Lecture 6

ANTIBACTERIAL ANTIBIOTICS

Phenicols
Phuong-Thuy Thi PHAN, M.S.
 Recommended Reading

1) Beale, J.M., Block, J.H. (2011). Wilson and Gisvold’s Textbook of

Organic Medicinal and Pharmaceutical Chemistry 12th edition,
Lippincott Williams & Wilkins: Baltimore. Chapter 8. Antibacterial
antibiotics, p.p. 258-329.

2) Thomas L.L., David A.W. (2013). Foye’s Principle of Medicinal

Chemistry 7th edition, Lippincott Williams & Wilkins: Baltimore.
Chapter 33. Antibiotics and antimicrobial agents, p.p. 1073-1124.

3) Lê Minh Trí, Huỳnh Thị Ngọc Phương (2017). Hóa dược 1 (Dùng cho
đào tạo dược sĩ đại học), NXB Giáo Dục Việt Nam. Bài 10. Kháng
sinh họ phenicol, p.p. 231-237.
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 Goals
1) Indentify the structural features of phenicol antibitotics

2) Describe the mechanism of action of phenicol antibiotics

3) Analysis of the synthetic process of chloramphenicol

4) Know the background information of phenicols

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 1.1. GENERAL STRUCTURE

Thiamphenicol

Chloramphenicol
originally produced by
Streptomyces venezuelae

Azidamfenicol

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 1.2. MECHANISM OF ACTION-BACTERIOSTATIC

Simplified schematic of mRNA translation

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 1.3. MECHANISM OF BACTERIAL RESISTANCE

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 1.4. ANTI-INFECTIVE SPECTRUM

✓ Broad spectrum with activity against gram-positive and gram-

negative bacteria: Salmonella typhi (typhoid fever), Haemophilus
influenza, Streptococcus pneumoniae, Neisseria meningitidis
(meningitis, epiglottitis).

✓ Anaerobes (anaerobic bacteria): Chlamydia, Mycoplasma spp

(sexually transmitted infections, pelvic inflammatory disease).

✓ Activity against Enterobacteriaceae is unpredictable, and activity

against Pseudomonas is poor

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 2. CHLORAMPHENICOL - STRUCTURE

Chloramphenicol

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 2. CHLORAMPHENICOL - SYNTHESIS

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 2. CHLORAMPHENICOL - SYNTHESIS

Allegra Franchino et al. Org. Biomol. Chem., 2016, 14, 93

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 2. CHLORAMPHENICOL - SYNTHESIS

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 2. CHLORAMPHENICOL - CHEMICAL PROPERTIES

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 2. CHLORAMPHENICOL - CHEMICAL PROPERTIES

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 2. CHLORAMPHENICOL - PRODRUG FORMS

Chloramphenicol palmitate Chloramphenicol sodium succinate

oral suspension, less bitter water-soluble sodium salt
intravenous (IV) preparation

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 2. CHLORAMPHENICOL - SIDE EFFECTS

• Digestive disorders

• Bone marrow disorders/ Pancytopenia

• Grey syndrom

• Herxheimer

• Allergic

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 3. THIAMPHENICOL

Thiamphenicol

Gornorrhea
Urinary tract infection

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