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

CC(C)CC(=O)OCC1=CO[C@@H](OC(=O)CC(C)C)[C@H]2[C@@H]1C[C@H](OC(C)=O)[C@]23CO3

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	5 / 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 8583	VALMANE Approved Use Unknown Launch Date 1983
Kidney cancer 10 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8583	VALMANE Approved Use Unknown Launch Date 1983
Breast cancer 432 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8583	VALMANE Approved Use Unknown Launch Date 1983
Mesothelioma 4 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8583	VALMANE Approved Use Unknown Launch Date 1983
Lung cancer 70 Sources: http://customers.hbci.com/~wenonah/new/nieper.htm	Primary	Approved 8583	VALMANE Approved Use Unknown Launch Date 1983

PubMed

Title	Date	PubMed
Effect of didrovaltrate on I-calcium current in rabbit ventricular myocytes.	2012-09	23297570
Effect of valepotriates on the behavior of rats in the elevated plus-maze during diazepam withdrawal.	1994-08-01	7988648
High-yield production of valepotriates by hairy root cultures of Valeriana officnalis L. var. sambucifolia Mikan.	1992-07	24201434
Valerian-derived sedative agents. I. On the structure and spectral assignment of the constituents of valmane using the selective INEPT nuclear magnetic resonance technique.	1991-09	1788154
Effects of thiol compounds versus the cytotoxicity of valepotriates on cultured hepatoma cells.	1990-04	2353067
The Structure of New Valepotriates from Tissue Cultures of Valeriana wallichii.	1984-06	17340305
[The synthesis of valperinol and various 3-aminomethyl derivatives of 2,9-dioxatricyclo[4,3,1,0(3,7)]decane from didrovaltrate].	1984	6543120
Valepotriate content in different in vitro cultures of Valerianaceae and characterization of Valeriana officinalis L. callus during a growth period.	1983-10-21	6646985
Antispasmodic effects of valeriana compounds: an in-vivo and in-vitro study on the guinea-pig ileum.	1982-06	7114974
HPCL Separation and quantitative determination of valepotriates from Valeriana kilimandascharica.	1981-10	17402032
[In vitro- and vivo-metabolism of 14C-didrovaltrate (author's transl)].	1980-04	7367495

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 `Mon Mar 31 18:32:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:26 GMT 2025`
Record UNII	KEN63D125F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIDROVALTRATE

Official Name

English

NSC-335756

Preferred 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

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