Lecture 14

Drugs affecting the immune system

Drugs used to treat gout
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 24. Analgesics, p.p.
809-811.

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

Chemistry 7th edition, Lippincott Williams & Wilkins: Baltimore.
Medicinal
Chapter 31. Nonsteroidal anti-inflammarory drugs, p.p. 1034-1044.

3) Trương Phương, Trần Thành Đạo (2017). Hóa dược 2 (Dùng cho đào
tạo dược sĩ đại học), NXB Giáo Dục Việt Nam. Bài 50. Thuốc trị bệnh
gout, p.p. 392-400.

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 Goals
1) Indentify the structural features of drugs used to treat gout

2) Know the background information of drugs used to treat gout

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 Gout

• Gout is a metabolic disorder of purine metabolism,

characterized by intermittent attacks of acute pain, swelling
and inflammation.
• It always preceded by hyperuricaemia.

• Acute gout vs. chronic gout.

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 Acute gout

• Painful arthritic attack of sudden onset

• Usually occurring at night or in early morning

• Arthritic pain worsen progressively

• Generally involves one or few joints

• Most common site of attack

initial metatarsophalangeal joint

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 Chronic gout
• Frequency of attacks increases, continuous deposit leads to damage
joints and chronic pain
• Patients may develop large subacutenous tophi in pinna of external
ear, eyelids, nose and around joints
• Articular cartiage may be destroyed result in joint deformities

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 Risk factors

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 Treatmen
t Drugs For example
NSAIDs - Indomethacin
- Diclofenac
Acute gout - Ibuprofen
- Naproxen

Colchicine
Corticoid - Prednisolone
- Methylprednisolone

Inhibit uric acid synthesis - Allopurinol

- Febuxostat
Chronic gout Increase uric acid excretion - NaHCO3
- Probenecid
- Sulfinpyrazone

Decompose uric acid - Uricase

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 Colchicine - MOA
• Neither analgesic anti-inflammatory, but specific for gouty
nor inflammation

• It is only effective in prophylaxis of acute gout

• It has no effect on synthesis or promote excretion

• Colchicine binds to intracellular protein “Tubulin” and causes

depolymerisation and disappearance of microtubules in granulocytes
and inhibit granulocyte migration so dec phagocytic activity

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 Colchicine - Side effects
o Diarrhea, vomiting, abdominal pain

o Agranulocytosis

o Myopathy

o Peripheral neuritis

o Renal tubular necrosis

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 Colchicine - Contraindicated
• Pregnant

• Severe liver failure, severe renal failure, heart

failure, digestive disorders

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 Colchicine - Structure

Alkaloid from Cochium autumnale

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 Colchicine - Chemical properties

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 Colchicine - Chemical properties

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 Colchicine - Chemical properties

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 Colchicine - Identification

o IR, optical rotation

o UV, melting point, TLC, reaction with FeCl3

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 Colchicine – Related substances

• Colchicinic acid
• β-lumicolchicine
• Colchicoside
• N-deacetyl-N-formylcolchicine

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 Colchicine - Assay

o Titration method
o UV

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 Allopurinol - MOA

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 Allopurinol - Identification

• IR
• UV, TLC
• Reaction with Ag

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 Drugs used to treat gout

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