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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H52O3
Molecular Weight 472.7428
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

InChIKey=ZAKOWWREFLAJOT-CEFNRUSXSA-N
InChI=1S/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1

HIDE SMILES / InChI

Molecular Formula C31H52O3
Molecular Weight 472.7428
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
Antioxidant capacity in Fasciola hepatica patients before and after treatment with triclabendazole alone or in combination with ascorbic acid (vitamin C) and tocofersolan (vitamin E).
2003
Bioavailability of oral vitamin E formulations in adult volunteers and children with chronic cholestasis or cystic fibrosis.
2009 Oct

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 Fri Dec 15 15:21:26 UTC 2023
Edited
by admin
on Fri Dec 15 15:21:26 UTC 2023
Record UNII
A7E6112E4N
Record Status Validated (UNII)
Record Version
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Name Type Language
.ALPHA.-TOCOPHEROL ACETATE, D-
Common Name English
RRR-ALPHA-TOCOPHERYL ACETATE
FCC  
Common Name English
TOCOPHERYL ACETATE, .ALPHA., D-
Common Name English
ALPHA-TOCOPHEROL ACETATE. D-
Common Name English
D-.ALPHA.-TOCOPHERYL ACETATE
Common Name English
ALPHA-TOCOPHERYL ACETATE, D-
Common Name English
D-ALPHA TOCOFERIL ACETATE [MART.]
Common Name English
(+)-ALFA-TOCOPHEROL ACETATE
Common Name English
TOCOPHERYL ACETATE, D-ALPHA
Common Name English
2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-, 6-ACETATE, (2R)-
Common Name English
D-ALPHA TOCOPHERYL ACETATE
Common Name English
.ALPHA.-TOCOPHEROL ACETATE [MI]
Common Name English
NSC-755840
Code English
TOCOPHERYL ACETATE,D-ALPHA [VANDF]
Common Name English
Tocopheryl acetate [WHO-DD]
Common Name English
ALPHA-TOCOPHEROL ACETATE, D-
Common Name English
D-ALPHA TOCOFERIL ACETATE
MART.  
Common Name English
RRR-ALPHA-TOCOPHERYL ACETATE [FCC]
Common Name English
RRR-ALPHA-TOCOPHERYL ACETATE CONCENTRATE [FCC]
Common Name English
RRR-ALPHA-TOCOPHERYL ACETATE CONCENTRATE
FCC  
Common Name English
.ALPHA.-TOCOPHEROL ACETATE. D-
Common Name English
J24.807J
Code English
Classification Tree Code System Code
DSLD 2349 (Number of products:2130)
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
Code System Code Type Description
WIKIPEDIA
α-Tocopheryl acetate
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
DAILYMED
A7E6112E4N
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
CAS
58-95-7
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
FDA UNII
A7E6112E4N
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
EVMPD
SUB22088
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-405-4
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
RXCUI
1441649
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID1031096
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
EVMPD
SUB16136MIG
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
SMS_ID
100000085417
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
PUBCHEM
86472
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
MERCK INDEX
m10923
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY Merck Index
NSC
755840
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
NCI_THESAURUS
C74962
Created by admin on Fri Dec 15 15:21:26 UTC 2023 , Edited by admin on Fri Dec 15 15:21:26 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY