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Drug

D0432 | tetracyclines

Molecular Formula C22H24N2O8
Molecular Weight 444.4
Structure
State solid
Route of elimination They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.
Protein binding 20 - 67% protein bound
Half life 6-12 hours
Absorption Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.
Trade names Sumycin
Description broad spectrum polyketide antibiotic; binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site

S

J

A

D

S03AA02 Tetracycline


[S03AA] Antiinfectives


[S03A] ANTIINFECTIVES


[S03] OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS


[S] Sensory organs

S02AA08 Tetracycline


[S02AA] Antiinfectives


[S02A] ANTIINFECTIVES


[S02] OTOLOGICALS


[S] Sensory organs

S01AA09 Tetracycline


[S01AA] Antibiotics


[S01A] ANTIINFECTIVES


[S01] OPHTHALMOLOGICALS


[S] Sensory organs

J01RA08 Tetracycline and oleandomycin


[J01RA] Combinations of antibacterials


[J01R] COMBINATIONS OF ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J01AA20 Combinations of tetracyclines


[J01AA] Tetracyclines


[J01A] TETRACYCLINES


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J01AA07 Tetracycline


[J01AA] Tetracyclines


[J01A] TETRACYCLINES


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

D06AA04 Tetracycline


[D06AA] Tetracycline and derivatives


[D06A] ANTIBIOTICS FOR TOPICAL USE


[D06] ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE


[D] Dermatological drugs

A02BD08 Bismuth subcitrate, tetracycline and metronidazole


[A02BD] Combinations for eradication of Helicobacter pylori


[A02B] DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)


[A02] DRUGS FOR ACID RELATED DISORDERS


[A] Alimentary tract and metabolism

A02BD02 Lansoprazole, tetracycline and metronidazole


[A02BD] Combinations for eradication of Helicobacter pylori


[A02B] DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)


[A02] DRUGS FOR ACID RELATED DISORDERS


[A] Alimentary tract and metabolism

A01AB13 Tetracycline


[A01AB] Antiinfectives and antiseptics for local oral treatment


[A01A] STOMATOLOGICAL PREPARATIONS


[A01] STOMATOLOGICAL PREPARATIONS


[A] Alimentary tract and metabolism

Toxicity Dose Time Species Model Method Action Positive criterion Reference
PROTONOPHORIC UNCOUPLING 278
MEMBRANE POTENTIAL decrease 307
ELECTRON TRANSPORT CHAIN decrease 307
TCA mouse liver mitochondria Tricarboxylic acid cycle activity was assessed by the in vitro formation of [14C]CO2 from [1-14C]acetylcoenzyme A by mouse liver mitochondria. affect 236
MITOCHONDRIAL FATTY ACID BETA OXIDATION mouse liver mitochondria affect 236
MITOCHONDRIAL PROTEIN TRANSLATION 2.1 ± 0.5 μM rat liver mitochondria Mitochondrial protein synthesis assay (The incorporation of [35S]methionine into mitochondrial protein was determined by a filter paper disk assay ) IC50 281
MITOCHONDRIAL PROTEIN TRANSLATION decrease 307

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 49 companies from 2 notifications to the ECHA C&L Inventory.


H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P264, P270, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 195, 1996.
mouse LD50 subcutaneous > 4gm/kg (4000mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 195, 1996.
mouse LD50 oral > 5gm/kg (5000mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 195, 1996.
rat LD50 oral > 5gm/kg (5000mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 195, 1996.
mouse LD50 intravenous 1638mg/kg (1638mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 195, 1996.
rat LD50 intravenous 1310mg/kg (1310mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 27, Pg. 195, 1996.


  • (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 (4S,4aS,5aS,6S,12aS)-2-[Amino(hydroxy)methylene]-4beta-(dimethylamino)-1,2,3,4,4a,5,5a,6,11,12a-decahydro-6alpha,10,12,12abeta-tetrahydroxy-6-methylnaphthacene-1,3,11-trione (4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
    (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide (4S,6S,12aS,4aS,5aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,1 1-dioxo-4,5,6,12a,4a,5a-hexahydronaphthacene-2-carboxamide;
    1369-EP2269978A2 1369-EP2269985A2 1369-EP2269991A2
    1369-EP2270008A1 1369-EP2275420A1 1369-EP2284150A2
    1369-EP2284151A2 1369-EP2284152A2 1369-EP2284153A2
    1369-EP2284155A2 1369-EP2284156A2 1369-EP2284164A2
    1369-EP2287140A2 1369-EP2287148A2 1369-EP2287150A2
    1369-EP2289871A1 1369-EP2289891A2 1369-EP2292088A1
    1369-EP2292590A2 1369-EP2292612A2 1369-EP2292617A1
    1369-EP2295402A2 1369-EP2295419A2 1369-EP2298732A1
    1369-EP2301534A1 1369-EP2301912A2 1369-EP2301913A1
    1369-EP2301914A1 1369-EP2301916A2 1369-EP2305637A2
    1369-EP2305640A2 1369-EP2305662A1 1369-EP2307027A1
    1369-EP2308832A1 1369-EP2308863A1 1369-EP2308883A1
    1369-EP2311451A1 1369-EP2311796A1 1369-EP2311797A1
    1369-EP2311798A1 1369-EP2311799A1 1369-EP2311822A1
    1369-EP2314583A1 1369-EP2316450A1 1369-EP2371797A1
    1369-EP2371798A1 1369-EP2371800A1 1369-EP2371804A1
    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,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))-
    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 60-54-8
    6416-04-2 (3H2O) AB00053550-04 AB00053550_05
    AB00053550_06 AKOS024277860 AKOS026749977
    Abramycin Abricycline Achromycin
    Achromycin (naphthacene derivative) Achromycin V Agromicina
    Ambramicina Ambramycin Amycin
    BDBM50237605 BPBio1_000242 BSPBio_000220
    BSPBio_001950 Bio-tetra Biocycline
    C06570 CAS-60-54-8 CCRIS 9483
    CHEBI:27902 CPD003601804 CS-8188
    Cefracycline Cefracycline suspension Centet (base)
    Ciclibion Copharlan Criseociclina
    Cyclomycin D00201 DB00759
    DSSTox_CID_3645 DSSTox_GSID_23645 DSSTox_RID_77127
    DTXSID7023645 Democracin Deschlorobiomycin
    DivK1c_000827 E701 EC 200-481-9
    EINECS 200-481-9 Economycin F8VB5M810T
    FT-0696567 HMS2090B04 HSDB 3188
    HY-A0107 Hostacyclin IDI1_000827
    KBio1_000827 KBio2_001514 KBio2_004082
    KBio2_006650 KBio3_001450 KBioGR_000783
    KBioSS_001514 Lexacycline Limecycline
    Liquamycin (Veterinary) MCULE-3752961261 MFCD00151232
    Mericycline Micycline NCGC00017323-03
    NCGC00017323-04 NCGC00017323-05 NCGC00017323-07
    NCGC00142507-02 NCGC00254063-01 NINDS_000827
    NSC-108579 NSC108579 NWXMGUDVXFXRIG-WESIUVDSSA-N
    Neocycline OFVLGDICTFRJMM-WESIUVDSSA-N Omegamycin
    Orlycycline Piracaps (base) Polycycline
    Polycycline (VAN) Polycycline (antibiotic) Polyotic
    Prestwick0_000140 Prestwick1_000140 Prestwick2_000140
    Prestwick3_000140 Purocyclina Q193045
    RKL10088 Roviciclina SAM002554934
    SBI-0051530.P003 SC-81153 SCHEMBL2116649
    SCHEMBL2116661 SCHEMBL21271987 SCHEMBL3098
    SCHEMBL537050 SK-Tetracycline SPBio_001457
    SPBio_002159 SR-01000000212 SR-01000000212-3
    ST019403 Solvocin Spectrum2_001329
    Spectrum3_000565 Spectrum4_000352 Spectrum5_001112
    Spectrum_001034 Sumycin (TN) Sumycin syrup
    Supramycin Sustamycin T-125
    Tetra-Co Tetrabid Organon Tetrabon
    Tetraciclina Tetraciclina [INN-Spanish] Tetracycl
    Tetracyclin Tetracycline (JAN/USP/INN) Tetracycline (internal use)
    Tetracycline I Tetracycline II Tetracycline [USP:INN:BAN:JAN]
    Tetracycline base Tetracycline, >=88.0% (HPLC) Tetracycline, >=98.0% (NT)
    Tetracycline, EP grade Tetracyclinehydrate Tetracyclinum
    Tetracyclinum [INN-Latin] Tetracyn Tetradecin
    Tetrafil Tetraverine Tetrazyklin
    Tetrex Tox21_300150 Tsiklomistsin
    Tsiklomitsin UNII-F8VB5M810T Veracin
    Vetacyclinum Vetquamycin Vetquamycin-324 (free base)
    Z2144222809 ZINC100303069 ZINC102229720
    ZINC84441937 tetracycline

    DrugBank Name Tetracycline
    DrugBank DB00759
    CAS Number 115074-43-6, 60-54-8, 64-75-5
    PubChem Compound 54675776
    KEGG Drug D00201
    ChEBI 27902
    PharmGKB PA451640
    ChemSpider 10257122
    BindingDB 50237605.0
    TTD DAP001527
    Wikipedia Tetracycline