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Substance Name: Methacycline [USAN:BAN]
RN: 914-00-1
UNII: IR235I7C5P
InChIKey: MHIGBKBJSQVXNH-IWVLMIASSA-N

Note

  • A broad-spectrum semisynthetic antibiotic related to TETRACYCLINE but excreted more slowly and maintaining effective blood levels for a more extended period.

Molecular Formula

  • C22-H22-N2-O8

Molecular Weight

  • 442.4218
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Mutation Data
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Names and Synonyms

Name of Substance

  • Metacycline [INN]
  • Methacycline
  • Methacycline [USAN:BAN]

MeSH Heading

  • Methacycline

Synonyms

  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-
  • 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
  • 6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline
  • 6-Deoxy-6-demethyl-6-methylene-5-oxytetracycline
  • 6-Methylene-5-hydroxytetracycline
  • 6-Methylene-5-oxytetracycline
  • 6-Methyleneoxytetracycline
  • Bialatan
  • EINECS 213-017-5
  • GS 2876
  • GS-2876
  • HSDB 3118
  • Metaciclina
  • Metaciclina [INN-Spanish]
  • Metacycline
  • Metacyclinum
  • Metacyclinum [INN-Latin]
  • Methacycline
  • Methacycline amphoteric
  • Methacycline base
  • Methacyclinum
  • Methylenecycline
  • Oxytetracycline, 6-methylene-
  • Rondomycin
  • Tri-methacycline
  • UNII-IR235I7C5P

Systematic Names

  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-
  • Metacycline

Registry Numbers

CAS Registry Number

  • 914-00-1

FDA UNII

  • IR235I7C5P

Related Registry Number

  • 3963-95-9 (mono-hydrochloride)

System Generated Number

  • 0000914001

Structure Descriptors

InChI

1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1

InChIKey

MHIGBKBJSQVXNH-IWVLMIASSA-N

Smiles

CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)c4cccc(c4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intraperitoneal 660mg/kg (660mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.370 (none)   EST
Water Solubility 7550 mg/L 21 EXP
Atmospheric OH Rate Constant 2.71E-10 cm3/molecule-sec 25 EST

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