PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)

Antimicrobial Property of Penicilins and Celphalosporins

1. What is the product of acid hydrolysis of penicilins? Cephalosporins?

PENICILINS:

In addition to acids, penicillins are susceptible to hydrolysis of the B-lactam ring

by enzymes called B-lactamase or penicilinases. This cause an inactivation of
A. the compound because the antibacterial properties of these molecules reside the
ring itself (Calderon and Sabundayo, 2007) REFERENCE: MANUAL PAGE 87

B.
https://books.google.com.ph/books?
id=kwGsuSEZBkYC&pg=PA27&dq=acid+hydrolysis+of+penicillin&hl=en&sa=X&ved=0ahUKEwjsxYmqzuD
oAhWFBIgKHbycCioQ6AEIQzAD#v=onepage&q=acid%20hydrolysis%20of%20penicillin&f=false

C.

https://pharmafactz.com/medicinal-chemistry-of-beta-lactam-antibiotics/

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PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
CEPHALOSPORINS:

A.

https://books.google.com.ph/books?
id=uf_FRSFrccgC&pg=PA180&dq=acid+hydrolysis+cephalosporins&hl=en&sa=X&ved=0ahUKEwi
Ao-uH2ODoAhXOPXAKHV8_D6AQ6AEIMzAB#v=onepage&q=acid%20hydrolysis
%20cephalosporins&f=false

B.

https://pharmafactz.com/medicinal-chemistry-of-beta-lactam-antibiotics/

AALA & OLARVE

 PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
2. How do penicillinase inhibitors like clavulanic acid, sulbactam, and tazobactam
affect the activity of penicillins against penicillin-resistant microorganism?

CLAVULANIC ACID:

A.

id=FaXRAQAAQBAJ&pg=PA192&dq=clavulanic
+acid+affect+penicillin+resistant&hl=en&sa=X
&ved=0ahUKEwinwfOa3eDoAhWzIqYKHfV1Cd
w4FBDoAQgnMAA#v=onepage&q=clavulanic
%20acid%20affect%20penicillin
%20resistant&f=false

B.

https://books.google.com.ph/books?
id=qq83AT5aQ1wC&pg=PT56&dq=clavulanic+
acid+affect+penicillin+resistant&hl=en&sa=X&
ved=0ahUKEwjvopn52DoAhUUIIgKHZljACAQ6
AEITDAE#v=onepage&q&f=false

AALA & OLARVE

 PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
SULBACTAM:

A.
https://books.google.com.ph/books?
id=vshQDwAAQBAJ&pg=PA77&dq=SULBACTA
M+affect+penicillin&hl=en&sa=X&ved=0ahUK
EwjAw86D3DoAhWDUN4KHXVZDT0Q6AEIKD
AA#v=onepage&q=SULBACTAM%20affect
%20penicillin&f=false

B.

https://books.google.com.ph/books?
id=UGqjFPQ_LkgC&pg=PA308&dq=Ampicillin/sulbactam+is+a+combination+of+the+common+penicillin
derived&hl=en&sa=X&ved=0ahUKEwisyJ6S4ODoAhWHFogKHTZ9BPsQ6AEIMDAB#v=onepage&q=Ampici
llin%2Fsulbactam%20is%20a%20combination%20of%20the%20common%20penicillin-derived&f=false

AALA & OLARVE

 PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
TAZOBACTAM:

A.

https://books.google.com.ph/books?
id=JcCEDwAAQBAJ&pg=PA827&dq=tazobactam+affect+penicillin&hl=en&sa=X&ved=0ahUKEwj9s9ae4e
DoAhWSNKYKHfz0BToQ6AEIMDAB#v=onepage&q=tazobactam%20affect%20penicillin&f=false

AALA & OLARVE

PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
CLAVULANIC ACID, SULBACTAM & TAZOBACTAM

https://books.google.com.ph/books?
id=HdA4dl8m_T4C&pg=PA387&dq=tazobactam+penicillin&hl=en&sa=X&ved=0ahUKEwi_o4q04
uDoAhXZxYsBHQPqDA0Q6AEIKDAA#v=onepage&q=tazobactam%20penicillin&f=false

AALA & OLARVE

PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
3. How do molecular modifications in penicilins and cephalosporins affect the acid-
resistance and penicillinase-resistance of these antibiotics?

The solubility and other physicochemical properties of the penicillins are affected
by the nature of the acyl side chain and by the cations used to make salts of the
acid. Improved microbiological and pharmacokinetic properties in penicillins have
focused on acyl functionalities that would minimize the sensitivity of β-lactam ring
to acid hydrolysis while maintaining antibacterial activity. Increasing the steric
hindrance at the α-carbon of the acyl group increased resistance to
staphylococcal β-lactamase, with maximal resistance being observed with
quaternary substitution.

*Penicillinases have two general types: β-lactamases and acylases

In certain cephalosporins, oral activity can also be conferred by esterification of

the 3-carboxylic acid group to form acid-stable, lipophilic esters that undergo
hydrolysis in the plasma. The introduction of polar substituents in the aminoacyl
moiety as well as the steric factors of cephalosporins appear to confer stability
and resistance to some β-lactamases.

Beale, J. Jr. & Block, J. (2011). Wilson and Gisvold’s Textbook of: Organic
Medicinal and Pharmaceutical Chemistry. Philadelphia: Lippincott Williams &
Wilkins, a Wolters Kluwer business

AALA & OLARVE

PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins

4. How are microorganism categorized as susceptible, intermediate, and resistant

by agar disk diffusion method?

A.

https://www.slideshare.net/doctorrao/kirby-bauer-antibiotic-sensitivity-testing

AALA & OLARVE

 PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins

B.

https://amrls.cvm.msu.edu/microbiology/detecting-antimicrobial-resistance/test-methods/examples-
of-antibiotic-sensitivity-tesing-methods

AALA & OLARVE

PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins

C.

AALA & OLARVE

PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins

AALA & OLARVE

PH-PHR 222(Pharmaceutical and Medical Organic Chemistry)
Antimicrobial Property of Penicilins and Celphalosporins
https://www.slideshare.net/doctorrao/kirbybauer-disc-diffusion-method-antibiotic-susceptibility-
testing-skill-based-learning

AALA & OLARVE