MIY

(4S,4AS,5AR,12AS)-4,7-BIS(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2- CARBOXAMIDE

Created: 2006-06-09
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count60
Chiral Atom Count4
Bond Count63
Aromatic Bond Count6
2D diagram of MIY

Chemical Component Summary

Name(4S,4AS,5AR,12AS)-4,7-BIS(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2- CARBOXAMIDE
SynonymsMINOCYCLINE
Systematic Name (OpenEye OEToolkits)(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
FormulaC23 H27 N3 O7
Molecular Weight457.476
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(N)C1=C(O)C(N(C)C)C2CC4C(=C(O)C2(O)C1=O)C(=O)c3c(c(ccc3O)N(C)C)C4
SMILESCACTVS3.341CN(C)[CH]1[CH]2C[CH]3Cc4c(ccc(O)c4C(=O)C3=C(O)[C]2(O)C(=O)C(=C1O)C(N)=O)N(C)C
SMILESOpenEye OEToolkits1.5.0CN(C)c1ccc(c2c1CC3CC4C(C(=C(C(=O)C4(C(=C3C2=O)O)O)C(=O)N)O)N(C)C)O
Canonical SMILESCACTVS3.341 CN(C)[C@H]1[C@@H]2C[C@@H]3Cc4c(ccc(O)c4C(=O)C3=C(O)[C@]2(O)C(=O)C(=C1O)C(N)=O)N(C)C
Canonical SMILESOpenEye OEToolkits1.5.0 CN(C)c1ccc(c2c1C[C@H]3C[C@H]4[C@@H](C(=C(C(=O)[C@]4(C(=C3C2=O)O)O)C(=O)N)O)N(C)C)O
InChIInChI1.03 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
InChIKeyInChI1.03 DYKFCLLONBREIL-KVUCHLLUSA-N

Drug Info: DrugBank

DrugBank IDDB01017 
NameMinocycline
Groups
  • approved
  • investigational
DescriptionMinocycline was first described in the literacture in 1966.[A190681] It is a second generation tetracycline antibiotic that is active against gram-negative and gram-positive bacteria.[A190723] Like other semisynthetic tetracyclines, minocycline has modifications to carbons 7-9 on the D ring to generate higher efficacy than previous tetracyclines.[A190723] Minocycline was granted FDA approval on 30 June 1971.[L11695]
Synonyms
  • 7-Dimethylamino-6-demethyl-6-deoxytetracycline
  • Minocyclin
  • (4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  • Minocycline
  • Minocycline hydrochloride
Brand Names
  • Ximino
  • Minocin Cap 100mg
  • Enca 100mg
  • PMS-minocycline
  • Sandoz Minocycline
IndicationOral and topical minocycline are indicated to treat inflammatory lesions of acne vulgaris.[L11701,L11704,L11719] Subgingival microspheres are indicated as an adjunct treatment in the reduction of pocket depth in adults with periodontitis.[L11716] Oral and intravenous formulations are indicated to treat infections of susceptible microorganisms.[L11707,L11710,L11713] These include rickettsiae, _Mycoplasma pneumoniae_, _Chlamydia trachomatis_, _Chlamydophila psittaci_, _Chlamydia trachomatis_, _Ureaplasma urealyticum_, _Borrelia recurrentis_, _Haemophilus ducreyi_, _Yersinia pestis_, _Francisella tularensis_, _Vibrio cholerae_, _Campylobacter fetus_, _Brucella_ species, _Bartonella bacilliformis_, _Klebsiella granulomatis_, _Escherichia coli_, _Enterobacter aerogenes_, _Shigella_ species, _Acinetobacter_ species, _Haemophilus influenzae_, and _Kelbsiella_ species.[L11710]
Categories
  • Agents Causing Muscle Toxicity
  • Agents that produce neuromuscular block (indirect)
  • Alimentary Tract and Metabolism
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Topical Use
ATC-Code
  • D10AF07
  • J01AA08
  • J01AA20
  • A01AB23
CAS number10118-90-8

Drug Targets

NameTarget SequencePharmacological ActionActions
30S ribosomal protein S9MAENQYYGTGRRKSSAARVFIKPGNGKIVINQRSLEQYFGRETARMVVRQ...unknowninhibitor
30S ribosomal protein S4MARYLGPKLKLSRREGTDLFLKSGVRAIDTKCKIEQAPGQHGARKPRLSD...unknowninhibitor
16S ribosomal RNA-unknowninhibitor
Interleukin-1 betaMAEVPELASEMMAYYSGNEDDLFFEADGPKQMKCSFQDLDLCPLDGGIQL...unknownmodulator
Arachidonate 5-lipoxygenaseMPSYTVTVATGSQWFAGTDDYIYLSLVGSAGCSEKHLLDKPFYNDFERGA...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682