Details of the Drug

General Information of Drug (ID: DMZA017)

Drug Name

Tetracycline

Synonyms

Amycin; Biocycline; Bristaciclin; Bristaciclina; Bristacycline; Ciclibion; Copharlan; Cyclomycin; Cytome; Dumocyclin; Enterocycline; Medocycline; Resteclin; Robitet; Sanclomycine; Tetrachel; Veracin; Bristaciclin alpha; Cefracycline suspension; Component of Tetrastatin; Sumycin syrup; Tetracycline Free Base; Tetracycline I; Tetracycline II; Tetracycline Monohydrochloride; Achromycin (naphthacene derivative); Achromycin, naphthacene derivative; Centet (base); Lemtrex (base); Liquamycin (Veterinary); Liquamycin, veterinary; Panmycin (TN); Piracaps (base); Polycycline (VAN); Polycycline (antibiotic); Polycycline, antibiotic; SK-Tetracycline; Sumycin (TN); T-125; Tetra-Co; Tetraciclina [INN-Spanish]; Tetracycline & VRC3375; Tetracycline (internal use); Tetracyclinum [INN-Latin]; Tetracyn (TN); Vetquamycin-324 (free base); Tetracycline (JAN/USP/INN); Tetracycline [USAN:INN:BAN:JAN]; Methyl-1,11-dioxo-2-naphthacenecarboxamide; 6-Methyl-1,11-dioxy-2-naphthacenecarboxamide

Indication

Disease Entry	ICD 11	Status	REF
Acne vulgaris	ED80	Approved	[1]
Actinomycosis	N.A.	Approved	[1]
Acute gonococcal cervicitis	N.A.	Approved	[1]
Acute gonococcal epididymo-orchitis	N.A.	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Bronchitis	CA20	Approved	[1]
Brucellosis	N.A.	Approved	[1]
Lymphogranuloma venereum	N.A.	Approved	[1]
Ornithosis	N.A.	Approved	[1]
Pneumonia	CA40	Approved	[1]
Q fever	N.A.	Approved	[1]
Relapsing fever	N.A.	Approved	[1]
Rickettsialpox	N.A.	Approved	[1]
Rocky mountain spotted fever	N.A.	Approved	[1]
Syphilis	N.A.	Approved	[1]
Trachoma	N.A.	Approved	[1]
Typhus	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[1]
Yaws	N.A.	Approved	[1]
Pelvic inflammatory disease	GA05	Investigative	[1]
Sinusitis	CA0A.Z	Investigative	[1]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

444.4

Logarithm of the Partition Coefficient (xlogp)

-2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 77% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 1.5 mL/min/kg [5]
Elimination: 58% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 6 - 12 hours [5]
Metabolism: The drug is not metabolised []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 74.92487 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.78% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.2 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 1.7 mg/mL [3]

Chemical Identifiers

Formula: C22H24N2O8
IUPAC Name: (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
Canonical SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
InChI: InChI=1S/C22H24N2O8/c1-21(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/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKey: NWXMGUDVXFXRIG-WESIUVDSSA-N

Cross-matching ID

PubChem CID: 54675776
ChEBI ID: CHEBI:27902
CAS Number: 60-54-8
DrugBank ID: DB00759
TTD ID: D08NQZ
VARIDT ID: DR00127
ACDINA ID: D00668

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2)	TTQ8KVI	F4NA87_STAAU	Binder	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic anion transporter 2 (SLC22A7)	DT0OC1Q	S22A7_HUMAN	Substrate	[8]
Organic anion transporter 4 (SLC22A11)	DT06JWZ	S22AB_HUMAN	Substrate	[8]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[9]
Organic anion transporter 3 (SLC22A8)	DTVP67E	S22A8_HUMAN	Substrate	[8]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[10]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[11]
Alpha-1-antichymotrypsin (SERPINA3)	OT9BP2S0	AACT_HUMAN	Gene/Protein Processing	[12]
Alternative prion protein (PRNP)	OTE85L1Q	APRIO_HUMAN	Protein Interaction/Cellular Processes	[13]
Angiotensin-converting enzyme 2 (ACE2)	OTTRZGU7	ACE2_HUMAN	Gene/Protein Processing	[14]
AP-1 complex subunit sigma-1A (AP1S1)	OTQ2H8DN	AP1S1_HUMAN	Gene/Protein Processing	[12]
Asparagine synthetase (ASNS)	OT8R922G	ASNS_HUMAN	Gene/Protein Processing	[12]
ATP-binding cassette sub-family C member 4 (ABCC4)	OTO27PAL	MRP4_HUMAN	Regulation of Drug Effects	[15]
Claudin-10 (CLDN10)	OT2CVAKY	CLD10_HUMAN	Gene/Protein Processing	[16]
Claudin-11 (CLDN11)	OTNN6UTL	CLD11_HUMAN	Gene/Protein Processing	[16]
Claudin-15 (CLDN15)	OT9K0KI7	CLD15_HUMAN	Gene/Protein Processing	[16]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Tetracycline (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Tetracycline and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[17]
Sodium bicarbonate	DMMU6BJ	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tetracycline caused by Sodium bicarbonate mediated altered urine pH.	Acidosis [5C73]	[18]
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tetracycline caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[18]
Isotretinoin	DM4QTBN	Major	Increased risk of pseudotumor cerebri by the combination of Tetracycline and Isotretinoin.	Acne vulgaris [ED80]	[19]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Tetracycline and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[20]
Aminophylline	DML2NIB	Moderate	Decreased metabolism of Tetracycline caused by Aminophylline mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[21]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Tetracycline and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[22]
Mestranol	DMG3F94	Moderate	Decreased absorption of Tetracycline due to formation of complexes caused by Mestranol.	Contraceptive management [QA21]	[23]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Tetracycline and Atracurium.	Corneal disease [9A76-9A78]	[24]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Tetracycline and Mivacurium.	Corneal disease [9A76-9A78]	[24]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Tetracycline and Pancuronium.	Corneal disease [9A76-9A78]	[24]
Oxtriphylline	DMLHSE3	Moderate	Decreased metabolism of Tetracycline caused by Oxtriphylline mediated inhibition of CYP450 enzyme.	Cough [MD12]	[21]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Tetracycline due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[25]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tetracycline caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[18]
Digitoxin	DMWVIGP	Moderate	Altered absorption of Tetracycline due to GI flora changes caused by Digitoxin.	Heart failure [BD10-BD1Z]	[26]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Tetracycline and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[27]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Tetracycline and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[28]
Quinapril	DMR8H31	Moderate	Decreased absorption of Tetracycline due to formation of complexes caused by Quinapril.	Hypertension [BA00-BA04]	[29]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tetracycline caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[18]
Iron	DMAP8MV	Moderate	Decreased absorption of Tetracycline due to formation of complexes caused by Iron.	Iron deficiency anaemia [3A00]	[30]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Tetracycline and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[31]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Tetracycline and Idelalisib.	Mature B-cell leukaemia [2A82]	[32]
Ethinyl estradiol	DMODJ40	Moderate	Decreased absorption of Tetracycline due to formation of complexes caused by Ethinyl estradiol.	Menopausal disorder [GA30]	[23]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Tetracycline due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[33]
Metoclopramide	DMFA5MY	Minor	Altered absorption of Tetracycline due to GI dynamics variation caused by Metoclopramide.	Nausea/vomiting [MD90]	[17]
Ranitidine	DM0GUSX	Moderate	Decreased absorption of Tetracycline due to formation of complexes caused by Ranitidine.	Peptic ulcer [DA61]	[34]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Tetracycline and Vecuronium.	Tonus and reflex abnormality [MB47]	[24]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Butylparaben	E00142	7184	Antimicrobial preservative
D&C red no. 22	E00206	11048	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Edetate calcium disodium	E00487	6093170	Complexing agent
Ethylene glycol ethyl ether	E00164	8076	Solubilizing agent; Solvent
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium propionate	E00445	2723816	Antimicrobial preservative
Soybean lecithin	E00637	Not Available	Other agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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⏷ Show the Full List of 26 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tetracycline 250 mg capsule	250 mg	Oral Capsule	Oral
Tetracycline 500 mg capsule	500 mg	Oral Capsule	Oral

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References

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2	How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	The glycylcyclines: a comparative review with the tetracyclines. Drugs. 2004;64(1):63-88.
8	Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76.
9	Arginine-482 is not essential for transport of antibiotics, primary bile acids and unconjugated sterols by the human breast cancer resistance protein (ABCG2). Biochem J. 2005 Jan 15;385(Pt 2):419-26.
10	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
11	Synthesis and in vitro evaluation of targeted tetracycline derivatives: effects on inhibition of matrix metalloproteinases. Bioorg Med Chem. 2007 Mar 15;15(6):2368-74. doi: 10.1016/j.bmc.2007.01.026. Epub 2007 Jan 19.
12	Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells. Toxicol Sci. 2007 Mar;96(1):101-14.
13	Tetracycline affects abnormal properties of synthetic PrP peptides and PrP(Sc) in vitro. J Mol Biol. 2000 Jul 28;300(5):1309-22. doi: 10.1006/jmbi.2000.3840.
14	Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
15	Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharm Res. 2007 Dec;24(12):2281-96.
16	Effects of residual levels of tetracycline on the barrier functions of human intestinal epithelial cells. Food Chem Toxicol. 2017 Nov;109(Pt 1):253-263. doi: 10.1016/j.fct.2017.09.004. Epub 2017 Sep 4.
17	Cerner Multum, Inc. "Australian Product Information.".
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20	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
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22	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
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27	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
28	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
29	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
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31	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
32	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
33	Canadian Pharmacists Association.
34	Albert KS, Welch RD, DeSante KA, DiSanto AR "Decreased tetracycline bioavailability caused by a bismuth subsalicylate antidiarrheal mixture." J Pharm Sci 68 (1979): 586-8. [PMID: 435335]