cido 6-aminopenicilnico

El cido 6-aminopenicilnico (6-APA) es un compuesto qumico que forma el ncleo

fundamental de la molcula de los antibiticos del grupo de las penicilinas y usado en la
fabricacion de penicilinas sintticas.1 2 La estructura comprende un anillo betalactmico
unido a un anillo tiazolidnico. La adicin de diferentes molculas sobre el 6aminopenicilnico determina la farmacologa esencial y las propiedades antibacterianas
de los compuestos as formados.3

cido 6-aminopenicilnico
Aviso mdico

Nombre (IUPAC) sistemtico

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

Identificadores
Nmero CAS

1203-85-6

Cdigo ATC

PubChem

592657

ChEBI

Datos qumicos
Frmula

C8H12N2O3S

Peso mol.

216.2575 gr/mol

SMILES

CC1(C(N2C(S1)C(C2=O)N)C(=O)O)C

Sinnimos

Penicina o penina

Datos fsicos
P. fusin

198 C (388 F)

Punto de
ebullicin

209 C (408 F)

Farmacocintica
Biodisponibilidad ?
Metabolismo

Vida media

Excrecin

Consideraciones teraputicas
Cat. embarazo

Estado legal

Vas adm.

Intramuscular y oral

6-AMINOPENICILLANIC ACID
PRODUCT IDENTIFICATION
CAS NO.
551-16-6
EINECS NO.
208-993-4
FORMULA
C8H12N2O3S
MOL WT.
216.25
H.S. CODE
2941.10
TOXICITY
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-2carboxylic acid; Acido 6-aminopenicillanico (Italian); 6-Amino-3,3-dimethyl-7-oxo-4-thia-1 -azabicyclo
[3.2.0]heptane-2- carboxylic acid;
PRICE
CLASSIFICATION
PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE
white powder
MELTING POINT
198 - 200 C
BOILING POINT
> 200 C(Decomposes)
SPECIFIC GRAVITY
SOLUBILITY IN WATER
pH
VAPOR DENSITY
AUTOIGNITION
> 250 C
NFPA RATINGS
Health: 1; Flammability: 0; Reactivity: 0
REFRACTIVE INDEX
FLASH POINT
STABILITY
Stable under ordinary conditions
APPLICATIONS
6-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 SPECIFICATION
APPEARANCE
white to off white free flowing crystalline powder
IDENTIFICATION
Complies
OPTICAL ROTATION
+260 ~ +280
ASSAY
98.0 - 101.0 %
PENICILLIN G
0.6 % max
PHENYLACETIC ACID
0.6 % max
SULPHATED ASH
0.5% max
WATER
0.3% max

pH
3.5 - 5.5
N,N-DIMETHYLANILINE Absent
TRANSPORTATION
PACKING
25kgs in Bag
HAZARD CLASS
Not regulated
UN NO.
OTHER INFORMATION
Hazard Symbols: n/a, Risk Phrases: n/a, Safety Phrases: 24/25
GENERAL 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-(2phenylacetamido)-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-(2phenylacetamido)-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid with 2-(Diethylamino)ethyl paminobenzoate (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 15001750 U per
mg; administered intramuscularly and intravenously.
Penicillin N (also called adicillin, CAS RN: 525-94-0]: a cephalosporin that is more active against gramnegative 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-1azabicyclo[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%202009/19.91-2008G.D.Najafpour.pdf