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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H54O5
Molecular Weight 530.7789
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-TOCOPHEROL SUCCINATE, 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(=O)CCC(O)=O)=C2C

InChI

InChIKey=IELOKBJPULMYRW-NJQVLOCASA-N
InChI=1S/C33H54O5/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-20-33(8)21-19-28-27(7)31(25(5)26(6)32(28)38-33)37-30(36)18-17-29(34)35/h22-24H,9-21H2,1-8H3,(H,34,35)/t23-,24-,33-/m1/s1

HIDE SMILES / InChI

Molecular Formula C33H54O5
Molecular Weight 530.7789
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
Treatment of cholestatic children with water-soluble vitamin E (alpha-tocopheryl polyethylene glycol succinate): effects on serum vitamin E, lipid peroxides, and polyunsaturated fatty acids.
1997 Feb
Final report on the safety assessment of Tocopherol, Tocopheryl Acetate, Tocopheryl Linoleate, Tocopheryl Linoleate/Oleate, Tocopheryl Nicotinate, Tocopheryl Succinate, Dioleyl Tocopheryl Methylsilanol, Potassium Ascorbyl Tocopheryl Phosphate, and Tocophersolan.
2002
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
Determination of alpha-tocopherol in plasma by high performance liquid chromatography with fluorescence detection and stability of alpha-tocopherol under different conditions.
2004
Bioavailability of oral vitamin E formulations in adult volunteers and children with chronic cholestasis or cystic fibrosis.
2009 Oct
Dosage and formulation issues: oral vitamin E therapy in children.
2010 Feb
Guidelines for the diagnosis and management of chylomicron retention disease based on a review of the literature and the experience of two centers.
2010 Sep 29
Effect of hydrosoluble vitamin E on erythrocyte membrane lipid composition in patients with advanced cirrhosis: An open-label pilot trial.
2015 Aug
Oral Tocofersolan Corrects or Prevents Vitamin E Deficiency in Children With Chronic Cholestasis.
2016 Dec
Efficacy of two vitamin E formulations in patients with abetalipoproteinemia and chylomicron retention disease.
2018 Sep

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 15:00:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:19 GMT 2023
Record UNII
LU4B53JYVE
Record Status Validated (UNII)
Record Version
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Name Type Language
.ALPHA.-TOCOPHEROL SUCCINATE, D-
Common Name English
Tocopheryl acid succinate [WHO-DD]
Common Name English
.ALPHA.-TOCOPHERYL SUCCINATE
Common Name English
VITAMIN E (ALPHA-TOCOPHERYL SUCCINATE)
Common Name English
RRR-ALPHA-TOCOPHERYL ACID SUCCINATE
FCC  
Common Name English
BUTANEDIOIC ACID, 1-((2R)-3,4-DIHYDRO-2,5,7,8-TETRAMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-YL) ESTER
Common Name English
TOCOPHERYL SUCCINATE
INCI  
INCI  
Official Name English
NSC-173849
Code English
J24.824J
Code English
TOCOPHEROL SUCCINATE
Common Name English
TOCOPHERYL ACID SUCCINATE,D-ALPHA [VANDF]
Common Name English
VITAMINE E SUCCINATE
Common Name English
RRR-ALPHA-TOCOPHERYL ACID SUCCINATE [FCC]
Common Name English
VITAMIN E HEMISUCCINATE
Common Name English
ALPHA-TOCOPHEROL SUCCINATE
Common Name English
TOCOPHERYL ACID SUCCINATE, D-ALPHA
Common Name English
RRR-.ALPHA.-TOCOPHERYL HYDROGEN SUCCINATE
EP  
Common Name English
ALPHA-TOCOPHEROL SUCCINATE, D-
Common Name English
.ALPHA.-TOCOPHEROL SUCCINATE [MI]
Common Name English
TOCOPHERYL SUCCINATE [INCI]
Common Name English
D-ALPHA TOCOFERIL ACID SUCCINATE [MART.]
Common Name English
.ALPHA.-TOCOPHERYL SUCCINATE, D-
Common Name English
VITAMIN E SUCCINATE
Common Name English
TOCOPHERYL ACID SUCCINATE [VANDF]
Common Name English
.ALPHA.-TOCOPHEROL SUCCINATE
MI  
Common Name English
RRR-.ALPHA.-TOCOPHERYL HYDROGEN SUCCINATE [EP IMPURITY]
Common Name English
Classification Tree Code System Code
DSLD 2439 (Number of products:1456)
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
DSLD 3277 (Number of products:274)
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
DSLD 3107 (Number of products:36)
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
DSLD 3090 (Number of products:111)
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
Code System Code Type Description
PUBCHEM
20353
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
NSC
173849
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
SMS_ID
100000129677
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
CAS
4345-03-3
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
DRUG CENTRAL
2690
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
RS_ITEM_NUM
1667803
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
MERCK INDEX
m10923
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB14001
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
RXCUI
39626
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
ALTERNATIVE
NCI_THESAURUS
C74963
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
EVMPD
SUB39880
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID2026151
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
DAILYMED
LU4B53JYVE
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
RXCUI
1426447
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
RXCUI
314875
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
ALTERNATIVE
FDA UNII
LU4B53JYVE
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
224-403-8
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
PRIMARY
EVMPD
SUB12264MIG
Created by admin on Fri Dec 15 15:00:19 GMT 2023 , Edited by admin on Fri Dec 15 15:00:19 GMT 2023
ALTERNATIVE
Related Record Type Details
ACTIVE MOIETY