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Chemical Compound Review

ADOSTEROL     (3S,6S,8S,9S,13R,14S,17R)-6- (iodomethyl)...

Synonyms: NP-59, SureCN10006975, AC1L25V7, 55623-03-5, 6-Iodomethylnorcholesterol
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Disease relevance of ADOSTEROL

  • In the presence of normal biochemistry, a concordant NP-59 imaging pattern is diagnostic of a nonhypersecretory benign adrenal adenoma and requires no immediate therapeutic intervention [1].
  • The adrenal gland uptake of 131I-6-beta-iodomethyl-19-norcholesterol (NP-59) was calculated using a semioperator-independent computer algorithm in 17 patients with Cushing's syndrome (CS) [2].
  • NP-59 adrenal uptake values were 0.20 +/- 0.02%/dose (range, 0.03-0.72), 0.28 +/- 0.04% (range, 0.10-0.65), and 0.14 +/- 0.02%/dose (range, 0.08-0.30) in AA, BAH, and essential hypertension, respectively [3].
  • The accuracy of NP-59 scintigraphy ranged from 71% in primary aldosteronism and 75% in euadrenal tumors, to 100% for Cushing's syndrome and hyperandrogenism [4].
  • With NP-59, nine of ten tumors were correctly located (90%) , correct distinction between tumor and hyperplasia was possible in 90%, and a locating DS scan was specific for tumor in 90% [5].

High impact information on ADOSTEROL

  • Bilateral, symmetric accumulation of NP-59 was seen in 17 patients, in whom the adrenal masses were shown to be metastatic malignancies in 2, and adenomas in 6 (the lesions in these cases being 2 cm or less in diameter), and lesions not truly involving the adrenal in the rest (periadrenal metastases in 4 and pseudoadrenal masses in 5) [6].
  • The elevation of adrenal cortical NP-59 uptake in PCO was quantitatively similar to that in women with ACTH-dependent Cushing's syndrome (0.64 +/- 0.11%; P greater than 0.1) [7].
  • A significant correlation was found between adrenal gland uptake of NP-59 and urinary aldosterone excretion in AA (r = 0.93; P less than 0.001) and BAH (r = 0.6; P less than 0.01) patients [3].
  • These data confirm that adrenal gland accumulation of NP-59 while on dexamethasone suppression can be used to characterize abnormal zona glomerulosa function in PA, in addition to localizing AA and differentiating AA from BAH [3].
  • Adrenocortical SPECT using iodine-131 NP-59 [8].

Chemical compound and disease context of ADOSTEROL


Biological context of ADOSTEROL

  • However, more than in most nuclear medicine studies, NP-59 imaging requires well-defined indications to be met for it to be efficacious, including the fulfillment of clear clinical, biochemical, and radiographic criteria [4].
  • Enterohepatic circulation and distribution of 131I-6 beta-iodomethyl-19-norcholesterol (NP-59) [13].

Anatomical context of ADOSTEROL

  • The mean adrenal gland uptake (percentage of administered dose) of NP-59 was 0.74 +/- 0.18% (range, 0.21-2.02%) in CS and was significantly higher than that of normal subjects (0.33 +/- 0.02%) [2].
  • The remaining adrenal cortex may be anatomically abnormal after unilateral adrenalectomy and demonstrate compensatory, increased NP-59 uptake in the presence of overall, normal adrenocortical function [14].
  • External scanning with NP-59 localized steroid production to the testes, and bilateral orchiectomy was performed [15].
  • Scanning the gonads with NP-59 may be a helpful imaging procedure in localizing possible sites for exploratory surgery in certain cases of gonadal neoplasia [16].
  • Imaging of the cortex is achieved by iodine-131-labeled iodomethyl nor-cholesterol (NP-59), while adrenal medulla imaging can be successfully accomplished by 131I-metaiodobenzylguanidine (MIBG), which localizes in the adrenergic nerve terminal with norepinephrine [17].

Associations of ADOSTEROL with other chemical compounds

  • NP-59 concentrates in steroid hormone synthesizing tissues, enabling scintigraphic localization and characterization of endocrine dysfunction in the adrenal cortex and ovary [4].
  • The chemical stabilities of the adrenal-scanning agents, 6beta-iodo-methyl-19-norcholest-5(10)-en-3beta-ol (6-iodomethylnorcholesterol) and 19-iodocholest-5-en-3beta-ol (19-iodocholesterol), and several of their derivatives were examined by 13C nuclear magnetic resonance [18].
  • In the course of recovery from o,p' DDD damage, the ability of the adrenal gland to take up NP-59 may be restored before the return of its biosynthetic and secretory functions [19].

Gene context of ADOSTEROL

  • This is the case of a large 2 x 1.5 cm adrenal tumor demonstrated on CT scan that was proven biochemically and surgically to be an aldosteronoma and that did not concentrate 6-beta(131I)-iodo-methyl-19-norcholesterol (NP-59) [20].

Analytical, diagnostic and therapeutic context of ADOSTEROL

  • Conversely, patients with discordant patterns of NP-59 scintigraphy have lesions that carry a significant risk for malignancy, and the pursuit of a tissue diagnosis is indicated, usually by means of FNA [1].
  • In 76 patients, NP-59 uptake lateralized to the abnormal adrenal seen on CT scans (concordant imaging), and in all of these patients, a diagnosis of adenoma was made by needle-aspiration biopsy, adrenalectomy, or extended follow-up with repeat CT scans that were unchanged at 6 months or later [6].
  • One-time evaluation with fine-needle aspiration (FNA) and combinations of chemical-shift MRI, noncontrast CT, 131I-6beta-iodomethylnorcholesterol (NP-59) scintigraphy, with or without FNA, in a hypothetical cohort of 1000 patients with incidentally discovered unilateral, nonhypersecretory adrenal masses [21].
  • Adrenal scintigraphy was performed using 1 mCi of NP-59 injected intravenously, with gamma camera imaging 5-7 days later [22].
  • Both adrenocortical scintigraphy with [131]6beta-iodomethylnorcholesterol (NP-59) and adrenomedullary imaging with 131I or 123I-labelled metaiodobenzylguanidine (MIBG) as function-dependant imaging techniques provide functional metabolic information for lesion characterization [23].


  1. Incidentally discovered adrenal masses. Kloos, R.T., Gross, M.D., Francis, I.R., Korobkin, M., Shapiro, B. Endocr. Rev. (1995) [Pubmed]
  2. The relationship of adrenal iodomethylnorcholesterol uptake to indices of adrenal cortical function in Cushing's syndrome. Gross, M.D., Valk, T.W., Freitas, J.E., Swanson, D.P., Schteingart, D.E., Beierwaltes, W.H. J. Clin. Endocrinol. Metab. (1981) [Pubmed]
  3. The relationship of adrenal gland iodomethylnorcholesterol uptake to zona glomerulosa function in primary aldosteronism. Gross, M.D., Shapiro, B., Grekin, R.J., Meyers, L., Swanson, D.P., Beierwaltes, W.H. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  4. Diagnostic accuracy and pitfalls of [iodine-131]6-beta-iodomethyl-19-norcholesterol (NP-59) imaging. Kazerooni, E.A., Sisson, J.C., Shapiro, B., Gross, M.D., Driedger, A., Hurwitz, G.A., Mattar, A.G., Petry, N.A. J. Nucl. Med. (1990) [Pubmed]
  5. Adrenal imaging with iodomethyl-norcholesterol (I-131) in primary aldosteronism. Freitas, J.E., Grekin, R.J., Thrall, J.H., Gross, M.D., Swanson, D.P., Beierwaltes, W.H. J. Nucl. Med. (1979) [Pubmed]
  6. Distinguishing benign from malignant euadrenal masses. Gross, M.D., Shapiro, B., Bouffard, J.A., Glazer, G.M., Francis, I.R., Wilton, G.P., Khafagi, F., Sonda, L.P. Ann. Intern. Med. (1988) [Pubmed]
  7. Scintigraphic evidence of adrenal cortical dysfunction in the polycystic ovary syndrome. Gross, M.D., Wortsman, J., Shapiro, B., Meyers, L.C., Woodbury, M.C., Ayers, J.W. J. Clin. Endocrinol. Metab. (1986) [Pubmed]
  8. Adrenocortical SPECT using iodine-131 NP-59. Hwang, I., Balingit, A.G., Georgitis, W.J., Sisson, J.C., Shapiro, B. J. Nucl. Med. (1998) [Pubmed]
  9. The relationship of serum lipids to adrenal-gland uptake of 6 beta-[131I]iodomethyl-19-norcholesterol in Cushing's syndrome. Valk, T.W., Gross, M.D., Freitas, J.E., Swanson, D.P., Schteingart, D.E., Beierwaltes, W.H. J. Nucl. Med. (1980) [Pubmed]
  10. Scintigraphic studies in adrenal hypertension. Gross, M.D., Shapiro, B. Seminars in nuclear medicine. (1989) [Pubmed]
  11. Visualization of adrenocortical carcinoma lung metastases with iodine-131 labeled 6B-iodomethylnorcholesterol (NP-59). Chow, C.K., Ziessman, H.A., Earll, J.M. Clinical nuclear medicine. (1987) [Pubmed]
  12. The relationship of I-131 6 beta-iodomethyl-19-norcholesterol (NP-59) adrenal cortical uptake to indices of androgen secretion in women with hyperandrogenism. Gross, M.D., Shapiro, B., Freitas, J.E., Ayers, J., Swanson, D.P., Woodbury, M.C., Schteingart, D.E., Beierwaltes, W.H. Clinical nuclear medicine. (1984) [Pubmed]
  13. Enterohepatic circulation and distribution of 131I-6 beta-iodomethyl-19-norcholesterol (NP-59). Lynn, M.D., Gross, M.D., Shapiro, B. Nuclear medicine communications. (1986) [Pubmed]
  14. Clinical significance of the solitary functioning adrenal gland. Gross, M.D., Shapiro, B., Freitas, J.E., Meyers, L., Francis, I., Thompson, N.W., Wortsman, J. J. Nucl. Med. (1991) [Pubmed]
  15. Massive hyperplasia of testicular adrenal rests in a patient with Nelson's syndrome. Johnson, R.E., Scheithauer, B. Am. J. Clin. Pathol. (1982) [Pubmed]
  16. Demonstration of steroid-producing gonadal tumors by external scanning with the use of NP-59. Carpenter, P.C., Wahner, H.W., Salassa, R.M., Duick, D.S. Mayo Clin. Proc. (1979) [Pubmed]
  17. Role of adrenal imaging in surgical management. Lamki, L.M., Haynie, T.P. Journal of surgical oncology. (1990) [Pubmed]
  18. Chemical and radiochemical stability of the adrenal-scanning agents, 6beta-iodomethyl-19-norcholest-5(10-en-3beta-ol and 19-iodocholest-5-en-3beta-ol. Scott, K.N., Mareci, T.H., Couch, M.W., Williams, C.M. Steroids (1977) [Pubmed]
  19. Positive iodine-131 6 beta-iodomethyl-19-norcholesterol (NP-59) adrenal images can precede return of adrenocortical function after o,p' DDD treatment. Sparagana, M., Ackerman, L. Clinical nuclear medicine. (1988) [Pubmed]
  20. Case report: failure of adrenal scintigraphy to exhibit 131I cholesterol uptake in a CT-demonstrated, surgically proven aldosteronoma. Salam, Z., Lubbos, H., Martinez, C., Mozley, P.D., Miller, J.L., Rose, L.I. Am. J. Med. Sci. (1996) [Pubmed]
  21. Diagnostic evaluation of the adrenal incidentaloma: decision and cost-effectiveness analyses. Dwamena, B.A., Kloos, R.T., Fendrick, A.M., Gross, M.D., Francis, I.R., Korobkin, M.T., Shapiro, B. J. Nucl. Med. (1998) [Pubmed]
  22. Scintigraphy of incidentally discovered bilateral adrenal masses. Gross, M.D., Shapiro, B., Francis, I.R., Bree, R.L., Korobkin, M., McLeod, M.K., Thompson, N.W., Sanfield, J.A. European journal of nuclear medicine. (1995) [Pubmed]
  23. Scintigraphic imaging of the adrenal glands. Kurtaran, A., Traub, T., Shapiro, B. European journal of radiology. (2002) [Pubmed]
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