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]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
A01AB25: Oxytetracycline
A01AB: Antiinfectives and antiseptics for local oral treatment
A01A: STOMATOLOGICAL PREPARATIONS
A01: STOMATOLOGICAL PREPARATIONS
A: ALIMENTARY TRACT AND METABOLISM
D06AA03: Oxytetracycline
D06AA: Tetracycline and derivatives
D06A: ANTIBIOTICS FOR TOPICAL USE
D06: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D: DERMATOLOGICALS
G01AA07: Oxytetracycline
G01AA: Antibiotics
G01A: ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
G01: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
G: GENITO URINARY SYSTEM AND SEX HORMONES
J01AA06: Oxytetracycline
J01AA: Tetracyclines
J01A: TETRACYCLINES
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J01AA06: Oxytetracycline
J01AA: Tetracyclines
J01A: TETRACYCLINES
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
S01AA04: Oxytetracycline
S01AA: Antibiotics
S01A: ANTIINFECTIVES
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
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) 2
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 10
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
CHEMBL27701
CAS Number
2058-46-0
UNII
SLF0D9077S
DrugBank ID
DB00595
TTD ID
D0J2NK
VARIDT ID
DR00635
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]

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]
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 [9]
Vascular endothelial growth factor A, long form OTIM9MZ3 VEGFA_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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] [10]
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] [11]
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] [11]
Tretinoin DM49DUI Major Increased risk of pseudotumor cerebri by the combination of Oxytetracycline and Tretinoin. Acne vulgaris [ED80] [12]
Isotretinoin DM4QTBN Major Increased risk of pseudotumor cerebri by the combination of Oxytetracycline and Isotretinoin. Acne vulgaris [ED80] [12]
Magnesium Sulfate DMVEK07 Moderate Decreased absorption of Oxytetracycline due to formation of complexes caused by Magnesium Sulfate. Acute pain [MG31] [13]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Oxytetracycline and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [14]
Aminophylline DML2NIB Moderate Decreased metabolism of Oxytetracycline caused by Aminophylline mediated inhibition of CYP450 enzyme. Asthma [CA23] [15]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Oxytetracycline and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [16]
Mestranol DMG3F94 Moderate Decreased absorption of Oxytetracycline due to formation of complexes caused by Mestranol. Contraceptive management [QA21] [17]
Atracurium DM42HXN Moderate Additive neuromuscular blocking effects by the combination of Oxytetracycline and Atracurium. Corneal disease [9A76-9A78] [18]
Mivacurium DM473VD Moderate Additive neuromuscular blocking effects by the combination of Oxytetracycline and Mivacurium. Corneal disease [9A76-9A78] [18]
Pancuronium DMB0VY8 Moderate Additive neuromuscular blocking effects by the combination of Oxytetracycline and Pancuronium. Corneal disease [9A76-9A78] [18]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Oxytetracycline due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [19]
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.] [11]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Oxytetracycline and Mipomersen. Hyper-lipoproteinaemia [5C80] [20]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Oxytetracycline and BMS-201038. Hyper-lipoproteinaemia [5C80] [21]
Quinapril DMR8H31 Moderate Decreased absorption of Oxytetracycline due to formation of complexes caused by Quinapril. Hypertension [BA00-BA04] [22]
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] [11]
Iron DMAP8MV Moderate Decreased absorption of Oxytetracycline due to formation of complexes caused by Iron. Iron deficiency anaemia [3A00] [23]
Porfimer Sodium DM7ZWNY Moderate Increased risk of photosensitivity reactions by the combination of Oxytetracycline and Porfimer Sodium. Lung cancer [2C25] [24]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Oxytetracycline and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [25]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Oxytetracycline and Idelalisib. Mature B-cell leukaemia [2A82] [26]
Ethinyl estradiol DMODJ40 Moderate Decreased absorption of Oxytetracycline due to formation of complexes caused by Ethinyl estradiol. Menopausal disorder [GA30] [17]
Lanthanum carbonate DMMJQSH Moderate Decreased absorption of Oxytetracycline due to formation of complexes caused by Lanthanum carbonate. Mineral absorption/transport disorder [5C64] [27]
Vecuronium DMP0UK2 Moderate Additive neuromuscular blocking effects by the combination of Oxytetracycline and Vecuronium. Tonus and reflex abnormality [MB47] [18]
Rocuronium DMY9BMK Moderate Additive neuromuscular blocking effects by the combination of Oxytetracycline and Rocuronium. Tonus and reflex abnormality [MB47] [18]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Oxytetracycline due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [19]
⏷ Show the Full List of 28 DDI Information of This Drug

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 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.
10 Cerner Multum, Inc. "Australian Product Information.".
11 Elliott GR "Sodium bicarbonate and oral tetracycline." Clin Pharmacol Ther 13 (1972): 459. [PMID: 5026384]
12 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]
13 Covington TR, Lawson LC, Young LL, eds. "Handbook of Nonprescription Drugs. 10th ed." Washington, DC: American Pharmaceutical Association (1993):.
14 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
15 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]
16 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
17 Friedman CI, Huneke AL, Kim MH, Powell J "The effect of ampicillin on oral contraceptive effectiveness." Obstet Gynecol 55 (1980): 33-7. [PMID: 7188714]
18 Multum Information Services, Inc. Expert Review Panel.
19 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
20 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
21 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
22 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
23 Campbell NR, Hasinoff BB "Iron supplements: a common cause of drug interactions." Br J Clin Pharmacol 31 (1991): 251-5. [PMID: 2054263]
24 Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]
25 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]
26 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
27 Canadian Pharmacists Association.