactam antibiotics, possess a four-ring beta-lactam structure shares a nitrogen and a carbon atom with fused a five-membered thiazolidine ring. These antibiotics have low toxicity for the host but effective against most gram-positive bacteria including pathogens (streptococci, staphylococci, pneumococci); clostridia; some gram-negative gonococci; some spirochetes (Treponema pallidum and T. pertenue); and some fungi. Certain strains of some target species, e.g., staphylococci, secrete the enzyme penicillinase, which inactivates penicillin and confers resistance to the antibiotic.

· Penicillic acid [CAS RN: 90-65-3]: an antibiotic substance produced by several species of Penicillium and Aspergillus; a white solid soluble in water; melting point 83 - 84 C; antibiotic and mycotoxin induceing DNA single-strand breaks, toxic to animal tissues also, causing nephrotoxicity and other damage.

· Penicillin G [also called benzylpenicillin, CAS RN: 61-33-6]: the first and the most widely used penicillin compound for medicinal use. It is used in the form of its stable salts (benzathine, potassium, procaine, and sodium) to treat principally the infections due to penicillin-susceptible gram-positive bacteria, gram-negative cocci, Treponema pallidum, and Actinomyces israelii.

· Penicillin G Benzathine [CAS RN: 41372-02-5]: the benzathine salt of penicillin G; having a long-sustained action, administered orally, intramuscularly. Chemically designation is (2S,5R,6R)- 3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid with N,N' -Dibenzylethylenediamine (2:1). It is a white crystalline powder; slightly soluble in water and sparingly soluble in alcohol.

· Penicillin G Potassium [CAS RN: 113-98-4]: the potassium salt of penicillin G; administered orally and by intravenously. It is a white crystalline powder; odorless, moderately hygroscopic; soluble in water.

· Penicillin G Procaine [CAS RN: 6130-64-9]: the procaine salt of penicillin G; having a long-sustained action, administered intramuscularly. Chemically designation is (2S,5R,6R)- 3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid with 2-(Diethylamino)ethyl p-aminobenzoate (1:1). It is a white crystalline powder; slightly soluble in water.

· Penicillin G sodium [CAS RN: 69-57-8]: the sodium salt of penicillin G having a potency of 1500–1750 U per mg; administered intramuscularly and intravenously.

· Penicillin N (also called adicillin, CAS RN: 525-94-0]: a cephalosporin that is more active against gram-negative organisms than penicillin G and is highly active against Neisseria; has been used in the treatment of typhoid fever and gonorrhea.

· Penicillin O: similar to penicillin G in antibiotic action but produced by adding a precursor to the

culture medium; penicillin O and its potassium and sodium salts are hypoallergenic.

· Penicillin V: [CAS RN: 87-08-1] a semisynthetic penicillin prepared from cultures of the mold Penicillium in the presence of 2-phenoxyethanol with an autolysate of yeast as the source of nitrogen; a white, crystalline powder, soluble in alcohol and acetone; resists destruction by high humidity (gastric juice), thus orally effective.

· Penicillin V Benzathine [CAS RN: 63690-57-3] : the benzathine salt of penicillin V, administered orally. Chemical designation is [2S-(2a,5a,6b)]-3,3 -dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4- thia-1- azabicyclo[3.2.0] heptane-2-carboxylic acid with N,N' -Dibenzylethylenediamine (2:1).

· Penicillin V Potassium [CAS RN: 132-98-9]: the potassium salt of penicillin V, administered orally. Chemical designation is [2S-(2a,5a,6b)]-3,3 -dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4- thia-1- azabicyclo[3.2.0] heptane-2-carboxylic acid, monopotassium salt.

Paginas web:

http://www.rmc.upm.edu.my/jpertanika/Pertanika%20PAPERS/Current%20Issues%202009/JST%20Current%20Issues%2017(1)%20Jan%202009/19.91-2008-G.D.Najafpour.pdf