Compound Detail

CHEMBL1440

TETRACYCLINE

💊 Approved Drug

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💊 Approved Drug

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]3C[C@@H]12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1440
Name	TETRACYCLINE
Phase	Approved
Structure Type	MOL
InChI Key	OFVLGDICTFRJMM-WESIUVDSSA-N
Therapeutic	✓ Yes

Known Names

Achromycin v E701 Economycin NSC-108579 Panmycin Supramycin Sustamycin Tetrabid organon Tetraciclina Tetracycline Tetracycline component of pylera Vetquamycin

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

444.4

MW (Da)

-0.21

ALogP

HBA

HBD

181.6

PSA (Å²)

0.34

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1953
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product

USAN Stem

-cycline

Extended Properties

Molecular Formula	C22H24N2O8
MW	444.44
Aromatic Rings	1
Heavy Atoms	32
NP-Likeness	1.70

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Bacterial 70S ribosome inhibitor	INHIBITOR	Bacterial 70S ribosome	✓	✓

Indications

Bacterial Infections Eye Infections Infections Candidiasis, Vulvovaginal Conjunctivitis, Inclusion Helicobacter Infections Periodontitis Vaginosis, Bacterial Burns Lyme Disease Lymphoma, Non-Hodgkin Multiple Sclerosis Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Relapsing-Remitting Acne Vulgaris Chalazion Osteomyelitis

ATC Classification

A01AB13

tetracycline

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: STOMATOLOGICAL PREPARATIONS

D06AA04

tetracycline

Level 1: DERMATOLOGICALS

Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

J01AA07

tetracycline

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

S01AA09

tetracycline

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

S02AA08

tetracycline

Level 1: SENSORY ORGANS

Level 2: OTOLOGICALS

S03AA02

tetracycline

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS

Activity Summary

IC50 42 meas. best 6.51

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Klebsiella pneumoniae CHEMBL350	IC50	6.51	6.51	312.0	1
Plasmodium falciparum CHEMBL364	IC50	6.49	6.23	323.9	5
Mycolicibacterium smegmatis CHEMBL613088	IC50	6.48	6.435	330.0	2
Dermabacter hominis CHEMBL1169592	IC50	5.92	5.92	1200.0	1
Bacillus subtilis CHEMBL359	IC50	5.9	5.9	1250.0	1
Pseudomonas aeruginosa CHEMBL348	IC50	5.9	5.9	1250.0	1
Escherichia coli CHEMBL354	IC50	5.85	5.306	1400.0	5
Bacterial 70S ribosome CHEMBL2363135	IC50	5.34	5.34	4580.0	1
Staphylococcus aureus CHEMBL352	IC50	5.24	5.24	5700.0	1
Alpha-synuclein CHEMBL6152	IC50	5.22	5.22	6060.0	1
HaCaT CHEMBL614392	IC50	5.1	5.1	8000.0	1
Tyrosine-protein phosphatase non-receptor type 7 CHEMBL2219	IC50	5.08	5.08	8330.0	1
Staphylococcus auricularis CHEMBL5291674	IC50	5.0	5.0	10000.0	1
Multidrug transporter MdfA CHEMBL4785	IC50	4.88	4.88	13200.0	1
Brevibacterium epidermidis CHEMBL1169591	IC50	4.86	4.86	13900.0	1
Heat shock protein HSP90 CHEMBL2095165	IC50	4.65	4.65	22447.4	1
ADMET CHEMBL612558	IC50	4.38	4.38	41600.0	1
HeLa CHEMBL399	IC50	4.29	4.29	51000.0	1
Unchecked CHEMBL612545	IC50	4.22	4.22	60300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	-	-	Mus musculus
AUC	802.0	ng.hr.mL-1	Rattus norvegicus
AUC	802.0	ng.hr.mL-1	Rattus norvegicus
AUC	3083.0	ng.hr.mL-1	Rattus norvegicus
AUC	4536.0	ng.hr.mL-1	Rattus norvegicus
CL	1.5	mL.min-1.kg-1	Homo sapiens
CL	1.5	mL.min-1.kg-1	Homo sapiens
CL	0.6	mL.min-1.kg-1	Homo sapiens
CL	1.5	mL.min-1.kg-1	Homo sapiens
CL	20.5	mL.min-1.kg-1	Rattus norvegicus
CL	20.5	mL.min-1.kg-1	Rattus norvegicus
CL	9.033	mL.min-1.kg-1	Rattus norvegicus
Cmax	-	-	Mus musculus
Cmax	3825.04	nM	Homo sapiens
Cmax	1311.76	nM	Rattus norvegicus
F	77.0	%	Homo sapiens
F	78.0	%	Homo sapiens
F	12.1	%	Rattus norvegicus
F	12.0	%	Rattus norvegicus
F	14.9	%	Rattus norvegicus
F	60.0	%	Homo sapiens
F	50.0	%	Homo sapiens
F	14.9	%	Rattus norvegicus
F	6.3	%	Mus musculus
Fu	0.78	-	Homo sapiens
Fu	0.78	-	Homo sapiens
MRT	12.0	hr	Homo sapiens
T1/2	9.4	hr	Homo sapiens
T1/2	4.5	hr	Rattus norvegicus
T1/2	4.5	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Klebsiella pneumoniae	IC50	=	312.0	nM	6.51	Antibacterial activity against Klebsiella pneumoniae assessed as reduction in ba...	30119011
Plasmodium falciparum	IC50	=	323.9	nM	6.49	Antimalarial activity after 96 hrs against azithromycin-resistant Plasmodium fal...	17110371
Mycolicibacterium smegmatis	IC50	=	330.0	nM	6.48	Antimycobacterial activity against Mycobacterium smegmatis by GFP-based fluoresc...	19786608
Plasmodium falciparum	IC50	=	364.7	nM	6.44	Antimalarial activity after 96 hrs against azithromycin-resistant Plasmodium fal...	17110371
Plasmodium falciparum	IC50	=	397.1	nM	6.4	Antimalarial activity after 96 hrs against Plasmodium falciparum Dd2 by [3H]hypo...	17110371
Mycolicibacterium smegmatis	IC50	=	410.0	nM	6.39	Antimycobacterial activity against Mycobacterium smegmatis assessed as growth in...	19786608
Plasmodium falciparum	IC50	=	696.7	nM	6.16	Antimalarial activity after 96hrs against Plasmodium falciparum 7G8 by [3H]hypox...	17110371
Dermabacter hominis	IC50	=	1200.0	nM	5.92	Antibacterial activity against Dermabacter hominis DSM 7083 after 48 hrs by micr...	20545334
Pseudomonas aeruginosa	IC50	=	1250.0	nM	5.9	Antibacterial activity against Pseudomonas aeruginosa assessed as reduction in b...	30119011
Bacillus subtilis	IC50	=	1250.0	nM	5.9	Antibacterial activity against Bacillus subtilis assessed as reduction in bacter...	30119011
Escherichia coli	IC50	=	1400.0	nM	5.85	Inhibition of transcription-translation process in Escherichia coli	26288696
Plasmodium falciparum	IC50	=	2190.0	nM	5.66	Inhibition of Plasmodium falciparum FCK2 growth as [3H]hypoxanthine uptake after...	17060533
Escherichia coli	IC50	=	2800.0	nM	5.55	Inhibition of protein synthesis in Escherichia coli S30 extracts by coupled tran...	16890435
Escherichia coli	IC50	=	2800.0	nM	5.55	Inhibition of protein synthesis in Escherichia coli by coupled transcription-tra...	17188860
Bacterial 70S ribosome	IC50	=	4580.0	nM	5.34	Inhibition of Escherichia coli ribosome-mediated translation after 60 mins by tr...	22148514
Staphylococcus aureus	IC50	=	5700.0	nM	5.24	Antimicrobial activity against Staphylococcus aureus ATCC 25923 after 16 hrs by ...	24856903
Alpha-synuclein	IC50	=	6060.0	nM	5.22	Inhibition of alpha-synuclein fibril formation (unknown origin) incubated for 24...	30743095
HaCaT	IC50	=	8000.0	nM	5.1	Cytotoxicity against human HaCaT cells after 24 hrs by MTT assay	34223166
Tyrosine-protein phosphatase non-receptor type 7	IC50	=	8330.0	nM	5.08	PUBCHEM_BIOASSAY: HTS Discovery of Chemical Inhibitors of HePTP, a Leukemia Targ...	-
Escherichia coli	IC50	=	10000.0	nM	5.0	Antibacterial activity against Escherichia coli assessed as reduction in bacteri...	30119011

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1453
-	10.6019/CHEMBL3885881	Rattus norvegicus	270
19164140	10.1128/aac.00822-08	Klebsiella aerogenes	62
17620376	10.1128/aac.00625-07	Escherichia coli	48
17043131	10.1128/aac.00600-06	Salmonella typhimurium	44
18443112	10.1128/aac.00084-08	Salmonella typhimurium	41
20713660	10.1128/aac.00009-10	Pseudomonas aeruginosa	36
17387155	10.1128/aac.00062-07	Cutibacterium acnes	36
19164140	10.1128/aac.00822-08	Klebsiella pneumoniae	34
20145081	10.1128/aac.00737-08	Bacillus anthracis	29
19738019	10.1128/aac.00724-09	NON-PROTEIN TARGET	28
19273677	10.1128/aac.01464-08	Streptococcus pneumoniae	27
17325224	10.1128/aac.00187-07	Streptococcus pneumoniae	26
18378705	10.1128/aac.01420-07	Neisseria gonorrhoeae	24
17158933	10.1128/aac.01052-06	Staphylococcus lugdunensis	23
19596873	10.1128/aac.00546-09	Streptococcus intermedius	23
19651906	10.1128/aac.00624-09	Staphylococcus simulans	18
19651906	10.1128/aac.00624-09	Staphylococcus hominis	18
19651906	10.1128/aac.00624-09	Staphylococcus aureus	18
18070962	10.1128/aac.00375-07	Escherichia coli	18

Data from ChEMBL 36 via Core Engine