CHLORTETRACYCLINE HYDROCHLORIDE

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Search structure


Trade Names	AUREOMYCIN
Synonyms	Aureomicina Aureomycin Aureomycin monohydrochloride Chlortet hcl Chlortetracycline hcl Chlortetracycline hydrochloride Chlortetracyclini hydrochloridum Fermycin Isaphamycin Isphamycin NSC-13252
Status
Molecule Category	Salt-form
UNII	O1GX33ON8R
EPA CompTox	DTXSID2045076


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

Structure


InChI Key	CBHYYLPALVVVEY-MRFRVZCGSA-N
Smiles	CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)ccc(Cl)c4[C@@](C)(O)[C@H]3C[C@@H]12.Cl
InChI	InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31);1H/t7-,8-,15-,21-,22-;/m0./s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H24Cl2N2O8
Molecular Weight	515.35
AlogP	0.44
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	6.0
Number of Rotational Bond	2.0
Polar Surface Area	181.62
Molecular species	ZWITTERION
Aromatic Rings	1.0
Heavy Atoms	33.0

Bioactivity

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

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	-	-	-	-	129

Assay Description	Organism	Bioactivity	Reference
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1900 (Counter Screen), 1677 (Project Summary), 1902 (Retest at Dose), 1662 (Primary HTS)]	Streptococcus	148.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)]	Streptococcus	60.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)]	Streptococcus pyogenes M1 GAS	65.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	128.75 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	95.91 %
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	-4.58 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-21.8 %
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	-0.27 %		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	-0.27 %

Cross References

Resources	Reference
ChEMBL	CHEMBL2146063
FDA SRS	O1GX33ON8R
SureChEMBL	SCHEMBL3841
ZINC	ZINC36372564

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).