Natural Product (NP) Details

General Information of the NP (ID: NP7529)
Name
Alitretinoin
Synonyms
Alitretinoin; 9-CIS-RETINOIC ACID; Panretin; 5300-03-8; 9-cis-Tretinoin; Panrexin; 9-cis Retinoic Acid; Panretyn; Panretin Gel; (9cis)-retinoic acid; Toctino; 9(Z)-Retinoic acid; Retinoic acid, 9-cis-; Panretin (TN); Alitretinoin (USAN); Alitretinoin [USAN]; ALRT-1057; AGN 192013; trans-Vitamin a acid; BAL-4079; LGD-1057; CHEMBL705; UNII-1UA8E65KDZ; AGN-192013; NSC-659772; 1UA8E65KDZ; Atragen; Effederm; Retinova; LG-100057; ALRT1057; CHEBI:50648; LGD1057; Aberela [Norway]; Avitoin [Norway]; Tretinoin (TN); Effederm [France]; (7E,9Z,11E,13E)-retinoic acid; MFCD00270072; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; A-Acido (Argentina); 9-cis-RA; Retin A (TN); LG100057; trans-Retinoate; beta-Retinoate; 9 Cis Retinoic Acid; alitretinoina; alitretinoine; alitretinoinum; Retinoic acid, cis-9,trans-13-; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid; Tretinoine [INN-French]; Tretinoinum [INN-Latin]; all-trans-b-Retinoic acid; Tretinoina [INN-Spanish]; Tretinoino [INN-Spanish]; ALRT 1057; 9-cis RA; 9CRA; Isotretinoin Retinoic acid; [3H]9-cis-retinoic acid; tretinoine (French) (EINECS); [3H]-9-cis-retinoic acid; 9-CRA; 9C-RA; Acide retinoique (French) (DSL); 15-Apo-beta-caroten-15-oic acid; B-retinoate; BML2-E06; CCRIS 7098; 9-Retinoate; 9-Retinoic acid; HSDB 7186; 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2E,4E,6Z,8E)-; Isotretinoin retinoate; All-trans-b-retinoate; NSC 659772; 9-cis- retinoic acid; Ro-04-4079; 9-(Z)-retinoic Acid; Tretinoin (JAN/USP); alpha-acido (argentina); All-trans-beta-retinoate; Spectrum5_001935; Retinoic acid 9-cis-form; alpha-vitaminsyre [denmark]; DSSTox_CID_20404; DSSTox_RID_79490; all-trans- Vitamin A1 acid; DSSTox_GSID_40404; SCHEMBL18666; BSPBio_001495; Tretinoin/all-trans retinoate; Tretinoin [USAN:BAN:INN]; 15-Apo-beta-caroten-15-oate; Alitretinoin [USAN:INN:BAN]; GTPL2645; GTPL5383; DTXSID6040404; UPCMLD-DP097:001; UPCMLD-DP097:002; BDBM31892; Alitretinoin; ; ; Retinoid analogues; HMS1361K17; HMS1791K17; HMS1989K17; HMS3402K17; (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic acid; 124510-04-9; AMY21903; Tox21_302195; LMPR01090022; NSC659772; STK801887; ZINC12661824; AKOS005622553; CCG-208266; DB00523; (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid; IDI1_033965; 9-cis-Retinoic acid, >=98% (HPLC); NCGC00161590-01; NCGC00161590-02; NCGC00161590-03; NCGC00161590-04; NCGC00161590-05; NCGC00161590-06; NCGC00161590-07; NCGC00255697-01; HY-15128; CAS-5300-03-8; BB 0261656; CS-0003780; C15493; D02815; 42156-EP2295426A1; 42156-EP2295427A1; 42156-EP2311808A1; 42156-EP2311829A1; 42156-EP2311840A1; 300R038; SR-05000013784; Q3611854; SR-05000013784-1; W-200595; BRD-K35483542-001-02-3
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Kaposi sarcoma [ICD-11: 2B57] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C20H28O2
PubChem CID
449171
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
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+
InChIKey
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
CAS Number
CAS 5300-03-8
ChEBI ID
CHEBI:50648
TTD Drug ID
D0G3PI
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Alitretinoin combined with topical 5-FU seems to be an interesting option in patients with DD, as it can allow a durable clinically complete remission with a good tolerance.
Target and Pathway
Target(s) Retinoic acid receptor beta (RARB)  Molecule Info  [3]
Retinoic acid receptor gamma (RARG)  Molecule Info  [3]
Retinoic acid receptor RXR-alpha (RXRA)  Molecule Info  [3]
Retinoic acid receptor RXR-beta (RXRB)  Molecule Info  [3]
Retinoic acid receptor RXR-gamma (RXRG)  Molecule Info  [3]
KEGG Pathway PPAR signaling pathway Click to Show/Hide
2 PI3K-Akt signaling pathway
3 Thyroid hormone signaling pathway
4 Adipocytokine signaling pathway
5 Non-alcoholic fatty liver disease (NAFLD)
6 Bile secretion
7 Hepatitis C
8 Pathways in cancer
9 Transcriptional misregulation in cancer
10 Thyroid cancer
11 Small cell lung cancer
12 Non-small cell lung cancer
Panther Pathway Vitamin D metabolism and pathway Click to Show/Hide
Pathway Interaction Database Regulation of Androgen receptor activity Click to Show/Hide
2 RXR and RAR heterodimerization with other nuclear receptor
3 Retinoic acid receptors-mediated signaling
4 a6b1 and a6b4 Integrin signaling
Reactome RORA activates gene expression Click to Show/Hide
2 BMAL1:CLOCK,NPAS2 activates circadian gene expression
3 Recycling of bile acids and salts
4 PPARA activates gene expression
5 Import of palmitoyl-CoA into the mitochondrial matrix
6 YAP1- and WWTR1 (TAZ)-stimulated gene expression
7 Regulation of pyruvate dehydrogenase (PDH) complex
8 Endogenous sterols
9 Transcriptional activation of mitochondrial biogenesis
10 Activation of gene expression by SREBF (SREBP)
11 Transcriptional regulation of white adipocyte differentiation
12 Nuclear Receptor transcription pathway
13 Regulation of lipid metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
14 Circadian Clock
WikiPathways Vitamin A and Carotenoid Metabolism Click to Show/Hide
2 NRF2 pathway
3 Nuclear Receptors Meta-Pathway
4 Farnesoid X Receptor Pathway
5 PPAR Alpha Pathway
6 Vitamin D Receptor Pathway
7 Pregnane X Receptor pathway
8 Constitutive Androstane Receptor Pathway
9 Liver X Receptor Pathway
10 Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
11 Transcriptional Regulation of White Adipocyte Differentiation
12 YAP1- and WWTR1 (TAZ)-stimulated gene expression
13 Activation of Gene Expression by SREBP (SREBF)
14 Integrated Pancreatic Cancer Pathway
15 Adipogenesis
16 Circadian Clock
17 Nuclear Receptors
18 Vitamin D Metabolism
19 Nuclear Receptors in Lipid Metabolism and Toxicity
20 Mesodermal Commitment Pathway
21 Endoderm Differentiation
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2645).
Reference 2 Combination of alitretinoin and topical 5-fluorouracil in Darier disease. JAAD Case Rep. 2018 Dec 11;5(1):75-77.
Reference 3 Retinoic acid receptors and retinoid X receptors: interactions with endogenous retinoic acids. Proc Natl Acad Sci U S A. 1993 Jan 1;90(1):30-4.
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