Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00699)
Name
Tretinoin
Synonyms    Click to Show/Hide the Synonyms of This API
Retinoic acid; tretinoin; 302-79-4; all-trans-Retinoic acid; Vitamin A acid; trans-Retinoic acid; 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; 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; MLS000028588; b-Retinoic acid; RETINOIC ACID, ALL TRANS; Tretinoine [INN-French]; Tretinoinum [INN-Latin]; Tretinoina [INN-Spanish]; Tretinoino [INN-Spanish]; CHEMBL38; NSC122758; Atragen; Retinova; SMR000058245; CHEBI:15367; 15-Apo-beta-caroten-15-oic acid; 5688UTC01R; Tretinoin (TN); beta-Ra; Acnavit [Denmark]; AGN 100335; 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]; 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; [3H]Retinoic acid; Renova (TN); CCRIS 3294; Avita (TN); HSDB 2169; SR-01000000239; 4759-48-2; EINECS 206-129-0; NSC 122758; BRN 2057223; Tretinoin (JAN/USP/INN); Retinoic acid, cis-9,trans-13-; TNP00194; BML2-E05; [3H]tretinoin; Tretinoin [USAN:USP:INN:BAN]; retinoic acid group; CAS-302-79-4; Prestwick_424; all-(E)-Retinoate; Tretinoine (French); ISORETINOIN; Retinoic acid, cis-; (5E)-Retinoic acid; [3H]Vitamin A acid; PubChem16466; 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; 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; ACT00012; BCP01405; US10188615, at-RA; Tox21_110812; Tox21_202330; Tox21_300305; Tox21_501061; All-trans Retinoic Acid (Tretinoin); CCG-39912; LMPR01090019; NSC759631; 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; BR-73126; HY-14649; Retinoic acid, >=98% (HPLC), powder; ST057075; SBI-0051031.P003; EU-0101061; 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; 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; 97950-17-9
Clinical Status
Approved
Disease Indication Acne vulgaris ICD-11: ED80 [1]
PubChem CID
444795
Formula
C20H28O2
Canonical SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=444795"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 300.4 Topological Polar Surface Area 37.3
XlogP 6.3 Complexity 567
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Tretinoin 10 mg capsule Click to Show/Hide the Full List of Formulation(s):          4 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
D&c yellow no. 10; Fd&c red no. 40; Alpha.-tocopherol; Fd&c blue no. 1; Fd&c blue no. 2; Indigotindisulfonate sodium; Butylated hydroxyanisole; Edetate disodium; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Polysorbate 80; Gelatin; Hydrogenated soybean oil; Shellac; Soybean oil; White wax
                   Dosage Form Oral Capsule
                   Company Barr Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Alpha-tocopherol DIG Info Glutathione S-transferase P (IC50 = 500 nM) [3]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [4]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [2]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Ascorbyl palmitate; Oleic acid; Sorbitol; Ammonia; Butylated hydroxyanisole; Edetate disodium; Ferric oxide red; Ferrosoferric oxide; Glycerin; Propylene glycol; Titanium dioxide; Lecithin, soybean; Medium-chain triglycerides; Gelatin; Hydrogenated soybean oil; Shellac; Soybean oil; Sunflower oil; Tocopherol; Yellow wax
                   Dosage Form Oral Capsule
                   Company Glenmark Pharmaceutials
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Oleic acid DIG Info Liver lipid-binding protein (Ki = 180 nM) [6]
Ascorbyl palmitate DIG Info Thiosulfate sulfurtransferase (IC50 = 53000 nM) [7]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [2]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [5]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [8]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxyanisole; Edetate disodium; Ferric oxide red; Ferric oxide yellow; Glycerin; Titanium dioxide; Water; Nitrogen; Lecithin, soybean; Medium-chain triglycerides; Alcohol; Gelatin; Soybean oil; Yellow wax
                   Dosage Form Oral Capsule
                   Company American Health Packaging; AvKARE; Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [2]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [5]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [8]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxyanisole; Edetate disodium; Ferric oxide red; Ferric oxide yellow; Glycerin; Titanium dioxide; Nitrogen; Lecithin, soybean; Medium-chain triglycerides; Alcohol; Gelatin; Soybean oil; Yellow wax
                   Dosage Form Oral Capsule
                   Company Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [2]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [5]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [8]
References
1 FDA label for approved tretinoin from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Reviewing Hit Discovery Literature for Difficult Targets: Glutathione Transferase Omega-1 as an Example. J Med Chem. 2018 Sep 13; 61(17):7448-7470.
4 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 Characterization of the drug binding specificity of rat liver fatty acid binding protein. J Med Chem. 2008 Jul 10; 51(13):3755-64.
7 HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules. Bioorg Med Chem Lett. 2019 May 1; 29(9):1106-1112.
8 Interactions between human multidrug resistance related protein (MRP2; ABCC2) and excipients commonly used in self-emulsifying drug delivery systems (SEDDS). Int J Pharm. 2013 Apr 15;447(1-2):192-8.

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