ETAROTENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H32O2S
Molecular Weight	396.585
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCS(=O)(=O)C1=CC=C(C=C1)\C=C(/C)C2=CC=C3C(=C2)C(C)(C)CCC3(C)C

InChI

InChIKey=UDAZCXVIYSIEFX-FBMGVBCBSA-N

InChI=1S/C25H32O2S/c1-7-28(26,27)21-11-8-19(9-12-21)16-18(2)20-10-13-22-23(17-20)25(5,6)15-14-24(22,3)4/h8-13,16-17H,7,14-15H2,1-6H3/b18-16+

HIDE SMILES / InChI

Molecular Formula	C25H32O2S
Molecular Weight	396.585
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11096376 | https://adisinsight.springer.com/drugs/800003576 | https://www.ncbi.nlm.nih.gov/pubmed/2446936

Etarotene (Ro 15-1570) is an arotinoid sulfone. Etarotene inhibits RNase P, a ribonucleoprotein that endonucleolytically cleaves all tRNA precursors to produce the mature 5' end, thereby affecting tRNA biogenesis. Etarotene has antikeratinizing potential. It was undergoing phase III clinical trials with Roche in the US for the treatment of psoriasis and other skin.

Originator

Approval Year

PubMed

Title	Date	PubMed
Quantitative analysis of retinoids in biological fluids by high-performance liquid chromatography using column switching. III. Determination of the arotinoid sumarotene and its Z-isomer in human and animal plasma.	1992 Apr 15	1500445
Pharmacological alterations of cellular transglutaminase activity and invasiveness in human colorectal carcinoma cells.	1993 Jun	7906610
Regulation of the induction of ornithine decarboxylase in keratinocytes by retinoids.	1995 Jul 1	7619051
Phorbol 12-myristate 13-acetate inhibits epidermal growth factor signalling in human keratinocytes, leading to decreased ornithine decarboxylase activity.	1996 Oct 15	8912706
Inhibitory effects of arotinoids on tRNA biogenesis.	2000 Nov-Dec	11096376

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:49:18 GMT 2023` Edited by `admin` on `Fri Dec 15 16:49:18 GMT 2023`
Record UNII	PD3817FE9N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETAROTENE

Official Name

English

etarotene [INN]

Common Name

English

RO-151570000

Code

English

6-((E)-P-(ETHYLSULFONYL)-.ALPHA.-METHYLSTYRYL)-1,2,3,4-TETRAHYDRONAPHTHALENE

Common Name

English

NAPHTHALENE, 6-(2-(4-(ETHYLSULFONYL)PHENYL)-1-METHYLETHENYL)-1,2,3,4-TETRAHYDRO-1,1,4,4-TETRAMETHYL-, (E)-

Common Name

English

ETAROTENE [USAN]

Common Name

English

RO 15-1570/000

Code

English

RO-15-1570/000

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C804