LONAPRISAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H29F5O3
Molecular Weight	508.5201
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(C(F)(F)C(F)(F)F)[C@@]1(C)C[C@H](C3=CC=C(C=C3)C(C)=O)C4=C5CCC(=O)C=C5CC[C@@]24[H]

InChI

InChIKey=VHZPUDNSVGRVMB-RXDLHWJPSA-N

InChI=1S/C28H29F5O3/c1-15(34)16-3-5-17(6-4-16)22-14-25(2)23(11-12-26(25,36)27(29,30)28(31,32)33)21-9-7-18-13-19(35)8-10-20(18)24(21)22/h3-6,13,21-23,36H,7-12,14H2,1-2H3/t21-,22+,23-,25-,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C28H29F5O3
Molecular Weight	508.5201
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/lonaprisan | https://adisinsight.springer.com/drugs/800017206 | https://www.ncbi.nlm.nih.gov/pubmed/23788750 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/18589542843c573d4bddaac8645fb730.html

Lonaprisan is an orally bioavailable pentafluoroethyl derivative of a mifepristone-related steroid with antiprogestagenic activity. Lonaprisan is a pure, highly receptor-selective progesterone receptor (PR) antagonist (both PR isoforms PR-A and PR-B); binding of this agent to PRs inhibits PR activation and the associated proliferative effects. Lonaprisan showed limited efficacy as second-line endocrine therapy in postmenopausal women with PR-positive metastatic breast cancer. Lonaprisan had been in phase II clinical trials by Bayer for the treatment of breast cancer and dysmenorrhea. However, this research has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Reversible suppression of menstruation with progesterone antagonists in rhesus macaques.	2001 Aug	11473944
Antiprogestin-releasing intrauterine devices: a novel approach to endometrial contraception.	2007 Jun	17531599
Intrauterine release of progesterone antagonist ZK230211 is feasible and results in novel endometrial effects: a pilot study.	2007 Sep	17636280
Global gene expression profiling of progesterone receptor modulators in T47D cells provides a new classification system.	2009 Jan	19130882
Progesterone receptor agonists and antagonists as anticancer agents.	2010 Jun	20370704
In vitro characterization of ZK 230211--A type III progesterone receptor antagonist with enhanced antiproliferative properties.	2010 Mar	20043998
The antiprogestin Lonaprisan inhibits breast cancer cell proliferation by inducing p21 expression.	2011 Feb 10	21138753
Progesterone reverts LPS-reduced FAAH activity in murine peripheral blood mononuclear cells by a receptor-mediated fashion.	2013 Dec 5	23906535
Randomized phase II study of lonaprisan as second-line therapy for progesterone receptor-positive breast cancer.	2013 Oct	23788750
Progesterone modulates the LPS-induced nitric oxide production by a progesterone-receptor independent mechanism.	2015 Dec 15	26548622
Acute exposure to progesterone attenuates cardiac contraction by modifying myofilament calcium sensitivity in the female mouse heart.	2017 Jan 1	27793852
Discovery of Vilaprisan (BAY 1002670): A Highly Potent and Selective Progesterone Receptor Modulator Optimized for Gynecologic Therapies.	2018 Nov 6	30407750

Patents

Sample Use Guides

In Vivo Use Guide

Once-daily 25 mg or 100 mg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:14:04 UTC 2023` Edited by `admin` on `Fri Dec 15 16:14:04 UTC 2023`
Record UNII	F5Z5EL4D26
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LONAPRISAN

Official Name

English

lonaprisan [INN]

Common Name

English

ZK-230211

Code

English

BAY86-5044

Code

English

11β-(4-Acetylphenyl)-20,20,21,21,21-pentafluoro-17-hydroxy-19-nor-17α-pregna-5,9-dien-3-one

Common Name

English

ZK230211

Code

English

Lonaprisan [WHO-DD]

Common Name

English

LONAPRISAN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1891