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Antibiotics Derived From

Acetate Metabolism
Catarina Cauilan
Angelene Kate Onate

Acetate Metabolism
Involves head-to-tail condensation of
2 carbon units or the formation of
some type of isoprenoid compound
Derived from polyketides
Deviates the tetracyclines, 2
macrolides, a few polyenes and
griseofulvin

TETRACYCLINES
A group of actinomycete antibiotics
that have a broad spectrum and
considerable therapeutic utility
Chlortetetracycline Demeclocycline
Doxycycline

Methacycline

Minocycline

Oxytetracylcine

Tetracycline

Chlortetetracycline
7-chlorotetracycline
From Streptomyces aureofaciens
First tetracycline antibiotic for
therapeutic responses
Employed in veterinary medicine (to
treat conjunctivitis in cats)
Example: Aureomycin

Demeclocycline

7-chloro-6-demethyltetracycline
Currently used in therapy
Used orally as the HCl Salt
Example: Declomycin

Doxycycline
6-deoxy-5-hydroxytetracycline
From oxytetracycline by chemical
dehydration and reduction
Example: Doxy, Doxychel, Vibramycin

Methacycline
From oxytetracycline by chemical
dehydration
Used orally as the HCl Salt
Example: Rondomycin

Minocycline
By reductive methylation of 7-nitro-6demethyl-6-deoxytetracylcine
For treating Neisseria gonoorhoeae
(when penicillin is unavailable)
For carrier states of N. meningitidis
Example: Minocin

Oxytetracycline
5-hydroxytetracycline
From Streptomyces rimosus
Example: Oxymycin, Uri-Tet

Tetracycline
Found in the antibiotic mixture of
Streptomyces aureofaciens (1953)
Least expensive and most
commonly utilized tetracycline
antibiotic
Examples: Achromycin, Cylcine,
Cyclopar, Tetra-C, Tetracap

ANTINEOPLASTIC
ANTHRACYCLINE
DERIVATIVES

Acetate-derived polycyclic metabolites of


actinomycetes
Produced by cultures of Streptomyces spp.
Inhibits DNA dependent RNA synthesis
SE: nausea, bone marrow depression, hair
loss, local tissue necrosis
Daunorobicin

Doxorubicin

Mitomycin C

Plicamycin

Daunorobicin
Streptomyces coeruleorubidus
Trx of acute lymphotic and
nonlymphotic leukemias, usually as a
component of combination
chemotherapeutic regimens
Example: Cerubidine

Doxorubicin
Streptomyces peucetius var. caesius
Promise in treatment of some acute
leukemia, soft tissue sarcomas, breast
cancer, and several types of carcinoma
Used as a component in combination with
chemotherapeutic regimens
Example: Adriamycin

Mitomycin C
Streptomyces caespitosus
Treatment of disseminated
adenocarcinoma of the stomach or
pancreas
Alternate drug in advanced
metastatic conditions of various types
that have become resistant to other
chemotherapeutic responses
Example: Mutamycin

Plicamycin
Streptomyces agrillaceus and S. plicatus
Treatment of disseminated testicular
carcinoma
For symptomatic control in patients with
hypercalcemia and hypercalcuira secondary
to a variety of advanced neoplasms
Example: Mithracin

MACROLIDE ANTIBIOTICS
Synthesized from acetate units
Products of both acetate and
carbohydrate metabolism linked to one or
more sugars
Mainly active against Gram-positive
bacteria and Mycoplasma spp.
Useful in patients with penicillin allergy
Protein synthesis inhibitors
Erythromycin and Oleandomycin
The only macrolide antibacterial agents
currently used in therapy

Erythromycin

Streptomyces erythreus
Treatment of Legionella pneumophila
Commercial product: Erythromycin A
Example: E-Mycin, Eryc, Wyamycin S.

Oleandomycin
Strain of Streptomyces antibioticus
Troleandomycin alternative
Example: Tao

POLYENES
Characterized by a large lactone ring
(20 to 44 membered) containing a
series of conjugated double bonds
Often mixtures of closely related
compounds
Candida albicans is susceptibe to the
polyenes
Cutaneous, intestinal and vaginal
infections of Candida

POLYENES
No antibacterial activity (polyenes have
a steroid component)
Antifungal action
Acts by destroying the integrity of the
cellular membrane of susceptible
organisms
Amphotericin B
Griseofulvin

Candicidin
Natamycin

Novobiocin

Nystatin

Rifampin

Amphotericin B
Streptomyces nodosus
Commercial product: must contain not less
than 750 mcg of Amphotericin B per mg
Topical purposes
IV: treatment of life-threatening,
disseminated mycotic infections, such as
blastomycosis, systemic candidiasis,
coccidiodomycosis, cryptococcosis,
histoplasmosis and moniliasis
Example: Fungizone

Candicidin
Streptomyces griseus
Ointment
Suppository for control of vaginal
candidiasis

Griseofulvin
Penicillium griseofulvin
Initially used in plant pathology as an
antifungal
Basic precursor: Polyketide
Early intermediate: Griseophenone C
Example: Fulvicin

Natamycin
Streptomyces natalensis
Classified as a macrolide polyene
antifungal
Treatment of fungal keratitis, an
infection of the eye
Effective against Aspergillus and
Fusarium corneal infections

Novobiocin
Streptomyces niveus & S. spheroides
Alternate means for controlling
penicillin-resistant staphylococci
Controls some strains of Proteus vulgaris
Pencillinase-resistant penicillins and
other available antibiotics have
eliminated its use.
Example: Albamycin

Nystatin
A polyene antifungal medication that
is derived from a bacterium,
Streptomyces noursei
Infections involving the skin, mouth,
esophagus, and vagina
Example: Nyamyc

Rifampin
From rifampicin B, a metabolite of
Streptomyces mediterranei
Should be used with another
antitubercular agent to avoid
development of resistant strains of
the tubercle bacillus
Treatment of pulmonary tuberculosis
Example: Rifadin

THE END