1 Dr. Harish & Purvi Kakrani

Dr.
Harish & Purvi Kakrani 1

Contents
 Introduction
 Classification
 Isolation
 Structure Determination
 Stereochemistry
 Biological Activity
Dr. Harish & Purvi Kakrani 2

INTRODUCTION…
 A chemical compound acting against life is

called an ‘Antibiotic’,obtained either from
natural source or by a synthetic method.
 The term ‘Antibiotic’ has been derived from

the word “antibiosis” which according to
biological concept means survival of fittest
means a process in which one organism
may destroy another to preserve itself.

 The word ‘Antibiotic’ was first
introduced by vuillemin in 1889 and
defined by waksman and latter
modified by benedict &langlykke.

 DEFINITION OF ANTIBIOTIC:
“It is a chemical substance

produced by or derived from living cell
which is capable ,in small
concentration ,of inhibiting the life
process or even distroying the
microorganism.”

 Conditions for chemical compound
being an antibiotic.
1)Originally ‘Antibiotic’ must have been a product of
metabolism although it might have been
synthesized.
2) If ‘Antibiotic’ is a synthetic product then it should
be a structural analogue of naturally occurred
‘Antibiotic’.
3) The ‘Antibiotic’ must be effective at low
concentration.
4)The ‘Antibiotic’ must be antagonise the growth
and/or survival of microorganism.

 In order for a particular ‘Antibiotic’ to act
as a therapeutic agent,it has to satisfy the
following conditions:
1) It must be effective against a pathogen.

2) It must not cause significant toxic effect.
3) It should be stored for a long time period
without loss of its activity.
4) Its stability must be high so that it can be
isolated and processed into suitable forms
of dosage which are readily absorbed in
to human body.
 IMPORTANCE OF ANTIBIOTIC:
• Clinically effective in protozoal infection

and fungal infection.
• Carcinostatic activity
• Antitumour activity
• Antibacterial activity
• Antiviral activity
• Important tool for study of biochemical
cellular mechanism

Three ‘ANTIBIOTICS’ should be
discussed here…
 PENICILLIN
 STREPTOMYCIN
 GRISEOFULVIN

CLASSIFICATION...
 First classification(the broad based
classification):
a) Broad spectrum Antibiotics:
PENICILLINS
Tetracycline
Chloramphenicol
b) Relative broad spectrum Antibiotics:
Ampicillin
Cephalosporin
c) Narrow spectrum Antibiotic:
STREPTOMYCIN(gm -ve)
GRESEOFULVIN(antifungal)
Amphotericin
 Second classification(type of bacteria
can antibiotic destroy):
a) Effective against Gm +ve bacteria:
PENICILLIN
Erythromycin
Bacitracin
b) Effective against Gm –ve bacteria:
STREPTOMYCIN
Neomycin
Gentamicin
c) Effective against both Gm +ve & Gm
–ve:
Ampicillin
Cephalosporin
Tetracycline
Chloramphenicol
 Third classification (chemical
structure):
a) PENICILLIN and related Antibiotics:
PENICILLIN
SEMISYNTHETIC
PENICILLIN
b) Aminoglycoside antibiotics:
STREPTOMYCIN
Neomycin
c) Macrolide Antobiotics:
Erythromycin
d) Tetracycline Antibiotics:
Tetracycline
Oxytetracycline
Chlorotetracycline
e) Peptide Antibiotics:
Bacitracin
Gramicidin
f) Chloramphenicol and its synthetic
analogues

g)Antifungal Antibiotics:
GRISEOFULVIN
Amphotericin
h) Unclassified Antibiotics:
Cycloserine
Fusidic acid
Vancomycin

PENICILLIN POWDER

 ‘Penicillin’ is the first antibiotic
discovered by alexander flemming .
 It was first extracted from P.notatum
then P.chrysogenum but now by
biofermentation process.
 It is also known as beta lactam
antibiotics.
 The basic structure of Penicillin
consists of thiazolidine ring(A) fused
with beta lactam ring(B).both these unit
form the 6-amino penicillinamic acid.

Penicillin has simillarity with L-cysteine and
D-valine

CLASSIFICATION…
 Acidresistant Penicillin:
Penicillin V
Phenethicillin
 Penicillinase resistant Penicillin:
Methicillin
Oxacillin
 Extended spectrum Penicillin:
Ampicillin
Amoxicillin

 Reversed spectrum Penicillin:
Temocillin
 β-lactamase inhibitors:
Clauvanic acid
Sulbactam

ISOLATION…
 Various culture method known which
are used to produce Penicillin.
 The strains of Penicillin species are
grown in a nutrient medium which is
obtained from sugary materials and
proteinous substance.
 P .chrysogenum (NRRL 1951,Stanford
25099,X-1612,176) are widely used
strains for the commercial production of
Penicillin.
Typical nutrient medium for penicillin
Component %
Corn steep liqour 3.5
solid
Lactose 3.5
Glucose 1
CaCO3 1
KH2PO4 0.4
Edible oil 0.25
Penicillin precursor
 Penicillin produced on larger scale by
3 methods:
 Liquid surface culture method
 Bran method
 Submerged method
In all these methods submerged

method is widely used.

 Liquid surface method:The molases
containing pH 7-8 is used as medium
for microorganisms.After few days the
growth of microorganism starts and
after 6-7 days,concentration of
Penicillin become 0.3-0.4 mg/ml.This
method mainly used for lab.studies.
 Bran method:The use of moist bran is
considered to be substrate for mould
growth and resultant Penicillin may be
extracted in a liquid or Penicillin
containing bran.
 Submerged culture method:This is
widely used method for commercial
production of Penicillin.In this method
P.chrysogenum is used for the
culture.Here culture and culture
medium are taken in large tanks.The
medium is agitated by a stream of
sterile air at 24 c for 2-3 days.After
that fermentation vessel is sealed and
positive air pressure is
maintained.under this condition mould
grows throughout the bulk of liquid.
 After fermentation the contents of
vessel should be rapidly cooled and
mycellium filtered on sterile rotary
filter.
 Adjust the pH of fitrate depends upon
the nature of solvent extraction that
carried out with amyl or butyl alcohol
now pet.ether is added and shaken
with dil.Na2CO3,adjust the pH 6-7 and
rapidly freeze evaporated to yield Na-
salt.
STRUCTURE
DETERMINATION…
 From analytical data the molecular
formula of Penicillin is C9H11N2O4SR.
 As Penicillin forms mono salts it
should be revealed that it contains
carboxyl group.
 From the chemical test it has been
proved that penicillin does not contain
free amino group.

 When penicillin are hydrolysed by hot
dilute inorganic acids,they degraded
to the equimolar amount of D-
penicillimine and penilloaldehyde.
 C9H11N2O4SR+2H2O
C5H11NO2S+C3H4NO2R+CO2

 Structure of D-Penicillamine:
• Molecular formula of Penicillamine is
C5H11NO2S.
• Penicillamine gives colour reaction
with sodium nitroprusside this reveals
that it contains thiol group so it is
probably substituted cysteine.

• When Penicilline is treated with
diazomethane, it is converted into its
methyl ester.the later compound
when treated with aqueous solution of
mercuric chloride gives methyl ester
of Penicillamine.this reaction reveals
that carboxyl group in Penicillamine is
carboxyl group in penicillin itself.

• Like cysteine D-Penicillamine also
react with acetone to yield
isopropylidene derivative.the later
compound does not contain a free
amino or thio group and reconverted
into Penicillamine on hydrolysis.
• Further the oxidation of Penicillamine
with bromine water gives sulphonic
acid.
So, D-Penicillamine is β ,β-
dimethylcysteine,which is confirmed
by its synthesis.
 Structure of Penilloaldehyde:
• Molecular formula of Penilloaldehyde
found to be C3H4NO2R.
• When hydrolysed vigorously,all
Penilloaldehyde yields a substituted
acetic acid and amino
acetaldehyde.this reaction reveals
that Penilloaldehyde are acyl
derivatives of amino acetaldehyde.

• The latter structure of Penilloaldehyde
has been confirmed by its synthesis
from corresponding acid chloride and
aminoacetal.
 RCONHCH2CHO+H2ORCOOH+
NH2CH2CHO
 RCOCl+NH2CH2CH(OC2H5)2→
RCONHCH2CHO.

D-Penicillimine - Penilloaldehyde
Penicillin

 Mode of linking of Penicillamine and
Penilloaldehyde:
• When Penicillin is hydrolysed with
dilute alkali it yields Penicilloic acid
which is dicarboxylic acid and readily
eliminates a CO2 to yield
monocarboxylic acid,Penilloic
acid.this suggests that in Penilloic
acid one of the carboxyl group is in β-
position with respect to electrone
attracting group.

• When Penilloic acid hydrolysed with
aqueous mercuric chloride,yields
Penicillamine and
Penilloaldehyde.this type of hydrolysis
is characteristic of compound having
a thiozolidine ring.

• if (і) is the structure of Penilloic acid
then the structure of Penicilloic acid
represented as (ii)
• (iii) and (iv)are also possible
structures of Penicillin.

 Desulphurisation of benzyl penicillin
with raney nickel to yield
desthiobenzylpenicillin which on
hydrolysis by acid gives
desthiobenzylpenicilloic acid it proves
existance of β-lactam ring in
Penicillin.

 The infrared spectral studies of
oxazolone and β-lactam structure,and
correlation between various band and
functional group is worked out.
 This could be understood by
considering the methyl ester and Na-
salt of benzylpenicillin.

Ir maxima of methyl ester & Na-salt
benzyl penicillin
Ir maxima of Ir maxima assignment
methyl ester of Na-salt
3333 3333 NH- group
1770 1770 β-lactam
1748 1613 >C=O
1684 1681 2ֹamide
1506 1515 2 ֹamide
 The ir spectra of number of β-lactam
& fused thiazolidine β-lactams are
recorded.
 The β-lactam do not exhibit band at
1770 cm ֿwhile the other exhibit band
at 1770 cmֿ,this explain the 5th band
so it would be concluded that (iv) is
the correct structure for penicillin.

So Finally Structure of Penicillin

STEREOCHEMISTRY…
 Penicillin contains a 4 membered lactam
ring which is fused through the nitrogen
and tetrahedral carbon to a second
heterocyclic ring.
 All the natural Penicillin are strongly
dextrorotatory .
 It has been denoted that there are 8
stereoisomers of benzyl
penicillin,achieved by changing the
orientation of three carbon in structure
namely 4,10,14.

Stereoisomer of benzylpenicillin

 The incorporation of an ionized or
polar group at the α- position of the
side chain benzyl carbon atom of
benzylpenicillin imparts clinical activity
against Gm –ve bacilli.
 If we were to find the stereochemistry
of cyclisation which forms the β-
lactam ring in Penicillin,we would
have to synthesized cysteine with
chiral tritium labelling at C-3 by cis-
addition of H atom to an olefin of well
defined stereochemistry.
3-D Structure of penicillin

BIOLOGICAL
ACTIVITY…
 Penicillin inhibits bacterial cell wall
formation.the cell wall of bacteria is
essential for their normal growth and
development.
 Peptidoglycan is a component of the cell
wall and provides rigid mechanical
stability by virtue of its highly crossed
linked lattice work structure.

 Penicillin inhibits the enzyme-
transpeptidase that brings about
cross linking between 5th glycine of
the already existing peptidoglycan in
the cell wall and 4th amino acid of
newly formed peptidoglycan.
 In addition, to the peptidoglycan
synthesis,Penicillin also inhibits
penicillin binding proteins at the cell
wall causing lysis of the bacterial cell
through autolysing enzymes.
 Penicillinis bactericidal in action.In its
presence the bacterial cell wall
become soft and finally undergoes
lysis.
 It is more effective on actively
multiplying organisms.

STREPTOMYCIN

STREPTOMYCIN POWDER

 Ineffectiveness of Penicillin towards
Gm –ve organisms leading to search
for newer antibiotics.
 Streptomycin was developed as a
result of a well planned scientific
research by waksman and coworkers
in 1944.

 It was first isolated from
Streptomyces griesus by schatz &
waksman in 1944.
 It is active against Gm –ve, Gm +ve
organism including acid fast bacteria.
 Streptomycin and other related
antibiotics like
kanamycin,Tobramycin,Framycetin
etc. are termed as aminoglycoside
antibiotics

 chemically aminoglycoside
antibiotics,consists of two or more
amino sugars joined in glycosidic
linkage to a hexose nucleus.
 This hexose is either Streptidine(in
streptomycin)or 2-Deoxy
streptamine(in other aminoglycoside
antibiotics).

 The number of the amino sugars
attached are also different.
 kanamycin ,Gentamicin,Tobramycin
consists two amino sugars,neomycin
consists three aminosugar.

ISOLATION…
 Initially,Streptomycinwas prepared by
surface culture technique but now a
days submerged culture technique is
widely used.
 The yield of Streptomycin depends
greatly on medium used.the addition of
corn steep liquor, meat extract,
soyabean meal enhances the yield.
 The medium composed of glucose ,
1% peptone, 0.3% meat extract, Nacl
0.5% in water.
 The culture solution is kept in large
vats. The growth of micro organism
begins at 24-28 ֹC and maximum yield
achieved after 3-5 days.
 After seperating mycellium and other
wastes,Streptomycin is extracted
from filtrate, either by adsorption on
charcoal or on base exchangable
resin.
 Sreptomycin is eluted from column by
means of dil.aqueous or alcoholic
mineral acid,then purify it by passing
through ion exchangable resin.
 The pure form of Streptomycin has
been isolated as sulphate or crystalline
double salt of calcium chloride.
 To get sterile drug crystaline
Streptomycin is dissolved to yield 25%
solution which is free from impurity by
passing through seitz filter and then
freeze dried then transferred
aseptically to small vials.

STRUCTURE
DETERMINATION…
 From essential analytical data
molecular formula of Streptomycin
has been found to be C21H39N7O12.
 As Streptomycin form tri
hydrochloride, this shows that its
three N atoms must be strongly basic
in nature.
 C21H39N7O12 +3Hcl→C21H39N7O12.3Hcl

 When Streptomycin is hydrolysed in
strongly acid solution,it yields one
molecule of Streptidine and one
molecule of Streptobiosamine.(folkers
et al)
 Streptomycin+H2O→Streptidine+
Streptobiosamine.
 On the other hand alkaline hydrolysis
gives maltol which is believed to be
derived from one of the fragment of
Streptobiosamine.

 Structure of Streptidine:
• From analytical data molecular
formula is found to be C8H18N6O4.
• When it is oxidised with pottasium
permenganate,it yields two molecules
of guanidine it reveals that Streptidine
has two guanidino groups.

• When Streptidine is subjected to
alkaline hydrolysis,it yields
Streptamine and ammonia.(brink et
al)
 Streptidine+4H2O→Streptamine+
4NH3+2CO2

•As Streptamine is obtained by alkaline
hydrolysis of Streptidine,the following
structure may be assigned to
Streptidine.this structure is confirmed
by its synthesis from
Streptamine(wolfrom et al)

• Streptidine is not opticaly
active,therefore it was assigned
mesoconfiguration with two guanidino
group in a cis position.

 Structure of Streptobiosamine:
• From analytical study the molecular
formula found to be C13H23NO9.
• When Streptomycin is subjected to
methanolysis then hydrolysed finally
acetylated,the penta acetate of N-
Methyl L-glucosamine which on
hydrolysis yields N-Methyl L-
glucosamine.

• When Streptomycin is reacted with
methanolic hydrochloric acid it gives
Streptidine di hydrochloride and
methyl streptobiosamine dimethyl
acetal.
• When methyl Streptobiosamine

dimethyl acetal is subjected to drastic
alkaline hydrolysis yields methyl
acetal,indicating the presence of
methyl amino group.

• On the other hand less drastic
degradation of the Methyl
Streptamine by means of acetic
anhydride and hydrochloric acid
yields N-Methyl glucosamine and
Streptose so it would be concluded
that Streptobiosamine may be
glycoside of N-Methylglucosamine
and Streptose.

• When N-Methylglucosamine is treated
with phenylhydrazine,it yields a
phenylhydrazone.the later can be
converted in to phenylosotriazole
which has same m.p and an equal but
opposite specific rotation as of D-
glucose phenylosotriazole.

• When Streptobiosamine is oxidised
with bromine,it yields a product which
on hydrolysis yields Streptosonic acid
monolactone.the lactone is converted
into amide which consumes two
moles of periodic acid ,indicating the
presence of three hydroxyl group.so
the structure of Streptosonic Acid
Diamide,Streptosonic Acid
Monolactone and Streptose may be
written as follows:

Streptobiosamine

Streptidine

Streptamine N-Methylglucosamine
-
Streptose
Streptidine Streptobiosamine
Streptomycin

 Point of linkage between Streptidine
and Streptobiosamine:
• In 1948-49 merck group of chemist
established the point of linkage
between Streptidine and
Streptobiosamine by carried out
hydrolysis of benzolyated
streptomycin very carefully without
disturbing the ester linkage to yield
optically active
heptabenzoylstreptidine.

• The oxidation product clearly
established the structure of dibenzoyl
derivative it reveals that –OH group is
adjacent to one of the carbon
attached to the guanidino group of
streptidine.

• C1 of Streptose unit is involved in
linkage between Streptidine and
Streptobiosamine.
• But later compound do not have
substituents on C1 it means that
substituent must be present for maltol
production.
• Hence,C1 of Streptose is linked
glycosidically to the C4 of the
Streptidine to yield following structure
of Streptomycin.
Point of linkage between Streptidine and
Streptobiosamine.

Structure of Streptomycin

STEREOCHEMISTRY…
 Streptomycin has two important
structural features namely aminosugar
portion and centrally placed hexose
ring.
 If Amino sugar portion at C-6 or C-2
position,serve as major target sites for
bacterial inactivating enzyme.
 If modification at C-1 carbon of
centrally placed hexose ring,helps to
retain the antibacterial potency.
Chair conformation

 Streptidine is not optically
active.therefore,it was assigned
mesoconfiguration with two guanidino
groups in a cis position.

Point of linkage

3-D structure of Streptomycin

BIOLOGICAL
ACTIVITY…
 Itis bactericidal in therapeutic dose
and bacteriostatic in lower dose.it
interferes with protein synthesis.
 The initial event is penetration of drug
into the cell.
 The 30s subunit of cell ribosomes is
primarily affected which in turn causes
inhibition of protein synthesis.it also
causes elongation of the cell without
permiting final division.

 Ribosomal protein synthesis is
inhibited by aminoglycoside by three
ways:
1)They interfere with the initiation
complex of peptide formation.
2)They induce misreading of the code
on the mRNA template.
3)They cause a break up of polysomes
into non-functional monosomes.

 Before producing inhibition of protein
synthesis ,it is necessary for
aminoglycoside to enter into cytosol
of the bacteria by diffusion through
aqueous channel or energy
dependent electrone transport.

 Non functional proteins produced
due to effect of Streptomycin,may be
incorporated into the cell membrane
leading to further stimulation of
aminoglycoside transport and leakage
of small and larger molecule.this is
the reason of bactericidal action of
Streptomycin.

GRISEOFULVIN

GRISEOFULVIN POWDER

 Griseofulvin is an antifungal agent
produced by the cultures of
P.griseofulvum other penicillium
species including
P.notatum,P.paltatum.
 Grisoefulvin is the drug of choice for
widespread or itractable
dermatophyte infection.

 Griseofulvin contain neither sulphur
nor nitrogen,but contains
chlorine.chlorine is supplied as
pottasium chloride throughout its
production,otherwise the product is
dechlorogriseofulvin which is identical
to griseofulvin.

ISOLATION…
 The principle in Griseofulvin
fermentation is to encourage early
growth and then,by nutrient
limitation,to maintain a cell population
just within the aeration potential of the
fermentor.
 Griseofulvin remains intracellular,at
harvest it is the cell that are
significant and the filtrate is no of
use.the cell can be easily removed by
fitration.
 The first step in the recovery of
Griseofulvin is to extract the cell with
acetone.
 The resulting extract is subjected to
concentration,thus a crude product is
obtained.

 This crude product is washed with
further organic solvent to remove
acetone soluble impurities.
 The washed Griseofulvin is
redissolved in acetone and solution is
mixed carefully with water so it would
be precipitated.the large volume of
acetone used are recovered for further
use.
STRUCTURE
DETERMINATION…
 There is no particular details about
structure determination for
Griseofulvin.
 From essential analytical data
molecular formula of Griseofulvin is
C17H17ClO6.
 By the usual chemical test it has been
shown that Griseofulvin do not have
free amino or thiol group.
 Initial
inspection of structure of
Griseofulvin shows the alternative
oxygenation pattern and also methyl
group which identifies the start of the
polyketide chain.

 From IR spectra studies of
Griseofulvin the principal peaks at
wave number
1220,1611,1210,1583,1135,800(KBr
disc).
 From Mass spectral studies of
Griseofulvin principal peaks acc. to
m/z 138,352,215,310,214,69,321,354.

Structure of Griseofulvin

BIOLOGICAL
ACTIVITY…
A prominent morphological
menisfastation of the action
Griseofulvin is the production of
multinucleate cells as the drug inhibit
fungal mitosis.the explanation for this
phenomenon appears to come from
the studies of effects on mammalian
cells of higher concentration of the
antibiotic.
 Griseofulvin causes disruption of
mitotic spindle by interacting with
polymerized microtubules,thus action
similar to colchicine and vinca
alkaloids.

 Griseofulvin‘s binding site on
microtubular protein is distinct.there is
evidence that it binds to a microtubule
associated protein in addition to its
binding to tubulin.
 Here,by destruction of microtubules
responsible for the synthesis of
various substance.

REFERANCE…
 Kar Ashutosh,Pharmacognosy &
Pharmabiotechnology 2nd revised
edition;New age international publisher.
Page:568-694.
 Kokate C K,Purohit A P,Pharmacognosy,27th

edition;Nirali prakashan Page:585-87.
 Agarwal O P,Organic Chemistry of Natural

Products Vol.2,28th edition;Goel publication
merut. Page:98-122.
 Comprehensive Medicinal Product,vol 4.
Page:100-02.
 Peter K,Volhardt C,Organic Chemistry:

Structure & Function, 3rd edition;W H
Freeman & Company,New york
Page:898,1102.
 Indian Pharmacopoiea’96 vol-1,Published by

controller of publication,Delhi.Page:353.
 British Pharmacopoiea’93 vol.1 International

edition,Page:316,635.
 Devik Paul,A Biosynthetic Approach to
Medicinal Natural Product,2nd edition;Willey
publication Page:78,437-444,478-480.
 Patel A H,Industrial Microbiology,Macmillan

India ltd, Page:112-22.
 Manfred Wollf,Berger’s Medicinal Chemistry

&Drug discovery vol-2:Therapeutic Agent ,
5th edition; Page:466-72,642-44.
 Kar Ashutosh,Medicinal Chemistry;2nd

edition, New age publication Page:455-61.
 Manfred Wollf,Berger’s Medicinal
Chemistry &Drug discovery vol
4:Therapeutic agent;5th edition Page:285-
93.
 Goyal R K, Element of Pharmacology 14th

edition 2004-05;B S Shah Prakashan,
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 Clarke’s Isolation &Identification of Drug in
Pharmaceutical Body Fluid and
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Pharmaceutical press.Page:645.
 Foye Willium,Williams A David,Principal of

Medicinal Chemistry 4th edition;B I Waverly
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Dr.

Harish & Purvi Kakrani 1

Dr. Harish & Purvi Kakrani 2

 A chemical compound acting against life is

 The term ‘Antibiotic’ has been derived from

Dr. Harish & Purvi Kakrani 3

Dr. Harish & Purvi Kakrani 4

“It is a chemical substance

Dr. Harish & Purvi Kakrani 5

Dr. Harish & Purvi Kakrani 6

1) It must be effective against a pathogen.

• Clinically effective in protozoal infection

Dr. Harish & Purvi Kakrani 8

Dr. Harish & Purvi Kakrani 9

Dr. Harish & Purvi Kakrani 14

Dr. Harish & Purvi Kakrani 15

Dr. Harish & Purvi Kakrani 17

Dr. Harish & Purvi Kakrani 19

Dr. Harish & Purvi Kakrani 20

Dr. Harish & Purvi Kakrani 21

Dr. Harish & Purvi Kakrani 22

In all these methods submerged

Dr. Harish & Purvi Kakrani 25

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• When methyl Streptobiosamine

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