Natural Product (NP) Details

General Information of the NP (ID: NP0082)
Name
Tretinoin
Synonyms
Retinoic acid; tretinoin; 302-79-4; all-trans-Retinoic acid; Vitamin A acid; trans-Retinoic acid; ATRA; Airol; Retin-A; Vesanoid; Renova; All-trans Retinoic Acid; all-trans-Vitamin A acid; Dermairol; Aknoten; Aberel; Eudyna; Aknefug; Cordes vas; Epi-aberel; TRETINON; Tretin M; Atralin; all-trans-Vitamin A1 acid; all-trans-Tretinoin; Retionic acid; All Trans Retinoic Acid; Vitamin A1 acid, all-trans-; Retin-A Micro; beta-Retinoic acid; all-(E)-Retinoic acid; Vitamin A acid, all-trans-; Retinoate; Retinoic acid, all-trans-; Alltrans-retinoic acid; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; Retacnyl; Vesnaroid; NSC-122758; Ro 1-5488; Tretinoin, all-trans-; all trans-Retinoic acid; Retin A; Stieva-A; Tretinoine; Solage; all-trans-beta-Retinoic acid; Effederm; .beta.-Retinoic acid; Tretinoin/All-Trans Retinoic Acid; Aberela [Norway]; Avitoin [Norway]; Effederm [France]; MFCD00001551; UNII-5688UTC01R; A-Acido (Argentina); 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic acid; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; MLS000028588; b-Retinoic acid; RETINOIC ACID, ALL TRANS; Tretinoine [INN-French]; Tretinoinum [INN-Latin]; AT-RA; Tretinoina [INN-Spanish]; Tretinoino [INN-Spanish]; CHEMBL38; 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-; NSC122758; Atragen; Retinova; SMR000058245; CHEBI:15367; 15-Apo-beta-caroten-15-oic acid; 5688UTC01R; Tretinoin (TN); beta-Ra; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid; Acnavit [Denmark]; AGN 100335; REA; 9-cis-RA; Retin A (TN); NCGC00017280-10; Tretinoinum; Aberela; Acnavit; Avitoin; Betarretin; Tretinoina; Tretinoino; A-Vitaminsyre; all-trans-b-Retinoic acid; DSSTox_CID_1239; Cordes VAS [Germany]; A-Vitaminsyre [Denmark]; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL); DSSTox_RID_76031; DSSTox_GSID_21239; trans-Retinoate; beta-Retinoate; all-trans-Retinoic acid, 97%; tretinoine (French) (EINECS); cis-Retinoic acid; Acide retinoique (French) (DSL); Refissa; Nexret; Vitamin a acid, trans-; Retisol-A; Acid A Vit (Belgium, Netherlands); 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid; 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid; (11Z)-retinoic acid; (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; [3H]Retinoic acid; Renova (TN); CCRIS 3294; Avita (TN); HSDB 2169; SR-01000000239; EINECS 206-129-0; NSC 122758; BRN 2057223; Tretinoin (JAN/USP/INN); Retinoic acid, cis-9,trans-13-; TNP00194; BML2-E05; 1cbr; [3H]tretinoin; [All-E]-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; Tretinoin [USAN:USP:INN:BAN]; retinoic acid group; (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetr aenoic acid; CAS-302-79-4; Prestwick_424; all-(E)-Retinoate; Tretinoine (French); Retinoic acid, cis-; (5E)-Retinoic acid; [3H]Vitamin A acid; PubChem16466; 1n4h; CPD000058245; Retinoic acid all trans; 6-s-trans-retinoic acid; Vitamin-A-sA currencyure; Opera_ID_1055; Prestwick2_000257; Prestwick3_000257; Spectrum5_001746; Spectrum5_001933; acide retinoique (French); Vesanoid (TN) (Roche); Tretinoin - Retinoic Acid; bmse000562; UPCMLD-DP097; R 2625; Renova (0.02% cream); SCHEMBL3145; (9Z,13Z)-Retinoic acid; 3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid; Altreno (0.05% lotion); BIDD:PXR0081; Lopac0_001061; Avita (0.025% gel); BSPBio_000074; BSPBio_001500; MLS001076515; MLS002207234; MLS002222211; MLS002548861; MLS006010222; ARONIS25153; BIDD:GT0483; SPECTRUM1502016; 9-cis-retinoic acid (9cRA); [3H]RA; BPBio1_000082; cid_444795; GTPL2644; .beta.-all-trans-Retinoic acid; all-trans-retinoic acid (ATRA); DTXSID7021239; SCHEMBL19091395; BDBM31883; HMS502N05; QCR-120; BCPP000036; BDBM323588; HMS1361K22; HMS1568D16; HMS1791K22; HMS1921D14; HMS1989K22; HMS2089D20; HMS2092N11; HMS2095D16; HMS2236N03; HMS3259E11; HMS3263E04; HMS3402K22; HMS3411B09; HMS3675B09; HMS3712D16; Pharmakon1600-01502016; Retinoic acid, all-trans- (8CI); 124510-04-9; 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2E,4E,6Z,8E)-; ACT00012; BCP01405; US10188615, at-RA; Tox21_110812; Tox21_202330; Tox21_300305; Tox21_501061; All-trans Retinoic Acid (Tretinoin); CCG-39912; LMPR01090019; NSC759631; s1653; SBB065722; ZINC12358651; AKOS000280845; Tox21_110812_1; AB03039; AC-6824; CS-1269; DB00755; GS-3578; LP01061; NC00481; NSC-759631; SDCCGSBI-0051031.P004; IDI1_000903; IDI1_033970; NCGC00017280-05; NCGC00017280-06; NCGC00017280-07; NCGC00017280-08; NCGC00017280-09; NCGC00017280-12; NCGC00017280-15; NCGC00017280-16; NCGC00017280-17; NCGC00017280-18; NCGC00017280-19; NCGC00017280-20; NCGC00017280-23; NCGC00017280-38; NCGC00021808-04; NCGC00021808-05; NCGC00021808-06; NCGC00021808-07; NCGC00021808-09; NCGC00021808-11; NCGC00021808-14; NCGC00021808-15; NCGC00254179-01; NCGC00259879-01; NCGC00261746-01; trans-Retinoic acid; ; ; Retinoid analogues; BP-20401; HY-14649; Retinoic acid, >=98% (HPLC), powder; ST057075; SBI-0051031.P003; EU-0101061; R0064; SW203749-4; 02T794; 5914-EP2275412A1; 5914-EP2292576A2; A10944; C00777; D00094; J10054; Q29417; S-1635; 33998-EP2275420A1; 33998-EP2295055A2; 33998-EP2295416A2; 33998-EP2295426A1; 33998-EP2295427A1; 33998-EP2298748A2; 33998-EP2298764A1; 33998-EP2298765A1; 33998-EP2298768A1; 33998-EP2301928A1; 33998-EP2305642A2; 33998-EP2308833A2; 33998-EP2308861A1; 33998-EP2311453A1; 33998-EP2311808A1; 33998-EP2311829A1; 33998-EP2311840A1; AB00052318-15; AB00052318-16; AB00052318-17; AB00052318_18; AB00052318_19; L000833; Q-200610; SR-01000000239-3; SR-01000000239-4; SR-01000000239-6; SR-01000000239-7; BRD-K06926592-001-01-7; BRD-K71879491-001-15-0; BRD-K71879491-001-22-6; SR-01000000239-12; SR-01000000239-13; SR-01000000239-14; SR-01000000239-15; WLN: L6UTJ A1 B1U1Y1&U2U1Y1&U1VQ C1 C1; Tretinoin, European Pharmacopoeia (EP) Reference Standard; WLN: L6UTJ A1 B1U1Y1 & U2U1Y1 & U1VQ C1 C1; Tretinoin, United States Pharmacopeia (USP) Reference Standard; 3,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; Tretinoin, Pharmaceutical Secondary Standard; Certified Reference Material; (2E,4E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenoic acid; (4E,6E,8E)-9-(2,6,6-Trimethyl-1-cyclohexenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate; 2,4,6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 2,6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2E,4E,6E,8E,-nonatetraenoic acid; all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid; 2,4, 6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-, (2E, 4E, 6E, 8E)-; 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)--, (all trans)-; 2,4,6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all trans)-; 2,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid-, (all trans)-; 97950-17-9
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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 Acne vulgaris [ICD-11: ED80] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C20H28O2
PubChem CID
444795
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-YCNIQYBTSA-N
CAS Number
CAS 302-79-4
ChEBI ID
CHEBI:15367
Herb ID
HBIN046885
TTD Drug ID
D02DGU
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder 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
                    Molecule(s)
                    Regulation		 Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
                    In-vitro Model LT73 CVCL_VU37 Lung adenocarcinoma Homo sapiens
                    In-vivo Model Patient-Derived Xenograft Tumor Models were used in this study.
                    Experimental
                    Result(s)		 Combination treatment with All-Trans Retinoic Acid prevents cisplatin-induced enrichment of CD133+ tumor-initiating cells and reveals heterogeneity of cancer stem cell compartment in lung cancer.
          Atorvastatin      Cardiovascular disease     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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
                    In-vivo Model MOG35-55 in female C57BL/6 mice were used in this study.
                    Experimental
                    Result(s)		 Combined atorvastatin and ATRA have immunomodulatory synergistic benefits.
          Paricalcitol      Hyper-parathyroidism     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression SNAI1  Molecule Info 
Pathway MAP
Down-regulation Expression VIM  Molecule Info 
Pathway MAP
                    In-vivo Model The animal model was established by unilateral ureteral obstruction (UUO) in male CD-1 mice.
                    Experimental
                    Result(s)		 Combination therapy of paricalcitol and trandolapril had additive efficacy in retarding renal scar formation during obstructive nephropathy.
          Primaquin      Malaria     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
                    In-vivo Model C57BL/6 micemice were transtracheally instilled with 2*106 of Pc organisms in 50 uL sterile PBS.
                    Experimental
                    Result(s)		 All-trans retinoic acid in combination with primaquine clears pneumocystis infection.
          Daratumumab      Multiple myeloma     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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression NOTCH1  Molecule Info 
Pathway MAP
                    In-vitro Model MV4-11 CVCL_0064 Childhood acute monocytic leukemia Homo sapiens
OCI-AML-3 CVCL_1844 Adult acute myeloid leukemia Homo sapiens
MOLM-13 CVCL_2119 Adult acute myeloid leukemia Homo sapiens
U-937 CVCL_0007 Adult acute monocytic leukemia Homo sapiens
                    In-vivo Model For the leukemic model, 3.0 * 105 spleen cells from MV4-11-engrafted mice were injected intravenously into 75 NSG mice.
                    Experimental
                    Result(s)		 The combination of ATRA plus DARA induced Fc-dependent conjugate formation and cytotoxicity among AML blasts in vitro. Combination treatment also led to reduction in tumor volume and resulted in increased overall survival in murine engraftment models of AML.
          1,25-dihydroxyvitamin D3      Congenital alopecia     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 [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model HL-60 CVCL_0002 Adult acute myeloid leukemia Homo sapiens
                    Experimental
                    Result(s)		 Yomogin may be useful in combination with 1,25-(OH)(2) D(3) or all- trans-RA in the differentiation therapy for myeloid leukemias.
          Hydroquinone + Fluocinolone acetonide     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 [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 Combination therapy with hydroquinone, tretinoin, and fluocinolone is the most cost-effective treatment when compared with any of its dyads or with hydroquinone alone.
          Imiquimod + 5-fluorouracil     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 [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model A case report
                    Experimental
                    Result(s)		 Combination of imiquimod, 5-fluorouracil, and tretinoin is an effective viable treatment modality for treating melanoma in situ during a pandemic with telemedicine.
Target and Pathway
Target(s) Retinoic acid receptor gamma (RARG)  Molecule Info  [10]
Reactome Nuclear Receptor transcription pathway Click to Show/Hide
WikiPathways Vitamin A and Carotenoid Metabolism Click to Show/Hide
2 Nuclear Receptors in Lipid Metabolism and Toxicity
3 Mesodermal Commitment Pathway
4 Endoderm Differentiation
5 Nuclear Receptors
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: 2644).
Reference 2 Combination Treatment with All-Trans Retinoic Acid Prevents Cisplatin-Induced Enrichment of CD133+ Tumor-Initiating Cells and Reveals Heterogeneity of Cancer Stem Cell Compartment in Lung Cancer. J Thorac Oncol. 2015 Jul;10(7):1027-36.
Reference 3 Synergistic effects of atorvastatin and all-trans retinoic acid in ameliorating animal model of multiple sclerosis. Immunol Invest. 2014;43(1):54-68.
Reference 4 Combination therapy with paricalcitol and trandolapril reduces renal fibrosis in obstructive nephropathy. Kidney Int. 2009 Dec;76(12):1248-57.
Reference 5 All-trans retinoic acid in combination with primaquine clears pneumocystis infection. PLoS One. 2013;8(1):e53479.
Reference 6 Anti-leukemic effects of all-trans retinoic acid in combination with Daratumumab in acute myeloid leukemia. Int Immunol. 2018 Jul 24;30(8):375-383.
Reference 7 Synergistic induction of 1,25-dihydroxyvitamin D(3)- and all-trans-retinoic acid-induced differentiation of HL-60 leukemia cells by yomogin, a sesquiterpene lactone from Artemisia princeps. Planta Med. 2002 Oct;68(10):886-90.
Reference 8 Cost-effectiveness of a hydroquinone/tretinoin/fluocinolone acetonide cream combination in treating melasma in the United States. J Dermatolog Treat. 2010 Sep;21(5):276-81.
Reference 9 Treating Melanoma in Situ During a Pandemic with Telemedicine and a Combination of Imiquimod, 5-Fluorouracil, and Tretinoin. Dermatol Ther (Heidelb). 2021 Feb;11(1):307-314.
Reference 10 Targacept active conformation search: a new method for predicting the conformation of a ligand bound to its protein target. J Med Chem. 2004 Dec 30;47(27):6831-9.
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