TOSAGESTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24O2
Molecular Weight	308.4141
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC(=C)[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C

InChI

InChIKey=YJSTYQGZKJHXLN-OLGWUGKESA-N

InChI=1S/C21H24O2/c1-4-21(23)10-9-18-17-7-5-14-11-15(22)6-8-16(14)19(17)13(2)12-20(18,21)3/h1,9-11,16-19,23H,2,5-8,12H2,3H3/t16-,17-,18-,19+,20-,21-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10822023 | https://www.ncbi.nlm.nih.gov/pubmed/11438328 | https://www.ncbi.nlm.nih.gov/pubmed/9806953 | https://apps.who.int/iris/bitstream/handle/10665/67830/WHO_EDM_QSM_2003.2.pdf | https://adisinsight.springer.com/drugs/800012399

Tosagestin (Org 30659) is a synthetic 19-nortestosterone derived progestogen. It was under clinical development by NV Organon for use in oral contraceptive and hormone replacement therapy. After oral administration of [14C]-Org 30659 to postmenopausal women, the compound was extensively metabolized. The dosed radioactivity was predominantly excreted via urine. Org 30659 was to a large extent metabolized at the C3- and the C17-positions. Species comparison of the metabolic routes of Org 30659 after oral administration indicated that the monkey seems to be a better representative species than the rat for the metabolism of Org 30659 in humans. Daily oral administration of Org 30659 suppresses ovarian function to a level sufficient to inhibit ovulation. This effect is dose-dependent, and the suppressive effect is readily reversible at all doses tested. Tosagestin had been in phase II clinical trial for the treatment of the menopausal syndrome. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pharmacokinetic differences between Caucasian and Japanese subjects after single and multiple doses of a potential combined oral contraceptive (Org 30659 and EE).	2003-09	14561540
Identification of the human P450 enzymes involved in the in vitro metabolism of the synthetic steroidal hormones Org 4060 and Org 30659.	2002-02	11871398
Ovarian function during and after treatment with the new progestagen Org 30659.	2001-07	11438328
Excretion balance and metabolism of the progestagen Org 30659 in healthy postmenopausal women.	2000-05	10822023
In vitro and in vivo metabolism of the progestagen Org 30659 in several species.	1998-11	9806953
Effects of two classes of progestagens, pregnane and 19-nortestosterone derivatives, on cell growth of human breast tumor cells: II. T47D cell lines.	1995-12	8541241
Effects of two classes of progestagens, pregnane and 19-nortestosterone derivatives, on cell growth of human breast tumor cells: I. MCF-7 cell lines.	1995-12	8541240
Effects of progestins on the proliferation of estrogen-dependent human breast cancer cells under growth factor-defined conditions.	1992-06	1616875

Sample Use Guides

In Vivo Use Guide

Daily administration of 0.060, 0.120, 0.180, or 0.240 mg for 21 days

Route of Administration: Oral

Name

Type

Language

TOSAGESTIN

Official Name

English

ORG-30659

Preferred Name

English

TOSAGESTIN [USAN]

Common Name

English

ORG30659

Code

English

tosagestin [INN]

Common Name

English

17-Hydroxy-11-methylene-19-nor-17?-pregna-4,15-dien-20-yn-3-one

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C776