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Details

Stereochemistry ACHIRAL
Molecular Formula C20H28O2
Molecular Weight 300.4351
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ALITRETINOIN

SMILES

CC(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(C)=C\C(O)=O

InChI

InChIKey=SHGAZHPCJJPHSC-ZVCIMWCZSA-N
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+

HIDE SMILES / InChI

Description

All-trans retinoic acid (ATRA) also known as tretinoin is an active metabolite of vitamin A that has been demonstrated to inhibit the growth of cancer cells, some types of epithelial cells, and vascular smooth muscles. It is medication used for the treatment of acne. Tretinoin capsules are indicated for the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant), characterized by the presence of the t(15;17) translocation and/or the presence of the PML/RARα gene who are refractory to, or who have relapsed from, anthracycline chemotherapy, or for whom anthracycline based chemotherapy is contraindicated. Tretinoin is for the induction of remission only. For acne it is applied to the skin as a cream or ointment. For leukemia it is taken by mouth for up to three months. The exact mechanism of action of tretinoin in APL and acne treatment is unknown, but is known, that tretinoin activates three members of the retinoid acid (RAR) nuclear receptors (RARα, RARβ, and RARγ) which act to modify gene expression, subsequent protein synthesis, and epithelial cell growth and differentiation. It has not been established whether the clinical effects of tretinoin are mediated through activation of retinoic acid receptors, other mechanisms, or both.

CNS Activity

Originator

Approval Year

Sample Use Guides

In Vivo Use Guide
Panretin (Alitretinoin) gel should initially be applied two (2) times a day to cutaneous KS lesions. The application frequency can be gradually increased to three (3) or four (4) times a day according to individual lesion tolerance.
Route of Administration: topical; oral
In Vitro Use Guide
The addition of 5 nM Alitretinoin to the maturation medium was beneficial for parthenogenetic pig embryo production.
Name Type Language
ALITRETINOIN
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
PANRETIN
Brand Name English
RETINOIC ACID 9-CIS-FORM [MI]
Common Name English
LG-100057
Code English
ALITRETINOIN [MART.]
Common Name English
9-CIS-RETINOIC ACID
Common Name English
ALITRETINOIN [USAN]
Common Name English
ALRT-1057
Code English
ALITRETINOIN [ORANGE BOOK]
Common Name English
ALRT1057
Code English
LGD-1057
Code English
LGD1057
Code English
ALITRETINOIN [MI]
Common Name English
ALITRETINOIN [WHO-DD]
Common Name English
ALITRETINOIN [VANDF]
Common Name English
ALITRETINOIN [INN]
Common Name English
LG100057
Code English
(2E,4E,6Z,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-2,4,6,8-NONATETRAENOIC ACID
Systematic Name English
TRETINOIN IMPURITY D [EP]
Common Name English
ALITRETINOIN [HSDB]
Common Name English
9-CIS RETINOIC ACID
Common Name English
AGN 192013
Code English
NSC-659772
Code English
AGN-192013
Code English
ALITRETINOIN [EMA EPAR]
Common Name English
BAL-4079
Code English
Classification Tree Code System Code
WHO-ATC D11AX19
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-VATC QL01XX22
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-VATC QD11AH04
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NCI_THESAURUS C804
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
FDA ORPHAN DRUG 101296
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-ATC D11AH04
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
EMA ASSESSMENT REPORTS PANRETIN (AUTHORIZED: SARCOMA, KAPOSI)
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
FDA ORPHAN DRUG 110998
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
WHO-ATC L01XX22
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000175607
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
FDA ORPHAN DRUG 66592
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C1574
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
INN
7781
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
HSDB
5300-03-8
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL705
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
MERCK INDEX
M1511
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY Merck Index
MERCK INDEX
M9558
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
MESH
C103303
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
EPA CompTox
5300-03-8
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
CAS
5300-03-8
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
DRUG BANK
DB00523
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
RXCUI
81864
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY RxNorm
IUPHAR
2645
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
WIKIPEDIA
ALITRETINOIN
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
EVMPD
SUB00344MIG
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY
PUBCHEM
449171
Created by admin on Mon Oct 21 19:53:24 UTC 2019 , Edited by admin on Mon Oct 21 19:53:24 UTC 2019
PRIMARY