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Substance Name: Tetracycline [USP:INN:BAN:JAN]
RN: 60-54-8
UNII: F8VB5M810T
InChIKey: OFVLGDICTFRJMM-WESIUVDSSA-N

Note

  • A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.

Molecular Formula

  • C22-H24-N2-O8

Molecular Weight

  • 444.4376
 

Classification Codes

  • Anti-Amebic
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antirickettsial
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Protein Synthesis Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Tetracycline
  • Tetracycline [USP:INN:BAN:JAN]

MeSH Heading

  • Tetracycline

Synonyms

  • (4S,4aS,5aS,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-
  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-
  • 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,1 0,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
  • 6-Methyl-1,11-dioxy-2-naphthacenecarboxamide
  • Abramycin
  • Abricycline
  • Achromycin
  • Achromycin (naphthacene derivative)
  • Agromicina
  • Ambramicina
  • Ambramycin
  • Amycin
  • Bio-tetra
  • Biocycline
  • CCRIS 9483
  • Cefracycline
  • Cefracycline suspension
  • Centet (base)
  • Ciclibion
  • Copharlan
  • Criseociclina
  • Cyclomycin
  • Cyclopar
  • Democracin
  • Deschlorobiomycin
  • EC 200-481-9
  • EINECS 200-481-9
  • Hostacyclin
  • HSDB 3188
  • Lexacycline
  • Limecycline
  • Liquamycin
  • Liquamycin (Veterinary)
  • Mericycline
  • Micycline
  • Neocycline
  • NSC 108579
  • Omegamycin
  • Orlycycline
  • Panmycin
  • Piracaps (base)
  • Polycycline
  • Polycycline (antibiotic)
  • Polycycline (VAN)
  • Polyotic
  • Purocyclina
  • Robitet
  • Roviciclina
  • SK-Tetracycline
  • Solvocin
  • Sumycin
  • Sumycin syrup
  • T-125
  • Tetra-co
  • Tetrabon
  • Tetraciclina
  • Tetraciclina [INN-Spanish]
  • Tetracycl
  • Tetracycline
  • Tetracycline I
  • Tetracycline II
  • Tetracyclinum
  • Tetracyclinum [INN-Latin]
  • Tetracyn
  • Tetradecin
  • Tetrafil
  • Tetraverine
  • Tsiklomistsin
  • Tsiklomitsin
  • UNII-F8VB5M810T
  • Veracin
  • Vetacyclinum
  • Vetquamycin-324 (free base)

Systematic Names

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

Superlist Names

  • Tetracycline
  • Tetracycline (internal use)

Mixture Names

  • Mysteclin-F
  • Talsutin

Registry Numbers

CAS Registry Number

  • 60-54-8

FDA UNII

  • F8VB5M810T

Other Registry Number

  • 6591-49-7

Related Registry Number

  • 64-75-5 (mono-hydrochloride)

System Generated Number

  • 0000060548

Structure Descriptors

InChI

1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

InChIKey

OFVLGDICTFRJMM-WESIUVDSSA-N

Smiles

C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 1875mg/kg (1875mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 109, 1982.
mouse LD50 intraperitoneal 120mg/kg (120mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 134, 1967.
mouse LD50 intravenous 157mg/kg (157mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 346, 1955.
mouse LD50 oral 678mg/kg (678mg/kg)   American Journal of Tropical Medicine and Hygiene. Vol. 2, Pg. 254, 1953.
mouse LD50 subcutaneous 400mg/kg (400mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 3, Pg. 42, 1980.
rat LD50 intraperitoneal 310mg/kg (310mg/kg)   Drugs in Japan Vol. 6, Pg. 493, 1982.
rat LD50 intravenous 129mg/kg (129mg/kg)   Antibiotics and Chemotherapy Vol. 4, Pg. 411, 1954.
rat LD50 oral 807mg/kg (807mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
women LDLo multiple routes 310mg/kg (310mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

GASTROINTESTINAL: NAUSEA OR VOMITING
New England Journal of Medicine. Vol. 270, Pg. 157, 1964.
women TDLo oral 600mg/kg/15D (600mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Southern Medical Journal. Vol. 71, Pg. 961, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 172.5 dec deg C   EXP
pKa Dissociation Constant 3.3 (none) 25 EXP
log P (octanol-water) -1.30E+00 (none)   EXP
Water Solubility 231 mg/L 25 EXP
Vapor Pressure 3.09E-23 mm Hg 25 EST
Henry's Law Constant 4.66E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.56E-10 cm3/molecule-sec 25 EST

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