organic medicinal chem

Medicinal Chemistry

Medicinal Chemistry

it is devoted to the DISCOVERY and DEVELOPMENT of new agents for treating diseases.

Drug

An agent intended for use in the DIAGNOSIS, MEDICATION, TREATMENT, CURE, or PREVENTION of disease in humans or in other animals.

Antibiotic

is a substance produced by microorganisms, which has the capacity of inhibiting the growth and even of destroying other microorganisms. - Waksman

P. NOTATUM

microbrial source of Penecillin

S. GRISEUS

microbrial source of Streptomycin

S. VENEZUELAE

microbrial source of Chlormaphenicol

S. ORIENTALIS

microbrial source of Vancomycin

TRUE

TRUE OR FALSE

Antibiotic Characteristics

It is a product of METABOLISM (although it may be duplicated or even have been anticipated by chemical synthesis).

FALSE

TRUE OR FALSE

Antibiotic Characteristics

It is a synthetic product produced as a PURE SYNTHETIC of a naturally occurring antibiotic.

TRUE

TRUE OR FALSE

Antibiotic Characteristics

It antagonizes the growth or survival of one or more species of microorganisms.

FALSE

TRUE OR FALSE

Antibiotic Characteristics

It is effective in HIGH concentrations.

FALSE

TRUE OR FALSE

Gram positive has a COMPLEX CELL wall

FALSE

TRUE OR FALSE

Gram positive is easier to destroy than gram negative

NAM and NAG

Cell wall contains TWO sugars called

n-acetylmuramic acid

NAM means?

n-acetylglucosamine

NAG means?

penicillin, cephalosporins, carbapenem, monobactam, polypeptides/glycopeptides

Cell wall inhibitors includes:

cell wall synthesis inhibitor

bacteriocidal that kills the bacteria

protein synthesis inhibitor

bacteriostatic/ prevents growth

Aminoglycoside & tetracycline

30 s inhibitors are:

chloramphenicol, erythromycin, lincosamides

50s inhibitors

Sir Alexander Fleming

Penicillin was accidentally discovered by

Howard Florey and Ernst Chain

____ introduced penicillin into therapy in 1928. They isolated penicillin using the process called “freeze drying”.

freeze drying

Florey & Chain isolated penicillin using the process called”

beta lactam ring, thiazolidine, 6 aminopenicillanic acid

penicillin contains:

penicillum chrysogenum

microbrial source that can produce a lot of penicillins

cross linking

Transpepditation is known as

salt

Certain issues with penicillin:

WATER INSOLUBLE

They added ____ to penicillin. (Sodium and Potassium salt of Penicillins are soluble in water)

Probenecid

Certain issues with penicillin:

Easily excreted

Combined Penicillin with __ (a uricosuric agent that competes with the active tubular secretion of drugs including Penicillin.)

Depot forms

Certain issues with penicillin:

2nd solution: ___ ( benzathine, procaine)

uricosuric

Probenecid is a __ agent that competes with the active tubular secretion of drugs including Penicillin

B-lactamases

enzymes that catalyze the hydrolytic opening of the B-lactam ring of penicillins to produce inactive penicilloic acids.

CLAVULANIC ACID, SULBACTAM, TAZOBACTAM

examples of b-lactamase inhibitors

TRUE

TRUE OR FALSE

TAZOBACTAM is more potent B-lactamase inhibitor than sulbactam and has a slightly broader spectrum of activity than clavulanic acid.

benzathine

Which of the following is a depot penicillin preparation? A. Phenoxymethylpenicillin B. Benzathine penicillin C. Benzyl penicillin D. Cloxacillin

Pen G and Pen V

Natural penicillins

BENZYLPENICILLIN

pen G aka

parenteral

pen g is administred through

SYPHILIS

pen G is DOC for

Phenoxymethylpenicillin

pen V is known as

stable

pen V is acid ___

ORALLY

pen V is administred through

repository

pen G is rapidly eliminated from the bloodstream leading to the use of the

EXTENDED SPECTRUM PENICILLINS

AMINO PENICILLINS IS KNOWN AS

a-amino group

Amino penicillins contain ____ (ionized/polar group) that can penetrate the outer cell membrane of Gram negative bacteria.

D-a-Amino-p hydroxybenzylpenicillin

chemical name of amoxicillin

FALSE

TRUE OR FALSE

Ampicillin has better oral bioavailability than Amoxicillin

D-a-aminobenzylpenicillin

Ampicillin is known as

Hetacillin

Ampicillin prodrugs that react penicillin with acetone

Bacampicillin Cyclacillin Hetacillin

Prodrugs of Ampicillin

ANTI-STAPHYLOCOCCAL AGENTS

Penicillinase Resistant Penicillin IS KNOWN AS

bulky group

Penicillinase Resistant Penicillin contains __ that serves as Steric hindrance

Staphylococcus aureus

Halophilic (meaning: salt-loving)

Usually found in the nose

Gram positive bacteria

Produces Beta-lactamase enzyme

It causes toxic shock syndrome (rare)

It causes scalded skin syndrome (causes outer layer of skin to blister and peel

2,6-dimethoxyphenylpenicillin

chemical name for methicillin

Methicillin

DOC for Penicillin-resistant Staphylococcus aureus

vancomycin

MRSA

Linezolid

VRSA

INTERSTITIAL NEPHRITIS

side effects of methicillin

Nafcillin

ALTERNATIVE FOR METHICILLIN

2-ethoxy-1-naphthylpenicillin

chemical name for nafcillin

5-Methyl-3-phenyl-4 isoxazolylpenicillin

chemical name for oxacillin

5-Methyl-3-(2-chlorophenyl)-4 isoxazolylpenicillin

chemical name for Cloxacillin

5-Methyl-3-(2,6 dichlorophenyl)-4-isoxazolylpenicillin

chemical name for dicloxacillin

Pseudomonas aeruginosa

Nosocomial infection (Hospital-acquired)

Opportunistic gram negative pathogen

Causes severe soft tissue infection

red

Pyorubin

brown

Pyomelanin

greenish yellow

Pyoverdin

blue green

Pyocyanin

a-Carboxybenzylpenicillin

chemical name for Carbenicillin

TRUE

TRUE OR FALSE

Carbenicillin has a broad range of antimicrobial activity, broader than any other known penicillin (attributed by carboxyl group)

a-Carboxy-3-thienylpenicillin

chemical name for Ticarcillin

Ticarcillin

higher serum levels and a longer duration of action, and has greater potency against Gram -

Tionentin

BN for Clavulanate

Piperacillin

The most potent of all ureidopenicillin

Tazobactam

Piperacillin is usually combine with

PIPTAZ & ZOSYN

tazobactam BN

dihydrothiazine ring

Cephalosporins contains a beta lactam ring called

7-aminocephalosparanic acid

Cephalosporins contains a nucleus called

CEPHALOSPORIUM ACREMONIUM

Microbrial source of cepholosporins

TRUE

TRUE OR FALSE

Cephalosporins are much more resistant to inactivation by beta-lactamases (Penicillinase)

ERYTHROMYCIN

alternative if you are penicillin sensitive

HYPOPROTHROMBINEMIA, DISULDIRAM LIKE REACTIONS

ADR for cephalosporins

pyrroline ring

carbapenem contains ___ ring

Thienamycin

First Carbapenem to be discovered.

streptomyces cattleya

Thienamycin was First isolated from the fermentation of

N-formimidoylthienamycin

imipinem is known as

1b & 2

imipinem inhibits of cell wall synthesis associated with PBPs

Imipinem

The most successful of a series of chemically stable derivatives of thienamycin.

dehydropeptidase enzyme

problem of imipinem is that it is easily degraded by _

seizure

imipinem causes __ to patients with renal failure

cilastatin

Inhibits dihydropeptidase-I enzyme

primaxin

Imipenem + Cilastatin BN

Meropenem

Second generation Carbapenem that Does not cause seizure

Monobactams

Beta-lactam ring is not fused to another ring

Aztreonam

Monobactam prepared by total synthesis

PBP3

Monobactam binds with high affinity to _____ in Gram negati ve bacteria only

PBPs 1A AND 1B

involved in peptidoglycan synthesis associated with CELL ELONGATION.

PBP 2

involved in maintaining the ROD SHAPE of bacilli.

rapid cell lysis

WhenPBP 1 and b inhibited, it will lead to spheroplast forma tion and

delayed lysis

When PBP2 inhibited, it will result to ovoid or round forms that undergo