MINOCYCLINE

ID: ALA1434

Max Phase: Approved

First Approval: 1971

Molecular Formula: C23H27N3O7

Molecular Weight: 457.48

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (1): Minocycline
Synonyms from Alternative Forms(1):

    Canonical SMILES:  CN(C)c1ccc(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C2=O

    Standard InChI:  InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1

    Standard InChI Key:  DYKFCLLONBREIL-KVUCHLLUSA-N

    Associated Targets(Human)

    Serum albumin 2651 Activities

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    Adrenergic receptor beta 1214 Activities

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    CCRF-CEM 65223 Activities

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    Homo sapiens 32628 Activities

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    Protein-arginine deiminase type-4 309 Activities

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    Proteinase-activated receptor 2 703 Activities

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    Serum 1292 Activities

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    Cytochrome P450 3A4 53859 Activities

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    Cytochrome P450 2D6 33882 Activities

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    Cytochrome P450 2C19 29246 Activities

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    Cytochrome P450 2C9 32119 Activities

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    Cytochrome P450 1A2 26471 Activities

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    Liver microsomes 16955 Activities

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    Solute carrier family 22 member 7 39 Activities

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    Solute carrier family 22 member 8 241 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Solute carrier family 22 member 11 82 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Solute carrier family 22 member 6 265 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glutaminase kidney isoform, mitochondrial 16997 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tyrosyl-DNA phosphodiesterase 1 345557 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cytochrome P450 2J2 258 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    N9 414 Activities

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    microRNA 21 64692 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Poly [ADP-ribose] polymerase 15 178 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Poly [ADP-ribose] polymerase 14 380 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Matrix metalloproteinase 3 3433 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Matrix metalloproteinase 7 1073 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Matrix metalloproteinase 9 6779 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D1 receptor 9720 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HERG 29587 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine transporter 10535 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Bile salt export pump 2311 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Estrogen receptor alpha 17718 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Acetylcholinesterase 18204 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Norepinephrine transporter 10102 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin transporter 12625 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alpha-2a adrenergic receptor 9450 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mu opioid receptor 19785 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine oxidase A 11911 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1a (5-HT1a) receptor 14969 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vascular endothelial growth factor receptor 2 20924 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Phosphodiesterase 3A 3309 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D3 receptor 14368 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Muscarinic acetylcholine receptor M2 10671 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thrombin 11687 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thromboxane A2 receptor 5717 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Adenosine A3 receptor 15931 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histamine H3 receptor 10389 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2b (5-HT2b) receptor 10323 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 1034 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Androgen Receptor 11781 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Progesterone receptor 8562 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cyclooxygenase-1 9233 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Phosphodiesterase 4A 1943 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alpha-1a adrenergic receptor 8359 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Muscarinic acetylcholine receptor M1 12690 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Multidrug translocase mdfA 30 Activities

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    Escherichia coli 133304 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Staphylococcus aureus 210822 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Enterococcus faecalis 29875 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Enterococcus 1748 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Enterococcus faecium 13803 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Candida parapsilosis 8521 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Burkholderia cepacia 649 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nocardia cyriacigeorgica 11 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nocardia farcinica 74 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nocardia otitidiscaviarum 9 Activities

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    Nocardia nova 9 Activities

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    Nocardia transvalensis 9 Activities

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    Nocardia carnea 11 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nocardia brasiliensis 50 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nocardia sp. 39 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycobacterium tuberculosis 203094 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus pyogenes 16140 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Neisseria meningitidis 411 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus pneumoniae 31063 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Human immunodeficiency virus type 1 integrase 9041 Activities

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    Human immunodeficiency virus 1 70413 Activities

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    Acinetobacter baumannii 41033 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycoplasmoides pneumoniae 351 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Staphylococcus epidermidis 22802 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Moraxella catarrhalis 3334 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Haemophilus influenzae 8812 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus intermedius 230 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Peptoniphilus asaccharolyticus 368 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Peptostreptococcus anaerobius 347 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Finegoldia magna 323 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Clostridium perfringens 1165 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cutibacterium acnes 887 Activities

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    Rattus norvegicus 775804 Activities

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    Signal transducer and activator of transcription 1 5 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Interferon regulatory factor 1 3 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Protein kinase C alpha 23 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus pasteurianus 62 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus equinus 217 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine oxidase A 498 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Acinetobacter 437 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Metamycoplasma hominis 88 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ureaplasma 3 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Plasmodium falciparum 966862 Activities

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    Salmonella enterica 1497 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Pseudomonas aeruginosa 123386 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Listeria monocytogenes 2626 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium amycolatum 49 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium jeikeium 106 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium pseudodiphtheriticum 105 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium striatum 66 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium urealyticum 43 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Prescottella equi 132 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium minutissimum 39 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium xerosis 106 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Klebsiella pneumoniae 43867 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Proteus mirabilis 3894 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corynebacterium sp. 83 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Staphylococcus 1598 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus sp. 'group A' 3417 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus sp. 'group B' 533 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycolicibacterium smegmatis 8003 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Streptococcus mitis 390 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Enterobacter cloacae 7976 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    RAW264.7 28094 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Acetylcholinesterase 12221 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cholinesterase 8742 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mus musculus 284745 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Leishmania donovani 89745 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypanosoma cruzi 99888 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypanosoma brucei rhodesiense 7991 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Klebsiella pneumoniae subsp. pneumoniae 55 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    BV-2 3710 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SARS-CoV-2 38078 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Salmonella typhimurium 15756 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Brugia malayi 1377 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Stenotrophomonas maltophilia 1743 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: YesChemical Probe: NoParenteral: Yes
    Molecule Type: Small moleculeTopical: YesFirst In Class: NoBlack Box: No
    Chirality: YesAvailability: YesProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 457.48Molecular Weight (Monoisotopic): 457.1849AlogP: 0.19#Rotatable Bonds: 3
    Polar Surface Area: 164.63Molecular Species: ACIDHBA: 9HBD: 5
    #RO5 Violations: 0HBA (Lipinski): 10HBD (Lipinski): 6#RO5 Violations (Lipinski): 1
    CX Acidic pKa: 2.90CX Basic pKa: 7.90CX LogP: -2.54CX LogD: -2.61
    Aromatic Rings: 1Heavy Atoms: 33QED Weighted: 0.40Np Likeness Score: 1.30

    References

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    10. Weigel LM, Donlan RM, Shin DH, Jensen B, Clark NC, McDougal LK, Zhu W, Musser KA, Thompson J, Kohlerschmidt D, Dumas N, Limberger RJ, Patel JB..  (2007)  High-level vancomycin-resistant Staphylococcus aureus isolates associated with a polymicrobial biofilm.,  51  (1): [PMID:17074796] [10.1128/aac.00576-06]
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    12. Zhou J, Chen Y, Tabibi S, Alba L, Garber E, Saiman L..  (2007)  Antimicrobial susceptibility and synergy studies of Burkholderia cepacia complex isolated from patients with cystic fibrosis.,  51  (3): [PMID:17158942] [10.1128/aac.00954-06]
    13. Cercenado E, Marín M, Sánchez-Martínez M, Cuevas O, Martínez-Alarcón J, Bouza E..  (2007)  In vitro activities of tigecycline and eight other antimicrobials against different Nocardia species identified by molecular methods.,  51  (3): [PMID:17194827] [10.1128/aac.01102-06]
    14. Izdebski R, Sadowy E, Fiett J, Grzesiowski P, Gniadkowski M, Hryniewicz W..  (2007)  Clonal diversity and resistance mechanisms in tetracycline-nonsusceptible Streptococcus pneumoniae isolates in Poland.,  51  (4): [PMID:17210772] [10.1128/aac.01384-06]
    15. Cho SH, Warit S, Wan B, Hwang CH, Pauli GF, Franzblau SG..  (2007)  Low-oxygen-recovery assay for high-throughput screening of compounds against nonreplicating Mycobacterium tuberculosis.,  51  (4): [PMID:17210775] [10.1128/aac.00055-06]
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    25. Peleg AY, Adams J, Paterson DL..  (2007)  Tigecycline Efflux as a Mechanism for Nonsusceptibility in Acinetobacter baumannii.,  51  (6): [PMID:17420217] [10.1128/aac.01198-06]
    26. Raad I, Hanna H, Jiang Y, Dvorak T, Reitzel R, Chaiban G, Sherertz R, Hachem R..  (2007)  Comparative activities of daptomycin, linezolid, and tigecycline against catheter-related methicillin-resistant Staphylococcus bacteremic isolates embedded in biofilm.,  51  (5): [PMID:17353249] [10.1128/aac.00350-06]
    27. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]
    28. Nikodemova M, Watters JJ, Jackson SJ, Yang SK, Duncan ID..  (2007)  Minocycline down-regulates MHC II expression in microglia and macrophages through inhibition of IRF-1 and protein kinase C (PKC)alpha/betaII.,  282  (20): [PMID:17395590] [10.1074/jbc.m611907200]
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