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103 Cards in this Set
- Front
- Back
chemical nucleus for estrogens
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estrane C18
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chemical nucleus for androgens
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androstane C19
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chemical nucleus for progestrogens and corticosteroids
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pregnane C21
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chemical nucleus for cholesterol
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cholestane C27
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Ring ___ must be aromatic for estrogens
____ hybridization at all carbons in this ring gives estrogens their selectivity. |
A
sp2 |
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Natural estrogens produced by the ovaries:
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Estradiol (Estrace)
Estrone (Theelin) Estriol |
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Semi-synthetic estrogens include:
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Estradiol cypionate (Depo-estradiol)
Ethinyl estradiol (Estinyl) Mestranol Estropipate (Ogen) Conjugated Estrogens (Premarin) |
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Synthetic estrogens (nonsteroidal nucleus)
non-serms |
Diethylstilbestrol (DES)
Dienestrol (Ortho-dienestrol) Chlorotrianisene (TACE) |
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SERMs
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Clomiphene (Clomid)
Tamoxifene (Nolvadex) Raloxifene (Evista) |
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The hypothalamus releases ____ stimulating the pituitary to release ___ which causes the ovaries to release estrogen. Estrogens are responsible for:
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FSRH
FSH maturation of follicles / ovum |
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The hypothalamus releases ____ stimulating the pituitary to release ___ which causes the ovaries to produce progersterone. Progesterone is responsible for
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LHRF
LH release ovum, maintaining pregnancy or shedding the endometrium during menstruation |
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Oral contraceptives work via:
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Negative feedback on the HPA axis
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Natural estrogen functions
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Maturation of sex hormones
Regulation of ovulation Bone growth |
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Potential therapeutic uses of estrogens
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HRT during menopause
Male prostate cancer Hirsutism |
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Estrone is produced from the _________ of estradiol
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Oxidation
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_________ + _________ of estrone will produce estriol
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enolization + Hydration
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Diethylstilbestrol requires _______ bonds at the ethyl groups to maintain activity.
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Trans
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This synthetic estrogen led to the development of SERMs which has high affinity for receptors but low intrinsic activity
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Chlorotrianisene (TACE)
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SERMs are used to treat _________ and ________
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breast cancer
osteoporosis |
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Tamoxifen is metabolized via aromatic hydoxylation and N-dealkylation, and its para-hydroxylated metabolite is ________
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Active
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Ethinyl Estradiol was developed to prevent
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First pass oxidation
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Mestranol is a derivative of ethinyl estradiol that was developed to:
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Limit phase II metabolism as well as first pass oxidation
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This semi-synthetic estrogen is a prodrug given PO or by injection, activated via phase II metabolism.
Salt of estrone-sulfate |
Estropipate (Ogen)
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True or False
Synthetic estrogens are steroids that have high affinity for estrogen receptors with low intrinsic activity. |
False
NOT steroids, with variable activity |
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Clomiphene's agonistic effect is used to treat _______ or _______, while its antagonistic effect is good for _________
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osteoporosis / infertility
cancer |
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Exogenous progestins will cause feedback inhibition of ____
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LH
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Side effects of progestins are associated with
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Androgenic nucleus
acne, hirsutism, decreased bone density, decreased HDL, high LDL |
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Progesterone has high absorption but first pass metabolism.__________ is progesterones active metabolite
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Hydroxyprogesterone
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This progestin contains ethinyl group giving it high androgenic activity due to its similarity to androstane nucleus
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Ethisterone
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Removal of ______ from position __ on ethisterone will block the androgenic effects.
This hormone is called |
methyl
C10 (carbon19) Norethisterone |
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Modified hydroxyprogesterone given as a depot IM injection
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Hydroxyprogesterone capoate
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hydroxyprogesterone capoate is no longer used in the US. Instead ____________ was made by removing long chained fatty acid and adding an additional methyl at C6 to resist 1st pass
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medroxyprogesterone acetate
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Common ingredient in many oral contraceptives, resists first pass metabolism, sold as a racemic mix
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norgestrel
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Plan B
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levonorgestrel
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This abortive agent works to block progesterones endometrial effects after ovulation
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Mifepristone
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testosterone is metabolized by 5-alpha reductase into
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dihydrotestosterone
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Testosterone decanoate is an IM injection indicated for
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hypogonadism + anemia
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Effects of testosterone
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Male sex characteristics
Spermatogenesis Protein synthesis - anabolic |
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__________ is an oral testosterone derivative designed to avoid first pass metabolism,
7-10X more potent, also sublingual |
methyltestosterone
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________ is 20X more potent than testosterone, anabolic effects aid in anemia also used for hypogonadism
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fluoxymesterone
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Anabolic steroid lacking a methyl at C____ which is essential for androgenic effects, in order to isolate anabolic effect
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C10 (carbon19)
Nandrolone |
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1-2 double bonds in ring A, or an additional ring with double bonds will give steroid structures more activity at ________ receptors due to ___ hybridization and flattening structure
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Anabolic
sp2 |
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Explain why dihydrotestosterone is 10 times more active at androgenic receptors than testosterone
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alpha reductase removes the double bond in ring a creating sp3 hybridization all around the ring (chair) which is more selective towards androgenic receptors
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Estrogen receptor affinity is associated with ___ double bonds (_______) in ring A
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3
Benzene |
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Danazol has no effect for hypogonadism. It is an anabolic steroid used to treat ___________. Side effects are caused by its _________ effects.
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hemolytic anemia
progesterone |
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These steroids have no androgenic activity but will not come up positive on anabolic steroid testing.
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Oxandrolone + Testolactone
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Nandrolone (Deca-durabolin) is used for
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breast cancer + anemia
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Anabolic steroids ______ nitrogen balance
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increase
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Anti-androgens are used for:
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acne
hirsutism prostate cancer |
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Cyproterone + Flutamide are:
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competitive androgen receptor antagonists
acne / hirsutism / prostate cancer |
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Insulin is a ___ amino acid polypeptide consisting of 2 separate chains connected by 2 ______ bonds
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51
disulfide |
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Chain A of insulin polypeptide is ___ amino acids long and contains an ______molecular disulfide bond.
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21
INTRA molecular |
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Chain B on insulin is ___ amino acids long
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30
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True or False
Insulin has no plasma protein binding when distributed in the body |
True
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In order for insulin to be active it must be in its ______ form
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monomer
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Insulin metabolism happens where?
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Liver, kidney, muscles
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________ cleaves intermolecular disulfide bonds, giving insulin a t1/2 of ___ minutes
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Insulin-glutathione transhydrogenase
6 minutes |
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Polypeptide hormones produced by gastric mucosa when you eat, stimulating the release of insulin
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Incretins
GIP (glucose dependent insulin releasing peptide) GLP-1 (glucagon-like peptide) |
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Glucagon stimulates __________ and ________ through a receptor-mediated action in the liver.
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glycogenolysis
gluconeogenesis |
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________ serves as a mediator between glucagon and insulin.
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Somatostatin
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Iletin = ______ insulin differing from human insulin structure by __ amino acid(s)
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Pork
1 AA |
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Regular human insulin has an onset of ___ minutes and a duration of ______ hours
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30 minute onset
5-8 hour duration |
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Rapid acting insulin has an onset of ___ minutes and a duration of ____ hours
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15-30 minute
2-6 hour duration |
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Lispro is a derivative of regular insulin but dissociates from its hexamer form more rapidly because of alterations at positions ___ + ___
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28 lysine
29 proline |
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Aspart contains _____ at position 28.
Glulisine contains _____ at position 3 and _____ at position 28 |
Aspartate
Lysine + Glutamate |
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Lispro and Aspart are contained in a _______ buffer, while ________ is contained in distilled water
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phosphate buffer
glulisine |
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_______ is a fast acting insulin not used in the US. Its amorphous shape provides a larger surface area for dissolution when zinc is low.
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Semilente
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Ultralente is long acting. When _____ levels are high it is crystalline with less surface area for dissolution.
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zinc
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Intermediate acting insulins have an onset of ____ hours and a duration of _____ hours
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3-4 hour onset
18-24 hour duration |
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Aspart is more negative due to aspartic residue which aids in ________ rate
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dissolution
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Ultra-lente is contained in a ______ buffer
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Acetate
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4 Major classes of anti-diabetics
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Secretagogues
Glucosidase inhibitors Biguanides Insulin Sensitizers |
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Secretagogues include
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Sulfonylureas
Meglitinides GLP-1 agonists / DPP-IV inhib |
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________ is the longest acting of the 1st generation sulfonylureas with QD dosing.
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Chlorpropamide (Diabenese)
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2nd generation sulfonylureas are 100x more potent than first generation. __________ allows for qd dosing
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enterohepatic circulation
|
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Adverse effects associated with 2nd generation sulfonylureas.
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hyperinsulinemia
hypoglycemia |
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Normal glucose levels should be
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90-110mg/dL
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Meglitinides are 5-10x more potent than sulfonylureas and work via the same mechanism. They have a _____ onset and _____ duration and do not cause __________
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rapid onset
shorter duration hyperinsulinemia |
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True or False
Stronger effect: Meglitinides > Sulfonylureas |
False
|
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________ only work when glucose is high. (Antihyperglycemics)
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Biguanides
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While metformin is the safest to use, biguanides adverse effects can include:
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Muscle ache, lactic acidosis
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Biguanides work by:
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Inhibit gluconeogenesis
Inhibit glycogenolysis Promote glycolysis |
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True or False
Biguanides are excreted unchanged |
True - very polar
|
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True or False
Thiazolidindiones when used alone, effectively increase insulin release |
False
PPARγ agonist / insulin sensitizer! need to be used in combo to have any effect |
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True or False
Sulfonylureas can be used in combination with biguanides |
True
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_________ metabolite has a similar structure to vitamin E, it can cause severe hepatotoxicity.
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Troglitazone
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metformin + rosiglitazone
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Avandamet
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metformin + glipizide
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Metaglip
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metformin + glyburide
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Glucovance
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Metformin has _______ oral absorption due to its polarity
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low
food decreases absorption too |
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These antidiabetic drugs are very safe for elderly because they are not absorbed
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Glucosidase Inhibitors
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Thyroid functions include:
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Regulating metabolism BMR
Growth Homeostasis |
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Another name for hyperthyroidism
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Graves Disease
|
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True or False
Hyperthyroidism or Hypothyroidism can cause goiter |
True
|
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Thyroid hormones are iodinated amino acids derived from ________. They are synthesized in the thyroid gland and stored as amino acid residues of _________.
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tyrosine
thyroglobulin |
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T3 and T4 tyrosine rings are perpendicular to eachother due to
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Steric hinderance from Iodination - required conformation for receptor activity
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T4 is _____ acidic and lipophilic than T3. T4 undergoes enterohepatic circulation and has a t1/2 of about ____
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more
7 days |
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Which is more active at thyroid receptor?
T3 vs. T4 |
T3 more active, higher affinity for receptor, low ppb, no enterohepatic circulation
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The overall ratio of T4:T3 in the body
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4:1
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After uptake of iodide into the thyroid gland via iodide pump, iodide is ________ by peroxidase into elemental iodine.
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oxidized
|
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Goitrin found in cabbage exists as a tautamer that can interfere with peroxidase enzyme leading to _______
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goiter
|
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hypothyroidism is also called
|
myxedema
|
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Types of Anti-thyroid drugs
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Peroxidase inhibitors
Iodide pump inhibitors |