Synthesis of 16α‐ethyl‐21‐hydroxy‐19‐norpregn‐4‐ene‐3,20‐dione (Org 2058)

Zeelen, F. J.; Broek, Albert

doi:10.1002/recl.19851040907

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…We began our development of PgR PET probes knowing that progesterone itself is not a very high-affinity ligand for PgR (K d = 8 nM) [ 6 , 69 ]. Hence, we focused on two much higher affinity ligands that had been developed by pharmaceutical companies, the Roussel compound R5020 (K d = 1 nM) [ 70 ] and the Organon compound ORG2058 (K d = 0.5 nM) [ 71 ] ( Figure 7 ). As will be noted below, to some degree, structural changes that boost the binding affinity of androgens for AR also worked for the progestins: ORG2058 is a 19-nor analog of progesterone with an additional 16α-ethyl group, and R5020 has an extended A,B-ring dienone with flanking methyl groups at the 17α and 21 positions [ 6 , 69 ].…”

Section: Ffnp a Pet Imaging Agent For Progesterone Receptors In Bmentioning

confidence: 99%

PET Imaging Agents (FES, FFNP, and FDHT) for Estrogen, Androgen, and Progesterone Receptors to Improve Management of Breast and Prostate Cancers by Functional Imaging

Katzenellenbogen

2020

Cancers

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Many breast and prostate cancers are driven by the action of steroid hormones on their cognate receptors in primary tumors and in metastases, and endocrine therapies that inhibit hormone production or block the action of these receptors provide clinical benefit to many but not all of these cancer patients. Because it is difficult to predict which individuals will be helped by endocrine therapies and which will not, positron emission tomography (PET) imaging of estrogen receptor (ER) and progesterone receptor (PgR) in breast cancer, and androgen receptor (AR) in prostate cancer can provide useful, often functional, information on the likelihood of endocrine therapy response in individual patients. This review covers our development of three PET imaging agents, 16α-[18F]fluoroestradiol (FES) for ER, 21-[18F]fluoro-furanyl-nor-progesterone (FFNP) for PgR, and 16β-[18F]fluoro-5α-dihydrotestosterone (FDHT) for AR, and the evolution of their clinical use. For these agents, the pathway from concept through development tracks with an emerging understanding of critical performance criteria that is needed for successful PET imaging of these low-abundance receptor targets. Progress in the ongoing evaluation of what they can add to the clinical management of breast and prostate cancers reflects our increased understanding of these diseases and of optimal strategies for predicting the success of clinical endocrine therapies.

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Section: Ffnp a Pet Imaging Agent For Progesterone Receptors In Bmentioning

confidence: 99%

PET Imaging Agents (FES, FFNP, and FDHT) for Estrogen, Androgen, and Progesterone Receptors to Improve Management of Breast and Prostate Cancers by Functional Imaging

Katzenellenbogen

2020

Cancers

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“…This is also illustrated by the two steroids Org2058 and R5020 (promegestone), currently used for PR radioimmunoassay (see Fig. 17); their affinity for PR is only 5 to 15 times higher than that of progesterone itself [175,[232][233][234][235].…”

Section: Influence Of Progesterone Structural Substitutions On Pr Binmentioning

confidence: 99%

“…(17). [ 18 F]FENP is a fluoro substituted analogue of the potent high affinity progestin ORG2058 49 (16 -ethyl-21-hydroxy-19-nor pregn-4-ene-3,10-dione) in which the 21-hydroxyl group is replaced by a radiofluorine atom [234]. [ 18 F]FENP is a potent progestin, possessing a high binding affinity (60 times that of progesterone) for the progesterone receptor (700% relative to R5020=100%) [304].…”

Section: -[ 18 F]fluoro-16 -Ethyl-19-norprogesterone ([ 18 F]fenp)mentioning

confidence: 99%

Steroid Receptor Ligands for Breast Cancer Targeting: An Insight into Their Potential Role As Pet Imaging Agents

Oliveira¹,

Neto²,

Morais³

et al. 2012

CMC

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The design and development of radiolabelled steroid derivatives has been an important area of research due to their wellknown value in breast cancer targeting. The estrogen receptor (ER) and progesterone receptor (PR) are important biomarkers in the diagnosis, prognosis and follow-up of the therapeutic response of breast tumours. Thus, several radioligands based on estrogens and progestins have been proposed for targeted functional ER imaging. The aim of this review is to survey and analyze the developments in this field, which have led to the design of a number of PET steroid-based imaging agents, a few of which seem to be promising as radiopharmaceuticals for detection of ER-positive breast tumours.

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ChemInform Abstract: Synthesis of 16a‐Ethyl‐2l‐hydroxy‐19‐norpregn‐4‐ene‐3,20‐dione(Org 2058) (Synthese und Untersuchung der biologischen Aktivität der Titelverbindung (X)).

Zeelen¹,

Broek²

1986

Chemischer Informationsdienst

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Synthesis of 16α‐ethyl‐21‐hydroxy‐19‐norpregn‐4‐ene‐3,20‐dione (Org 2058)

Abstract: Abstract.norprogesterone derivatives show interesting progestational activities.The syntheses of the title compound and of some ester derivatives are described. These

Cited by 9 publications

References 21 publications

PET Imaging Agents (FES, FFNP, and FDHT) for Estrogen, Androgen, and Progesterone Receptors to Improve Management of Breast and Prostate Cancers by Functional Imaging

PET Imaging Agents (FES, FFNP, and FDHT) for Estrogen, Androgen, and Progesterone Receptors to Improve Management of Breast and Prostate Cancers by Functional Imaging

Steroid Receptor Ligands for Breast Cancer Targeting: An Insight into Their Potential Role As Pet Imaging Agents

ChemInform Abstract: Synthesis of 16a‐Ethyl‐2l‐hydroxy‐19‐norpregn‐4‐ene‐3,20‐dione(Org 2058) (Synthese und Untersuchung der biologischen Aktivität der Titelverbindung (X)).

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