Supplementary Material for - How Many Drugs Are Catecholics, by Da-Peng Yang, Hong-Fang Ji, Guang-Yan Tang, Wei Ren, Hong-Yu Zhang*, Molecules, 2007, 12, 878-884 Table S1. Catecholics identified from CMC. No CMC Number Name Structure Activity O H HO N 1 MCMC00000595 adrenalone CH3 adrenergic HO HO OH Chiral HO O OH antiviral; 2 MCMC00009836 aphloiol O OH HO antiinflammatory HO O OH Chiral N CH H 3 3 MCMC00000177 apomorphine HO emetic HO HO OH diagnostic aid; 4 MCMC00006456 arbutamine N OH cardiotonic H OH HO O antioxidant; 5 MCMC00010715 baicalein analgesic; HO OH O antiallergic OH O Chiral HO O O antiasthmatic; 6 MCMC00010411 baicalin OH O antiallergic HO OH O OH OH HO OH O H enzyme inhibitor 7 MCMC00000976 benserazide H2N N N (decarboxylase) H OH OH OH caffeic acid phenethyl antiviral; 8 MCMC00006778 ester enzyme inhibitor O O Molecules, 2007, 12, Molecules, 2007, 12, 878-884 2 Table S1. Cont. O OH enzyme inhibitor 9 MCMC00010571 carbidopa CH H N 3 (decarboxylase) HO NH2 OH HO OChiral O O N S N S antibiotic; 10 MCMC00006131 cefetecol H H H2N N N H antibacterial O O HO OH H HO O Chiral HO O 11 MCMC00010530 chf-1301 antiparkinsonian NH CH HO 2 3 OH Chiral HO antiviral; 12 MCMC00000898 cianidol HO O OH antineoplastic HO OH O O OH O O HO phagocyte stimulant; 13 MCMC00007713 cichoric acid O O OH HO antineoplastic HO HO O O HO 14 MCMC00009461 citromycetin O antibiotic HOO CH3 HO OH antispasmodic; 15 MCMC00004237 clofeverine O Cl anticholinergic N H H3C CH3 CH3 16 MCMC00003077 colterol N bronchodilator HO H OH HO HOHO O O 17 MCMC00001729 cynarine O choleretic HO O OH HO OH O OH Molecules, 2007, 12, Molecules, 2007, 12, 878-884 3 Table S1. Cont. O HO OH O 18 MCMC00006608 digalloyl trioleate HO ultraviolet screen O HO HO OH HO CH3 CH 3 antitussive; 19 MCMC00001167 dioxethedrin HO N adrenergic OH H HO CH3 20 MCMC00002622 dioxifedrine CH3 bronchodilator HO N OH H OH OH H C 21 MCMC00009077 dl-methyldopa 3 antihypertensive OH H2N O HO CH3 22 MCMC00003673 dobutamine HO N cardiotonic H OH H HO N 23 MCMC00003884 dopamantine O antiparkinsonian HO HNHO 2 24 MCMC00000060 dopamine adrenergic HO N N H 25 MCMC00005460 dopexamine H cardioprotective HO OH Chiral OH H O HO 26 MCMC00003277 droxidopa OH antiparkinsonian H NH2 HO OH O O OH 27 MCMC00001113 ellagic acid hemostatic HO O O OH Molecules, 2007, 12, Molecules, 2007, 12, 878-884 4 Table S1. Cont. O O + enzyme inhibitor N O N CH 3 (catechol-O-methyl- 28 MCMC00006466 entacapone HO H C transferase); N 3 OH antiparkinsonian Chiral HO bronchodilator; 29 MCMC00006922 epinephrine N adrenergic HO H OH OH OH HO O 30 MCMC00007320 eriodictyol bioflavanoid OH O O Chiral N OH O O OH O OH 31 MCMC00003555 ethoxazorutoside OH O antihemorrhagic O OH O O H3C OH OH HO OH HO OH HCHO 3 32 MCMC00001273 ethylnorepinephrine bronchodilator H2N O Chiral O CH3 33 MCMC00010602 etilevodopa NH antiparkinsonian HO 2 OH OH HO OH 34 MCMC00004116 exifone HO OH antiparkinsonian OH O H dopamine receptor N antagonist; 35 MCMC00004827 fenoldopam OH dopamine receptor Cl agonist; HO OH antihypertensive 18F Chiral NH 2 diagnostic aid (brain O 36 MCMC00007665 fluorodopa f 18 imaging); H HO OH diagnostic aid OH Molecules, 2007, 12, Molecules, 2007, 12, 878-884 5 Table S1. Cont. HO O O HO 37 MCMC00002916 folescutol capillary protectant N O O Chiral H H O O H OH O N O N CH3 N N CH antibiotic; H S 3 38 MCMC00005667 fomidacillin O N H N antibacterial O H3C HO OH O OH 39 MCMC00006710 gallic acid astringent HOHO OH H3C CH3 O H C OH OH3 spermaticide; HO insecticide; 40 MCMC00010223 gossypol OH OH antimalarial; HO CH3 O antioxidant H3C CH3 OH HO N HO H 41 MCMC00001935 hexoprenaline bronchodilator H N HO HO OH OH Chiral HO OH CH O 3 O OH 42 MCMC00006852 huangqioside-e O O sweetener O O OH HO OH OH OH HO HO OH HO 43 MCMC00001257 isoetharine bronchodilator H N CH3 CH3 CH3 Molecules, 2007, 12, Molecules, 2007, 12, 878-884 6 Table S1. Cont. OH H HO N CH 44 MCMC00002560 isoproterenol 3 adrenergic CH3 HO OH HO O OH 45 MCMC00001123 leucocianidol capillary protectant OH OH OH OH Chiral HO 46 MCMC00006244 levdobutamine cardiotonic H HO N CH3 H OH H Chiral N CH bronchodilator; 47 MCMC00000050 levisoprenaline HO 3 antiasthmatic CH3 HO O Chiral OH NH 2 48 MCMC00006962 levodopa HO antiparkinsonian OH Chiral NH2 HO CH3 vasoconstrictor; 49 MCMC00007083 levonordefrin adrenergic OH OH CH3 CH3 H H HO OH 50 MCMC00005851 masoprocol antineoplastic HO OH OHChiral H HO O OH antispasmodic; 51 MCMC00004738 meciadanol O CH3 H anticholinergic OH HO OH Chiral 52 MCMC00007071 methyldopa CH3 antihypertensive OH H2N O Molecules, 2007, 12, Molecules, 2007, 12, 878-884 7 Table S1. Cont. Chiral HO NH2 O CH 53 MCMC00001852 methyldopate 3 antihypertensive H C O HO 3 OH Chiral OH OH O O O CH O 3 54 MCMC00003289 monoxerutin O O antidote OH O OH OH HO OH OH OH O CH3 HO N CH 55 MCMC00002973 n-methyladrenalone 3 antineoplastic HO O + O N HO O 56 MCMC00006082 nitecapone antineoplastic HO H3C CH3 O HO 57 MCMC00002903 norbudrine N bronchodilator HO H HO OH CH3 NH 2 58 MCMC00002427 nordefrin HO vasoconstrictor OH OH Chiral HO 59 MCMC00000052 norepinephrine NH adrenergic HO 2 OH O Chiral HO CH O 3 O O O coronary HO O O OH vasodilator; CH 60 MCMC00010143 oleuropein 3 antispasmodic; antihypertensive OH OH HO NH2 61 MCMC00001601 oxidopamine adrenergic HO OH Molecules, 2007, 12, Molecules, 2007, 12, 878-884 8 Table S1. Cont. HO N HO vascular disorders 62 MCMC00001354 papaveroline (therapeutic) OH OH HO O HO 63 MCMC00003471 phenisonone CH3 bronchodilator H N CH3 H3C HO N HO 64 MCMC00002868 pipratecol N vasodilator HO H3C O HO O 65 MCMC00000711 propyl gallate HO antioxidant O HO CH3 O O OH 66 MCMC00000809 protokylol HO adrenergic N HO H CH3 OH HO O HO 67 MCMC00009540 quercetin antihemorrhagic OH HO O HO H3C H N 68 MCMC00005810 racepinephrine bronchodilator HO OH OH H 69 MCMC00003621 rimiterol bronchodilator N H HO OH OH Chiral OH CH HO O 3 OH O 70 MCMC00000892 rutin O O capillary protectant O OH OH O OH HO OH OH Molecules, 2007, 12, Molecules, 2007, 12, 878-884 9 Table S1. Cont. OH Chiral OH CH3 enzyme inhibitor 71 MCMC00007657 tetracyclic catechols1 (cholesteryl ester CH3 transfer protein) CH CH 3 H3C 3 OHChiral CH3 OH enzyme inhibitor H CH 72 MCMC00007656 tetracyclic catechols2 3 (cholesteryl ester transfer protein) CHH H3C 3 H N OH N N CNS stimulant; 73 MCMC00002703 theodrenaline H3C N antihypertensive O N O CH3 HO OH O O + N O enzyme inhibitor 74 MCMC00006484 tolcapone (catechol-O-methyl- HO CH3 OH transferase) CH3 O CH3 O bronchodilator; 75 MCMC00003539 tretoquinol O antiallergic HO H CH3 N HO Cl Chiral HO Vasodilator; N H HO dopamine receptor 76 MCMC00010810 (r)-(+)-fenoldopam agonist; antihypertensive HO HO H Chiral N CH 77 MCMC00010809 (r)-isoproterenol HO 3 antiasthmatic CH3 HO HO 1-(p-hydroxybenzyl)- N enzyme inhibitor HO H 78 MCMC00008199 6,7-dihydroxy-1,2,3,4- (dihydropteridine tetrahydroisoquin reductase enzyme ) OH Molecules, 2007, 12, Molecules, 2007, 12, 878-884 10 Table S2. Catecholic drugs recorded in US FDA database. Catecholic Drug name (usage/strength) Marketing status apomorphine (1) apokyn (injectable; subcutaneous/10MG/ML) prescription arbutamine (1) genesa (injectable; injection/0.05MG/ML) discontinued carbidopa (1) carbidopa and levodopa (tablet; oral/Multiple Strengths); discontinued (2) carbilev (tablet, for suspension; oral/10MG; 25MG; 100MG; 250MG); prescription (3) lodosyn (tablet; oral/25MG); prescription (4) parcopa (tablet, orally disintegrating; oral/10MG; 25MG; 100MG; prescription 250MG); (5) sinemet (tablet; oral/10MG; 25MG; 100MG; 250MG); prescription (6) sinemet cr (tablet, extended release; oral/25MG; 50MG; 100MG; prescription 200MG); (7) stalevo 100 (tablet; oral/25MG; 200MG; 100MG); prescription (8) stalevo 150 (tablet; oral/37.5MG; 200MG; 150MG); prescription (9) stalevo 50 (tablet; oral/12.5MG; 200MG; 50MG) prescription dobutamine (1) dobutamine hydrochloride (injectable; injection/EQ 12.5MG prescription BASE/ML; EQ 1.25GM BASE/100ML); (2) dobutamine hydrochloride in dextrose 5% (injectable; injection/EQ prescription 50MG BASE/100ML; EQ 100MG BASE/100ML; EQ 200MG BASE/200ML); (3) dobutamine hydrochloride in dextrose 5% in plastic container prescription (injectable; injection/Multiple Strengths); (4) dobutrex (injectable; injection/EQ 12.5MG BASE/ML) discontinued dopamine (1) dopamine hydrochloride (injectable; injection/Multiple Strengths); prescription (2) dopamine hydrochloride and dextrose 5%(injectable; prescription injection/40MG/100ML; 80MG/100ML; 160MG/100ML; 320MG/100ML); (3) dopamine hydrochloride and dextrose 5% in plastic container prescription (injectable; injection/40MG/100ML; 80MG/100ML; 160MG/100ML; 320MG/100ML); (4) dopamine hydrochloride in dextrose 5% (injectable; discontinued injection/1.6MG/ML); (5) dopamine hydrochloride in dextrose 5% in plastic container prescription (injectable; injection/Multiple Strengths); (6) intropin (injectable; injection/40MG/ML; 80MG/ML; 160MG/ML) discontinued entacapone (1) comtan (tablet; oral/200MG); prescription (2) stalevo 100 (tablet; oral/25MG; 200MG; 100MG); prescription (3) stalevo 150 (tablet; oral/37.5MG; 200MG; 150MG); prescription (4) stalevo 50 (tablet; oral/12.5MG; 200MG; 50MG) prescription epinephrine (1) alphacaine hydrochloride w/ epinephrine (injectable; discontinued injection/0.01MG/ML; 0.02MG/ML; 2%); (2) bronitin mist (aerosol, metered; inhalation/0.3MG/INH; 0.2MG/INH); over-the-counter (3) bronkaid mist (aerosol, metered; inhalation/0.25MG/INH); discontinued (4) bupivacaine hydrochloride and epinephrine (injectable; injection/ prescription 0.005MG/ML; 0.0091MG/ML; 0.25%; 0.5%; 0.75%); (5) bupivacaine hydrochloride w/epinephrine (injectable; prescription injection/0.0091MG/ML; 0.5%); (6) citanest forte (injectable; injection/0.005MG/ML; 4%); prescription (7) duranest (injectable; injection/Multiple Strengths); discontinued (8) epi e z pen jr (injectable; intramuscular/0.15MG/DELIVERY; discontinued 0.3MG/DELIVERY); (9) epinephrine ( aerosol, metered; inhalation/0.2MG/INH); over-the-counter (10) epipen (injectable; injection/0.15MG/DELIVERY; prescription 0.3MG/DELIVERY); (11) epipen e z pen (injectable; intramuscular/0.15MG/DELIVERY; discontinued 0.3MG/DELIVERY); (12) epipen jr.