UZARIGENIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H34O4
Molecular Weight	374.5137
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C5=CC(=O)OC5

InChI

InChIKey=XZTUSOXSLKTKJQ-CIXPXFMPSA-N

InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16-,17+,18-,19+,21-,22+,23-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21479205 | https://www.ncbi.nlm.nih.gov/pubmed/25193007
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21421322

Uzarigenin is a Na(+), K(+)-ATPase inhibitor; potential anticancer drug. Uzarigenin is a component of Uzara, which has been used for a long time in traditional medicine to treat diarrheal disorders, but the mode of action is not fully known. In Germany, Uzara (Stada, Bad Vilbel, Germany) is frequently used as over-the-counter preparation of the Uzara root, containing 40 mg glycosides/ml.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21421322 \| https://www.ncbi.nlm.nih.gov/pubmed/10882359 \| https://www.ncbi.nlm.nih.gov/pubmed/10784099 \| https://www.ncbi.nlm.nih.gov/pubmed/21479205	Inhibitor 8297
MCF7 21 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21421322	Inhibitor 8297	0.6 µM [IC50]
Bursaphelenchus xylophilus 1 Target ID: CHEMBL613331 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19319871	Inhibitor 8297
Caenorhabditis elegans 3 Target ID: CHEMBL613135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19319871	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diarrhea 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?21479205 https://www.ncbi.nlm.nih.gov/pubmed/25193007	Primary		Approved 8429	Uzara Approved Use Diarrhea

PubMed

Title	Date	PubMed
Anti-diarrheal mechanism of the traditional remedy Uzara via reduction of active chloride secretion.	2011 Mar 30	21479205
Xysmalobium undulatum (uzara) - review of an antidiarrhoeal traditional medicine.	2014 Oct 28	25193007

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The median lethal concentrations (LC(50)) of Uzarigenin against the nematodes Bursaphelenchus xylophilus, Panagrellus redivivus, and Caenorhabditis elegans at 72 h were 49.0, 62.7, and 29.1, mg/l, respectively

Name

Type

Language

UZARIGENIN

Common Name

English

ODORIGENI

Common Name

English

NSC-277290

Code

English

(3.BETA.,5.ALPHA.)-3,14-DIHYDROXYCARD-20(22)-ENOLIDE

Common Name

English

UZARIGENIN [MI]

Common Name

English

CARD-20(22)-ENOLIDE, 3,14-DIHYDROXY-, (3.BETA.,5.ALPHA.)-

Common Name

English

ODORIGENIN

Common Name

English

NSC-119993

Code

English

URARIGENIN

Common Name

English

Code System Code Type Description

MERCK INDEX

m11353