U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H50O2
Molecular Weight 430.7061
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-TOCOPHEROL, D-

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C

InChI

InChIKey=GVJHHUAWPYXKBD-IEOSBIPESA-N
InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula C29H50O2
Molecular Weight 430.7061
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000920/WC500047919.pdf http://www.ema.europa.eu/docs/en_GB/document_library/Medicine_QA/2009/11/WC500014528.pdf https://www.medicines.org.uk/emc/medicine/24235 https://www.ncbi.nlm.nih.gov/pubmed/12537931

Tocophersolan (Vedrop, tocofersolan) or d-alpha-Tocopheryl Polyethylene Glycol 1000 Succinate (TPGS) is a watersoluble derivative of the natural active (d-alpha) isomer of vitamin E. The active constituent of the medicinal product is essentially vitamin E (alpha tocopherol). Chronic congenital or hereditary cholestasis is a clinical condition where vitamin E deficiency results from an impaired bile secretion. Decreased intestinal absorption observed in chronic congenital or hereditary cholestatic patients is due to decreased bile secretion and the resulting decrease in intestinal cellular absorption. As a result, fatsoluble vitamins (i.e. vit. E) are not absorbed properly and deficiency can occur. Tocophersolan (Vedrop) is used to treat or prevent vitamin E deficiency (low vitamin E levels). It is used in children up to the age of 18 years who have congenital or hereditary chronic cholestasis and who cannot absorb vitamin E from the gut. Tocophersolan (Tocofersolan) can be absorbed from the gut in children who have difficulty absorbing fats and vitamin E from the diet. This can increase vitamin E levels in the blood and help to prevent neurological deterioration (problems in the nervous system) due to vitamin E deficiency. No treatment-related findings were reported, as all clinical observations and findings at autopsy were similar in treatment and control groups. In many of the studies, the LD50 was not determined as tocofersolan was well tolerated.

CNS Activity

Curator's Comment: Neurological symptoms were either improved or stabilized in 96% of patients with chronic congenital or hereditary cholestasis (pages 19-20)

Originator

Curator's Comment: Tocophersolan or d-a-tocopheryl polyethylene glycol succinate (TPGS, CAS Registry Number 9002-96-4) was invented by Eastman Kodak in 1950.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Vedrop

Approved Use

Tocophersolan (Vedrop) is used to treat or prevent vitamin E deficiency (low vitamin E levels). The recommended total daily dose in paediatric patients suffering from congenital chronic cholestasis or hereditary chronic cholestasis is 0.34 ml/kg/day (17 mg/kg of d-alpha-tocopherol in the form of tocofersolan). The dose should be prescribed in ml.
Palliative
Vedrop

Approved Use

Tocophersolan (Vedrop) is used to treat or prevent vitamin E deficiency (low vitamin E levels). The recommended total daily dose in paediatric patients suffering from congenital chronic cholestasis or hereditary chronic cholestasis is 0.34 ml/kg/day (17 mg/kg of d-alpha-tocopherol in the form of tocofersolan). The dose should be prescribed in ml.
Palliative
Vedrop

Approved Use

Unknown
Palliative
Vedrop

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Determination of alpha-tocopherol in plasma by high performance liquid chromatography with fluorescence detection and stability of alpha-tocopherol under different conditions.
2004
Dosage and formulation issues: oral vitamin E therapy in children.
2010 Feb

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Tocophersolan (Vedrop) is given with or without water. This dose should be adjusted depending on the amount of vitamin E in the child’s blood. This should be checked regularly.
The recommended total daily dose in paediatric patients suffering from congenital chronic cholestasis or hereditary chronic cholestasis is 0.34 ml/kg/day (17 mg/kg of d-alpha-tocopherol in the form of tocofersolan). The dose should be prescribed in ml.
Route of Administration: Oral
In vitro studies using fibroblasts, enterocytes and Caco-2 cells conclude that Tocophersolan (tocofersolan) is taken up as the intact molecule and undergoes a slow hydrolysis reaction, intracellularly, to give PEG 1000 and Vitamin E (d-α tocopherol).
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:00:08 GMT 2023
Edited
by admin
on Sat Dec 16 05:00:08 GMT 2023
Record UNII
N9PR3490H9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-TOCOPHEROL, D-
Common Name English
RRR-ALPHA-TOCOPHEROL CONCENTRATE
FCC  
Common Name English
5,7,8-TRIMETHYLTOCOL
Common Name English
INS NO.307A
Code English
.ALPHA.-TOCOPHEROL [MI]
Common Name English
TOCOPHEROL, D-ALPHA-
Common Name English
D-ALPHA TOCOPHEROL
MART.  
Common Name English
D-ALPHA TOCOPHEROL [MART.]
Common Name English
RRR-ALPHA-TOCOPHEROL CONCENTRATE [FCC]
Common Name English
(+)-ALPHA-TOCOPHEROL-
Common Name English
ALPHA-TOCOPHEROL, D-
Common Name English
J24.260H
Code English
INS-307A
Code English
ALPHA-TOCOPHEROL (CONSTITUENT OF LYCOPENE AND TOMATO EXTRACT CONTAINING LYCOPENE) [DSC]
Common Name English
NSC-20812
Code English
ALPHA-TOCOPHEROL [HSDB]
Common Name English
R,R,R-.ALPHA.-TOCOPHEROL
Common Name English
D-ALPHA-TOCOPHEROL
Common Name English
VITAMIN E D-ALPHA
Common Name English
E-307A
Code English
2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-, (2R)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C74960
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
JECFA EVALUATION INS-307A
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
CODEX ALIMENTARIUS (GSFA) INS-307A
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
Code System Code Type Description
SMS_ID
100000145646
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
DAILYMED
N9PR3490H9
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
RXCUI
220892
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-412-2
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
NSC
20812
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
CAS
59-02-9
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
PUBCHEM
14985
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
WIKIPEDIA
α-Tocopherol
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
EVMPD
SUB124293
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID0026339
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
FDA UNII
N9PR3490H9
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
CHEBI
18145
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
MERCK INDEX
m10923
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY Merck Index
HSDB
2556
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
DRUG BANK
DB00163
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
NCI_THESAURUS
C2832
Created by admin on Sat Dec 16 05:00:09 GMT 2023 , Edited by admin on Sat Dec 16 05:00:09 GMT 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (GC)
EP
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
ACTIVE MOIETY