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Substance Name: Demeclocycline [USP:INN:BAN]
RN: 127-33-3
UNII: 5R5W9ICI6O
InChIKey: FMTDIUIBLCQGJB-SEYHBJAFSA-N

Note

  • A TETRACYCLINE analog having a 7-chloro and a 6-methyl. Because it is excreted more slowly than TETRACYCLINE, it maintains effective blood levels for longer periods of time.

Molecular Formula

  • C21-H21-Cl-N2-O8

Molecular Weight

  • 464.8559
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Demeclocycline
  • Demeclocycline [USP:INN:BAN]

MeSH Heading

  • Demeclocycline

Synonyms

  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-
  • 6-Demethyl-7-chlorotetracycline
  • 6-Demethyl-7-chlortetracycline
  • 6-Demethylchlorotetracycline
  • 6-Demethylchlortetracycline
  • 6-Demetil-7-clorotetraciclina
  • 6-Demetil-7-clorotetraciclina [Italian]
  • 7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide
  • 7-Chloro-6-demethyltetracycline
  • Bioterciclin
  • Chlortetracycline, 6-demethyl-
  • Clortetrin
  • Deganol
  • Demeclociclina
  • Demeclociclina [INN-Spanish]
  • Demeclocycline
  • Demeclocyclinum
  • Demeclocyclinum [INN-Latin]
  • Demeclor
  • Demethylchlorotetracycline
  • Demethylchlortetracyclin
  • Demethylchlortetracycline
  • Demethylchlortetracycline base
  • Demethylchlortetracyclinum
  • Demetraclin
  • Diuciclin
  • DMCT
  • DMCT (antibiotic)
  • EINECS 204-834-8
  • HSDB 3051
  • Ledermycin
  • Mexocine
  • Novotriclina
  • Perciclina
  • RP 10192
  • Sumaclina
  • Tetracycline, 7-chloro-6-demethyl-
  • Tri-demethylchlortetracycline
  • UNII-5R5W9ICI6O

Systematic Names

  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-
  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-
  • Demeclocycline

Registry Numbers

CAS Registry Number

  • 127-33-3

FDA UNII

  • 5R5W9ICI6O

Other Registry Numbers

  • 16204-02-7
  • 8059-70-9

Related Registry Number

  • 64-73-3 (mono-hydrochloride)

System Generated Number

  • 0000127333

Structure Descriptors

InChI

1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1

InChIKey

FMTDIUIBLCQGJB-SEYHBJAFSA-N

Smiles

CN(C)[C@H]1[C@@H]2C[C@@H]3[C@H](O)c4c(Cl)ccc(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
human TDLo oral 10mg/kg (10mg/kg)   British Medical Journal. Vol. 2, Pg. 96, 1977.
human TDLo oral 10mg/kg (10mg/kg) SKIN AND APPENDAGES (SKIN): NAILS: OTHER

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
British Medical Journal. Vol. 2, Pg. 96, 1977.
human TDLo oral 68mg/kg/8D (68mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Current Therapeutic Research, Clinical & Experimental. Vol. 15, Pg. 734, 1973.
human TDLo oral 420mg/kg/6W (420mg/kg)   Annals of Internal Medicine. Vol. 79, Pg. 679, 1973.
human TDLo oral 420mg/kg/6W (420mg/kg) ENDOCRINE: DIABETES INSIPIDUS (NEPHROGENIC OR CNS) Annals of Internal Medicine. Vol. 79, Pg. 679, 1973.
mouse LD50 intraperitoneal 454mg/kg (454mg/kg)   Drugs in Japan Vol. 6, Pg. 497, 1982.
mouse LD50 intravenous 79mg/kg (79mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 281, 1970.
mouse LDLo oral 4gm/kg (4000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 350, 1960.
mouse LDLo subcutaneous 2500mg/kg (2500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 350, 1960.
rat LD50 intraperitoneal 358mg/kg (358mg/kg)   Drugs in Japan Vol. 6, Pg. 497, 1982.
rat LD50 intravenous 146mg/kg (146mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
rat LD50 oral > 6750mg/kg (6750mg/kg)   Drugs in Japan Vol. 6, Pg. 497, 1982.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. 6, Pg. 497, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.140 (none)   EST
Water Solubility 1520 mg/L 21 EXP
Atmospheric OH Rate Constant 2.12E-10 cm3/molecule-sec 25 EST

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