Iodocholesterol

Last updated
Iodocholesterol
19-Iodocholesterol.png
Clinical data
Other namesIodocholesterol; 19-Iodocholesterol; Iodocholesterol (131I); 19-Iodocholest-5-en-3β-ol
ATC code
Identifiers
  • (3S,8S,9S,10S,13R,14S,17R)-10-(iodomethyl)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.048.618 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H45IO
Molar mass 512.560 g·mol−1
3D model (JSmol)
  • CC(C)CCC[C@@H](C)[C@H]3CC[C@H]2[C@@H]4C\C=C1\C[C@@H](O)CC[C@]1(CI)[C@H]4CC[C@@]23C
  • InChI=1S/C27H45IO/c1-18(2)6-5-7-19(3)23-10-11-24-22-9-8-20-16-21(29)12-15-27(20,17-28)25(22)13-14-26(23,24)4/h8,18-19,21-25,29H,5-7,9-17H2,1-4H3/t19-,21+,22+,23-,24+,25+,26-,27-/m1/s1 Yes check.svgY
  • Key:FIOAEFCJGZJUPW-FTLVODPJSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Iodocholesterol, or 19-iodocholesterol, also as iodocholesterol (131I) (INN) and NP-59, is a derivative of cholesterol with an iodine atom in the C19 position and a radiopharmaceutical. [1] [2] When the iodine atom is a radioactive isotope (iodine-125 or iodine-131), it is used as an adrenal cortex radiotracer in the diagnosis of patients suspected of having Cushing's syndrome, hyperaldosteronism, [3] pheochromocytoma, and adrenal remnants following total adrenalectomy. [1] [2]

Related Research Articles

<span class="mw-page-title-main">Astatine</span> Chemical element, symbol At and atomic number 85

Astatine is a chemical element with the symbol At and atomic number 85. It is the rarest naturally occurring element in the Earth's crust, occurring only as the decay product of various heavier elements. All of astatine's isotopes are short-lived; the most stable is astatine-210, with a half-life of 8.1 hours. Consequently, a solid sample of the element has never been seen, because any macroscopic specimen would be immediately vaporized by the heat of its radioactivity.

<span class="mw-page-title-main">Halogen</span> Group of chemical elements

The halogens are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group (XVII) or group (VII).

<span class="mw-page-title-main">Iodine</span> Chemical element, symbol I and atomic number 53

Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at 114 °C (237 °F), and boils to a violet gas at 184 °C (363 °F). The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek Ιώδης 'violet-coloured'.

<span class="mw-page-title-main">Cushing's syndrome</span> Symptoms from excessive exposure to glucocorticoids such as cortisol

Cushing's syndrome is a collection of signs and symptoms due to prolonged exposure to glucocorticoids such as cortisol. Signs and symptoms may include high blood pressure, abdominal obesity but with thin arms and legs, reddish stretch marks, a round red face due to facial plethora, a fat lump between the shoulders, weak muscles, weak bones, acne, and fragile skin that heals poorly. Women may have more hair and irregular menstruation. Occasionally there may be changes in mood, headaches, and a chronic feeling of tiredness.

<span class="mw-page-title-main">Nonmetal</span> Chemical element that mostly lacks the characteristics of a metal

A nonmetal is a chemical element that mostly lacks metallic properties. There is a general consensus on seventeen elements as nonmetals. Some authors recognize more or fewer elements as nonmetals depending on the properties they consider most representative of metallic or nonmetallic character. Some borderline elements further complicate the situation.

<span class="mw-page-title-main">Addison's disease</span> Endocrine disorder

Addison's disease, also known as primary adrenal insufficiency, is a rare long-term endocrine disorder characterized by inadequate production of the steroid hormones cortisol and aldosterone by the two outer layers of the cells of the adrenal glands, causing adrenal insufficiency. Symptoms generally come on slowly and insidiously and may include abdominal pain and gastrointestinal abnormalities, weakness, and weight loss. Darkening of the skin in certain areas may also occur. Under certain circumstances, an adrenal crisis may occur with low blood pressure, vomiting, lower back pain, and loss of consciousness. Mood changes may also occur. Rapid onset of symptoms indicates acute adrenal failure, which is a clinical emergency. An adrenal crisis can be triggered by stress, such as from an injury, surgery, or infection.

<span class="mw-page-title-main">Primary aldosteronism</span> Medical condition

Primary aldosteronism (PA), also known as primary hyperaldosteronism or Conn's syndrome, refers to the excess production of the hormone aldosterone from the adrenal glands, resulting in low renin levels and high blood pressure. This abnormality is caused by hyperplasia or tumors. Many experience fatigue, potassium deficiency and high blood pressure which may cause poor vision, confusion or headaches. Symptoms may also include: muscular aches and weakness, muscle spasms, low back and flank pain from the kidneys, trembling, tingling sensations, dizziness/vertigo, nocturia and excessive urination. Complications include cardiovascular disease such as stroke, myocardial infarction, kidney failure and abnormal heart rhythms.

<span class="mw-page-title-main">Hydrocortisone</span> Glucocorticoid and Mineralocorticoid hormone Cortisol supplied as a medication

Hydrocortisone is the name for the hormone cortisol when supplied as a medication. Uses include conditions such as adrenocortical insufficiency, adrenogenital syndrome, high blood calcium, thyroiditis, rheumatoid arthritis, dermatitis, asthma, and COPD. It is the treatment of choice for adrenocortical insufficiency. It can be given by mouth, topically, or by injection. Stopping treatment after long-term use should be done slowly.

<span class="mw-page-title-main">Fludrocortisone</span> Mineralocorticoid Hormone used as a Medicine

Fludrocortisone, sold under the brand name Florinef, among others, is a corticosteroid used to treat adrenogenital syndrome, postural hypotension, and adrenal insufficiency. In adrenal insufficiency, it is generally taken together with hydrocortisone. Fludrocortisone is taken by mouth and is most commonly used in its acetate form.

In chemistry, an interhalogen compound is a molecule which contains two or more different halogen atoms and no atoms of elements from any other group.

<span class="mw-page-title-main">Sodium thiosulfate</span> Chemical compound

Sodium thiosulfate is an inorganic compound with the formula Na2S2O3·xH2O, where x indicates the number of water molecules in the compound. Typically it is available as the white or colorless pentahydrate, Na2S2O3·5H2O. The solid is an efflorescent crystalline substance that dissolves well in water.

<span class="mw-page-title-main">17α-Hydroxyprogesterone</span> Chemical compound

17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.

<span class="mw-page-title-main">Multiple endocrine neoplasia type 1</span> Medical condition

Multiple endocrine neoplasia type 1 (MEN-1) is one of a group of disorders, the multiple endocrine neoplasias, that affect the endocrine system through development of neoplastic lesions in pituitary, parathyroid gland and pancreas. Individuals suffering from this disorder are prone to developing multiple endocrine and nonendocrine tumors. It was first described by Paul Wermer in 1954.

Iodine-125 (125I) is a radioisotope of iodine which has uses in biological assays, nuclear medicine imaging and in radiation therapy as brachytherapy to treat a number of conditions, including prostate cancer, uveal melanomas, and brain tumors. It is the second longest-lived radioisotope of iodine, after iodine-129.

<span class="mw-page-title-main">Mitotane</span> Chemical compound

Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a derivative of the early insecticide DDT and an isomer of p,p'-DDDTooltip dichlorodiphenyldichloroethane (4,4'-dichlorodiphenyldichloroethane) and is also known as 2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD).

<span class="mw-page-title-main">Adrenal crisis</span> Medical condition

Adrenal crisis is a potentially life-threatening medical condition requiring immediate emergency treatment. It is a constellation of symptoms that indicate severe adrenal insufficiency. This may be the result of either previously undiagnosed or untreated Addison's disease, a disease process that suddenly affects adrenal function, suddenly stopping intake of glucocorticoids or an intercurrent problem in someone known to have Addison's disease, congenital adrenal hyperplasia (CAH), or another form of primary adrenal insufficiency.

<span class="mw-page-title-main">Thyroid hormones</span> Hormones produced by the thyroid gland

Thyroid hormones are any hormones produced and released by the thyroid gland, namely triiodothyronine (T3) and thyroxine (T4). They are tyrosine-based hormones that are primarily responsible for regulation of metabolism. T3 and T4 are partially composed of iodine, derived from food. A deficiency of iodine leads to decreased production of T3 and T4, enlarges the thyroid tissue and will cause the disease known as simple goitre.

<span class="mw-page-title-main">Alsactide</span> Chemical compound

Alsactide (INN) (brand name Synchrodyn 1-17 or simply Synchrodyn, former development code name Hoechst 433), also known as alisactide, is a synthetic peptide and analogue of adrenocorticotropic hormone (ACTH) which is used in Italy as a diagnostic agent in kidney function for adrenal insufficiency. Like ACTH, alsactide is thought to act as a non-selective agonist of the melanocortin receptors, including the ACTH receptor (MC2R). However, it appears to show a different profile of receptor selectivity relative to ACTH, as it apparently demonstrated no evidence of inhibition of endogenous ACTH in Addison's disease patients.

<span class="mw-page-title-main">Prothipendyl</span> Chemical compound

Prothipendyl, also known as azapromazine or phrenotropin, is an anxiolytic, antiemetic, and antihistamine of the azaphenothiazine group which is marketed in Europe and is used to treat anxiety and agitation in psychotic syndromes. It differs from promazine only by the replacement of one carbon atom with a nitrogen atom in the tricyclic ring system. Prothipendyl is said to not possess antipsychotic effects, and in accordance, appears to be a weaker dopamine receptor antagonist than other phenothiazines.

<span class="mw-page-title-main">Delmadinone acetate</span> Chemical compound

Delmadinone acetate (DMA), sold under the brand name Tardak among others, is a progestin and antiandrogen which is used in veterinary medicine to treat androgen-dependent conditions such as benign prostatic hyperplasia. It must be used with care as it has the potential to cause adrenal insufficiency via inhibition of adrenocorticotropic hormone (ACTH) secretion from the pituitary gland. DMA is the C17α acetate ester of delmadinone, which, in contrast to DMA, was never marketed for medical use.

References

  1. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 692–. ISBN   978-1-4757-2085-3.
  2. 1 2 Clark OH, American Cancer Society (2003). Endocrine Tumors. PMPH-USA. pp. 124–. ISBN   978-1-55009-134-2.
  3. Fischer M, Rosenbach EA, Glaser B, Stokar J (2023-02-24). "NP-59 Scintigraphy for Primary Aldosteronism Lateralization in a Patient With Polycystic Kidney Disease". AACE Clinical Case Reports. 9 (3): 97–98. doi:10.1016/j.aace.2023.02.006. PMC   10213608 . PMID   37251975. S2CID   257212197.