TORIPRISTONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H39NO2
Molecular Weight	457.6469
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@H](C[C@]12C)C5=CC=C(C=C5)N(C)C(C)C

InChI

InChIKey=LOIYXTZQBQVHSF-PABOLRIOSA-N

InChI=1S/C31H39NO2/c1-6-16-31(34)17-15-28-26-13-9-22-18-24(33)12-14-25(22)29(26)27(19-30(28,31)4)21-7-10-23(11-8-21)32(5)20(2)3/h7-8,10-11,18,20,26-28,34H,9,12-15,17,19H2,1-5H3/t26-,27+,28-,30-,31-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C31H39NO2
Molecular Weight	457.6469
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12890569 | https://www.ncbi.nlm.nih.gov/pubmed/11238624 | https://www.ncbi.nlm.nih.gov/pubmed/9607777 | https://www.ncbi.nlm.nih.gov/pubmed/1336944

Toripristone has a high inhibiting activity against the cortisol receptors. Toripristone enhanced the antibacterial activities of the sparfloxacin in combination with ethambutol in the treatment of M. avium complex infections. Also, toripristone is a glucocorticoid type II receptor and progesterone receptor antagonist. Toripristone treatment was estimated to selectively occupy approximately 50% of glucocorticoid receptors in rat brain.

Approval Year

PubMed

Title	Date	PubMed
Suppressive effect of dexamethasone on TIMP-1 production involves murine osteoblastic MC3T3-E1 cell apoptosis.	2010-04	19629637
Glucocorticoid receptor activation is involved in producing abnormal phenotypes of single-prolonged stress rats: a putative post-traumatic stress disorder model.	2007-08-10	17644267
Mouse calbindin-D(9k) gene expression in the uterus during late pregnancy and lactation.	2003-07-31	12890569
Acute exposure to a novel stressor further reduces the habituated corticosterone response to restraint in rats.	2001-12	22432149
The steroid receptor antagonists RU40555 and RU486 activate glucocorticoid receptor translocation and are not excreted by the steroid hormones transporter in L929 cells.	2001-05	11312148
Endogenous glucocorticoids play a positive regulatory role in the anti-keyhole limpet hemocyanin in vivo antibody response.	2001-03-15	11238624
Selective blockade of the mineralocorticoid receptor impairs hypothalamic-pituitary-adrenal axis expression of habituation.	2000-10	11012846
Immunodynamics of methylprednisolone induced T-cell trafficking and deactivation using whole blood lymphocyte proliferation techniques in the rat.	1999-07	10594870
Influence of gender on prednisolone effects on whole blood T-cell deactivation and trafficking in rats.	1999-01	9874701
Evaluation of RU28318 and RU40555 as selective mineralocorticoid receptor and glucocorticoid receptor antagonists, respectively: receptor measures and functional studies.	1998-11	9879980
Evidence for mineralocorticoid receptor facilitation of glucocorticoid receptor-dependent regulation of hypothalamic-pituitary-adrenal axis activity.	1998-06	9607777
Restraint stress slows cutaneous wound healing in mice.	1998-03	9570862
Type II glucocorticoid receptor antagonists impair contextual but not auditory-cue fear conditioning in juvenile rats.	1997-01	9013504

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:36:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:36:35 GMT 2025`
Record UNII	711D76P884
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TORIPRISTONE

Official Name

English

RU-40555

Preferred Name

English

RU40555

Code

English

toripristone [INN]

Common Name

English

17.BETA.-HYDROXY-11.BETA.-(P-(ISOPROPYLMETHYLAMINO)PHENYL)-17-(1-PROPYNYL)ESTRA-4,9-DIEN-3-ONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1891