Tetracyclines Structure, IUPAC Name, Uses, Adverse Effects Notes B.Pharmacy 6th Semester 2021 (2020-2021) Previous Year's Question Papers/Notes Download - HK Technical PGIMS

1. Clinical Uses of Tetracyclines • Tetracyclines are bacteriostatic antibacterial with a wide spectrum of activity and have been used in the treatment of a large number of infection caused by susceptible organism. • In the treatment of Gonorrhoea, respiratory tract, ear infection and acne vulgaris etc • To treat infections caused by bacteria such as pneumonia and respiratory tract infections. Certain infections of skin, eye, lymphatic, intestinal, genital and urinary systems. • To treat certain infection spread by ticks, lice, mites, and infected animals • With other medication to treat acne. • To treat plague and tularemia. • To treat certain type of food poisoning where can’t be treat with penicillin. • It will not work for colds, flu, or other viral infections. 1 HK Technical PGIMS Dosages Drugs Dose Tetracycline[Capsule] Adult: 500mg b.i.d 250mg q.i.d Child(>8yrs): 25-50mg/kg body wt. Oxytetracycline[Capsule] Adult: 1-2g daily dose Child(>8yrs): 25-50mg/kg daily dose Chlortetracycline[Per Oral] 250mg in every 6hrs. Minocycline[Tablet] Paediatric: 4 mg/kg initially followed by 2 mg/kg every 12 hours. Adult: 100 mg b.i.d. Doxycycline[Tablet] Adult: first Dose:200mg/day Maintenance dose: 100mg/day HK Technical PGIMS 2. HK Technical PGIMS 2 Adverse Effects of Tertacyclines Oesophageal ulceration Teeth decolouration Intracranial Hypertension Dental Hypoplasia Nausea & Vomiting Nail Decolouration Photo Sensitivity Headaches HK Technical PGIMS 3. HK Technical PGIMS 3 Drugs Adverse effects Tetracycline[1] • Tetracyclines can cause hepatotoxicity • Might exacerbate preexisting renal failure • Oesophageal ulceration and strictures • Intracranial hypertension (IH, pseudotumor cerebri) • Discoloration of teeth & inhibition of bone growth in children may occur • Abdominal discomfort, epigastric pain, nausea, vomiting, and anorexia • Some patients experience photosensitivity, which can manifest as a red rash or skin blistering. Oxytetracycline[2] • Stomach or bowel upsets and rarely allergic reactions • Very rarely severe headache and vision problems may be signs of dangerous intracranial hypertension. Chlortetracycline[3] • Gastrointestinal disturbances, and staining of teeth and bone • Some occurrences of dental hypoplasia and bone deformity have been noted . • In pregnant women tetracyclines may produce hepatotoxicity. Minocycline[4] • Gastrointestinal distress and photosensitivity. • Hyperpigmentation of skin and discoloration of nails • Staining of teeth and bone growth inhibition(more in children) • Hepatotoxicity, and exacerbation of preexisting renal failure. • Pill esophagitis, odynophagia, and dysphagia Doxycycline[5] • Gastrointestinal symptoms and photosensitivity include nausea, abdominal pain, vomiting, and diarrhea. • With tetracycline: onycholysis, benign intracranial hypertension, skin hyper-pigmentation, post- inflammatory elastolysis, tooth discoloration, vertigo, ataxia, clostridium difficile diarrhea, visual disturbances, and phlebitis. HK Technical PGIMS 4. 4 HK Technical PGIMS IUPAC Name: (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a pentahydroxy-6-methyl-1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide IUPAC Name: (4S,4aR,5aR,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl 1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide IUPAC Name: (45,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Structure and IUPAC Name HK Technical PGIMS 5. HK Technical PGIMS 5 IUPAC Name: (4S,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-6-methyl-1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide IUPAC Name: (45,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11 dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Structure and IUPAC Name HK Technical PGIMS 6. Reference • https://medlineplus.gov/druginfo/meds/a682098.html • Arora P., Arora V., Kumar D., ‘Medicinal Chemistry-III’, PV Books, Edition 2020, Page No. 52,56. • https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=54d1720d-edfc- 4eb4-8388-f61bd5971336 • https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6b4de8c9-8a32- 4a07-9183-419d6177ea08 • https://www.sciencedirect.com/topics/agricultural-and-biological- sciences/chlortetracycline • https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4f243e45-a1e6- 4246-95f8-196f2b491185 • https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9b52e0a7-f024- 4d8a-a59e-374946e60b44 • https://www.ncbi.nlm.nih.gov/books/NBK549905/ • https://pubchem.ncbi.nlm.nih.gov/compound/Oxytetracycline#section=Antid ote-and-Emergency-Treatment • https://pubchem.ncbi.nlm.nih.gov/compound/Chlortetracycline#section=Acut e-Effects • https://www.ncbi.nlm.nih.gov/books/NBK554519/ • https://www.ncbi.nlm.nih.gov/books/NBK556599/ 6 HK Technical PGIMS HK Technical PGIMS