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Substance Name: Minocycline [USAN:INN:BAN]
RN: 10118-90-8
UNII: FYY3R43WGO
InChIKey: DYKFCLLONBREIL-KVUCHLLUSA-N

Note

  • A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.

Molecular Formula

  • C23-H27-N3-O7

Molecular Weight

  • 457.4803
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Natural Product

Names and Synonyms

Name of Substance

  • Minocycline
  • Minocycline [USAN:INN:BAN]

MeSH Heading

  • Minocycline

Synonyms

  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,12aalpha))-
  • 4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
  • 7-Dimethylamino-6-demethyl-6-deoxytetracycline
  • Borymycin
  • BRN 3077644
  • CL 59806
  • Dynacin
  • HSDB 3130
  • Minociclina
  • Minociclina [INN-Spanish]
  • Minocyclin
  • Minocycline
  • Minocyclinum
  • Minocyclinum [INN-Latin]
  • Minocyn
  • Minoz
  • NSC 141993
  • Tri-minocycline
  • UNII-FYY3R43WGO

Systematic Names

  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
  • 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,12aalpha))-

Registry Numbers

CAS Registry Number

  • 10118-90-8

FDA UNII

  • FYY3R43WGO

Other Registry Numbers

  • 1071761-03-9
  • 146440-73-5
  • 17175-40-5
  • 24058-90-0

Related Registry Number

  • 13614-98-7 (mono-hydrochloride)

System Generated Number

  • 0010118908

Structure Descriptors

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

InChIKey

DYKFCLLONBREIL-KVUCHLLUSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo oral 12mg/kg/2D-I (12mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE

GASTROINTESTINAL: NAUSEA OR VOMITING
Therapie. Vol. 38, Pg. 93, 1983.
man TDLo oral 343mg/kg/17W- (343mg/kg) BLOOD: EOSINOPHILIA

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"
American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
mouse LD50 intracrebral 38mg/kg (38mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES
Chemotherapy Vol. 26, Pg. 196, 1980.
mouse LD50 intraperitoneal 310mg/kg (310mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
mouse LD50 intravenous 140mg/kg (140mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
mouse LD50 oral 3100mg/kg (3100mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
women TDLo oral 8mg/kg (8mg/kg)   American Journal of Medicine. Vol. 109, Pg. 340, 2000.
women TDLo oral 8mg/kg (8mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" American Journal of Medicine. Vol. 109, Pg. 340, 2000.
women TDLo oral 28mg/kg/2W-I (28mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)"

BEHAVIORAL: HEADACHE
Annals of Internal Medicine. Vol. 127, Pg. 168, 1997.
women TDLo oral 100mg/kg (100mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: PROTEINURIS
British Medical Journal. Vol. 1, Pg. 524, 1979.
women TDLo oral 112mg/kg/4W-I (112mg/kg)   American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
women TDLo oral 112mg/kg/4W-I (112mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
women TDLo oral 730mg/kg/1Y-I (730mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ANOREXIA (HUMAN

LIVER: LIVER FUNCTION TESTS IMPAIRED
American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996.
women TDLo oral 1204mg/kg/86W (1204mg/kg) MUSCULOSKELETAL: JOINTS British Journal of Rheumatology. Vol. 33, Pg. 674, 1994.
women TDLo oral 17520mg/kg/12 (17520mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES
American Journal of Ophthalmology. Vol. 125, Pg. 396, 1998.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 0.05 (none)   EXP
Water Solubility 5.20E+04 mg/L 25 EXP
Vapor Pressure 3.71E-23 mm Hg 25 EST
Henry's Law Constant 1.53E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.17E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.