Details of the Drug

General Information of Drug (ID: DMOVH1M)

Drug Name

Oxytetracycline

Synonyms

Adamycin; Biostat; Dabicycline; Dalimycin; Fanterrin; Geomycin; Geotilin; Hydroxytetracycline; Imperacin; Lenocycline; Macocyn; OTC; Oksisyklin; Ossitetraciclina; Oxacycline; Oxitetraciclina; Oxitetracyclin; Oxitetracycline; Oxitetracyclinum; Oxymycin; Oxymykoin; Oxypam; Oxyterracin; Oxyterracine; Oxyterracyne; Oxytetracid; Oxytetracyclin; Oxytetracyclinum; Proteroxyna; Riomitsin; Ryomycin; Solkaciclina; Tarocyn; Tarosin; Teravit; Terrafungine; Terramitsin; Terramycin; Tetran; Unimycin; Ursocyclin; Ursocycline; Vendarcin; Biostat PA; Ossitetraciclina [DCIT]; Oxytetracycline HCl; Oxytetracycline [INN]; Oxytetracycline amphoteric; Oxytetracycline anhydrous; Oxytetracycline calcium; Terramycin im; Antibiotic TM 25; LA 200; Liquamycin LA 200; Mycoshield TMQTHC 20; Pennox 200; TM 5; Terramycin Q50; Geomycin (Streptomyces vimosus); OTC (antibiotic); Oxitetraciclina [INN-Spanish]; Oxytetracycline (anhydrous); Oxytetracycline (internal use); Oxytetracyclinum [INN-Latin]; Terramycin, Liquamycin, Oxytetracycline; (2E,4S,4aR,5S,5aR,6S,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2E,4S,6S,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2Z)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2Z,4S,4aR,5S,5aR,6S,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; 5-Hydroxytetracycline

Indication

Disease Entry	ICD 11	Status	REF
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]
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)

460.4

Logarithm of the Partition Coefficient (xlogp)

-1.6

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: 58% 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 2 mL/min/kg [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 10 hours [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 72.3214 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.9% [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 1.7 L/kg [5]

Chemical Identifiers

Formula: C22H24N2O9
IUPAC Name: (4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
Canonical SMILES: C[C@@]1([C@H]2[C@@H]([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)O
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/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChIKey: OWFJMIVZYSDULZ-PXOLEDIWSA-N

Cross-matching ID

PubChem CID: 54675779
ChEBI ID: CHEBI:27701
CAS Number: 2058-46-0
DrugBank ID: DB00595
TTD ID: D0J2NK
VARIDT ID: DR00635

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 Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[8]
C-C motif chemokine 3 (CCL3)	OTW2H3ND	CCL3_HUMAN	Gene/Protein Processing	[8]
C-C motif chemokine 4 (CCL4)	OT6B8P25	CCL4_HUMAN	Gene/Protein Processing	[8]
C-C motif chemokine 5 (CCL5)	OTSCA5CK	CCL5_HUMAN	Gene/Protein Processing	[8]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Gene/Protein Processing	[9]
Interleukin-6 receptor subunit alpha (IL6R)	OTCQL07Z	IL6RA_HUMAN	Gene/Protein Processing	[8]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[8]
Type I iodothyronine deiodinase (DIO1)	OTFYLYJ0	IOD1_HUMAN	Gene/Protein Processing	[10]
Vascular endothelial growth factor A, long form	OTIM9MZ3	VEGFA_HUMAN	Gene/Protein Processing	[8]

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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 Oxytetracycline (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Oxytetracycline and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[11]
Sodium bicarbonate	DMMU6BJ	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Oxytetracycline caused by Sodium bicarbonate mediated altered urine pH.	Acidosis [5C73]	[12]
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Oxytetracycline caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[12]
Tretinoin	DM49DUI	Major	Increased risk of pseudotumor cerebri by the combination of Oxytetracycline and Tretinoin.	Acne vulgaris [ED80]	[13]
Isotretinoin	DM4QTBN	Major	Increased risk of pseudotumor cerebri by the combination of Oxytetracycline and Isotretinoin.	Acne vulgaris [ED80]	[13]
Magnesium Sulfate	DMVEK07	Moderate	Decreased absorption of Oxytetracycline due to formation of complexes caused by Magnesium Sulfate.	Acute pain [MG31]	[14]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Oxytetracycline and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[15]
Aminophylline	DML2NIB	Moderate	Decreased metabolism of Oxytetracycline caused by Aminophylline mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[16]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Oxytetracycline and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[17]
Mestranol	DMG3F94	Moderate	Decreased absorption of Oxytetracycline due to formation of complexes caused by Mestranol.	Contraceptive management [QA21]	[18]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Oxytetracycline and Atracurium.	Corneal disease [9A76-9A78]	[19]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Oxytetracycline and Mivacurium.	Corneal disease [9A76-9A78]	[19]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Oxytetracycline and Pancuronium.	Corneal disease [9A76-9A78]	[19]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Oxytetracycline due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[20]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Oxytetracycline caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[12]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Oxytetracycline and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[21]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Oxytetracycline and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[22]
Quinapril	DMR8H31	Moderate	Decreased absorption of Oxytetracycline due to formation of complexes caused by Quinapril.	Hypertension [BA00-BA04]	[23]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Oxytetracycline caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[12]
Iron	DMAP8MV	Moderate	Decreased absorption of Oxytetracycline due to formation of complexes caused by Iron.	Iron deficiency anaemia [3A00]	[24]
Porfimer Sodium	DM7ZWNY	Moderate	Increased risk of photosensitivity reactions by the combination of Oxytetracycline and Porfimer Sodium.	Lung cancer [2C25]	[25]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Oxytetracycline and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[26]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Oxytetracycline and Idelalisib.	Mature B-cell leukaemia [2A82]	[27]
Ethinyl estradiol	DMODJ40	Moderate	Decreased absorption of Oxytetracycline due to formation of complexes caused by Ethinyl estradiol.	Menopausal disorder [GA30]	[18]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Oxytetracycline due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[28]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Oxytetracycline and Vecuronium.	Tonus and reflex abnormality [MB47]	[19]
Rocuronium	DMY9BMK	Moderate	Additive neuromuscular blocking effects by the combination of Oxytetracycline and Rocuronium.	Tonus and reflex abnormality [MB47]	[19]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Oxytetracycline due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[20]
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References

1	Oxytetracycline FDA Label
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 060634.
3	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional 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	Detection of tetracycline resistance genes by PCR methods. Methods Mol Biol. 2004;268:3-13.
8	Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. Leuk Res. 2010 Jul;34(7):917-24. doi: 10.1016/j.leukres.2009.12.002. Epub 2010 Feb 8.
9	Phototoxic effect of oxytetracycline on normal human melanocytes. Toxicol In Vitro. 2018 Apr;48:26-32. doi: 10.1016/j.tiv.2017.12.008. Epub 2017 Dec 15.
10	Screening the ToxCast Phase 1 Chemical Library for Inhibition of Deiodinase Type 1 Activity. Toxicol Sci. 2018 Apr 1;162(2):570-581. doi: 10.1093/toxsci/kfx279.
11	Cerner Multum, Inc. "Australian Product Information.".
12	Elliott GR "Sodium bicarbonate and oral tetracycline." Clin Pharmacol Ther 13 (1972): 459. [PMID: 5026384]
13	Gardner K, Cox T, Digre KB "Idiopathic intracranial hypertension associated with tetracycline use in fraternal twins: case reports and review." Neurology 45 (1995): 6-10. [PMID: 7824136]
14	Covington TR, Lawson LC, Young LL, eds. "Handbook of Nonprescription Drugs. 10th ed." Washington, DC: American Pharmaceutical Association (1993):.
15	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
16	Gotz VP, Ryerson GG "Evaluation of tetracycline on theophylline disposition in patients with chronic obstructive airways disease." Drug Intell Clin Pharm 20 (1986): 694-6. [PMID: 3757782]
17	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
18	Friedman CI, Huneke AL, Kim MH, Powell J "The effect of ampicillin on oral contraceptive effectiveness." Obstet Gynecol 55 (1980): 33-7. [PMID: 7188714]
19	Multum Information Services, Inc. Expert Review Panel.
20	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
21	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
22	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
23	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
24	Campbell NR, Hasinoff BB "Iron supplements: a common cause of drug interactions." Br J Clin Pharmacol 31 (1991): 251-5. [PMID: 2054263]
25	Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]
26	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]
27	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
28	Canadian Pharmacists Association.