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

Stem definitionDrug idCAS RN
antibiotics, protein-synthesis inhibitors, tetracycline derivatives 2661 220620-09-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • CL-331002
  • CL 331002
  • tigecycline
  • tygacil
  • glycylcycline
Tigecycline inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. In general, tigecycline is considered bacteriostatic; however, tigecycline has demonstrated bactericidal activity against isolates of S. pneumoniae and L. pneumophila.
  • Molecular weight: 585.66
  • Formula: C29H39N5O8
  • CLOGP: -0.03
  • LIPINSKI: 3
  • HAC: 13
  • HDO: 7
  • TPSA: 205.76
  • ALOGS: -3.11
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 295 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 22 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.80 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.20 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 48 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 15, 2005 FDA PF PRISM CV

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
Pathogen resistance 213.72 30.77 56 3493 6004 46676509
Pancreatitis acute 146.35 30.77 59 3490 24813 46657700
Pancreatitis 120.42 30.77 61 3488 43566 46638947
Drug resistance 97.97 30.77 40 3509 17328 46665185
Klebsiella infection 80.96 30.77 27 3522 6635 46675878
Thrombocytopenia 63.52 30.77 62 3487 126519 46555994
Hypofibrinogenaemia 63.37 30.77 15 3534 1055 46681458
Acinetobacter infection 59.13 30.77 15 3534 1407 46681106
Multiple organ dysfunction syndrome 56.92 30.77 40 3509 51670 46630843
Sepsis 47.55 30.77 55 3494 135959 46546554
Adjusted calcium decreased 46.64 30.77 8 3541 106 46682407
Septic shock 44.20 30.77 36 3513 57857 46624656
Biloma 43.59 30.77 7 3542 60 46682453
Globulins decreased 41.57 30.77 8 3541 207 46682306
Haemodynamic instability 40.84 30.77 17 3532 7708 46674805
Morganella infection 40.81 30.77 9 3540 461 46682052
Haemostasis 40.50 30.77 8 3541 238 46682275
Systemic inflammatory response syndrome 39.50 30.77 15 3534 5356 46677157
Hepatotoxicity 38.82 30.77 24 3525 24985 46657528
Coma hepatic 38.39 30.77 9 3540 607 46681906
Drug ineffective 38.08 30.77 125 3424 677713 46004800
Multiple-drug resistance 37.65 30.77 12 3537 2553 46679960
Immunosuppressant drug level increased 34.75 30.77 12 3537 3270 46679243
Escherichia infection 32.35 30.77 16 3533 10801 46671712
Blood fibrinogen decreased 32.05 30.77 8 3541 702 46681811
Nephropathy toxic 31.49 30.77 14 3535 7440 46675073
Wound haemorrhage 31.42 30.77 10 3539 2117 46680396
Blood urea increased 31.14 30.77 21 3528 25331 46657182

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
Pathogen resistance 165.23 25.22 58 4468 8352 29939600
Hypofibrinogenaemia 143.51 25.22 36 4490 1609 29946343
Septic shock 135.38 25.22 96 4430 63511 29884441
Drug ineffective 126.93 25.22 201 4325 340186 29607766
Multiple organ dysfunction syndrome 93.47 25.22 77 4449 63410 29884542
Drug resistance 93.26 25.22 50 4476 20083 29927869
Enterococcal infection 76.57 25.22 33 4493 8191 29939761
Klebsiella infection 71.97 25.22 30 4496 6857 29941095
Mycobacterium chelonae infection 66.76 25.22 16 4510 589 29947363
Sepsis 60.35 25.22 91 4435 146304 29801648
Treatment failure 55.03 25.22 44 4482 34635 29913317
Thrombocytopenia 54.78 25.22 84 4442 136960 29810992
Pancreatitis acute 50.42 25.22 37 4489 25658 29922294
Ototoxicity 49.20 25.22 15 4511 1381 29946571
Pancreatitis 46.91 25.22 41 4485 36449 29911503
Mycobacterium abscessus infection 42.11 25.22 11 4515 577 29947375
Acinetobacter infection 40.55 25.22 12 4514 998 29946954
Klebsiella bacteraemia 40.01 25.22 12 4514 1045 29946907
Multiple-drug resistance 38.25 25.22 15 4511 2926 29945026
Gallstone ileus 37.55 25.22 6 4520 22 29947930
Coagulopathy 34.85 25.22 26 4500 18461 29929491
Fungaemia 31.22 25.22 12 4514 2219 29945733
Deafness neurosensory 30.40 25.22 12 4514 2381 29945571
Anuria 30.10 25.22 19 4507 10297 29937655
Flavobacterium infection 29.98 25.22 6 4520 93 29947859
Candida infection 29.84 25.22 22 4504 15340 29932612
Product use in unapproved indication 29.11 25.22 45 4481 73648 29874304
Haematological malignancy 29.04 25.22 6 4520 110 29947842
Acoustic neuroma 27.91 25.22 6 4520 134 29947818
Staphylococcal infection 27.40 25.22 28 4498 30196 29917756
Bacteraemia 27.37 25.22 21 4505 15539 29932413
Hepatotoxicity 26.60 25.22 22 4504 18123 29929829
Nausea 25.35 25.22 100 4426 296857 29651095

Pharmacologic Action:

SourceCodeDescription
ATC J01AA12 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
TETRACYCLINES
Tetracyclines
FDA CS M0021223 Tetracyclines
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011500 Protein Synthesis Inhibitors
FDA EPC N0000175938 Tetracycline-class Antibacterial

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pneumonia due to Streptococcus indication 34020007
Haemophilus influenzae pneumonia indication 70036007
Abdominal abscess indication 75100008
Infectious disease of abdomen indication 128070006
Complicated appendicitis indication 418171008
Complicated Skin and Skin Structure E. Coli Infection indication
Complicated Skin and Skin Structure Staphylococcus Aureus Infection indication
Complicated Skin and Skin Structure Infection indication
Complicated Skin and Skin Structure Streptococcus Pyogenes Infection indication
Legionella Pneumophila Pneumonia indication
Complicated Bacterial Peritonitis indication
Complicated Skin and Skin Structure Enterococcus Faecalis Infection indication
Complicated Skin and Skin Structure Streptococcus Agalactiae Infection indication
Hyperbilirubinemia contraindication 14783006 DOID:2741
Gastrointestinal perforation contraindication 51875005
Hepatic failure contraindication 59927004
Pancreatitis contraindication 75694006 DOID:4989
Pregnancy, function contraindication 289908002
Pseudomembranous enterocolitis contraindication 397683000
Antibiotic-Induced Hypoprothrombinemia contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.13 acidic
pKa2 8.64 acidic
pKa3 11.14 acidic
pKa4 11.96 acidic
pKa5 13.08 acidic
pKa6 13.93 acidic
pKa7 9.41 Basic
pKa8 7.96 Basic
pKa9 7.31 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

IDSource
4024922 VUID
N0000171604 NUI
D01079 KEGG_DRUG
4024922 VANDF
C0255348 UMLSCUI
CHEBI:142708 CHEBI
T1C PDB_CHEM_ID
CHEMBL376140 ChEMBL_ID
D000078304 MESH_DESCRIPTOR_UI
C087533 MESH_SUPPLEMENTAL_RECORD_UI
54686193 PUBCHEM_CID
8115 INN_ID
DB00560 DRUGBANK_ID
70JE2N95KR UNII
10929 IUPHAR_LIGAND_ID
384455 RXNORM
20166 MMSL
230306 MMSL
69774 MMSL
d05537 MMSL
010833 NDDF
418313005 SNOMEDCT_US
418631002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tygacil HUMAN PRESCRIPTION DRUG LABEL 1 0008-4990 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 33 sections
Tygacil HUMAN PRESCRIPTION DRUG LABEL 1 0008-4994 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 30 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 0781-3481 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 26 sections
TIGECYCLINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-364 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 31 sections
Tigecycline Human Prescription Drug Label 1 55150-228 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 28 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 60505-6098 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 sections
Tigecycline Human Prescription Drug Label 1 63323-960 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 27 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 70121-1647 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 22 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 70594-035 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 33 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 71288-019 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 30 sections