tigecycline 🐶 Veterinary Use | 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: -0.19
  • 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 222.08 27.95 57 3790 5632 50595645
Pancreatitis acute 159.37 27.95 62 3785 23750 50577527
Pancreatitis 124.70 27.95 62 3785 42552 50558725
Drug resistance 111.47 27.95 45 3802 18944 50582333
Hypofibrinogenaemia 84.02 27.95 19 3828 1093 50600184
Thrombocytopenia 80.49 27.95 71 3776 127602 50473675
Multiple organ dysfunction syndrome 65.05 27.95 43 3804 50294 50550983
Sepsis 52.00 27.95 57 3790 132868 50468409
Septic shock 48.89 27.95 38 3809 57137 50544140
Klebsiella infection 45.48 27.95 18 3829 7176 50594101
Adjusted calcium decreased 45.35 27.95 8 3839 126 50601151
Morganella infection 44.21 27.95 10 3837 575 50600702
Biloma 43.59 27.95 7 3840 60 50601217
Haemodynamic instability 43.57 27.95 18 3829 8006 50593271
Globulins decreased 41.39 27.95 8 3839 212 50601065
Haemostasis 40.46 27.95 8 3839 239 50601038
Systemic inflammatory response syndrome 40.40 27.95 15 3832 5034 50596243
Coma hepatic 38.38 27.95 9 3838 607 50600670
Vomiting 38.38 27.95 98 3749 460660 50140617
Deafness 37.63 27.95 20 3827 15671 50585606
Blood urea increased 37.54 27.95 23 3824 23562 50577715
Hepatotoxicity 36.95 27.95 24 3823 27202 50574075
Wound haemorrhage 35.79 27.95 11 3836 2079 50599198
Immunosuppressant drug level increased 35.49 27.95 12 3835 3070 50598207
Multiple-drug resistance 34.63 27.95 12 3835 3302 50597975
Hepatic failure 33.24 27.95 24 3823 32259 50569018
Pain 33.17 27.95 3 3844 578900 50022377
Blood fibrinogen decreased 32.74 27.95 8 3839 643 50600634
Drug ineffective 32.42 27.95 135 3712 819198 49782079
Agranulocytosis 31.84 27.95 20 3827 21401 50579876
Acinetobacter infection 30.88 27.95 9 3838 1418 50599859
Nephropathy toxic 30.49 27.95 14 3833 8015 50593262
Nausea 30.05 27.95 119 3728 705279 49895998
Enterococcal infection 29.28 27.95 13 3834 6885 50594392
Escherichia infection 29.24 27.95 15 3832 10926 50590351

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 189.86 25.99 66 5056 8050 29561355
Hypofibrinogenaemia 146.84 25.99 37 5085 1464 29567941
Septic shock 138.36 25.99 102 5020 62458 29506947
Drug ineffective 131.25 25.99 228 4894 362942 29206463
Drug resistance 110.71 25.99 60 5062 21480 29547925
Multiple organ dysfunction syndrome 98.75 25.99 84 5038 63032 29506373
Klebsiella infection 95.88 25.99 39 5083 7310 29562095
Sepsis 72.25 25.99 105 5017 142577 29426828
Thrombocytopenia 66.47 25.99 98 5024 134725 29434680
Treatment failure 65.67 25.99 53 5069 36886 29532519
Enterococcal infection 59.75 25.99 29 5093 8239 29561166
Deafness neurosensory 56.53 25.99 20 5102 2558 29566847
Mycobacterium chelonae infection 54.58 25.99 14 5108 594 29568811
Pancreatitis acute 49.82 25.99 38 5084 24347 29545058
Ototoxicity 45.50 25.99 15 5107 1550 29567855
Pancreatitis 44.05 25.99 41 5081 34473 29534932
Fungaemia 40.62 25.99 15 5107 2166 29567239
Clostridium difficile colitis 39.53 25.99 26 5096 13186 29556219
Myasthenia gravis crisis 37.77 25.99 10 5112 481 29568924
Coagulopathy 36.77 25.99 28 5094 17879 29551526
Gallstone ileus 36.73 25.99 6 5116 22 29569383
Candida infection 36.19 25.99 26 5096 15199 29554206
Off label use 34.40 25.99 122 5000 300678 29268727
Product use in unapproved indication 34.14 25.99 57 5065 86818 29482587
Multiple-drug resistance 32.20 25.99 15 5107 3885 29565520
Staphylococcal infection 32.13 25.99 32 5090 29208 29540197
Flavobacterium infection 30.01 25.99 6 5116 80 29569325
Nausea 29.41 25.99 113 5009 289142 29280263
Geotrichum infection 29.22 25.99 8 5114 437 29568968
Anuria 29.08 25.99 19 5103 9522 29559883
Drug reaction with eosinophilia and systemic symptoms 27.78 25.99 29 5093 27963 29541442
Acoustic neuroma 26.57 25.99 6 5116 147 29569258

FDA Adverse Event Reporting System (Geriatric)

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 325.71 25.64 102 7989 12441 64478200
Drug resistance 201.71 25.64 95 7996 35007 64455634
Septic shock 176.58 25.64 128 7963 105309 64385332
Pancreatitis acute 166.61 25.64 89 8002 42766 64447875
Hypofibrinogenaemia 152.43 25.64 37 8054 1741 64488900
Drug ineffective 151.72 25.64 327 7764 839920 63650721
Klebsiella infection 135.68 25.64 54 8037 13227 64477414
Thrombocytopenia 133.76 25.64 152 7939 223649 64266992
Multiple organ dysfunction syndrome 125.64 25.64 103 7988 101310 64389331
Sepsis 112.18 25.64 141 7950 230200 64260441
Pancreatitis 105.68 25.64 75 8016 59532 64431109
Enterococcal infection 77.94 25.64 37 8054 13829 64476812
Acinetobacter infection 72.48 25.64 22 8069 2407 64488234
Coagulopathy 67.98 25.64 45 8046 31875 64458766
Multiple-drug resistance 58.01 25.64 24 8067 6478 64484163
Hepatotoxicity 56.68 25.64 44 8047 39918 64450723
Blood fibrinogen decreased 55.74 25.64 16 8075 1442 64489199
Mycobacterium chelonae infection 53.83 25.64 17 8074 2120 64488521
Off label use 53.34 25.64 187 7904 632619 63858022
Blood urea increased 50.75 25.64 43 8048 44110 64446531
Ototoxicity 49.78 25.64 17 8074 2706 64487935
Treatment failure 49.66 25.64 67 8024 116749 64373892
Pain 48.99 25.64 6 8085 553505 63937136
Clostridium difficile colitis 45.32 25.64 33 8058 27190 64463451
Morganella infection 42.79 25.64 12 8079 994 64489647
Deafness neurosensory 42.01 25.64 19 8072 6355 64484286
Haemodynamic instability 41.72 25.64 25 8066 14887 64475754
Pseudomonas infection 39.98 25.64 26 8065 17857 64472784
Adjusted calcium decreased 39.73 25.64 8 8083 156 64490485
Drug reaction with eosinophilia and systemic symptoms 39.53 25.64 41 8050 54176 64436465
Product use in unapproved indication 38.78 25.64 75 8016 176543 64314098
Nephropathy toxic 38.02 25.64 25 8066 17489 64473152
Pneumonia pseudomonal 36.77 25.64 16 8075 4887 64485754
Fall 35.69 25.64 5 8086 416821 64073820
Haemostasis 35.52 25.64 8 8083 270 64490371
Myasthenia gravis crisis 35.14 25.64 10 8081 874 64489767
Biloma 34.14 25.64 7 8084 150 64490491
Fungaemia 33.86 25.64 14 8077 3771 64486870
Coma hepatic 33.80 25.64 10 8081 1002 64489639
Globulins decreased 33.16 25.64 8 8083 366 64490275
Klebsiella bacteraemia 32.83 25.64 12 8079 2328 64488313
Headache 32.39 25.64 13 8078 529454 63961187
Aspergillus infection 32.24 25.64 22 8069 16357 64474284
Renal failure 31.48 25.64 70 8021 181618 64309023
Flavobacterium infection 31.22 25.64 6 8085 91 64490550
Immunosuppressant drug level increased 30.79 25.64 16 8075 7243 64483398
Hepatitis cholestatic 30.47 25.64 19 8072 12136 64478505
Hepatic failure 30.22 25.64 36 8055 55358 64435283
Endocarditis 29.59 25.64 17 8074 9361 64481280
Staphylococcal infection 29.41 25.64 34 8057 50644 64439997
Hypertriglyceridaemia 29.32 25.64 18 8073 11187 64479454
Escherichia infection 28.97 25.64 20 8071 15148 64475493
Candida infection 28.93 25.64 27 8064 31392 64459249
Acute kidney injury 28.85 25.64 122 7969 449118 64041523
Electrocardiogram QT prolonged 28.45 25.64 42 8049 79406 64411235
Wound haemorrhage 28.37 25.64 12 8079 3419 64487222
Systemic inflammatory response syndrome 28.22 25.64 17 8074 10218 64480423
Abdominal infection 26.73 25.64 11 8080 2929 64487712
Pneumonia klebsiella 26.50 25.64 12 8079 4025 64486616
Liver abscess 26.37 25.64 13 8078 5267 64485374
Acinetobacter bacteraemia 26.35 25.64 6 8085 213 64490428
Eosinophilic pneumonia acute 26.32 25.64 8 8083 879 64489762
Geotrichum infection 26.05 25.64 8 8083 910 64489731
Acoustic neuroma 25.88 25.64 6 8085 231 64490410

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
C1260298 UMLSCUI
CHEBI:142708 CHEBI
T1C PDB_CHEM_ID
CHEMBL376140 ChEMBL_ID
D000078304 MESH_DESCRIPTOR_UI
DB00560 DRUGBANK_ID
C087533 MESH_SUPPLEMENTAL_RECORD_UI
10929 IUPHAR_LIGAND_ID
8115 INN_ID
70JE2N95KR UNII
54686904 PUBCHEM_CID
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 27 sections
Tigecycline Human Prescription Drug Label 1 55150-228 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 27 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