General Information of API (ID: D00836)
Name
Amlexanox
Synonyms    Click to Show/Hide the Synonyms of This API
amlexanox; 68302-57-8; Amoxanox; Aphthasol; 2-Amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid; Amlenanox; Amlexanoxum [Latin]; AA-673; Amlexanoxo [Spanish]; Amlexanoxo; Amlexanoxum; CHX 3673; AA 673; CHX-3673; UNII-BRL1C2459K; 2-amino-5-oxo-7-propan-2-ylchromeno[2,3-b]pyridine-3-carboxylic acid; 2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid; 2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acid; AA673;Amoxanox;CHX3673; BRL1C2459K; CHEBI:31205; 2-Amino-7-isopropyl-5-oxo-5H-chromeno-[2,3-b]pyridine-3-carboxylic acid; 2-amino-7-(1-methylethyl)-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid; MFCD00864790; 2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid; NCGC00167472-01; Elics; Amlexanox [USAN:INN:JAN]; DSSTox_CID_2595; 5H-(1)Benzopyrano(2,3-b)pyridine-3-carboxylic acid, 2-amino-7-(1-methylethyl)-5-oxo-; DSSTox_RID_76651; DSSTox_GSID_22595; Aptheal; Apthera; OraRinse; 2-Amino-7-isopropyl-5-oxochromeno[2,3-b]pyridine-3-carboxylic Acid; OraDisc A; Aphthasol (TN); ANW; SMR000466352; CAS-68302-57-8; CCRIS 2686; Solfa (TN); BRN 0556384; 4wbo; 5H-[1]Benzopyrano[2,3-b]pyridine-3-carboxylic acid, 2-amino-7-(1-methylethyl)-5-oxo-; Amlexanox [USAN:INN:BAN:JAN]; AA-673(Amlexanox); CHEMBL1096; SCHEMBL29642; ZINC928; MLS000759466; MLS001424059; MLS006010129; BIDD:GT0709; US10214536, Amlexanox; GTPL7113; Amlexanox (JP17/USAN/INN); Amlexanox, >=98% (HPLC); DTXSID2022595; BDBM357857; HMS2051F13; HMS2235M08; HMS3393F13; HMS3715B14; ACN-S001255; BCP28222; HY-B0713; Tox21_112476; ANW-44913; CA0192; s3648; AKOS015900498; Tox21_112476_1; AC-1192; CCG-100953; DB01025; DS-1396; NC00203; NCGC00167472-02; NCGC00167472-03; NCGC00167472-14; AK-72823; H834; AB0013295; FT-0641176; D01828; J90008; M-8361; AB00639947-06; AB00639947_08; 302A578; A836094; L001037; Q695611; Amlexanox, United States Pharmacopeia (USP) Reference Standard; 2-amino-5-oxo-7-propan-2-yl-3-[1]benzopyrano[2,3-b]pyridinecarboxylic acid; 2-Amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b] pyridine-3-carboxylic acid; 2-azanyl-5-oxidanylidene-7-propan-2-yl-chromeno[2,3-b]pyridine-3-carboxylic acid
Clinical Status
Approved
PubChem CID
2161
Formula
C16H14N2O4
Canonical SMILES
CC(C)C1=CC2=C(C=C1)OC3=NC(=C(C=C3C2=O)C(=O)O)N
InChI
1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21)
InChIKey
SGRYPYWGNKJSDL-UHFFFAOYSA-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=2161"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 298.29 Topological Polar Surface Area 103
XlogP 3.1 Complexity 467
Heavy Atom Count 22 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Amlexanox 2mg Patch Click to Show/Hide the Full List of Formulation(s):          1 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
Ethylcellulose; Fd&C Blue 1; Fd&C Red 40; Hydroxyethylcellulose; Hypromellose; Methylparaben; Modified Starch; Polycarbophil; Povidone; Propylene Glycol; Propylene Glycol Monostearate; Purified Water; Sodium Benzoate; Sodium Carboxymethylcellulose
                   Dosage Form Patch
                   Company Uluru
                   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) [1]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [4]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Carboxymethylcellulose sodium DIG Info Albendazole monooxygenase (EC50 = 12.6 uM) [6]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [6]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Propylene glycol monostearate DIG Info Multidrug resistance protein 1 (Inhibition ratio = 25 %) [7]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [8]
          Amlexanox 5% paste Click to Show/Hide the Full List of Formulation(s):          1 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
Benzyl Alcohol; Gelatin; Glyceryl Monostearate; Mineral Oil; Pectin; Petrolatum; Sodium Carboxymethylcellulose
                   Dosage Form Paste
                   Company Uluru
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [9]
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [10]
Carboxymethylcellulose sodium DIG Info Albendazole monooxygenase (EC50 = 12.6 uM) [6]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [6]
References
1 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
2 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.
3 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
4 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
7 Modulation of intestinal P-glycoprotein function by polyethylene glycols and their derivatives by in vitro transport and in situ absorption studies. Int J Pharm. 2006 Apr 26;313(1-2):49-56.
8 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
9 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
10 Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. J Nat Prod. 2002 Feb; 65(2):206-9.

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