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Substance Name: Oxytetracycline [INN]
RN: 79-57-2
UNII: SLF0D9077S
InChIKey: IWVCMVBTMGNXQD-PXOLEDIWSA-N

Note

  • A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES rimosus and used in a wide variety of clinical conditions.

Molecular Formula

  • C22-H24-N2-O9

Molecular Weight

  • 460.4366
 

Classification Codes

  • Agricultural Chemical
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Germicide, Bactericide, Disinfectant
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Results Name

  • Oxytetracycline [INN]

Name of Substance

  • Oxytetracycline (anhydrous)
  • Oxytetracycline [INN]

MeSH Heading

  • Oxytetracycline

Synonyms

  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-
  • 4-14-00-02633 (Beilstein Handbook Reference)
  • 5-Hydroxytetracycline
  • Adamycin
  • Antibiotic TM 25
  • Berkmycen
  • Biostat
  • Biostat PA
  • BRN 2714587
  • Dabicycline
  • EINECS 201-212-8
  • Fanterrin
  • Geomycin
  • Geomycin (Streptomyces vimosus)
  • Geotilin
  • HSDB 3145
  • Imperacin
  • LA 200
  • Lenocycline
  • Liquamycin
  • Liquamycin LA 200
  • Macocyn
  • Mycoshield TMQTHC 20
  • NCI-C56473
  • NSC-9169
  • Oksisyklin
  • Ossitetraciclina
  • Ossitetraciclina [DCIT]
  • OTC
  • OTC (antibiotic)
  • Oxitetraciclina
  • Oxitetraciclina [INN-Spanish]
  • Oxitetracyclin
  • Oxitetracyclinum
  • Oxy-kesso-tetra
  • Oxymycin
  • Oxymykoin
  • Oxypam
  • Oxysteclin
  • Oxyterracin
  • Oxyterracine
  • Oxyterracyne
  • Oxytetracyclin
  • Oxytetracycline
  • Oxytetracycline amphoteric
  • Oxytetracyclinum
  • Oxytetracyclinum [INN-Latin]
  • Pennox 200
  • Proteroxyna
  • Riomitsin
  • Ryomycin
  • Solkaciclina
  • Stevacin
  • Tarocyn
  • Tarosin
  • Teravit
  • Terrafungine
  • Terramicina Oftalmica
  • Terramitsin
  • Terramycin
  • Terramycin im
  • Terramycin Q50
  • Tetrachel
  • Tetracycline, 5-hydroxy-
  • Tetran
  • UNII-SLF0D9077S
  • Ursocyclin
  • Ursocycline
  • Vendarcin

Systematic Names

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

Superlist Names

  • Oxytetracycline
  • Oxytetracycline (internal use)

Registry Numbers

CAS Registry Number

  • 79-57-2

FDA UNII

  • SLF0D9077S

Other Registry Numbers

  • 102287-29-6
  • 103351-03-7
  • 105145-10-6
  • 106216-57-3
  • 1135442-00-0
  • 1256964-22-3
  • 1405-95-4
  • 21645-09-0
  • 52214-46-7
  • 856305-69-6
  • 909261-39-8
  • 96310-42-8

Related Registry Numbers

  • 2058-46-0 (mono-hydrochloride)
  • 6153-64-6 (di-hydrate)
  • 6153-65-7 (di-hydrochloride salt, di-hydrate)
  • 64038-91-1 (sulfate (2:1))
  • 69766-62-7 (hydrochloride salt)
  • 7179-50-2 (calcium (1:1) salt)

System Generated Number

  • 0000079572

Structure Descriptors

InChI

InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

InChIKey

IWVCMVBTMGNXQD-PXOLEDIWSA-N

Smiles

CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(=O)N)C(=O)c4c(O)cccc4[C@@]3(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 220mg/kg (220mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Antibiotics and Chemotherapy Vol. 3, Pg. 1015, 1953.
guinea pig LDLo intraperitoneal 2250mg/kg (2250mg/kg)   Antibiotiki. Vol. 20, Pg. 793, 1975.
infant TDLo parenteral 136mg/kg (136mg/kg) MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES Lancet. Vol. 1, Pg. 827, 1962.
man TDLo oral 114mg/kg/4D (114mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BLOOD: HEMORRHAGE		 JAMA, Journal of the American Medical Association. Vol. 231, Pg. 734, 1975.
mouse LD50 intraperitoneal 5706mg/kg (5706mg/kg)   Antibiotiki. Vol. 20, Pg. 793, 1975.
mouse LD50 intravenous 140mg/kg (140mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse LD50 oral 2240mg/kg (2240mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse LD50 subcutaneous 700mg/kg (700mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 3, Pg. 44, 1980.
rat LD50 intravenous 260mg/kg (260mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
rat LD50 oral 4800mg/kg (4800mg/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 24mg/kg/6D-I (24mg/kg) BLOOD: THROMBOCYTOPENIA American Journal of Hematology. Vol. 43, Pg. 333, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 184.5 deg C   EXP
pKa Dissociation Constant 3.27 (none) 25 EXP
log P (octanol-water) -0.9 (none)   EXP
Water Solubility 313 mg/L 25 EXP
Vapor Pressure 9.68E-25 mm Hg 25 EST
Henry's Law Constant 1.70E-25 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.65E-10 cm3/molecule-sec 25 EST

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