tetracycline Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, protein-synthesis inhibitors, tetracycline derivatives 2611 60-54-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tetracycline phosphate complex
  • achromycin
  • tetracycline metaphosphate
  • tetracycline
  • tetracycline hydrochloride
  • tetracycline HCl
A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.
  • Molecular weight: 444.44
  • Formula: C22H24N2O8
  • CLOGP: -0.90
  • LIPINSKI: 1
  • HAC: 10
  • HDO: 6
  • TPSA: 181.62
  • ALOGS: -2.52
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O
1 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1.70 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 58 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 74.92 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 77 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.78 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 9.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 19, 1953 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 4344.44 58.08 855 333 45788 2311109
Rash 233.20 58.08 102 1086 59456 2297441
Urticaria 101.99 58.08 44 1144 24217 2332680
Nausea 77.77 58.08 63 1125 112126 2244771
Vomiting 66.58 58.08 48 1140 71554 2285343

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 568.18 43.57 119 196 15016 1731450

Pharmacologic Action:

SourceCodeDescription
ATC A01AB13 ALIMENTARY TRACT AND METABOLISM
STOMATOLOGICAL PREPARATIONS
STOMATOLOGICAL PREPARATIONS
Antiinfectives and antiseptics for local oral treatment
ATC D06AA04 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
ANTIBIOTICS FOR TOPICAL USE
Tetracycline and derivatives
ATC J01AA07 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
TETRACYCLINES
Tetracyclines
ATC S01AA09 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antibiotics
ATC S02AA08 SENSORY ORGANS
OTOLOGICALS
ANTIINFECTIVES
Antiinfectives
ATC S03AA02 SENSORY ORGANS
OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
ANTIINFECTIVES
Antiinfectives
ATC A02BD02 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC A02BD08 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Combinations for eradication of Helicobacter pylori
ATC J01RA08 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
FDA EPC N0000175505 Tetracycline-class Antimicrobial
FDA Chemical/Ingredient N0000007948 Tetracyclines
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011500 Protein Synthesis Inhibitors
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:35820 antiprotozoal drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Trachoma indication 2576002 DOID:11265
Actinomycotic infection indication 11817007 DOID:8478
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Gingivostomatitis indication 20607006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Granuloma inguinale indication 28867007 DOID:9113
Acute gonococcal urethritis indication 29864006
Acute gonococcal epididymo-orchitis indication 30168008 DOID:10802
Bronchitis indication 32398004 DOID:6132
Neonatal conjunctivitis indication 34298002 DOID:9699
Sinusitis indication 36971009
Gonorrhea of rectum indication 42746002
Acute gonococcal endometritis indication 65295003 DOID:7527
Urinary tract infectious disease indication 68566005
Yaws indication 70647001 DOID:10371
Gonorrhea of pharynx indication 74372003
Rickettsialpox indication 75096007 DOID:11103
Ornithosis indication 75116005 DOID:11262
Brucellosis indication 75702008 DOID:11077
Syphilis indication 76272004
Acne vulgaris indication 88616000
Bacterial conjunctivitis indication 128350005 DOID:9700
Rocky Mountain spotted fever indication 186772009
Q fever indication 186788009 DOID:11100
Lymphogranuloma venereum indication 186946009 DOID:13819
Pneumonia indication 233604007 DOID:552
Inclusion conjunctivitis indication 266109000
Infective otitis media indication 312218008
Bacterial keratitis indication 314557000
Pharyngitis indication 405737000 DOID:2275
Anthrax indication 409498004 DOID:7427
Relapsing fever indication 420079008 DOID:13034
Chlamydia trachomatis infection of genital structure indication 428015005
Typhus Infections indication
Sexually Transmitted Epididymo-Orchitis indication
Female Urethral Syndrome indication
Rectal Chlamydia Trachomatis Infection indication
Inflammatory Disease of Female Pelvic Organs indication
Superficial Ocular Infection indication
Minor Bacterial Skin Infections indication
Duodenal Ulcer due to H. Pylori indication
Tularemia off-label use 19265001
Enterocolitis off-label use 43752006
Pneumonia due to Mycoplasma pneumoniae off-label use 46970008
Tropical sprue off-label use 47384003 DOID:10607
Plague off-label use 58750007 DOID:3482
Malaria off-label use 61462000 DOID:12365
Blepharoconjunctivitis off-label use 68659002 DOID:2456
Cholangitis off-label use 82403002 DOID:9446
Chlamydial infection off-label use 105629000
Infectious disease of abdomen off-label use 128070006
Ocular rosacea off-label use 200933006
Meibomianitis off-label use 309779001
Infective blepharitis off-label use 312219000
Rosacea off-label use 398909004 DOID:8881
Helicobacter pylori-associated gastritis off-label use 708164002
Chloroquine Resistant Plasmodium Falciparum Malaria off-label use
Alcoholism contraindication 7200002
Lowered convulsive threshold contraindication 19260006
Alcohol intoxication contraindication 25702006
Complete atrioventricular block contraindication 27885002
Shock contraindication 27942005
Hypovolemia contraindication 28560003
Glomerulonephritis contraindication 36171008 DOID:2921
Acute hepatitis contraindication 37871000
Hypokalemia contraindication 43339004
Uremia contraindication 44730006 DOID:4676
Stokes-Adams syndrome contraindication 46935006
Chronic heart failure contraindication 48447003
Atrial fibrillation contraindication 49436004 DOID:0060224
Sinus bradycardia contraindication 49710005
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Diabetes mellitus contraindication 73211009 DOID:9351
Wolff-Parkinson-White pattern contraindication 74390002 DOID:384
Decreased respiratory function contraindication 80954004
Disorder of brain contraindication 81308009 DOID:936
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Seizure disorder contraindication 128613002
Hypomagnesemia contraindication 190855004
Partial atrioventricular block contraindication 195039008
Non-infective meningitis contraindication 230155003
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Peripheral nerve disease contraindication 302226006
Neutropenic disorder contraindication 303011007 DOID:1227
Hypoxia contraindication 389086002
Pseudomembranous enterocolitis contraindication 397683000
Breastfeeding (mother) contraindication 413712001
Lidocaine Toxicity contraindication
Reduced Hepatic Blood Flow contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.26 acidic
pKa2 7.44 acidic
pKa3 8.06 acidic
pKa4 11.92 acidic
pKa5 12.84 acidic
pKa6 13.45 acidic
pKa7 9.49 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
30S ribosomal protein S4 Ribosomal protein WOMBAT-PK
30S ribosomal protein S9 Ribosomal protein WOMBAT-PK

External reference:

IDSource
4017625 VUID
N0000146005 NUI
C0039644 UMLSCUI
D00201 KEGG_DRUG
6B7BK5H33B UNII
1336-20-5 SECONDARY_CAS_RN
66261008 SNOMEDCT_US
4017625 VANDF
10395 RXNORM
372809001 SNOMEDCT_US
d00041 MMSL
002738 NDDF
CHEMBL1440 ChEMBL_ID
DB00759 DRUGBANK_ID
CHEMBL454950 ChEMBL_ID
298 INN_ID
TAC PDB_CHEM_ID
CHEBI:77932 CHEBI
CHEMBL1201071 ChEMBL_ID
D013752 MESH_DESCRIPTOR_UI
54675776 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0440-8505 CAPSULE 250 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-2474 CAPSULE 250 mg ORAL ANDA 12 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-2475 CAPSULE 500 mg ORAL ANDA 12 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-590 CAPSULE 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16590-216 CAPSULE 250 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16590-217 CAPSULE 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-302 CAPSULE 250 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-640 CAPSULE 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-017 CAPSULE 250 mg ORAL NDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-018 CAPSULE 500 mg ORAL NDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-766 CAPSULE 250 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-767 CAPSULE 500 mg ORAL ANDA 13 sections
Diabecline HUMAN OTC DRUG LABEL 1 24471-200 OINTMENT 30 mg TOPICAL OTC monograph final 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-798 CAPSULE 250 mg ORAL NDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-799 CAPSULE 500 mg ORAL NDA 13 sections
TETRA-ABC HUMAN OTC DRUG LABEL 1 43074-103 OINTMENT 0.03 mg TOPICAL OTC monograph final 12 sections
Dyabetex HUMAN OTC DRUG LABEL 1 43074-108 OINTMENT 0.03 mg TOPICAL OTC monograph final 12 sections
Diabecline HUMAN OTC DRUG LABEL 1 43074-112 OINTMENT 30 mg TOPICAL OTC monograph final 13 sections
Tetracycline-ABC HUMAN OTC DRUG LABEL 1 43074-115 OINTMENT 0.03 mg TOPICAL OTC monograph final 12 sections
Acnecycline HUMAN OTC DRUG LABEL 1 43074-116 OINTMENT 0.03 mg TOPICAL OTC monograph final 12 sections
TetraStem HUMAN OTC DRUG LABEL 1 43074-301 OINTMENT 30 mg TOPICAL OTC monograph final 9 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 47781-508 CAPSULE 250 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 47781-509 CAPSULE 500 mg ORAL ANDA 13 sections
SUMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 49884-732 TABLET, FILM COATED 250 mg ORAL ANDA 13 sections
SUMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 49884-733 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51991-906 CAPSULE 250 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51991-907 CAPSULE 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52959-336 CAPSULE 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-0877 CAPSULE 500 mg ORAL ANDA 13 sections
Tetracycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-0024 CAPSULE 250 mg ORAL ANDA 13 sections