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Tetracyclines: Dr. Md. Rageeb Md. Usman Associate Professor Department of Pharmacognosy

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Tetracyclines are a class of broad-spectrum antibiotic commonly used to treat bacterial infections and acne. The first tetracycline discovered was chlortetracycline. Tetracyclines have a tetracyclic ring structure and include both naturally occurring and semisynthetic derivatives. Their mechanism of action involves inhibiting bacterial protein synthesis by binding to the 30S ribosomal subunit. Common side effects include gastrointestinal issues, skin reactions, and discoloration of teeth when used by children.

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Tetracyclines: Dr. Md. Rageeb Md. Usman Associate Professor Department of Pharmacognosy

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Tetracyclines are a class of broad-spectrum antibiotic commonly used to treat bacterial infections and acne. The first tetracycline discovered was chlortetracycline. Tetracyclines have a tetracyclic ring structure and include both naturally occurring and semisynthetic derivatives. Their mechanism of action involves inhibiting bacterial protein synthesis by binding to the 30S ribosomal subunit. Common side effects include gastrointestinal issues, skin reactions, and discoloration of teeth when used by children.

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Tetracyclines

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Tetracyclines

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Tetracyclines are a class of broad-spectrum antibiotic commonly used to treat bacterial infections and acne. The first tetracycline discovered was chlortetracycline. Tetracyclines have a tetracyclic ring structure and include both naturally occurring and semisynthetic derivatives. Their mechanism of action involves inhibiting bacterial protein synthesis by binding to the 30S ribosomal subunit. Common side effects include gastrointestinal issues, skin reactions, and discoloration of teeth when used by children.

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47 views21 pages

Tetracyclines: Dr. Md. Rageeb Md. Usman Associate Professor Department of Pharmacognosy

Uploaded by

Anonymous TCbZigVq
Tetracyclines are a class of broad-spectrum antibiotic commonly used to treat bacterial infections and acne. The first tetracycline discovered was chlortetracycline. Tetracyclines have a tetracyclic ring structure and include both naturally occurring and semisynthetic derivatives. Their mechanism of action involves inhibiting bacterial protein synthesis by binding to the 30S ribosomal subunit. Common side effects include gastrointestinal issues, skin reactions, and discoloration of teeth when used by children.

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TETRACYCLINES

Dr. Md. Rageeb Md. Usman


(M. Pharm., Ph.D., FAPP, FICPHS, FSRHCP, FRSH, FSPER)
Associate Professor
Department of Pharmacognosy

Smt. Sharadchandrika Suresh Patil


College of Pharmacy,
Chopda, Maharashtra, India
Tetracyclines:
-a broad-spectrum antibiotics.

-It is commonly used to treat acne,


infection, and other infections caused by
bacteria.

-The first of these compounds was


chlortetracycline followed by
oxytetracycline and tetracycline.
Tetracycline divided into:
a) Naturally occurring:

1-tetracycline 2-chlortetracycline

3-oxytetracycline 4-demeclocycline
Semisynthetic occurring:

1-doxycycline 2-minocycline

3-meclocycline 4-lymecycline

5-methacycline 6-rolitetracycline
Total Synthesis of the
Tetracyclines:
Structure and chemical characteristics

•
Structure activity relationship
•
R5 R4 R3 R2 R1.
Chlortetracycline H H OH CH3 Cl
Oxytetracycline H OH OH CH3 H
Tetracycline H H OH CH3 H
Demethylchlortetracycline H H OR H CI
Rolitetracycline + H OH CH3 H
Metacycline H OH CH2 H
Doxycycline H OH H CH3 H
Minocycline H H H N(CH3)2
• Retention of the configuration of the
asymmetric centres C-4, C-4a and C-12a is
essential, whereas the configurations at C-5,
C-5a and C-6 may be altered:

• 1- The amide hydrogen may be replaced


with a methyl group, but larger groups have
a deleterious effect except for those which
are eliIminated spontaneously in water .
• 2-The dimethyl amino group may be
replaced by a primary amino group
without loss of in vitro activity but all
other changes so far lead to decreased
bacteriostatic action .
• The hydrophobic part of the molecule
from C-5 to C-9 may be altered in
various ways:
• modifications at C-6 and C-7 in
particular afford products having
greater chemical stability.
• increased antibiotic activity and more
favourable pharmacokinetics
• Dehydrogenation to form a double
bond between C-5a and C-11a
markedly decreases activity

• Polar substituents at C-5 and C-6


contribute decreased lipid versus water
solubility to the tetracycline
• . The drugs are amphoteric, meaning
they will form salts with both strong
acids and bases. Thus, they may exist
as salts of sodium or chloride.
Uses:
-treat cancer patients with SIADH.

-treat hyponatremia.

-combined with hydrocortisone in a paste used


by dentists .

-treat trachoma.
Side effect:
Dermatological:-Skin reactions, photosensitivity

GIT:-nausea, vomiting, and diarrhea.

CNS:-Dizziness,visualdisturbances .

Immune System:-allergic reactions.

Other:-yellowish-grayish-brown discoloration of the


teeth.
Pharmacodynamics/Kinetics:
-Absorption: ~50% to 80%.

-Protein binding: 41% to 50%

-Metabolism: Hepatic.

-Half-life elimination: 10-17 hours

-Time to peak, serum: 3-6 hours

-Excretion: Urine
Side effects:
-Gastrointestinal: anorexia, nausea,
vomiting, diarrhea,
-Skin: rashes, dermatitis.
-Renal Toxicity
-Hepatic Cholestasis:
-Hypersensitivity
Reactions:Anaphylaxis,
Miscellaneous: Dizziness and headache
Side effects:
-Hypersensitivity reactions:Urticaria,anaphylaxis.

-GI :Anorexia, nausea, vomiting, diarrhea.

-Hepatic toxicity: Hyperbilirubinemia.

-Respiratory:Cough, dyspnea.

-Blood:Agranulocytosis, hemolytic anemia.

-CNS: Convulsions, dizziness,sedation.

-Oral cavity discoloration.

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