Details of the Drug Inactive Ingredient (DIG)

General Information of DIG (ID: E0M1QY)
DIG Name
Caffeine
Synonyms    Click to Show/Hide the Synonyms of This DIG
caffeine; 58-08-2; 1,3,7-Trimethylxanthine; Guaranine; Thein; Methyltheobromine; Cafeina; Theine; Koffein; Mateina; Alert-pep; Caffein; Cafipel; Coffeine; Refresh'n; Caffedrine; Stim; Cafamil; Cafecon; Caffine; Dexitac; Nodaca; Anhydrous caffeine; No-Doz; Eldiatric C; 7-Methyltheophylline; Hycomine; Organex; Vivarin; Nix Nap; Methyltheobromide; 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; Coffein; Phensal; Caffeine, synthetic; Quick-Pep; Coffeinum; Tirend; 1,3,7-Trimethyl-2,6-dioxopurine; Theophylline, 7-methyl; DHCplus; Tri-Aqua; 1,3,7-Trimethylpurine-2,6-dione; 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-; Kofein; Miudol; Caffeine, anhydrous; Theobromine, 1-methyl-; Propoxyphene Compound 65; 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione; Kofein [Czech]; Coffein [German]; Koffein [German]; 1-methyltheobromine; Caffeine (natural); Xanthine, 1,3,7-trimethyl; Caffeina [Italian]; Theophylline Me; Methylxanthine theophylline; Theobromine Me; NCI-C02733; SK-65 Compound; Anacin; Anacin Maximum Strength; P-A-C Analgesic Tablets; C8H10N4O2; HSDB 36; FEMA No. 2224; BRN 0017705; 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; NSC 5036; A.S.A. and Codeine Compound; UNII-3G6A5W338E; 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione; AI3-20154; MFCD00005758; CHEMBL113; CFF; CHEBI:27732; 3G6A5W338E; NSC-5036; caffenium; SK 65 Compound; Caffeina; DSSTox_CID_232; Caffeine [BAN:JAN]; CAFFEINE-D3; DSSTox_RID_75448; DSSTox_GSID_20232; 1,3,7-trimethyl-1,3,7-trihydropurine-2,6-dione; cafeine; peyona; teina; CAS-58-08-2; Caffeine (USP); SMR000326667; CCRIS 1314; 72238-85-8; SR-01000075187; Anhydrous caffeine (TN); EINECS 200-362-1; Monomethyl derivative of Theophylline; Caffeine [USP:BAN:JAN]; Anhydrous caffeine (JP15); Caffeine, 98.5%, specified according to the req. of USP/BP; 1gfz; Caffeine, BioXtra; TNP00310; Caffeine-[d9]; Monohydrate Caffeine; Respia (TN); 1-methyl-Theobromine; 7-methyl Theophylline; PubChem9436; 202282-98-2; 78072-66-9; Cafergot (Salt/Mix); Caffeine-[13C3]; 1,7-Trimethylxanthine; Spectrum_001301; 1l5q; 1l7x; 2a3b; 3g6m; 3,7-dihydro-1,3,7-trimethyl-1H-purine; Xanthine,3,7-trimethyl; Theine, methyltheobromine; Spectrum2_001261; Spectrum3_000321; Spectrum4_001782; Spectrum5_000423; Lopac-C-0750; bmse000206; MolMap_000054; Probes1_000150; Probes2_000128; C 0750; EC 200-362-1; SCHEMBL5671; Anhydrous caffeine (JP17); NCIOpen2_008255; BIDD:PXR0172; Lopac0_000228; 1, 3, 7-Trimethylxanthine; BSPBio_001921; GTPL407; KBioGR_002325; KBioSS_001781; 5-26-13-00558 (Beilstein Handbook Reference); MLS001055341; MLS001056714; MLS001066409; ARONIS25359; BIDD:ER0554; BIDD:GT0632; Caffeine, 1mg/ml in methanol; DivK1c_000730; SPECTRUM1500155; CU-01000012617-3; SPBio_001222; Caffeine melting point standard; MEGxp0_001350; ZINC1084; 1,3,7-trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine; component of Dilone (Salt/Mix); DTXSID0020232; 1,7-Trimethyl-2,6-dioxopurine; ACon1_000085; BDBM10849; HMS502E12; KBio1_000730; KBio2_001781; KBio2_004349; KBio2_006917; KBio3_001141; Caffeine 1.0 mg/ml in Methanol; NSC5036; Caffeine, powder, ReagentPlus(R); component of Percodan (Salt/Mix); NINDS_000730; Bio1_000473; Bio1_000962; Bio1_001451; HMS1920I09; HMS2091O11; HMS2232M13; HMS3260N17; HMS3372J18; HMS3435F10; HMS3715D13; Pharmakon1600-01500155; NoDoz Caplets and Chewable Tablets; Caffeine 10 microg/mL in Methanol; CS-M0795; Tox21_201685; Tox21_300010; Tox21_500228; BBL016491; caffeine (1,3,7-trimethylxanthine); Caffeine 100 microg/mL in Methanol; CCG-38825; NSC755917; PDSP1_001016; PDSP1_001235; PDSP2_001000; PDSP2_001219; SBB006474; STK177283; Propoxyphene Compound 65 (Salt/Mix); AKOS000121334; 5-26-13-00558 (Beilstein); ACN-034787; Bayer Select Headache Pain (Salt/Mix); Caffeine, anhydrous, 99%, FCC, FG; DB00201; LP00228; MCULE-3362813910; NSC-755917; SDCCGMLS-0064595.P001; SDCCGMLS-0064595.P002; SDCCGSBI-0050216.P005; IDI1_000730; 3,3,7-trimethyl-1H-purine-2,6-dione; NCGC00015208-01; NCGC00015208-02; NCGC00015208-03; NCGC00015208-04; NCGC00015208-05; NCGC00015208-06; NCGC00015208-07; NCGC00015208-08; NCGC00015208-10; NCGC00015208-11; NCGC00015208-12; NCGC00015208-13; NCGC00015208-14; NCGC00015208-15; NCGC00015208-16; NCGC00015208-17; NCGC00015208-18; NCGC00015208-20; NCGC00015208-29; NCGC00090699-01; NCGC00090699-02; NCGC00090699-03; NCGC00090699-04; NCGC00090699-05; NCGC00090699-06; NCGC00090699-07; NCGC00090699-08; NCGC00090699-09; NCGC00168808-01; NCGC00168808-02; NCGC00254057-01; NCGC00259234-01; NCGC00260913-01; AC-12774; AS-15340; Caffeine, SAJ special grade, >=98.5%; component of P-A-C Compound (Salt/Mix); O926; ST057528; component of A.S.A. Compound (Salt/Mix); SBI-0050216.P004; DB-023002; WLN: T56 BN DN FNVNVJ B1 F1 H1; EU-0100228; FT-0664195; H2815; N1379; N2379; 3378-EP2269610A2; 3378-EP2275420A1; 3378-EP2277848A1; 3378-EP2277867A2; 3378-EP2280003A2; 3378-EP2284160A1; 3378-EP2289510A1; 3378-EP2295409A1; 3378-EP2295434A2; 3378-EP2301937A1; 3378-EP2305219A1; 3378-EP2305662A1; 3378-EP2305671A1; 3378-EP2305677A1; 3378-EP2305682A1; 3378-EP2305695A2; 3378-EP2305696A2; 3378-EP2305697A2; 3378-EP2305698A2; 3378-EP2308562A2; 3378-EP2308840A1; 3378-EP2308867A2; 3378-EP2308870A2; 3378-EP2308879A1; 3378-EP2311801A1; 3378-EP2311802A1; 3378-EP2311803A1; 3378-EP2311806A2; 3378-EP2311808A1; 3378-EP2311829A1; 3378-EP2311842A2; 3378-EP2314588A1; 3378-EP2314590A1; 3378-EP2314593A1; 3378-EP2316457A1; 3378-EP2316458A1; 3378-EP2316825A1; 3378-EP2316826A1; 3378-EP2316827A1; 3378-EP2316828A1; 3378-EP2371814A1; BIM-0050216.0001; C07481; D00528; Q60235; 1,3,7-trimethyl-3,7-dihydropurine-2,6-dione; 1H-Purine-2, 3,7-dihydro-1,3,7-trimethyl-; AB00051930-09; AB00051930_10; Caffeine, purum, anhydrous, >=99.0% (HPLC); 3,7-dihydro-1,3,7-trimethyl-1H-purine (9CI); Caffeine, anhydrous, tested according to Ph.Eur.; L000155; 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion; Caffeine, Sigma Reference Standard, vial of 250 mg; SR-01000075187-1; SR-01000075187-4; SR-01000075187-7; SR-01000075187-8; BRD-K02404261-001-02-7; BRD-K02404261-001-03-5; BRD-K02404261-001-07-6; Caffeine, certified reference material, TraceCERT(R); Caffeine, meets USP testing specifications, anhydrous; Melting point standard 235-237C, analytical standard; 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione #; Caffeine, British Pharmacopoeia (BP) Reference Standard; Caffeine, European Pharmacopoeia (EP) Reference Standard; F3371-0262; Z112207564; Caffeine 2000 microg/mL in Water:Methanol (81:19 g/g); 07E4FB58-FD79-4175-8E3D-05BF96954522; 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion (coffein); Caffeine solution, analytical standard, 1.0 mg/mL in methanol; Caffeine, United States Pharmacopeia (USP) Reference Standard; Caffeine, Pharmaceutical Secondary Standard; Certified Reference Material; Caffeine for system suitability, European Pharmacopoeia (EP) Reference Standard; Caffeine melting point standard, United States Pharmacopeia (USP) Reference Standard; Caffeine solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material; 114303-55-8; Caffeine Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material; Caffeine, PharmaGrade, EP, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production; Mettler-Toledo Calibration substance ME 18872, Caffeine, analytical standard, for the calibration of the thermosystem 900, traceable to primary standards (LGC)
DIG Function
Other agent
PubChem CID
2519
Formula
C8H10N4O2
Canonical SMILES
CN1C=NC2=C1C(=O)N(C(=O)N2C)C
InChI
1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChIKey
RYYVLZVUVIJVGH-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This DIG
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=2519"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 194.19 Topological Polar Surface Area 58.4
XlogP -0.1 Complexity 293
Heavy Atom Count 14 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Full List of Biological Targets of DIG (DBTs) Regulated by This DIG
      G-protein coupled receptor (GPCR)
            DBT Name: Adenosine receptor (ADOR) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 15000 nM (tested by experiment) [1]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA1R_RAT ; AA2AR_RAT ; AA2BR_RAT ; AA3R_RAT
            DBT Name: Adenosine receptor A1 (AA1R) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment (1) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki > 10000 nM (tested by experiment) [2]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AA1R_HUMAN
               Experiment (2) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 130000 nM (tested by experiment) [1]
                    Tested Species Bos taurus (Bovine)
                    UniProt ID AA1R_BOVIN
               Experiment (3) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 100000 nM (tested by experiment) [3]
                    Tested Species Cavia porcellus (Guinea pig)
                    UniProt ID AA1R_CAVPO
               Experiment (4) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki > 10000 nM (tested by experiment) [2]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA1R_RAT
            DBT Name: Adenosine receptor A2 (ADORA2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 27000 nM (tested by experiment) [4]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA2AR_RAT ; AA2BR_RAT
            DBT Name: Adenosine receptor A2a (AA2AR) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment (1) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 2480 nM (tested by experiment) [5]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AA2AR_HUMAN
               Experiment (2) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 50000 nM (tested by experiment) [6]
                    Tested Species Cavia porcellus (Guinea pig)
                    UniProt ID AA2AR_CAVPO
               Experiment (3) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 9400 nM (tested by experiment) [7]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA2AR_RAT
            DBT Name: Adenosine receptor A2b (AA2BR) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment (1) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 10000 nM (tested by experiment) [8]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AA2BR_HUMAN
               Experiment (2) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 23000 nM (tested by experiment) [2]
                    Tested Species Mus musculus (Mouse)
                    UniProt ID AA2BR_MOUSE
               Experiment (3) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 30000 nM (tested by experiment) [2]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA2BR_RAT
            DBT Name: Adenosine receptor A3 (AA3R) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment (1) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki = 13300 nM (tested by experiment) [9]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AA3R_HUMAN
               Experiment (2) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity Ki > 100000 nM (tested by experiment) [10]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID AA3R_RAT
      Oxidoreductase (ORase)
            DBT Name: Monoamine oxidase A (MAO-A) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 50000 nM (tested by experiment) [11]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AOFA_HUMAN
            DBT Name: Monoamine oxidase B (MAO-B) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 50000 nM (tested by experiment) [11]
                    Tested Species Homo sapiens (Human)
                    UniProt ID AOFB_HUMAN
      Transferase (TFase)
            DBT Name: Myophosphorylase (PYGM) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment (1) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 114000 nM (tested by experiment) [12]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PYGM_HUMAN
               Experiment (2) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 74900 nM (tested by experiment) [13]
                    Tested Species Oryctolagus cuniculus (Rabbit)
                    UniProt ID PYGM_RABIT
               Experiment (3) for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 182000 nM (tested by experiment) [14]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID PYGM_RAT
            DBT Name: PI3-kinase alpha (PIK3CA) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 400000 nM (tested by experiment) [15]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PK3CA_HUMAN
            DBT Name: PI3-kinase beta (PIK3CB) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 400000 nM (tested by experiment) [15]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PK3CB_HUMAN
            DBT Name: PI3-kinase delta (PIK3CD) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 75000 nM (tested by experiment) [15]
                    Tested Species Homo sapiens (Human)
                    UniProt ID PK3CD_HUMAN
      Hydrolase (HDase)
            DBT Name: Acetylcholinesterase (ACHE) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 7250 nM (tested by experiment) [16]
                    Tested Species Homo sapiens (Human)
                    UniProt ID ACES_HUMAN
            DBT Name: Cholinesterase (BCHE) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 > 50000 nM (tested by experiment) [16]
                    Tested Species Homo sapiens (Human)
                    UniProt ID CHLE_HUMAN
            DBT Name: Phosphodiesterase 1 (PDE1) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 70000 nM (tested by experiment) [17]
                    Tested Species Rattus norvegicus (Rat)
                    UniProt ID PDE1B_RAT ; PDE1C_RAT
      Primary active transporter (PAT)
            DBT Name: Multidrug resistance protein 3 (ABCC3) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 133000 nM (tested by experiment) [18]
                    Tested Species Homo sapiens (Human)
                    UniProt ID MRP3_HUMAN
            DBT Name: Bile salt export pump (BSEP) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 133000 nM (tested by experiment) [18]
                    Tested Species Homo sapiens (Human)
                    UniProt ID ABCBB_HUMAN
            DBT Name: Multidrug resistance protein 4 (ABCC4) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 133000 nM (tested by experiment) [18]
                    Tested Species Homo sapiens (Human)
                    UniProt ID MRP4_HUMAN
            DBT Name: Multidrug resistance protein 2 (ABCC2) Click to Show/Hide
               Detailed Information DBT Info click to show the detail info of this DBT
               Experiment for Assessing the Biological Activity of the Studied DIG on This DBT
                    Biological Activity IC50 = 133000 nM (tested by experiment) [18]
                    Tested Species Homo sapiens (Human)
                    UniProt ID MRP2_HUMAN
References
1 Adenosine receptors: targets for future drugs. J Med Chem. 1982 Mar; 25(3):197-207.
2 Fluorescent-Labeled Selective Adenosine A 2B Receptor Antagonist Enables Competition Binding Assay by Flow Cytometry. J Med Chem. 2018 May 24; 61(10):4301-4316.
3 8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors. J Med Chem. 1992 Mar 6; 35(5):924-30.
4 8-(Dicyclopropylmethyl)-1,3-dipropylxanthine: a potent and selective adenosine A1 antagonist with renal protective and diuretic activities. J Med Chem. 1991 Jan; 34(1):466-9.
5 Fluorescent ligands for adenosine receptors. Bioorg Med Chem Lett. 2013 Jan 1; 23(1):26-36.
6 Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors. J Med Chem. 1986 Jul; 29(7):1305-8.
7 Bioactive pyridoacridine alkaloids from the micronesian sponge Oceanapia sp. J Nat Prod. 1998 Feb; 61(2):301-5.
8 Novel non-xanthine antagonist of the A 2B adenosine receptor: From HTS hit to lead structure. Eur J Med Chem. 2019 Feb 1; 163:763-778.
9 1,3-Dialkyl-substituted tetrahydropyrimido[1,2-f]purine-2,4-diones as multiple target drugs for the potential treatment of neurodegenerative diseases. Bioorg Med Chem. 2013 Dec 1; 21(23):7435-52.
10 Adenosine A2A receptor as a drug discovery target. J Med Chem. 2014 May 8; 57(9):3623-50.
11 8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors. Bioorg Med Chem. 2016 Nov 1; 24(21):5462-5480.
12 Pentacyclic triterpenes. Part 1: the first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorg Med Chem Lett. 2005 Nov 15; 15(22):4944-8.
13 Terpenoids. III: Synthesis and biological evaluation of 23-hydroxybetulinic acid derivatives as novel inhibitors of glycogen phosphorylase. Bioorg Med Chem Lett. 2009 Dec 15; 19(24):6966-9.
14 Discovery of new nanomolar inhibitors of GPa: Extension of 2-oxo-1,2-dihydropyridinyl-3-yl amide-based GPa inhibitors. Eur J Med Chem. 2017 Feb 15; 127:341-356.
15 Small molecules targeting phosphoinositide 3-kinases. Med Chem Comm. (2012) 3:1337-1355.
16 Selective inhibition of human acetylcholinesterase by xanthine derivatives: in vitro inhibition and molecular modeling investigations. Bioorg Med Chem Lett. 2013 Aug 1; 23(15):4336-41.
17 4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants. J Med Chem. 1990 Aug; 33(8):2240-54.
18 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov; 136(1):216-41.

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