TETRACYCLINE PHOSPHATE COMPLEX

US Approved OTC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	5C22H24N2O8.Na.O3P.5HO3P
Molecular Weight	2724.034
Optical Activity	UNSPECIFIED
Defined Stereocenters	25 / 25
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TETRACYCLINE PHOSPHATE COMPLEX

Structure Search

SMILES

[Na+].OP(=O)=O.OP(=O)=O.OP(=O)=O.OP(=O)=O.OP(=O)=O.[O-]P(=O)=O.CN(C)[C@H]1[C@@H]2C[C@H]3C(C(=O)C4=C(C=CC=C4O)[C@@]3(C)O)=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O.CN(C)[C@H]5[C@@H]6C[C@H]7C(C(=O)C8=C(C=CC=C8O)[C@@]7(C)O)=C(O)[C@]6(O)C(=O)C(C(N)=O)=C5O.CN(C)[C@H]9[C@@H]%10C[C@H]%11C(C(=O)C%12=C(C=CC=C%12O)[C@@]%11(C)O)=C(O)[C@]%10(O)C(=O)C(C(N)=O)=C9O.CN(C)[C@H]%13[C@@H]%14C[C@H]%15C(C(=O)C%16=C(C=CC=C%16O)[C@@]%15(C)O)=C(O)[C@]%14(O)C(=O)C(C(N)=O)=C%13O.CN(C)[C@H]%17[C@@H]%18C[C@H]%19C(C(=O)C%20=C(C=CC=C%20O)[C@@]%19(C)O)=C(O)[C@]%18(O)C(=O)C(C(N)=O)=C%17O

InChI

InChIKey=DKNFPOTZPZOJHC-LBTQIPEASA-M

InChI=1S/5C22H24N2O8.Na.6HO3P/c5*1-21(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;;6*1-4(2)3/h5*4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);;6*(H,1,2,3)/q;;;;;+1;;;;;;/p-1/t5*9-,10-,15-,21+,22-;;;;;;;/m00000......./s1

HIDE SMILES / InChI

Molecular Formula	C22H24N2O8
Molecular Weight	444.4346
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	HO3P
Molecular Weight	79.9799
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050278s037lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22191524

Discovered as natural products from actinomycetes soil bacteria, the tetracyclines were first reported in the scientific literature in 1948. They were noted for their broad spectrum antibacterial activity and were commercialized with clinical success beginning in the late 1940s to the early 1950s. By catalytic hydrogenation of Aureomycin, using palladium metal and hydrogen, the C7 deschloro derivative was synthesized, producing a compound of higher potency, a better solubility profile, and favorable pharmacological activity; it was subsequently named tetracycline. Tetracyclines are primarily bacteriostatic and exert their antimicrobial effect by the inhibition of protein synthesis by binding to the 30S ribosomal subunit. Tetracycline is active against a broad range of gram-negative and gram-positive organisms. Tetracycline is indicated in the treatment of infections caused by susceptible strains. To reduce the development of drug-resistant bacteria and maintain the effectiveness of tetracycline hydrochloride and other antibacterial drugs, tetracycline hydrochloride should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050278s037lbl.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050278s037lbl.pdf	Curative		Approved 8583	TETRACYCLINE HYDROCHLORIDE Approved Use Tetracycline is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the conditions listed below: • Upper respiratory tract infections caused by Streptococcus pyogenes, Streptococcus pneumoniae and Hemophilus influenzae. Note: Tetracycline should not be used for streptococcal disease unless the organism has been demonstrated to be susceptible. • Lower respiratory tract infections caused by Streptococcus pyogenes, Streptococcus pneumoniae, Mycoplasma pneumoniae (Eaton agent, and Klebsiella sp.) • Skin and soft tissue infections caused by Streptococcus pyogenes, Staphylococcus aureaus. (Tetracyclines are not the drugs of choice in the treatment of any type of staphylococcal infections.) • Infections caused by rickettsia including Rocky Mountain spotted fever, typhus group infections, Q fever, rickettsialpox. • Psittacosis caused by Chlamydophila psittaci. • Infections caused by Chlamydia trachomatis such as uncomplicated urethral, endocervical or rectal infections, inclusion conjunctivitis, trachoma, and lymphogranuloma venereum. • Granuloma inquinale caused by Klebsiella granulomatis. • Relapsing fever caused by Borrelia sp. • Bartonellosis caused by Bartonella bacilliformis. • Chancroid caused by Hemophilus ducreyi. • Tularemia caused by Francisella tularensis. • Plaque caused by Yersinia pestis. • Cholera caused by Vibrio cholerae. • Brucellosis caused by Brucella species (tetracycline may be used in conjunction with an aminoglycoside). • Infections due to Campylobacter fetus. • As adjunctive therapy in intestinal amebiasis caused by Entamoeba histolytica. • Urinary tract infections caused by susceptible strains of Escherichia coli, Klebsiella, etc. • Other infections caused by susceptible gram-negative organisms such as E. coli, Enterobacter aerogenes, Shigella sp., Acinetobacter sp., Klebsiella sp., and Bacteroides sp. • In severe acne, adjunctive therapy with tetracycline may be useful. When penicillin is contraindicated, tetracyclines are alternative drugs in the treatment of the following infections: • Syphilis and yaws caused by Treponema pallidum and pertenue, respectively, • Vincent’s infection caused by Fusobacterium fusiforme, • Infections caused by Neisseria gonorrhoeae, • Anthrax caused by Bacillus anthracis, • Infections due to Listeria monocytogenes, • Actinomycosis caused by Actinomyces species, • Infections due to Clostridium species. Launch Date 1953

C_max

Value	Dose	Analyte	Population
2.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6487493/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
26.91 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6487493/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
27.27 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6487493/	300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TETRACYCLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
27 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
31.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
25.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
74.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
55.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
56.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
7.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6487493/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
7.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
8.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/856000/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	TETRACYCLINE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
1000 mg 1 times / day multiple, oral Recommended Dose: 1000 mg, 1 times / day Route: oral Route: multiple Dose: 1000 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2140332	unhealthy, 14 - 35 years Health Status: unhealthy Age Group: 14 - 35 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2140332	Sources: https://pubmed.ncbi.nlm.nih.gov/2140332
2.2 \|500 mg/mL\|mg 2 times / day multiple, topical\|oral Dose: 2.2 \|500 mg/mL\|mg, 2 times / day Route: topical\|oral Route: multiple Dose: 2.2 \|500 mg/mL\|mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2140332	unhealthy, 14 - 35 years Health Status: unhealthy Age Group: 14 - 35 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2140332	Other AEs: Discoloration skin... Other AEs: Discoloration skin Sources: https://pubmed.ncbi.nlm.nih.gov/2140332
250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8740345	unhealthy, 38 years Health Status: unhealthy Age Group: 38 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8740345	Disc. AE: Mucosal ulceration... AEs leading to discontinuation/dose reduction: Mucosal ulceration (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8740345
7 g multiple, intrapleural Overdose Dose: 7 g Route: intrapleural Route: multiple Dose: 7 g Sources: https://pubmed.ncbi.nlm.nih.gov/10571097	unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10571097	Disc. AE: Pleural disorder... AEs leading to discontinuation/dose reduction: Pleural disorder Sources: https://pubmed.ncbi.nlm.nih.gov/10571097
2 % 2 times / day multiple, intralesional Dose: 2 %, 2 times / day Route: intralesional Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24841733	unhealthy, 63 years (range: 53–72 years) Health Status: unhealthy Age Group: 63 years (range: 53–72 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24841733	Sources: https://pubmed.ncbi.nlm.nih.gov/24841733

AEs

AE	Significance	Dose	Population
Discoloration skin		2.2 \|500 mg/mL\|mg 2 times / day multiple, topical\|oral Dose: 2.2 \|500 mg/mL\|mg, 2 times / day Route: topical\|oral Route: multiple Dose: 2.2 \|500 mg/mL\|mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2140332	unhealthy, 14 - 35 years Health Status: unhealthy Age Group: 14 - 35 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2140332
Mucosal ulceration	1 patient Disc. AE	250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8740345	unhealthy, 38 years Health Status: unhealthy Age Group: 38 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8740345
Pleural disorder	Disc. AE	7 g multiple, intrapleural Overdose Dose: 7 g Route: intrapleural Route: multiple Dose: 7 g Sources: https://pubmed.ncbi.nlm.nih.gov/10571097	unhealthy, 41 years Health Status: unhealthy Age Group: 41 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10571097

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OAT4 93 OAT2 125 OAT3 391

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/epdf/10.1046/j.1365-2125.1997.t01-1-00619.x	yes [IC50 29 uM]

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884545/	likely
OAT2 125	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11855680/	yes
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11855680/	yes
OAT4 93	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11855680/	yes

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA003UKO	https://www.aablocks.com/goods/Goods/detail?id=AA003UKO
Aaron Chemicals	AR003VCG	http://www.aaronchem.com/60-54-8
abcr GmbH	AB349608	http://www.abcr.com/shop/en/AB349608
AK Scientific, Inc. (AKSCI)	67884	http://www.aksci.com/item_detail.php?cat=67884
Alfa Chemistry	ACM60548	https://www.alfa-chemistry.com/product/tetracycline-cas-60-54-8-1449.html
Aurora Fine Chemicals LLC	A17.890.739	http://online.aurorafinechemicals.com/info?ID=A17.890.739
BioCrick	BCC9176	http://www.biocrick.com/Tetracycline-BCC9176.html
Chem Scene	CS-8188	http://www.chemscene.com/60-54-8.html
Chemenu	CM110222	http://www.chemenu.com/products/CM110222
Chemspace	CSSB00020667474	https://chem-space.com/CSSB00020667474
Enamine	Z2144222809	https://www.enaminestore.com/catalog/Z2144222809
eNovation Chemicals	Y1053897	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1053897
Glentham Life Sciences	GA0548	http://www.glentham.com/products/product/GA0548/
Glentham Life Sciences	GA9779	http://www.glentham.com/products/product/GA9779/
Hairui	HR128188	http://www.hairuichem.com/en/product/60-54-8.html
Lab Network	LN01343680	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343680
mcule	MCULE-3752961261	https://mcule.com/MCULE-3752961261/
MedChem Express	HY-A0107	https://www.medchemexpress.com/Tetracycline.html
MolPort	MolPort-001-794-633	https://www.molport.com/shop/molecule-link/MolPort-001-794-633
MuseChem	A000279	https://www.musechem.com/product/A000279.html
MuseChem	R065761	https://www.musechem.com/product/R065761.html
Selleck Chemicals	S4490	http://www.selleckchem.com/products/tetracycline.html
Sigma-Aldrich	87128_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/87128?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T3258_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/t3258?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S545014	http://www.smolecule.com/products/s545014
THE BioTek	bt-283971	https://www.thebiotek.com/product/inhibitors/bt-283971

PubMed

Title	Date	PubMed
Megaloblastic anemia associated with long-term tetracycline therapy. Report of a case.	1973 Jun	4268307
Tetracycline-induced immune hemolytic anemia.	1974 May-Jun	4599404
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.	1975 Dec	1107297
Benign intracranial hypertension following tetracycline therapy.	1975 Jul	1184164
Fatty liver induced by tetracycline in the rat. Dose-response relationships and effect of sex.	1975 Sep	1158089
Tetracycline-associated intracranial hypertension in an adolescent: a complication of systemic acne therapy.	1978 Apr	147325
Acne.	1979 Dec	161830
Tetracycline-induced aplastic anemia.	1979 Mar	424834
Drug-induced myocarditis: a report of two cases.	1979 May-Jun	456966
Effect of toxic doses of progesterone on hepatotoxic effects of tetracycline.	1985 Apr	4024961
Selective absorption of ultraviolet laser energy by human atherosclerotic plaque treated with tetracycline.	1985 May 1	3993559
Minor complication of thyroid cyst sclerosis with tetracycline.	1986 Jan	3942454
Pseudotumor cerebri--a complication of tetracycline treatment of acne.	1986 Mar	2937759
An aborted, prospective, randomized trial of sclerotherapy for prolonged drainage after mastectomy.	1986 May	3704892
[Effectiveness of legalon and essentiale in a tetracycline-induced liver lesion].	1986 Oct	3789688
Tetracycline-induced renal hypophosphatemia in a patient with a syndrome of inappropriate secretion of antidiuretic hormone.	1988	3277077
Pseudotumor cerebri, a rare adverse reaction to tetracycline therapy. A case report.	1988 Dec	3225732
Anosmia after doxycycline use.	1990 Apr 16	2139490
Protective activity of tetracycline analogs against the cytopathic effect of the human immunodeficiency viruses in CEM cells.	1990 Jan-Feb	2326552
In vitro and in vivo effects of doxycycline on Toxoplasma gondii.	1990 May	2360817
[Clinical use of tetracyclines in the treatment of periodontal diseases].	2000 May-Jun	11089368
One-week regimens containing ranitidine bismuth citrate, furazolidone and either amoxicillin or tetracycline effectively eradicate Helicobacter pylori: a multicentre, randomized, double-blind study.	2001 Dec	11736729
Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity.	2001 Feb	11172685
Tetracycline-Cu(II) photo-induced fragmentation of serum albumin.	2002 Apr	11976059
In vitro activity of 11 antimicrobial agents, including gatifloxacin and GAR936, tested against clinical isolates of Mycobacterium marinum.	2002 Feb	11858912
Antimicrobial and anti-lipase activity of quercetin and its C2-C16 3-O-acyl-esters.	2002 Feb	11741775
Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance.	2002 Feb 10	11807801
Human organic anion transporters mediate the transport of tetracycline.	2002 Jan	11855680
Comparison of the in vitro activity of the glycylcycline tigecycline (formerly GAR-936) with those of tetracycline, minocycline, and doxycycline against isolates of nontuberculous mycobacteria.	2002 Oct	12234839
The outcome of pseudotumor cerebri induced by tetracycline therapy.	2004 Dec	15527455
Pyomyositis caused by methicillin-resistant Staphylococcus aureus.	2005 Apr 7	15814887
[Intracranial hypertension with severe and irreversible reduced acuity and impaired visual fields after oral tetracycline].	2005 Aug 20	16136745
Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]).	2005 May	15901346
Fatal brain abscess due to community-associated methicillin-resistant Staphylococcus aureus strain USA300.	2007 Nov 1	17918070
Acute hepatotoxicity: a predictive model based on focused illumina microarrays.	2007 Sep	17522070
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine.	2008 Aug	18505790
Meningitis due to hematogenous dissemination of community-associated methicillin-resistant Staphylococcus aureus (MRSA) in a patient with AIDS.	2008 Nov-Dec	18936290
Cellular imaging predictions of clinical drug-induced liver injury.	2008 Sep	18524759
Tetracycline-induced renal failure after dental treatment.	2009 Jan	19119167
Protective effect of bicyclol on tetracycline-induced fatty liver in mice.	2009 Jul 10	19427351
Gel entrapment culture of rat hepatocytes for investigation of tetracycline-induced toxicity.	2009 Jul 15	19463838
Decreased nanobacteria levels and symptoms of nanobacteria-associated interstitial cystitis/painful bladder syndrome after tetracycline treatment.	2010 Jan	19760079
Epidural abscess caused by community-associated methicillin-resistant Staphylococcus aureus strain USA300 in Japan.	2010 Oct	20364357
Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature.	2010 Sep	20592239
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.	2011 Aug	21576426
Fluorocyclines. 1. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: a potent, broad spectrum antibacterial agent.	2012 Jan 26	22148514
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs.	2012 May	22331495
Old drug, new target: ellipticines selectively inhibit RNA polymerase I transcription.	2013 Feb 15	23293027
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.	2013 Jun	22954530
A simple transcriptomic signature able to predict drug-induced hepatic steatosis.	2014 Apr	24469900

Patents

Sample Use Guides

In Vivo Use Guide

TETRACYCLINE HYDROCHLORIDE - tetracycline hydrochloride capsule Adults: Usual daily dose, 1 gram as 500 mg twice a day or 250 mg four times a day. Higher doses such as 500 mg four times a day may be required for severe infections or for those infections which do not respond to the smaller doses. For pediatric patients above eight years of age: Usual daily dose, 10 mg/lb to 20 mg/lb (25mg/kg to 50 mg/kg) body weight divided in four equal doses. TETRACYCLINE VISION 10 mg/g eye ointment Adults and children: depending on the severity of condition, a strip of the eye ointment with length of 1 – 1.5 cm is inserted into the conjunctival fold of the lower eyelid 3 - 4 times daily and in more severe cases, up to 6 times daily.

Route of Administration: Other

In Vitro Use Guide

Standard tetracycline powders should provide the following range of Minimal Inhibitory Concentration values: Enterococcus faecalis ATCC 29212 8 - 32 mcg/mL Escherichia coli ATCC 25922 0.5 - 2 mcg/mL Haemophilus influenzae ATCC 49247 4 - 32 mcg/mL Mycoplasma pneumoniae ATCC 29342 0.06-0.5 mcg/mL Staphylococcus aureus ATCC 29213 0.12 - 1 mcg/mL Streptococcus pneumoniae ATCC 49619 0.06 - 0.5 mcg/mL

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:20 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:20 GMT 2025`
Record UNII	6B7BK5H33B
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TETRACYCLINE METAPHOSPHATE

Preferred Name

English

TETRACYCLINE PHOSPHATE COMPLEX

Common Name

English

TETRACYCLINE HEXAMETAPHOSPHATE

Common Name

English

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-(4.ALPHA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,12A.ALPHA.))-, PHOSPHATE COMPLEX

Common Name

English

Tetracycline phosphate complex [WHO-DD]

Common Name

English

TETREX

Brand Name

English

TETRACYCLINE PHOSPHATE COMPLEX [MART.]

Common Name

English

TETRACYCLINE PHOSPHATE COMPLEX [MI]

Common Name

English

TETRACYCLINE PHOSPHATE COMPLEX [ORANGE BOOK]

Common Name

English

TETRACYCLINE METAPHOSPHATE [JAN]

Common Name

English

(4S,4aS,5aS,6S,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 phosphate complex

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.2345F