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Substance Name: Methacycline hydrochloride [USP]
RN: 3963-95-9
UNII: 9GJ0N7ZAP0
InChIKey: VZQARNDJLLWXGL-CCHMMTNSSA-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.Cl-H

Molecular Weight

  • 478.8827
 

Classification Codes

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

Name of Substance

  • Methacycline hydrochloride [USP]

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-, monohydrochloride, (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 monohydrochloride
  • Adriamicina
  • Ciclobiotic
  • EINECS 223-568-3
  • Germiciclin
  • Globociclina
  • Londomycin
  • Megamycine
  • Metacycline hydrochloride
  • Metadomus
  • Methacycline HCl
  • Methacycline hydrochloride
  • Methacycline monohydrochloride
  • Metilenbiotic
  • NSC 356465
  • Optimycin
  • Physiomycine
  • Rindex
  • Rondomycin
  • UNII-9GJ0N7ZAP0

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

Superlist Name

  • Methacycline hydrochloride

Registry Numbers

CAS Registry Number

  • 3963-95-9

FDA UNII

  • 9GJ0N7ZAP0

Other Registry Numbers

  • 101813-12-1
  • 2507-30-4
  • 60080-37-7
  • 857212-11-4

Related Registry Number

  • 914-00-1 (Parent)

System Generated Number

  • 0003963959

Molecular Formulas

Molecular Formula

  • C22-H22-N2-O8.Cl-H

Molecular Formula Fragments

  • C22-H22-N2-O8
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C22H22N2O8.ClH/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);1H/t10-,14-,15+,17+,22+;/m1./s1

InChIKey

VZQARNDJLLWXGL-CCHMMTNSSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 288mg/kg (288mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
mouse LD50 intravenous 193mg/kg (193mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.
mouse LD50 oral 3450mg/kg (3450mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.
rat LD50 intraperitoneal 252mg/kg (252mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 202mg/kg (202mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.
rat LD50 oral > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. 6, Pg. 818, 1982.