OXYTETRACYCLINE

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Search structure


Trade Names	TERRAMYCIN
Synonyms	5-hydroxytetracycline dihydrate Berkmycen Chemocycline E703 Galenomycin Hi-Tet Imperacin Microtet NSC-757262 NSC-9169 Nitox OXTC Oxitetracycline Oxymycin Oxytetracycline Oxytetracycline (anhydrous) Oxytetracycline anhydrous Oxytetracycline dehydrate Oxytetracycline dihydrate Oxytetracyclinum dihydras Oxytetramix-250 Terrafungine Terramycin Terramycine Tetraplex Unimycin
Status
Molecule Category	Free-form
ATC	D06AA03 G01AA07 J01AA06 S01AA04
UNII	SLF0D9077S
EPA CompTox	DTXSID1034260


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	IWVCMVBTMGNXQD-PXOLEDIWSA-N
Smiles	CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3[C@H](O)[C@@H]12
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H24N2O9
Molecular Weight	460.44
AlogP	-1.24
Hydrogen Bond Acceptor	10.0
Hydrogen Bond Donor	7.0
Number of Rotational Bond	2.0
Polar Surface Area	201.85
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	33.0

Pharmacology

Mechanism of Action	Action	Reference
Bacterial 70S ribosome inhibitor	INHIBITOR	KEGG

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	62
Unclassified protein	-	-	-	-	40

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	61.86 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	95.2 %
Inhibition of pre-miR-372 (unknown origin) cleavage assessed as reduction of oncogenic microRNAs biogenesis at 200 uM by measuring fluorescence every minute for 5 hrs using 5'-FAM,3'-dabcyl-pre-miRNA beacons by FRET assay in presence of recombinant Dicer	Not specified	10.0 %
Inhibition of pre-miR-373 (unknown origin) cleavage assessed as reduction of oncogenic microRNAs biogenesis at 200 uM by measuring fluorescence every minute for 5 hrs using 5'-FAM,3'-dabcyl-pre-miRNA beacons by FRET assay in presence of recombinant Dicer	Not specified	10.0 %
Inhibition of pre-miR-17 (unknown origin) cleavage assessed as reduction of oncogenic microRNAs biogenesis at 200 uM by measuring fluorescence every minute for 5 hrs using 5'-FAM,3'-dabcyl-pre-miRNA beacons by FRET assay in presence of recombinant Dicer	Not specified	10.0 %
Inhibition of pre-miR-21 (unknown origin) cleavage assessed as reduction of oncogenic microRNAs biogenesis at 200 uM by measuring fluorescence every minute for 5 hrs using 5'-FAM,3'-dabcyl-pre-miRNA beacons by FRET assay in presence of recombinant Dicer	Not specified	10.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-4.95 %
Inhibition of Dicer mediated biotinylated pre-miRNA-21 (unknown origin) maturation at 1 mM measured after 15 mins by cat-ELCCA relative to control	Not specified	40.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-19.37 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %

Related Entries

Cross References

Resources	Reference
ChEBI	27701
ChEMBL	CHEMBL1517
DrugBank	DB00595
DrugCentral	2041
FDA SRS	SLF0D9077S
Guide to Pharmacology	10919
KEGG	C06624
PDB	OTC
SureChEMBL	SCHEMBL2899
ZINC	ZINC000095626782

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).