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MED CHEM2 (Huigens)-MOD 02
SARs
149
Chemistry
Graduate
10/04/2016

Additional Chemistry Flashcards

 


 

Cards

Term
name this drug[image]
Definition
Largazole
Term
[image]list all func groups!
Definition
[image]
Term
name this drug[image]
Definition

Linezolid

purely synthetic 

[oxazolidenone antibacterial]

Term
[image]name this drug
Definition
Ciprofloxacin
Term
[image]name this drug
Definition
Tipranavir
Term
[image]name this drug
Definition
erythromycin
Term
[image]name this drug
Definition
Gefitinib
Term
[image]name this drug
Definition
Sorafenib
Term
[image]Name this drug
Definition
Quinine
Term
[image]name this drug
Definition
Cephalexin
Term
[image]name this drug
Definition
Penicillin G
Term
This pharmacophore represents what class of drugs[image]
Definition
Penicillins & derivatives
Term
name this drug[image]
Definition
tetracycline
Term

name the functional groups on this drug?

WHat drug is this anyway?

[image]

Definition

CIPROFLOXACIN

[image]

Term

name this drug 

[image]

Definition
Lipitor (atorvastatin)
Term

This Pharmacophore represents which drug class?

[image]

Definition
STATINS!
Term

Name this compound

[image]

Definition
Ageliferin (marine sponge derivative)
Term

name this drug

[image]

Definition
Lovastatin
Term

Magnesium Bromide (MgBr) is used as what type of reagent?

 

Definition
Grignard Reagent
Term

List in order of least to most reactive aka most to least stable

>>>

Amide, Aldehyde, Carboxylic Acid, Ester, Ketone

Definition

1.Carboxylic Acid

2. Amide

3. Ester

4. Ketone

5. Aldehyde

Term

Which Compound is found in many drugs?(most stable)

 

 

A. Amide

B. Aldehyde

C. Carboxylic Acid

D. Ester

E.Ketone

F. All of them

Definition
C. Carboxylic Acid
Term

Aromatic, Non-Aromatic, or ANti-Aromatic

[image]

Definition
Aromatic
Term

Aromatic, Non-Aromatic, or ANti-Aromatic

[image]
Definition
Aromatic
Term
Aromatic, Non-Aromatic, or ANti-Aromatic[image]
Definition
Aromatic
Term

Aromatic, Non-Aromatic, or ANti-Aromatic

 

[image]

Definition
Anti-aromatic
Term

Aromatic, Non-Aromatic, or ANti-Aromatic

 

[image]

Definition

Non aromatic

 

Term

Aromatic, Non-Aromatic, or ANti-Aromatic

[image]

Definition
Non aromatic
Term

Which of thes best describes Ciprofloxacins indication/function?

A. ANti-fungal

B. Anti-anginal

C. ANti-malarial

D. Anti-biotic

E. Anti-bacterial

Definition

E. Anti-bacterial

 

Anti bacterials are totally synthetic

Anti Biotics are nature derived

Term

Name this compound

[image]

Definition
Morphine
Term

Name this compound

[image]

Definition
Oxycodone
Term

name this compound

[image]

Definition
Hydrocodone
Term

Name this compound

[image]

Definition
Codeine
Term

name this drug

[image]

Definition
Heroin
Term

This structure is the pharmacophore for 40% of antibiotics. It is termed________

 

[image]

Definition
Beta-Lactam
Term

Irreversible Inhibition is characterized by what types of bonds?

(ex: ionic,hydrogen bonds....etc)

Definition
Covalent Bonds
Term

The process by which a quinoline is converted to a quinolone is known as __________.

 

ex: [image]

Definition
Tautomerization
Term

Name this functional group

[image]

Definition
Carbamate
Term

Name this functional group

[image]

Definition
Toluene
Term

Name this functional group

[image]

Definition
Aniline
Term

Name this functional group

[image]

Definition
Nitrile
Term

Name this functional group

[image]

Definition
Nitrosamine
Term

Name this functional group

[image]

Definition
Alkene/Olefin
Term

Name this functional group

[image]

Definition
Quinoline
Term

Name this functional group

[image]

Definition
Quinolone
Term

Name this functional group

[image]

Definition
pyridine
Term

name this functional group

[image]

Definition
Thioester
Term

Name this Functional Group

[image]

Definition
Nitrosos group
Term

This image depicts a carbapenem.

[image]

They are produced by

A. Bacteria

B. Fungi 

C. Humans

D. Fumigation

Definition
A. Bacteria
Term

Amines that are part of a conjugated system or with an adjacent electron withdrawing group are often___hybridized?

 

A. sp

B. sp2

C. sp1

D. sp3

Definition
B. sp2
Term
Erythromycin demonstrates selective targeting for bacterial______
Definition
Ribosomes
Term
Solubility, Absorption, Interaction with biological target, metabolism, excretion describe______properties of functional groups.
Definition
Physicochemical
Term

This drug is called ________.

It acts as a topoisomerase inhibitor.

[image]

Definition
TOPOTECAN
Term
Topotecan is a anticancer agent. It works as a ______________ inhibitor.
Definition

topoisomerase

[image]

Term

TRUE or FALSE.

 

Penicillins as well as statins come from fungi.

Definition
TRUE
Term

Name this 

[image]

Definition
imidazole
Term

name this structure

[image]

Definition
Pyrrole
Term

 

Name this structure

[image]

Definition
Furan
Term
[image]Name this structure
Definition
Thiophene
Term

Name this structure

[image]

Definition
Indole
Term

Name this structure

 

[image]

Definition
Benzofuran
Term

Name this structure 

[image]

Definition
Benzothiophene
Term
Taxol is an anti cancer agent and targets____
Definition
Microtubules (freezes/stabilizes)
Term
Quinine is an anti malaria agent and targets
Definition

Tat2p-mediated tryptophan transport and causes tryptophan starvation

Term
Statins target
Definition
HMG COA reductase (inhibitors of this enzyme)
Term
Ciprofloxacin inhibits bacterial DNA synthesis and  targets__________
Definition
topoisomerase II (responsible for supercoiling and uncoiling of DNA)
Term

Largazole (depicted below) comes from cyanobacteria and targets_________

[image]

Definition

Histone Deacetyleases aka HDACs

(Largazole is a Histone Deacetylase Inhibitor)

Term
Sorafenib is a kidney cancer drug that targets_____
Definition
Tyrosine protein Kinases
Term
Gefitinib(IRESSA) is a cancer drug that targets_______
Definition
EGFR and ERK 1/2
Term
Tipranavir treats multi drug resisitant HIV and targets______
Definition
HIV and CAAX Prenyl Proteases (protease inhibitor)
Term

Cephalasporin C is depicted below and targets______

[image]

Definition
Penicillin Binding Proteins PBPs(inhibits cell wall synthesis)
Term

Name this drug

[image]

Definition
Streptomycin (it is an aminoglycoside)
Term

Name this drug

[image]

Definition
Daptomycin (a lipopeptide antibiotic)
Term

Name the functional group

[image]

Definition
Guanidine
Term

Name the group

[image]

Definition
Pyrazole
Term

Name?

[image]

Definition
oxazole
Term

Name?

[image]

Definition
Pyrimidine
Term

Name?

[image]

Definition
Benzimidazole
Term

Name?

[image]

Definition
isoquinoline
Term

Rx name?

[image]

Definition

Epothilone A

[anticancer]

Term
Rx name?[image]
Definition
Camptothecin [anticancer]
Term

Rx name

[image]

Definition

Halfordinol

[anti-adipogenic activity, obesity]

Term

Rx name

[image]

Definition

ondansetron

[nausea from cancer tx]

Term

Rx name

[image]

Definition

Rivaroxaban (aka Xarelto)

[blood thinner, irregular heart beat]

Term

Rx name

[image]

Definition

Nexium (aka esomeprazole)

[ppi, tx for GERD]

Completely synthetic rx

Term

Rx name

[image]

Definition

AMIAS [hypertension, heart failure]

benzimidazole prodrug

Term

True or false

 

Carboxylic acids and Tetrazoles have similar acidities/pKa values

Definition
TRUE!!!
Term

Replacement or modification of specific pharmacophoric (functional) groups with other groups with similar properties is_____________.

 

 

Definition
Bioisosteric Replacement
Term

Rx name?

[image]

Definition

Tripelennamine

[1st generation antihistamine,antipruritic]

Term

Rx name

[image]

Definition

Methaphenilene

[antihistamine, anticholinergic]

Term

Rx name

[image]

Definition

a-tocopherol (aka Vitamin E)

[orally enhances immune system,antioxidant, topically promotes skin health]

Term

Group name?

[image]

Definition
catechol
Term

Rx name?

[image]

Definition

Isoproterenol

[tx for bradycardia aka slow heart rate, heart block]

Term

Rx name

[image]

Definition

Soterenol

[bronchodilator]

Term

Rx name

[image]

Definition

Estradiol

[female hormone hormone replacement, menopause]

Term

Rx name (this is the trans- version, not cis-)

[image]

Definition

Diethylstilbestrol (trans)

{synthetic estrogen}

The trans and cis version are equipotent to estrogen

Term
Acidity can be rationalized if you look at what type of organic structures?
Definition

Resonance structure

 

Term

Phenols PKA?

 

[image]

Definition
9-11
Term

Sulfonamide pKa (R2 is a hydrogen)?

 [image]

Definition
9-10
Term

Imide pKa?

[image]

 

Definition
9-10
Term

Alkylthiol pKa?

[image]

Definition
10-11
Term

Thiophenol pKa?

[image]

Definition
9-10
Term

N-aryl sulfonilamide pKa?

[image]

Definition
6-7
Term

Sulfonimide pKa?

[image]

Definition
5-6
Term

Alkylcarboxylic acid pKa?

[image]

Definition
5-6
Term

Arylcarboxylic acid pKa?

[image]

Definition
4-5
Term

Sulfonic Acid pKa?

[image]

Definition
0-1
Term

Rx name?

[image]

Definition

Irinotecan

[cancer Tx]

Topoisomerase 1 inhibitor

Term

Rx name

 

[image]

Definition

Cefaclor (Ceclor)

2nd generation cephalasporin antibiotic

Term

Water solubility is largely dependent on the # of _______'s

you are able to solubilize. They are accounted for by certain functional groups.

Definition
Carbon's
Term

Compound name 

 

[image]

Definition

Salicylic acid

[Monohydroxybenzoic acid derivative]

Term

This molecule may have trouble with dissolution due to _______________________.

[image]

Definition

INTRAmolecular hydrogen bonding

[of the carboxylic acid and alcohol] 

 

[image]

Term

Rx name?

 

[image]

Definition

NOVOCAINE

[local anesthetic]

Term

Based on pi values a molecule with a log p of 0.3 is _____

while a molecule with a pi value of 0.9 is ________

 

Definition

Soluble, insoluble (respectively)

 

 

Log p must be less than 0.5 for a molecule to be considered soluble in water. A molecule must have a Log p of less than 5 to have oral bioavailability. 

Term

Rx  name

 

[image]

Definition

Ibuprofen

[NSAID]

Term

Rx name

[image]

Definition

Captopril (Capoten)

[ACE inhibitor,hypertension]

Term

Rx name

[image]

Definition

Nadolol (Corgard)

 

[beta blocker, hypertension]

Term

Rx top selling drug of 2014

 

[image]

Definition

Synthroid (Levothyroxine)

 

[Thyroid hormone replacement]

T4 hormone produced naturally in our bodies

 

Term

Rx name

 

[image]

Definition

Zoloft

[selective serotonin reuptake inhibitor (AKA antidepressant)]

purely synthetic

Term

Name functional group

 

[image]

Definition
Napthalene
Term

Structural group? (HINT: 4)

 

[image]

Definition
tetrahydronaphthalene
Term

Functional group?

 

[image]

Definition

Piperizine

 

[It is a core functional group seen in LATUDA]

Term

Rx name?

 

[image]

Definition

LATUDA (Lurasidone)

 

[antipschotic, bipolar depression]

Term

Rx?

 

[image]

Definition

Testosterone

[T deficiency]

Term

Rx?

 

[image]

Definition

esterone

[estrogenic hormone secreted by the ovary as well as adipose tissue ]

Term

Rx?

 

[image]

Definition

progesterone

[endogenous steroid and progestogen sex hormone]

Term

Rx?

 

[image]

Definition

norethynodrel

 

[synthetic progestational hormone with actions and uses similar to those of PROGESTERONE]

Term

Rx?

 

[image]

Definition

mestranol

[synthetic steroidal estrogen]

Term

Rx?

 

[image]

Definition

Cortisone

 

[steroid, antiinflammatory]

 

NATURAL PRODUCT

Term

Rx?

 

[image]

Definition

Cortisol

 

[steroid hormone]

NATURAL PRODUCT

Term

Rx?

 

[image]

Definition

PREDNISONE

[synthetic steroid analog, ANTI INFLAMMATORY]

Term

Rx name?

 

[image]

Definition

Methicillin

 [β-lactam antibiotic of the penicillin class]

Term

In med chem we see in reversible reactions/equations that equilibrium lies with the more ________ species.

 

Definition
BASIC
Term

Rx?

 

[image]

Definition

Prostglandin

 

[lipids involved in injury and illness]

Term
pH =
Definition
pH = -log [H+]
Term
pOH =
Definition
pOH = -log[-OH]
Term
[H+] =
Definition

[H+] = 10= 10-pH

 

Term
[-OH] = 10= 10-pOH
Definition
[-OH] = 10= 10-pOH
Term
ALcohols hydrogen bond to water which can _______the water solubility
Definition
Increase
Term
Water solubility as described in the monofunctional model says the average functional group can account for about ___carbons
Definition
6
Term
Water solubility as described in the polyfunctional model says the average functional group can account for about ___carbons
Definition
3
Term

Molecule is?

[image]

Definition

Cytosine

[one of four main bases of DNA]

Term
pKa =
Definition

pKa = pH +log ([acid]/[base])

 

pKa = pH +log ([acid]/[base])

Term

Rx name?

 

[image]

Definition

Amobarbital

 

[sedative barbiturate, tranquilizer]

Term

Rx name?

 

[image]

Definition

Cetirizine (Zyrtec)

[antihistamine]

Term

Rx?

[image]

Definition

Phenylpropanolamine

[stimulant, decongestant, and anorectic]

Term

rx name?

[image]

Definition

crestor (rosuvastatin)

[hyperlipidemia]

synthetic derivative

 

Term

Rx?

 

[image]

Definition

Methadone

[Morphine Derivative]

opiod analgesic/treats pain or opiate withdrawals

Term

WHat is the name of the two methyl groups up top?

[image]

Definition
Gem-dimethyl
Term

Remember this position!!!!

 

[image]

Definition
[image]
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