TOCOPHERYL RETINOATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C49H76O3
Molecular Weight	713.1259
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

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)\C=C(C)\C=C\C=C(C)\C=C\C3=C(C)CCCC3(C)C)=C2C

InChI

InChIKey=RIQIJXOWVAHQES-UNAKLNRMSA-N

InChI=1S/C49H76O3/c1-34(2)19-14-20-35(3)21-15-22-36(4)25-17-31-49(13)32-29-43-42(10)46(40(8)41(9)47(43)52-49)51-45(50)33-38(6)24-16-23-37(5)27-28-44-39(7)26-18-30-48(44,11)12/h16,23-24,27-28,33-36H,14-15,17-22,25-26,29-32H2,1-13H3/b24-16+,28-27+,37-23+,38-33+/t35-,36-,49-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C49H76O3
Molecular Weight	713.1259
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	4
Optical Activity	UNSPECIFIED

Description
Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=35209
Curator's Comment: Decsription was created based on several sources including http://www.ncbi.nlm.nih.gov/pubmed/9250786 and https://www.jstage.jst.go.jp/article/skinresearch1959/36/2/36_2_209/_pdf

Tocopheryl retinoate (tocoretinate) is an alpha-tocopherol ester of all-trans retinoic acid (ATRA) and safely used to treat skin ulcers. Tocopheryl retinoate stimulates the formation of granulation tissue in the ulcer, and enhances the migration of guinea pig macrophages and stimulates the proliferation of human skin fibroblasts. It is usually used to treat pressure ulcer (bedsore) and skin ulcer (burn ulcer, diabetic ulcer, leg ulcer). Topical application of tocoretinate reduced the clinical symptoms of lichen amyloidosis and macular amyloidosis, and normalized disturbed epidermal differentiation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9616170	Agonist 2678
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9616170	Agonist 2678
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9616170	Agonist 2678
Collagen alpha-1(III) chain 1 Target ID: P02461\|\|\|Q6LDB3\|\|\|Q9UC91 Gene ID: 1281.0 Gene Symbol: COL3A1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/7865483	Activator 1430
Collagen alpha-1(IV) chain 1 Target ID: P02462 Gene ID: 1282.0 Gene Symbol: COL4A1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/7865483	Activator 1430
Collagen alpha-1(I) chain 11 Target ID: P02452\|\|\|Q15176\|\|\|Q9UML6 Gene ID: 1277.0 Gene Symbol: COL1A1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/7865483	Activator 1430
Fibronectin 1 Target ID: CHEMBL3810 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7865483	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Skin ulcer 8 Sources: http://adisinsight.springer.com/drugs/800001444	Primary	Approved 8429	Olcenon Ointment 0.25% Approved Use Usually used to treat pressure ulcer (bedsore) and skin ulcer (burn ulcer, diabetic ulcer, leg ulcer)
Acute promyelocytic leukemia 13 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9616170	Primary	Basic research	Unknown Approved Use Unknown
Lichen and macular amyloidosis 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21269316	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of tretinoin tocoferil on gene expression of the extracellular matrix components in human dermal fibroblasts in vitro.	1994 Dec	7865483
Tretinoin tocoferil as a possible differentiation-inducing agent against myelomonocytic leukemia.	1997 Jun	9250786
Induction of differentiation in acute promyelocytic leukemia cells by 9-cis retinoic acid alpha-tocopherol ester (9-cis tretinoin tocoferil).	1998 Jun 15	9616170
Clinical effect of tocoretinate on lichen and macular amyloidosis.	2011 Feb	21269316

Patents

Sample Use Guides

In Vivo Use Guide

In general, after cleaning up the affected area, put an appropriate amount of Tocopheryl retinoate ointment on gauze according to the symptom/size of the affected area and apply, or apply directly to the affected area, once to twice a day.

Route of Administration: Topical

In Vitro Use Guide

The mRNA levels of collagen I and flbronectin remarkably increased up to 90% of the controls at Tocopheryl retinoate concentrations of 10(-8) and 10(-6) M in human primary dermal tibroblast cultures.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:13:59 UTC 2023` Edited by `admin` on `Sat Dec 16 02:13:59 UTC 2023`
Record UNII	0WN694NBMM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOCOPHERYL RETINOATE

Official Name

English

D-.ALPHA.-TOCOPHERYL RETINOATE

Common Name

English

RETINOIC ACID, (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

.ALPHA.-TOCOPHERYL RETINOATE

Common Name

English

D-.ALPHA.-TOCOPHEROL RETINOATE

Common Name

English

TOCOPHERYL RETINOATE [INCI]

Common Name

English

Code System Code Type Description

PUBCHEM

5282180