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

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
Antiprogestin-releasing intrauterine devices: a novel approach to endometrial contraception.	2007 Jun	17531599
Progesterone reverts LPS-reduced FAAH activity in murine peripheral blood mononuclear cells by a receptor-mediated fashion.	2013 Dec 5	23906535
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

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