Sulfuric acid mono-((9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl) ester

ID: ALA494753

Cas Number: 481-97-0

PubChem CID: 3001028

Product Number: E610193, Order Now?

Max Phase: Approved

First Approval: 1977

Molecular Formula: C18H22O5S

Molecular Weight: 350.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Estrone Sulphate | Estrone sulfate|Estrone sulphate|Premarin|Estrone hydrogen sulfate|Estrone 3-sulfate|481-97-0|estrone-3-sulfate|estrone-3-sulphate|Conestoral|Estrone bisulfate|Estrone hemisulfate|evex|Hyhorin|Morestin|[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate|Par Estro|3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphate|Estrone, hydrogen sulfate|Estrone sulfate sodium|QTL48N278K|Sodium estrone 3-sulfate|CHEBI:17474|Show More⌵

Synonyms from Alternative Forms(18): Estropipate | Estrone sulfate piperazine salt | Piperazine estrone sulfate | Piperazine estrone sulphate | Sulestrex piperazine | NSC-758912 | Harmogen | Ogen | Ogen .625 | Ogen 1.25 | Ogen 2.5 | Ogen 5 | Ortho-est | Estrone sodium sulfate | Estrone sodium sulphate | Sodium estrone sulfate | Sodium estrone sulphate | NSC-18313

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(OS(=O)(=O)O)cc4CC[C@H]3[C@@H]1CCC2=O

Standard InChI:  InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1

Standard InChI Key:  JKKFKPJIXZFSSB-CBZIJGRNSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
   -3.1000   -2.2792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292    2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167    2.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    2.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -2.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208   -3.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -2.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    3.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1000    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750    3.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.2042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -0.1417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917    1.7625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 15  1  0
  7 18  1  0
  8  2  1  0
  9 10  1  0
 10  5  1  0
 11  3  1  0
 12 19  1  0
 13  1  1  0
 14  1  1  0
 15 23  2  0
 16  1  2  0
 17  1  2  0
 18 20  2  0
 19  7  1  0
 20 13  1  0
 21 11  1  0
 22  8  2  0
 23 20  1  0
  2 24  1  1
  5 25  1  6
  3 26  1  6
  4 27  1  1
  6  7  2  0
  4 12  1  0
  3  2  1  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA494753

   estrone-3-sulphate

2. Alternative Forms:

   

   ALA494753

   Estropipate
3. 

   ALA494753

   Potassium estrone sulfate
4. 

   ALA494753

   Estrone 3-sulfate sodium salt

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 350.44

Molecular Weight (Monoisotopic): 350.1188

AlogP: 3.29

#Rotatable Bonds: 2

Polar Surface Area: 80.67

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.75

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 1.46

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: 1.70

References

1. Chu GH, Peters A, Selcer KW, Li PK..  (1999)  Synthesis and sulfatase inhibitory activities of (E)- and (Z)-4-hydroxytamoxifen sulfamates.,  9  (2): [PMID:10021916] [10.1016/s0960-894x(98)00707-0]

2. Sarmiento M, Wu L, Keng YF, Song L, Luo Z, Huang Z, Wu GZ, Yuan AK, Zhang ZY..  (2000)  Structure-based discovery of small molecule inhibitors targeted to protein tyrosine phosphatase 1B.,  43  (2): [PMID:10649970] [10.1021/jm990329z]

3. Lapierre J, Ahmed V, Chen MJ, Ispahany M, Guillemette JG, Taylor SD..  (2004)  The difluoromethylene group as a replacement for the labile oxygen in steroid sulfates: a new approach to steroid sulfatase inhibitors.,  14  (1): [PMID:14684318] [10.1016/j.bmcl.2003.09.089]

4. Poirier D, Boivin RP..  (1998)  17 alpha-alkyl- or 17 alpha-substituted benzyl-17 beta-estradiols: a new family of estrone-sulfatase inhibitors.,  8  (14): [PMID:9873454] [10.1016/s0960-894x(98)00330-8]

5. Boivin RP, Luu-The V, Lachance R, Labrie F, Poirier D..  (2000)  Structure-activity relationships of 17alpha-derivatives of estradiol as inhibitors of steroid sulfatase.,  43  (23): [PMID:11087571] [10.1021/jm0001166]

6. Hamann LG, Meyer JH, Ruppar DA, Marschke KB, Lopez FJ, Allegretto EA, Karanewsky DS..  (2005)  Structure-activity relationships and sub-type selectivity in an oxabicyclic estrogen receptor alpha/beta agonist scaffold.,  15  (5): [PMID:15713407] [10.1016/j.bmcl.2004.12.077]

7. Pedersen JM, Matsson P, Bergström CA, Norinder U, Hoogstraate J, Artursson P..  (2008)  Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).,  51  (11): [PMID:18457386] [10.1021/jm7015683]

8. Kaler G, Truong DM, Khandelwal A, Nagle M, Eraly SA, Swaan PW, Nigam SK..  (2007)  Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.,  282  (33): [PMID:17553798] [10.1074/jbc.m703467200]

9. Puri N, Prakash O, Manoharlal R, Sharma M, Ghosh I, Prasad R..  (2010)  Analysis of physico-chemical properties of substrates of ABC and MFS multidrug transporters of pathogenic Candida albicans.,  45  (11): [PMID:20739103] [10.1016/j.ejmech.2010.07.050]

10. PubChem BioAssay data set, 

11. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

12. International Transporter Consortium, Giacomini KM, Huang SM, Tweedie DJ, Benet LZ, Brouwer KL, Chu X, Dahlin A, Evers R, Fischer V, Hillgren KM, Hoffmaster KA, Ishikawa T, Keppler D, Kim RB, Lee CA, Niemi M, Polli JW, Sugiyama Y, Swaan PW, Ware JA, Wright SH, Yee SW, Zamek-Gliszczynski MJ, Zhang L..  (2010)  Membrane transporters in drug development.,  9  (3): [PMID:20190787] [10.1038/nrd3028]

13. Bossuyt X, Müller M, Hagenbuch B, Meier PJ..  (1996)  Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver.,  276  (1): [PMID:8786566]

14. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T..  (2004)  Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier.,  309  (1): [PMID:14762099] [10.1124/jpet.103.063370]

15. Pang KS, Wang PJ, Chung AY, Wolkoff AW..  (1998)  The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein.,  28  (1): [PMID:9794920] [10.1002/hep.510280524]

16. Tohyama K, Kusuhara H, Sugiyama Y..  (2004)  Involvement of multispecific organic anion transporter, Oatp14 (Slc21a14), in the transport of thyroxine across the blood-brain barrier.,  145  (1): [PMID:15166123] [10.1210/en.2004-0058]

17. Nagata Y, Kusuhara H, Endou H, Sugiyama Y..  (2002)  Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.,  61  (1): [PMID:11961115] [10.1124/mol.61.5.982]

18. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H..  (2000)  Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.,  275  (1): [PMID:10660625] [10.1074/jbc.275.6.4507]

19. Eckhardt U, Schroeder A, Stieger B, Höchli M, Landmann L, Tynes R, Meier PJ, Hagenbuch B..  (1999)  Polyspecific substrate uptake by the hepatic organic anion transporter Oatp1 in stably transfected CHO cells.,  276  (1): [PMID:10198348] [10.1152/ajpgi.1999.276.4.g1037]

20. Noé B, Hagenbuch B, Stieger B, Meier PJ..  (1997)  Isolation of a multispecific organic anion and cardiac glycoside transporter from rat brain.,  94  (1): [PMID:9294213] [10.1073/pnas.94.19.10346]

21. Cui Y, König J, Leier I, Buchholz U, Keppler D..  (2001)  Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6.,  276  (1): [PMID:11134001] [10.1074/jbc.m004968200]

22. Hirohashi T, Suzuki H, Sugiyama Y..  (1999)  Characterization of the transport properties of cloned rat multidrug resistance-associated protein 3 (MRP3).,  274  (1): [PMID:10329726] [10.1074/jbc.274.21.15181]

23. Mori S, Takanaga H, Ohtsuki S, Deguchi T, Kang YS, Hosoya K, Terasaki T..  (2003)  Rat organic anion transporter 3 (rOAT3) is responsible for brain-to-blood efflux of homovanillic acid at the abluminal membrane of brain capillary endothelial cells.,  23  (1): [PMID:12679720] [10.1097/00004647-200304000-00007]

24. Suzuki M, Suzuki H, Sugimoto Y, Sugiyama Y..  (2003)  ABCG2 transports sulfated conjugates of steroids and xenobiotics.,  278  (1): [PMID:12682043] [10.1074/jbc.m212399200]

25. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H..  (1999)  Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.,  274  (1): [PMID:10224140] [10.1074/jbc.274.19.13675]

26. Youngblood GL, Sweet DH..  (2004)  Identification and functional assessment of the novel murine organic anion transporter Oat5 (Slc22a19) expressed in kidney.,  287  (1): [PMID:15068970] [10.1152/ajprenal.00012.2004]

27. Nozawa T, Tamai I, Sai Y, Nezu J, Tsuji A..  (2003)  Contribution of organic anion transporting polypeptide OATP-C to hepatic elimination of the opioid pentapeptide analogue [D-Ala2, D-Leu5]-enkephalin.,  55  (1): [PMID:12906759] [10.1211/0022357021440]

28. Cattori V, van Montfoort JE, Stieger B, Landmann L, Meijer DK, Winterhalter KH, Meier PJ, Hagenbuch B..  (2001)  Localization of organic anion transporting polypeptide 4 (Oatp4) in rat liver and comparison of its substrate specificity with Oatp1, Oatp2 and Oatp3.,  443  (1): [PMID:11713643] [10.1007/s004240100697]

29. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B..  (1998)  Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells.,  274  (1): [PMID:9486191] [10.1152/ajpgi.1998.274.2.g370]

30. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H..  (2001)  Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.,  59  (1): [PMID:11306713] [10.1124/mol.59.5.1277]

31. Bossuyt X, Müller M, Meier PJ..  (1996)  Multispecific amphipathic substrate transport by an organic anion transporter of human liver.,  25  (1): [PMID:8938553] [10.1016/s0168-8278(96)80246-7]

32. Hagenbuch B, Adler ID, Schmid TE..  (2000)  Molecular cloning and functional characterization of the mouse organic-anion-transporting polypeptide 1 (Oatp1) and mapping of the gene to chromosome X.,  345  (1): [PMID:10600646] [10.1042/0264-6021:3450115]

33. Imai Y, Asada S, Tsukahara S, Ishikawa E, Tsuruo T, Sugimoto Y..  (2003)  Breast cancer resistance protein exports sulfated estrogens but not free estrogens.,  64  (1): [PMID:12920197] [10.1124/mol.64.3.610]

34. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B..  (2001)  Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.,  120  (1): [PMID:11159893] [10.1053/gast.2001.21176]

35. Kullak-Ublick GA, Fisch T, Oswald M, Hagenbuch B, Meier PJ, Beuers U, Paumgartner G..  (1998)  Dehydroepiandrosterone sulfate (DHEAS): identification of a carrier protein in human liver and brain.,  424  (1): [PMID:9539145] [10.1016/s0014-5793(98)00168-9]

36. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y..  (2005)  Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B.,  33  (1): [PMID:15640378] [10.1124/dmd.104.002337]

37. Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I..  (2004)  Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human.,  308  (1): [PMID:14610227] [10.1124/jpet.103.060194]

38. Meier PJ, Eckhardt U, Schroeder A, Hagenbuch B, Stieger B..  (1997)  Substrate specificity of sinusoidal bile acid and organic anion uptake systems in rat and human liver.,  26  (1): [PMID:9398014] [10.1002/hep.510260641]

39. Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ..  (2002)  Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter.,  16  (1): [PMID:12351693] [10.1210/me.2001-0309]

40. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I..  (2003)  Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane.,  306  (1): [PMID:12724351] [10.1124/jpet.103.051300]

41. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A..  (2000)  Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family.,  273  (1): [PMID:10873595] [10.1006/bbrc.2000.2922]

42. Kontaxi M, Echkardt U, Hagenbuch B, Stieger B, Meier PJ, Petzinger E..  (1996)  Uptake of the mycotoxin ochratoxin A in liver cells occurs via the cloned organic anion transporting polypeptide.,  279  (1): [PMID:8968376]

43. Kouzuki H, Suzuki H, Ito K, Ohashi R, Sugiyama Y..  (1999)  Contribution of organic anion transporting polypeptide to uptake of its possible substrates into rat hepatocytes.,  288  (1): [PMID:9918568]

44. van Montfoort JE, Schmid TE, Adler ID, Meier PJ, Hagenbuch B..  (2002)  Functional characterization of the mouse organic-anion-transporting polypeptide 2.,  1564  (1): [PMID:12101011] [10.1016/s0005-2736(02)00445-5]

45. Sweet DH, Miller DS, Pritchard JB, Fujiwara Y, Beier DR, Nigam SK..  (2002)  Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.,  277  (1): [PMID:12011098] [10.1074/jbc.m203803200]

46. Nozawa T, Sugiura S, Nakajima M, Goto A, Yokoi T, Nezu J, Tsuji A, Tamai I..  (2004)  Involvement of organic anion transporting polypeptides in the transport of troglitazone sulfate: implications for understanding troglitazone hepatotoxicity.,  32  (1): [PMID:14977862] [10.1124/dmd.32.3.291]

47. Hirano M, Maeda K, Shitara Y, Sugiyama Y..  (2004)  Contribution of OATP2 (OATP1B1) and OATP8 (OATP1B3) to the hepatic uptake of pitavastatin in humans.,  311  (1): [PMID:15159445] [10.1124/jpet.104.068056]

48. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T..  (2004)  Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3.,  32  (1): [PMID:15100168] [10.1124/dmd.32.5.479]

49. Zelcer N, Reid G, Wielinga P, Kuil A, van der Heijden I, Schuetz JD, Borst P..  (2003)  Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4).,  371  (1): [PMID:12523936] [10.1042/bj20021886]

50. Lee TK, Koh AS, Cui Z, Pierce RH, Ballatori N..  (2003)  N-glycosylation controls functional activity of Oatp1, an organic anion transporter.,  285  (1): [PMID:12702494] [10.1152/ajpgi.00358.2002]

51. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y..  (2005)  Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein.,  314  (1): [PMID:15901800] [10.1124/jpet.105.085589]

52. Spears KJ, Ross J, Stenhouse A, Ward CJ, Goh LB, Wolf CR, Morgan P, Ayrton A, Friedberg TH..  (2005)  Directional trans-epithelial transport of organic anions in porcine LLC-PK1 cells that co-express human OATP1B1 (OATP-C) and MRP2.,  69  (1): [PMID:15652233] [10.1016/j.bcp.2004.09.026]

53. Chen ZS, Guo Y, Belinsky MG, Kotova E, Kruh GD..  (2004)  Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11).,  67  (1): [PMID:15537867] [10.1124/mol.104.007138]

54. Seward DJ, Koh AS, Boyer JL, Ballatori N..  (2003)  Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta.,  278  (1): [PMID:12719432] [10.1074/jbc.m301106200]

55. Tamai I, Nozawa T, Koshida M, Nezu J, Sai Y, Tsuji A..  (2001)  Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.,  18  (1): [PMID:11683238] [10.1023/a:1013077609227]

56. Gao B, Hagenbuch B, Kullak-Ublick GA, Benke D, Aguzzi A, Meier PJ..  (2000)  Organic anion-transporting polypeptides mediate transport of opioid peptides across blood-brain barrier.,  294  (1): [PMID:10871297]

57. Qian YM, Song WC, Cui H, Cole SP, Deeley RG..  (2001)  Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.,  276  (1): [PMID:11102445] [10.1074/jbc.m008251200]

58. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL..  (1996)  Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter.,  270  (1): [PMID:8779894] [10.1152/ajprenal.1996.270.2.f326]

59. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P..  (2012)  Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.,  55  (10): [PMID:22541068] [10.1021/jm300212s]

60. Carrigan CN, Patel SA, Cox HD, Bolstad ES, Gerdes JM, Smith WE, Bridges RJ, Thompson CM..  (2014)  The development of benzo- and naphtho-fused quinoline-2,4-dicarboxylic acids as vesicular glutamate transporter (VGLUT) inhibitors reveals a possible role for neuroactive steroids.,  24  (3): [PMID:24424130] [10.1016/j.bmcl.2013.12.086]

61. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

62. Liu X, Huang J, Sun Y, Zhan K, Zhang Z, Hong M..  (2013)  Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.,  41  (3): [PMID:23255551] [10.1124/dmd.112.047910]

63. Li J, Volpe DA, Wang Y, Zhang W, Bode C, Owen A, Hidalgo IJ..  (2011)  Use of transporter knockdown Caco-2 cells to investigate the in vitro efflux of statin drugs.,  39  (7): [PMID:21447733] [10.1124/dmd.111.038075]

64. Kimoto E, Chupka J, Xiao Y, Bi YA, Duignan DB..  (2011)  Characterization of digoxin uptake in sandwich-cultured human hepatocytes.,  39  (1): [PMID:20926619] [10.1124/dmd.110.034298]

65. Cheng Y, Vapurcuyan A, Shahidullah M, Aleksunes LM, Pelis RM..  (2012)  Expression of organic anion transporter 2 in the human kidney and its potential role in the tubular secretion of guanine-containing antiviral drugs.,  40  (3): [PMID:22190696] [10.1124/dmd.111.042036]

66. Zhang A, Wang C, Liu Q, Meng Q, Peng J, Sun H, Ma X, Huo X, Liu K..  (2013)  Involvement of organic anion-transporting polypeptides in the hepatic uptake of dioscin in rats and humans.,  41  (5): [PMID:23396419] [10.1124/dmd.112.049452]

67.  (2016)  7  (9): [10.1039/C6MD00235H]

68. Correia MSP, Ballet C, Meistermann H, Conway LP, Globisch D..  (2019)  Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.,  27  (6): [PMID:30738652] [10.1016/j.bmc.2019.01.031]

69. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database
• IMI-CARE SARS-CoV-2 Data