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You can watch this lecture video on youtube
https://www.youtube.com/watch?v=51OgNKXhbYc
Complete Chapter of
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Sulfonamide (also called sulphonamide, sulfa drugs or sulpha drugs) is the basis of several groups of drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the sulfonamide group.
Complete Chapter of Anti-malarial Drugs Part -2Anjali Bhardwaj
You can watch this lecture video on youtube
https://www.youtube.com/watch?v=51OgNKXhbYc
Complete Chapter of
Anti-malarial Drugs Part -2
-Synthesis of Important drugs
-Mechanism Of action
-Uses & Adverse effects
-Brand Name
Tetracyclines,Biological sources,History,Sturctures,SAR,Mechanism of action,Spectrum of activity,Important structural units and the three acidity constants in the tetracycline molucule,amphoteric nature,epimerisation, chelation with metals,toxicity and uses.
Tetracyclines,Biological sources,History,Sturctures,SAR,Mechanism of action,Spectrum of activity,Important structural units and the three acidity constants in the tetracycline molucule,amphoteric nature,epimerisation, chelation with metals,toxicity and uses.
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Performing procedures as directed by doctors.
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CHAPTER 1 SEMESTER V - ROLE OF PEADIATRIC NURSE.pdf
TB, historical perspective of anti TB drugs and medicinal chemistry of INH
1. Topic outline
• Brief introduction of TB
• Medicinal Chemistry of INH: Anti-TB drug
Dr. Khalid Hussain (hussain_761@yahoo.com)
2. Tuberculosis (TB)
• TB is a communicable disease caused by
Mycobacterium tuberculosis, which is a gram
positive, acid fast bacilli
• MT has characteristic cell wall that is made up
of peptydoglycan (amino acids and
sugars)covered by a lipopolisaccharide made
up of mainly mycolic acid
• Most of the antibiotics are not effective
against MT due to its characteristic cell wall
3. Anti-TB drugs
• First agent used as an anti-TB drug was
sulfanilamide, but, since, sulfonamides
are bacteriostatic, resistance occurred
rapidly
• Second agent tried was dapsone, though
it was effective, but in long-term therapy
found to be toxic…..discontinued
• In TB treatment, major breakthrough
was the development of streptomycin-an aminoglycoside, that
was highly effective against MT. Afterwards, many synthetic
drugs were developed to eradicate TB, despite such
developments, it is still prevailing due to emergence of multi-
drug resistant stains
4. Isoniazid
• It is synthetic anti-TB drug introduced in 1950
• Chemically, it is isonicotinic acid derivative-
combination of isonicotinic acid and hydrazine:
(Hydrazide)
• It is a prodrug- in body is converted into
electrophilic species which inhibit the synthesis
of mycolic acid
• It is effective against rapidly dividing MTB but
less effective against dormant and semi- dormant
MTB
Isonicotinyl
Hydrazine
Hydrazide
5. Structure activity relationship
• Pyridine ring, if replaced with piperidine then
the compound is less active than the original
• Hydrazide linkage when converted
into hydrazone derivatives, a series
of active compounds are produced.
Later it was found that in the body
Hydrzones are converted into
isoniazid
• If hydrazide is shifted to position 2 or 3 instead
of 4 then the compound is less active
6. • INH contains two nitrogen atoms, when
an alkyl group is introduced at N1 then
the compound became inactive
• When any alkyl group is introduced at N2
then a series of active compounds are
obtained but these are less active
• If hydarzide group is replaced totally by
alkyl or aryl then the compound remains
active but less than isonaizide
8. Chemical synthesis
4-cyano pyridine Isonicotinamide Isoniazid
Basic hydrolysis of 4-cyano pyridine
converts cyano/nitrile group to an amide-
Isonicotinamide- which then reacts with
hydrazine to produce isoniazid
9. Mechanism of action
• INH undergoes oxidation reaction by
endogenous catalyzing enzymes, producing
reactive species capable of acylating the
enzyme (inhA)-found in MT
• Under the influence of (kat G) a gene also
called (inhA), INH is converted into isonicotinic
aldehyde, isonicotinic acid and
isonicotinamide
10. • From these compounds, highly reactive
electrophilic species such as isonicotinyl radical
and isonicotinyl peroxy radical are formed
• These radicals acylate NADPH dependent β-
ketoacyl carrier protein reductase, involved in
elongation of mycolic acid. It results in the
inhibition of cell wall leading to cell death
11. • This enzyme selectively acts on fatty acids (more
than 26 carbon). Mycolic acid is a α-branched
fatty acids having short arm of 20-24 carbon and
long arm of 26-50 carbon
• Additionally, acylating agents combine with
position 4 of the NADPH and make it inactive for
reduction
• Its therapy causes peripheral
neuritis /neuropathy, hence
prescribed with vitamin-B6
12. Pyrazinamide (PZA )
• Contains pyrazine ring in its structure, which is
a six memberd heterocyclic ring containing
two nitrogen at a distance of 2 carbon atoms
• Pyrazinamide has amide group at position 2
• It is a prodrug and converted into pyrazinoic
acid in the body
13. • Activity is pH dependent and maximum activity
takes place at pH 5.5
• It can be considered a derivative of isonicotinic acid,
isonicotinic acid has 1 N while pyrazinamide has 2
• Both are called isosteres -those having same
biological and physicochemical properties.
• Nitrogen has atomic number 7 whereas CH also has
7, hence isosteres
• OH group of isonicotinic acid/pyrazinoic acid is
isosteric with NH2 group of PZA because both have
atomic number 9
• It is active against dormant MT
14. Structure activity relationship
• When pyrazine ring is replaced with alternate
heterocyclic ring e.g pyridine or pyrimidine, the
compound became less active
• Pyrazine ring is mono-substituted while di-
substituted derivatives are less active
-These were initial findings because later on due
to QSAR two di-substituted derivatives were
introduced –which were active
17. Therapeutic uses
• It is effective against dormant MT
• Activity is pH dependent, when administered
pH is lowered to 5.5 which is not suitable for
the growth of MT-suitable is 7.2- hence MT is
eradicated
• It is given in combination with other anti-TB
drugs