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Substance Name: Doxycycline [USAN:INN:BAN]
RN: 564-25-0
UNII: 334895S862
InChIKey: JBIWCJUYHHGXTC-AKNGSSGZSA-N

Note

  • A synthetic tetracycline derivative with similar antimicrobial activity.

Molecular Formula

  • C22-H24-N2-O8

Molecular Weight

  • 444.4376
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Results Name

  • Doxycycline [USAN:INN:BAN]

Name of Substance

  • Doxycycline
  • Doxycycline (anhydrous)
  • Doxycycline [USAN:INN:BAN]

MeSH Heading

  • Doxycycline

Synonyms

  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-
  • 5-Hydroxy-alpha-6-deoxytetracycline
  • 6-alpha-Deoxy-5-oxytetracycline
  • 6-Deoxyoxytetracycline
  • 6-Deoxytetracycline
  • 6alpha-Deoxy-5-oxytetracycline
  • alpha-6-Deoxy-5-hydroxytetracycline
  • alpha-6-Deoxyoxytetracycline
  • alpha-Doxycycline
  • Azudoxat
  • BMY 28689
  • BMY-28689
  • BMY28689
  • BU 3839T
  • BU-3839T
  • Deoxymykoin
  • Dossiciclina
  • Dossiciclina [DCIT]
  • Doxiciclina
  • Doxiciclina [INN-Spanish]
  • Doxiciclina [Italian]
  • Doxitard
  • Doxivetin
  • Doxy-Caps
  • Doxy-Puren
  • Doxy-Tabs
  • Doxycen
  • Doxychel
  • Doxycycline
  • Doxycyclinum
  • Doxycyclinum [INN-Latin]
  • Doxysol
  • Doxytetracycline
  • EINECS 209-271-1
  • HSDB 3071
  • Investin
  • Liviatin
  • Monodox
  • Nordox
  • Oracea
  • Oxytetracycline, 6-deoxy-
  • Ronaxan
  • Spanor
  • UNII-334895S862
  • Vibra-tabs
  • Vibramycin
  • Vibramycine
  • Vibravenos
  • Zenavod

Systematic Names

  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6R,12aS)-
  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-
  • 2-Naphthacenecarboxamide, 4-alpha-S-(dimethylamino)-1,4,4a-alpha-5,5a-alpha,6,11,12a-octahydro-3,5-alpha,10,12,12a-alpha-pentahydroxy-6-alpha-methyl-1,11-dioxo-
  • Doxycycline

Superlist Name

  • Doxycycline (internal use)

Registry Numbers

CAS Registry Number

  • 564-25-0

FDA UNII

  • 334895S862

Other Registry Numbers

  • 10597-92-9
  • 7164-70-7
  • 7264-10-0

Related Registry Numbers

  • 17086-28-1 (mono-hydrate)
  • 41411-66-9 (6-epimer, mono-hydrochloride)
  • 69935-17-7 (mono-hydrochloride, di-hydrate)
  • 94088-85-4 (calcium salt (1:2))

System Generated Number

  • 0000564250

Structure Descriptors

InChI

1S/C22H24N2O8/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/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

InChIKey

JBIWCJUYHHGXTC-AKNGSSGZSA-N

Smiles

C[C@H]1c2cccc(c2C(=O)C3=C([C@]4([C@@H]([C@H]([C@H]13)O)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 100mg/kg (100mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 305, 1979.
dog LD50 oral > 500mg/kg (500mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 305, 1979.
mouse LD50 intraperitoneal 410mg/kg (410mg/kg)   Giornale Italiano di Chemioterapia. Italian Journal of Chemotherapy. Vol. 17, Pg. 276, 1970.
mouse LD50 intravenous 241mg/kg (241mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 305, 1979.
mouse LD50 oral 1870mg/kg (1870mg/kg)   Giornale Italiano di Chemioterapia. Italian Journal of Chemotherapy. Vol. 17, Pg. 276, 1970.
rat LD50 intraperitoneal 378mg/kg (378mg/kg)   Therapie. Vol. 23, Pg. 575, 1968.
rat LD50 intravenous 228mg/kg (228mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 305, 1979.
rat LD50 oral > 2gm/kg (2000mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 305, 1979.
women TDLo oral 68mg/kg/24D-I (68mg/kg)   Postgraduate Medical Journal. Vol. 67, Pg. 313, 1991.
women TDLo oral 68mg/kg/24D-I (68mg/kg)   Postgraduate Medical Journal. Vol. 67, Pg. 313, 1991.
women TDLo oral 68mg/kg/24D-I (68mg/kg) MUSCULOSKELETAL: JOINTS Postgraduate Medical Journal. Vol. 67, Pg. 313, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.02 (none)   EXP
Water Solubility 630 mg/L 25 EXP
Vapor Pressure 1.42E-23 mm Hg 25 EST
Henry's Law Constant 4.66E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.66E-10 cm3/molecule-sec 25 EST

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