MED CHEM2 (Huigens)-MOD 02 – Flashcards
Unlock all answers in this set
Unlock answers| name this drug[image] |
| Largazole |
| [image]list all func groups! |
| [image] |
| name this drug[image] |
Linezolid purely synthetic [oxazolidenone antibacterial] |
| [image]name this drug |
| Ciprofloxacin |
| [image]name this drug |
| Tipranavir |
| [image]name this drug |
| erythromycin |
| [image]name this drug |
| Gefitinib |
| [image]name this drug |
| Sorafenib |
| [image]Name this drug |
| Quinine |
| [image]name this drug |
| Cephalexin |
| [image]name this drug |
| Penicillin G |
| This pharmacophore represents what class of drugs[image] |
| Penicillins & derivatives |
| name this drug[image] |
| tetracycline |
name the functional groups on this drug? WHat drug is this anyway? [image] |
CIPROFLOXACIN [image] |
name this drug [image] |
| Lipitor (atorvastatin) |
This Pharmacophore represents which drug class? [image] |
| STATINS! |
Name this compound [image] |
| Ageliferin (marine sponge derivative) |
name this drug [image] |
| Lovastatin |
Magnesium Bromide (MgBr) is used as what type of reagent?
|
| Grignard Reagent |
List in order of least to most reactive aka most to least stable >>> Amide, Aldehyde, Carboxylic Acid, Ester, Ketone |
1.Carboxylic Acid 2. Amide 3. Ester 4. Ketone 5. Aldehyde |
Which Compound is found in many drugs?(most stable)
A. Amide B. Aldehyde C. Carboxylic Acid D. Ester E.Ketone F. All of them |
| C. Carboxylic Acid |
Aromatic, Non-Aromatic, or ANti-Aromatic [image] |
| Aromatic |
Aromatic, Non-Aromatic, or ANti-Aromatic [image] |
| Aromatic |
| Aromatic, Non-Aromatic, or ANti-Aromatic[image] |
| Aromatic |
Aromatic, Non-Aromatic, or ANti-Aromatic
[image] |
| Anti-aromatic |
Aromatic, Non-Aromatic, or ANti-Aromatic
[image] |
Non aromatic
|
Aromatic, Non-Aromatic, or ANti-Aromatic [image] |
| Non aromatic |
Which of thes best describes Ciprofloxacins indication/function? A. ANti-fungal B. Anti-anginal C. ANti-malarial D. Anti-biotic E. Anti-bacterial |
E. Anti-bacterial
Anti bacterials are totally synthetic Anti Biotics are nature derived |
Name this compound [image] |
| Morphine |
Name this compound [image] |
| Oxycodone |
name this compound [image] |
| Hydrocodone |
Name this compound [image] |
| Codeine |
name this drug [image] |
| Heroin |
This structure is the pharmacophore for 40% of antibiotics. It is termed________
[image] |
| Beta-Lactam |
Irreversible Inhibition is characterized by what types of bonds? (ex: ionic,hydrogen bonds....etc) |
| Covalent Bonds |
The process by which a quinoline is converted to a quinolone is known as __________.
ex: [image] |
| Tautomerization |
Name this functional group [image] |
| Carbamate |
Name this functional group [image] |
| Toluene |
Name this functional group [image] |
| Aniline |
Name this functional group [image] |
| Nitrile |
Name this functional group [image] |
| Nitrosamine |
Name this functional group [image] |
| Alkene/Olefin |
Name this functional group [image] |
| Quinoline |
Name this functional group [image] |
| Quinolone |
Name this functional group [image] |
| pyridine |
name this functional group [image] |
| Thioester |
Name this Functional Group [image] |
| Nitrosos group |
This image depicts a carbapenem. [image] They are produced by A. Bacteria B. Fungi C. Humans D. Fumigation |
| A. Bacteria |
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 |
| B. sp2 |
| Erythromycin demonstrates selective targeting for bacterial______ |
| Ribosomes |
| Solubility, Absorption, Interaction with biological target, metabolism, excretion describe______properties of functional groups. |
| Physicochemical |
This drug is called ________. It acts as a topoisomerase inhibitor. [image] |
| TOPOTECAN |
| Topotecan is a anticancer agent. It works as a ______________ inhibitor. |
topoisomerase [image] |
TRUE or FALSE.
Penicillins as well as statins come from fungi. |
| TRUE |
Name this [image] |
| imidazole |
name this structure [image] |
| Pyrrole |
Name this structure [image] |
| Furan |
| [image]Name this structure |
| Thiophene |
Name this structure [image] |
| Indole |
Name this structure
[image] |
| Benzofuran |
Name this structure [image] |
| Benzothiophene |
| Taxol is an anti cancer agent and targets____ |
| Microtubules (freezes/stabilizes) |
| Quinine is an anti malaria agent and targets |
Tat2p-mediated tryptophan transport and causes tryptophan starvation |
| Statins target |
| HMG COA reductase (inhibitors of this enzyme) |
| Ciprofloxacin inhibits bacterial DNA synthesis and targets__________ |
| topoisomerase II (responsible for supercoiling and uncoiling of DNA) |
Largazole (depicted below) comes from cyanobacteria and targets_________ [image] |
Histone Deacetyleases aka HDACs (Largazole is a Histone Deacetylase Inhibitor) |
| Sorafenib is a kidney cancer drug that targets_____ |
| Tyrosine protein Kinases |
| Gefitinib(IRESSA) is a cancer drug that targets_______ |
| EGFR and ERK 1/2 |
| Tipranavir treats multi drug resisitant HIV and targets______ |
| HIV and CAAX Prenyl Proteases (protease inhibitor) |
Cephalasporin C is depicted below and targets______ [image] |
| Penicillin Binding Proteins PBPs(inhibits cell wall synthesis) |
Name this drug [image] |
| Streptomycin (it is an aminoglycoside) |
Name this drug [image] |
| Daptomycin (a lipopeptide antibiotic) |
Name the functional group [image] |
| Guanidine |
Name the group [image] |
| Pyrazole |
Name? [image] |
| oxazole |
Name? [image] |
| Pyrimidine |
Name? [image] |
| Benzimidazole |
Name? [image] |
| isoquinoline |
Rx name? [image] |
Epothilone A [anticancer] |
| Rx name?[image] |
| Camptothecin [anticancer] |
Rx name [image] |
Halfordinol [anti-adipogenic activity, obesity] |
Rx name [image] |
ondansetron [nausea from cancer tx] |
Rx name [image] |
Rivaroxaban (aka Xarelto) [blood thinner, irregular heart beat] |
Rx name [image] |
Nexium (aka esomeprazole) [ppi, tx for GERD] Completely synthetic rx |
Rx name [image] |
AMIAS [hypertension, heart failure] benzimidazole prodrug |
True or false
Carboxylic acids and Tetrazoles have similar acidities/pKa values |
| TRUE!!! |
Replacement or modification of specific pharmacophoric (functional) groups with other groups with similar properties is_____________.
|
| Bioisosteric Replacement |
Rx name? [image] |
Tripelennamine [1st generation antihistamine,antipruritic] |
Rx name [image] |
Methaphenilene [antihistamine, anticholinergic] |
Rx name [image] |
a-tocopherol (aka Vitamin E) [orally enhances immune system,antioxidant, topically promotes skin health] |
Group name? [image] |
| catechol |
Rx name? [image] |
Isoproterenol [tx for bradycardia aka slow heart rate, heart block] |
Rx name [image] |
Soterenol [bronchodilator] |
Rx name [image] |
Estradiol [female hormone hormone replacement, menopause] |
Rx name (this is the trans- version, not cis-) [image] |
Diethylstilbestrol (trans) {synthetic estrogen} The trans and cis version are equipotent to estrogen |
| Acidity can be rationalized if you look at what type of organic structures? |
Resonance structure
|
Phenols PKA?
[image] |
| 9-11 |
Sulfonamide pKa (R2 is a hydrogen)? [image] |
| 9-10 |
Imide pKa? [image]
|
| 9-10 |
Alkylthiol pKa? [image] |
| 10-11 |
Thiophenol pKa? [image] |
| 9-10 |
N-aryl sulfonilamide pKa? [image] |
| 6-7 |
Sulfonimide pKa? [image] |
| 5-6 |
Alkylcarboxylic acid pKa? [image] |
| 5-6 |
Arylcarboxylic acid pKa? [image] |
| 4-5 |
Sulfonic Acid pKa? [image] |
| 0-1 |
Rx name? [image] |
Irinotecan [cancer Tx] Topoisomerase 1 inhibitor |
Rx name
[image] |
Cefaclor (Ceclor) 2nd generation cephalasporin antibiotic |
Water solubility is largely dependent on the # of _______'s you are able to solubilize. They are accounted for by certain functional groups. |
| Carbon's |
Compound name
[image] |
Salicylic acid [Monohydroxybenzoic acid derivative] |
This molecule may have trouble with dissolution due to _______________________. [image] |
INTRAmolecular hydrogen bonding [of the carboxylic acid and alcohol]
[image] |
Rx name?
[image] |
NOVOCAINE [local anesthetic] |
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 ________
|
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. |
Rx name
[image] |
Ibuprofen [NSAID] |
Rx name [image] |
Captopril (Capoten) [ACE inhibitor,hypertension] |
Rx name [image] |
Nadolol (Corgard)
[beta blocker, hypertension] |
Rx top selling drug of 2014
[image] |
Synthroid (Levothyroxine)
[Thyroid hormone replacement] T4 hormone produced naturally in our bodies
|
Rx name
[image] |
Zoloft [selective serotonin reuptake inhibitor (AKA antidepressant)] purely synthetic |
Name functional group
[image] |
| Napthalene |
Structural group? (HINT: 4)
[image] |
| tetrahydronaphthalene |
Functional group?
[image] |
Piperizine
[It is a core functional group seen in LATUDA] |
Rx name?
[image] |
LATUDA (Lurasidone)
[antipschotic, bipolar depression] |
Rx?
[image] |
Testosterone [T deficiency] |
Rx?
[image] |
esterone [estrogenic hormone secreted by the ovary as well as adipose tissue ] |
Rx?
[image] |
progesterone [endogenous steroid and progestogen sex hormone] |
Rx?
[image] |
norethynodrel
[synthetic progestational hormone with actions and uses similar to those of PROGESTERONE] |
Rx?
[image] |
mestranol [synthetic steroidal estrogen] |
Rx?
[image] |
Cortisone
[steroid, antiinflammatory]
NATURAL PRODUCT |
Rx?
[image] |
Cortisol
[steroid hormone] NATURAL PRODUCT |
Rx?
[image] |
PREDNISONE [synthetic steroid analog, ANTI INFLAMMATORY] |
Rx name?
[image] |
Methicillin [?-lactam antibiotic of the penicillin class] |
In med chem we see in reversible reactions/equations that equilibrium lies with the more ________ species.
|
| BASIC |
Rx?
[image] |
Prostglandin
[lipids involved in injury and illness] |
| pH = |
| pH = -log [H+] |
| pOH = |
| pOH = -log[-OH] |
| [H+] = |
[H+] = 10x = 10-pH
|
| [-OH] = 10x = 10-pOH |
| [-OH] = 10x = 10-pOH |
| ALcohols hydrogen bond to water which can _______the water solubility |
| Increase |
| Water solubility as described in the monofunctional model says the average functional group can account for about ___carbons |
| 6 |
| Water solubility as described in the polyfunctional model says the average functional group can account for about ___carbons |
| 3 |
Molecule is? [image] |
Cytosine [one of four main bases of DNA] |
| pKa = |
pKa = pH +log ([acid]/[base])
pKa = pH +log ([acid]/[base]) |
Rx name?
[image] |
Amobarbital
[sedative barbiturate, tranquilizer] |
Rx name?
[image] |
Cetirizine (Zyrtec) [antihistamine] |
Rx? [image] |
Phenylpropanolamine [stimulant, decongestant, and anorectic] |
rx name? [image] |
crestor (rosuvastatin) [hyperlipidemia] synthetic derivative
|
Rx?
[image] |
Methadone [Morphine Derivative] opiod analgesic/treats pain or opiate withdrawals |
WHat is the name of the two methyl groups up top? [image] |
| Gem-dimethyl |
Remember this position!!!!
[image] |
| [image] |
