PHCH 2202: Steroid and Endocrine Products

Comprehensive vocabulary flashcards covering steroid and endocrine products, biosynthesis, commercial extraction pathways, adrenocorticoids, sex hormones, and hormone classifications based on PHCH 2202 Lesson 10.

Hormones

Chemical messengers secreted directly by the endocrine or ductless glands of animals to regulate physiological processes.

Victor Horsley (1891)

Demonstrated that patients presenting with myxedema and cretinism benefited clinically from the oral administration of animal thyroid glands.

Hormone Therapy

Therapeutic practice involving the administration of purified, active endocrine principles or their synthetic analogs.

Organotherapy

The medical use of whole animal endocrine glands or crude preparations derived from them rather than isolated active principles.

Prednisone

A synthetic steroid drug that chemically mimics the physiological glucocorticoid action of cortisone.

Steroid Hormones (Circulation Properties)

Lipid-soluble, water-insoluble hormones that are bound to transport proteins in the blood, allowing them to remain in circulation longer than peptide hormones.

Steroid Nucleus

A cyclopentanoperhydrophenanthrene (CPPP) framework consisting of four fused rings (A, B, C, and D) existing in $\alpha$ and $\beta$ stereochemical configurations.

Isopentenyl pyrophosphate

The fundamental biosynthetic precursor molecule from which steroids are formed via pathways involving squalene and lanosterol.

Sterols

Solid, high-molecular-weight steroid alcohols containing $27$ to $29$ carbon atoms; first isolated from human gallstones and also sourced from algae, fungi, and actinomyces.

Ergosterol

A $28$-carbon sterol that is the principal sterol of fungi; acts as provitamin $D_2$ and yields ergocalciferol (vitamin $D_2$) upon ultraviolet light irradiation.

7-Dehydrocholesterol

A provitamin (provitamin $D_3$) that undergoes photolysis upon ultraviolet light irradiation to produce cholecalciferol (vitamin $D_3$).

$\beta$-Sitosterol

A $29$-carbon compound that is the most common plant sterol, derived from plant oils such as corn and cottonseed oil.

Stigmasterol

A plant sterol closely related to $\beta$-sitosterol, isolated from Calabar bean and soybean oil, and used as a precursor in steroid drug synthesis.

Sitosterol (Drug)

An anti-hypercholesterolemic agent used clinically for the treatment and management of atherosclerosis.

Bile Acids

$C_{24}$ steroid carboxylic acids derived from cholesterol, stored in the gallbladder and secreted into the duodenum as conjugates to emulsify dietary lipids.

Ox Bile Extract

A product prepared by evaporating fresh ox bile, precipitating albuminous matter with alcohol, and drying at under $80\,^\circ\text{C}$; contains sodium salts of glycocholic and taurocholic acids equivalent to not less than $45\%$ cholic acid, used primarily as a laxative.

Primary Bile Acids

Bile acids synthesized directly by hepatocytes in the liver from cholesterol, consisting of cholic acid and chenodesoxycholic acid.

Intestinal Bile Acids

Secondary bile acids produced by bacterial action in the intestine, specifically deoxycholic acid (formed from cholic acid) and lithocholic acid (formed from chenodesoxycholic acid).

Chenodesoxycholic Acid (Chenodiol)

A primary bile acid that suppresses the hepatic synthesis of cholesterol and cholic acid, leading to biliary cholesterol desaturation and the dissolution of radiolucent cholesterol gallstones.

Sex Hormones

Steroid hormones produced primarily in the gonads that regulate the development, growth, maintenance, and functions of the reproductive tract and accessory sex organs.

Mineralocorticoids

Adrenocorticoid hormones produced in the outer cortex of the adrenal glands (chiefly aldosterone and desoxycorticosterone) that regulate electrolyte excretion, promoting sodium retention and potassium loss.

Glucocorticoids

Adrenal cortex hormones (such as cortisol and cortisone) that govern intermediary metabolism, notably carbohydrate and protein metabolism.

Russell Marker (1944)

Pioneered the chemical degradation method to convert diosgenin (a sapogenin found in the Mexican yam, Dioscorea spp.) into progesterone.

Rhizopus arrhizus (1952)

A fungus utilized to introduce an $11\alpha$-hydroxyl group microbiologically, dramatically reducing the chemical steps needed to synthesize cortisone and progesterone from plant steroids.

Cortesolone

A steroid intermediate prepared chemically from diosgenin that is hydroxylated to cortisol by Streptomyces fradiae or Cunninghamella blakesleeana.

Corynebacterium simplex and Fusarium spp.

Microorganisms employed in steroid production to dehydrogenate cortisol or cortisone into prednisone or prednisolone.

Addison's Disease

Chronic adrenocortical insufficiency characterized by bronze skin pigmentation, gonadal degeneration, increased capillary permeability, insulin sensitivity, weight loss, sodium wasting, and potassium retention.

Desoxycorticosterone

21-Hydroxypregn-4-ene-3,20-dione; a potent mineralocorticoid esterified with acetic acid at C-21, administered via buccal, intramuscular, or subcutaneous routes alongside glucocorticoids for Addison's disease.

Cortisone

17,21-Dihydroxypregn-4-ene-3,11,20-trione; a glucocorticoid used in arthritis, allergic disorders, and Addison's disease, commonly formulated as an acetate ester for oral, topical, or intramuscular use.

Cortisol (Hydrocortisone)

11$\beta$,17$\alpha$,21-Trihydroxypregn-4-ene-3,20-dione; the principal glucocorticoid secreted by the adrenal cortex, formulated as an acetate ester or water-soluble sodium phosphate/succinate salts for intravenous administration.

Eunuchoidism

A hypogonadal condition marked by inadequate development of the testes due to pituitary dysfunction, infection, or other systemic disease.

Testosterone

17$\beta$-Hydroxyandrost-4-ene-3-one; the primary endogenous male androgen, modified synthetically with a methyl substituent at C-17 to confer metabolic stability for androgenic therapy.

A-ring Aromaticity (Estrogens)

The distinctive structural hallmark of all estrogen steroids compared to other steroid hormones, containing a phenolic hydroxyl group at C-3 and no C-10 angular methyl group.

Estriol

The principal oxidative metabolic excretion product of estradiol and estrone; considered the best pure, naturally occurring estrogen for oral administration.

Conjugated Estrogens

A mixture containing the sodium salts of sulfate esters of estrogenic substances (principally estrone and equilin) obtained from the urine of pregnant mares.

Equilin

Estra-1,3,5(10),7-tetraen-3-ol-17-one; a distinctive unsaturated estrogen component found in conjugated estrogen preparations derived from pregnant mare urine.

Diethylstilbestrol (DES)

A synthetic nonsteroidal stilbene derivative with oral estrogenic potency, rapidly absorbed and slowly eliminated, but frequently associated with nausea and vomiting.

Progesterone

Pregn-4-ene-3,20-dione; the natural corpus luteum hormone essential for maintaining human pregnancy during the first half of the term; administered parenterally, buccally, or via intrauterine devices (IUD).

Synthetic Progestins

Analogs such as hydroxyprogesterone caproate, medroxyprogesterone acetate, and norethindrone used in contraception and for treating amenorrhea, dysmenorrhea, or endometriosis.

Amino Acid-Derived Hormones

Small signaling molecules synthesized from the amino acids tyrosine or tryptophan whose chemical nomenclature characteristically terminates with the suffix "-ine".

Epinephrine and Norepinephrine

Tyrosine-derived catecholamine hormones synthesized and secreted by the medulla of the adrenal glands in response to stress.

Melatonin

A tryptophan-derived amine hormone synthesized and secreted by the pineal gland in the brain to regulate sleep-wake cycles and circadian rhythms.

Peptide Hormones

Water-soluble, lipid-insoluble hormones composed of amino acid chains or glycoproteins that signal via cell-surface membrane receptors because they cannot permeate lipid bilayers.