Med Chem - Systemic Antibiotics for Acne

Question 1

what class of antibiotics are used for acne?
(systemic not topical)

Answer 1

tetracyclines

Question 2

name 4 tetracyclines used for acne

Answer 2

tetracycline
doxycycline
minocycline
sarecycline

Question 3

what severity of acne are systemic antibiotics indicated for?

how do they work in treating acne?

Answer 3

SEVERE ACNE

kill excess skin bacteria, and also show anti inflammatory activity

Question 4

all tetracyclines contain what?

Answer 4

naphthacene

highly functionalized, partially reduced naphthacene ring

Question 5

tetracyclines are ________ in nature

Answer 5

AMPHOTERIC - have both acidic and basic components

Question 6

by looking at the structure of a tetracycline, how can you determine which OH’s are acidic

Answer 6

look for “keto-enol” or enolic acid

OH has a double bond attached and a ketone next to it

acidic through tatomerization

Question 7

true or false

the naphthacene ring in tetracyclines is fully saturated

Answer 7

FALSE - partially saturated

the D ring is full unsaturated – has all double bonds

Question 8

name some requirements for tetracycline activity

(SAR)

Answer 8

1. C4 on ring A has dimethyl amino with (s) stereochemistry
2. linear naphthacene ring with C1-C3 keto enol and primary carboxamide on C2 (all on A ring)
3. C10-C11 keto enol and C11-C12 keto enol in conjunction with C12 alpha group

Question 9

which carbons on the general structure of a tetracycline CAN be chemically modified?
this mainly includes which ring?

Answer 9

carbons 5-9

D ring

Question 10

which ring of naphthacene on a tetracycline is the most flexible in terms of generating active derivatives

Answer 10

D ring

Question 11

tetracyclines are potent inhibitors of………

Answer 11

bacterial protein biosynthesis

Question 12

tetracyclines can’t be administered with what 2 things and why

Answer 12

high calcium rich foods and antacids

a portion of tetracyclines chelates with calcium and forms an insoluble chelate

Question 13

true or false

the top portion of tetracyclines is not as important to its activity and can be altered

Answer 13

FALSE

the bottom portion

top portion is essential and is the same across all the tetracyclines

Question 14

what kind of carboxamide is preferred on the 2nd carbon of tetracyclines

Answer 14

primary - UNSUBSTITUTED

Question 15

TRUE OR FALSE

the dimethylamino on ring A of tetracyclines is not essential for activity

Answer 15

FALSE - it is

must also have S stereochemistry