DIDROVALTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H32O8
Molecular Weight	424.4847
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@H](OC(C)=O)[C@]3(CO3)[C@@]1([H])[C@H](OC(=O)CC(C)C)OC=C2COC(=O)CC(C)C

InChI

InChIKey=PHHROXLDZHUIGO-PNBTUHDLSA-N

InChI=1S/C22H32O8/c1-12(2)6-18(24)26-9-15-10-27-21(30-19(25)7-13(3)4)20-16(15)8-17(29-14(5)23)22(20)11-28-22/h10,12-13,16-17,20-21H,6-9,11H2,1-5H3/t16-,17+,20-,21+,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H32O8
Molecular Weight	424.4847
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: ISBN-13: 978-0895298645
Curator's Comment: description was created based on several sources, including http://customers.hbci.com/~wenonah/new/nieper.htm

Didrovaltrate is an active compound derived from Valeriana plant. In experiments with rat HTC cells, didrovaltrate showed considerable cytotoxicity which made it a promising agent for the treatment of cancer. There are no clinical trials available on the drug, however, there are studies reporting its clinical use (under the name Valmane) in patients with kidney cancer, oral cavity cancer, breast cancer and lung cancer. It is believed that the drugs acts by inhibiting the protein synthesis. The current marketing status of the drug is unknown and supposed to be "discontinued".

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Tumors of the oral cavity 1 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8429	VALMANE Approved Use Unknown Launch Date 1983
Kidney cancer 10 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8429	VALMANE Approved Use Unknown Launch Date 1983
Breast cancer 434 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8429	VALMANE Approved Use Unknown Launch Date 1983
Mesothelioma 4 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8429	VALMANE Approved Use Unknown Launch Date 1983
Lung cancer 69 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8429	VALMANE Approved Use Unknown Launch Date 1983

PubMed

Title	Date	PubMed
[In vitro- and vivo-metabolism of 14C-didrovaltrate (author's transl)].	1980 Apr	7367495
HPCL Separation and quantitative determination of valepotriates from Valeriana kilimandascharica.	1981 Oct	17402032
Antispasmodic effects of valeriana compounds: an in-vivo and in-vitro study on the guinea-pig ileum.	1982 Jun	7114974
Valepotriate content in different in vitro cultures of Valerianaceae and characterization of Valeriana officinalis L. callus during a growth period.	1983 Oct 21	6646985
[The synthesis of valperinol and various 3-aminomethyl derivatives of 2,9-dioxatricyclo[4,3,1,0(3,7)]decane from didrovaltrate].	1984	6543120
Effect of didrovaltrate on I-calcium current in rabbit ventricular myocytes.	2012 Sep	23297570

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

HTC cells (rat cultured hepatoma cells) were incubated in 75 ml culture flasks at 37 C. After reacjing a density of 8*10(5) cells/ml (3-4 days), cells were treated with etanol solution of didrovaltrate (50 ul per 75 ml of culture flasks).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:36:30 GMT 2023` Edited by `admin` on `Fri Dec 15 16:36:30 GMT 2023`
Record UNII	KEN63D125F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIDROVALTRATE

Official Name

English

didrovaltrate [INN]

Common Name

English

BUTANOIC ACID, 3-METHYL-, (1S,2'R,4AS,6S,7AS)-6-(ACETYLOXY)-4A,5,6,7A-TETRAHYDRO-4-((3-METHYL-1-OXOBUTOXY)METHYL)SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'-OXIRAN)-1-YL ESTER

Common Name

English

NSC-335756

Code

English

DIDROVALTRATE [MART.]

Common Name

English

1,4A,5,7A-TETRAHYDRO-1,6-DIHYDROXYSPIRO(CYCLOPENTA(C)PYRAN-7(6H),2'-OXIRANE)-4-METHANOL 6-ACETATE 1,4-DIISOVALERATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29756