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) 0.45 mg/mL Bocci G, Oprea TI, Benet LZ
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 238.91 26.83 61 4436 6337 63478188
Pancreatitis acute 166.16 26.83 65 4432 27101 63457424
Drug resistance 151.35 26.83 58 4439 22875 63461650
Pancreatitis 126.34 26.83 64 4433 48991 63435534
Thrombocytopenia 104.52 26.83 86 4411 151071 63333454
Hypofibrinogenaemia 95.37 26.83 21 4476 1149 63483376
Multiple organ dysfunction syndrome 82.84 26.83 51 4446 56701 63427824
Septic shock 61.38 26.83 45 4452 66584 63417941
Klebsiella infection 57.65 26.83 22 4475 8544 63475981
Sepsis 57.23 26.83 62 4435 153061 63331464
Coagulopathy 44.78 26.83 24 4473 20520 63464005
Hepatic failure 44.39 26.83 29 4468 35627 63448898
Biloma 44.09 26.83 7 4490 60 63484465
Morganella infection 43.55 26.83 10 4487 661 63483864
Adjusted calcium decreased 43.12 26.83 8 4489 182 63484343
Haemodynamic instability 42.44 26.83 18 4479 9172 63475353
Drug ineffective 41.43 26.83 164 4333 1044601 62439924
Haemostasis 40.93 26.83 8 4489 242 63484283
Vomiting 40.42 26.83 108 4389 559509 62925016
Globulins decreased 40.35 26.83 8 4489 261 63484264
Systemic inflammatory response syndrome 39.86 26.83 15 4482 5606 63478919
Acinetobacter infection 39.57 26.83 11 4486 1572 63482953
Deafness 39.20 26.83 21 4476 17936 63466589
Pain 38.43 26.83 4 4493 740624 62743901
Coma hepatic 37.96 26.83 9 4488 684 63483841
Blood urea increased 36.66 26.83 23 4474 26356 63458169
Blood fibrinogen decreased 36.10 26.83 9 4488 844 63483681
Wound haemorrhage 34.54 26.83 11 4486 2505 63482020
Immunosuppressant drug level increased 34.36 26.83 12 4485 3626 63480899
Hepatotoxicity 34.04 26.83 25 4472 37016 63447509
Multiple-drug resistance 33.79 26.83 13 4484 5157 63479368
Agranulocytosis 32.64 26.83 21 4476 25113 63459412
Enterococcal infection 31.74 26.83 14 4483 7834 63476691
Nausea 31.24 26.83 131 4366 854340 62630185
Renal failure 31.19 26.83 40 4457 117612 63366913
Off label use 30.81 26.83 111 4386 674351 62810174
Nephropathy toxic 29.22 26.83 14 4483 9465 63475060
Lipase increased 28.64 26.83 14 4483 9886 63474639
Escherichia infection 28.07 26.83 15 4482 12739 63471786
Acute kidney injury 27.77 26.83 59 4438 263356 63221169
Arthralgia 27.26 26.83 4 4493 569706 62914819
Graft versus host disease 27.15 26.83 12 4485 6751 63477774

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 196.11 26.84 70 5862 9412 34941587
Hypofibrinogenaemia 148.19 26.84 38 5894 1648 34949351
Septic shock 138.38 26.84 107 5825 71727 34879272
Drug resistance 136.85 26.84 73 5859 25854 34925145
Drug ineffective 133.82 26.84 259 5673 456492 34494507
Multiple organ dysfunction syndrome 107.56 26.84 95 5837 76471 34874528
Coagulopathy 102.36 26.84 55 5877 19734 34931265
Klebsiella infection 101.03 26.84 42 5890 8489 34942510
Treatment failure 79.99 26.84 65 5867 46632 34904367
Off label use 76.07 26.84 197 5735 419327 34531672
Thrombocytopenia 69.35 26.84 107 5825 156140 34794859
Sepsis 68.31 26.84 110 5822 166451 34784548
Enterococcal infection 65.94 26.84 32 5900 9274 34941725
Pancreatitis acute 63.12 26.84 46 5886 28095 34922904
Drug reaction with eosinophilia and systemic symptoms 56.59 26.84 46 5886 32966 34918033
Mycobacterium chelonae infection 55.45 26.84 15 5917 800 34950199
Deafness neurosensory 54.82 26.84 20 5912 2851 34948148
Blood fibrinogen decreased 53.66 26.84 16 5916 1214 34949785
Trichosporon infection 47.56 26.84 13 5919 721 34950278
Ototoxicity 42.81 26.84 15 5917 1902 34949097
Pancreatitis 42.43 26.84 42 5890 38849 34912150
Staphylococcal infection 40.69 26.84 38 5894 32722 34918277
Clostridium difficile colitis 40.53 26.84 28 5904 15702 34935297
Fungaemia 38.53 26.84 15 5917 2553 34948446
Candida infection 37.54 26.84 28 5904 17687 34933312
Gallstone ileus 36.85 26.84 6 5926 22 34950977
Myasthenia gravis crisis 35.55 26.84 10 5922 617 34950382
Product use in unapproved indication 34.33 26.84 67 5865 117432 34833567
Klebsiella bacteraemia 31.53 26.84 11 5921 1377 34949622
Flavobacterium infection 30.13 26.84 6 5926 80 34950919
Bilirubin conjugated increased 28.57 26.84 13 5919 3258 34947741
Geotrichum infection 28.40 26.84 8 5924 496 34950503
Multiple-drug resistance 28.29 26.84 15 5917 5224 34945775
Nausea 28.19 26.84 123 5809 339785 34611214
Anuria 27.97 26.84 19 5913 10366 34940633
Blood bilirubin increased 27.18 26.84 33 5899 38263 34912736
Acinetobacter test positive 26.84 26.84 6 5926 143 34950856

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 350.51 24.85 110 9386 14232 79720660
Drug resistance 247.50 24.85 114 9382 42099 79692793
Septic shock 191.72 24.85 140 9356 122661 79612231
Pancreatitis acute 186.45 24.85 99 9397 49505 79685387
Drug ineffective 167.95 24.85 384 9112 1080529 78654363
Hypofibrinogenaemia 165.23 24.85 40 9456 1962 79732930
Thrombocytopenia 157.29 24.85 175 9321 265084 79469808
Coagulopathy 155.77 24.85 79 9417 35927 79698965
Multiple organ dysfunction syndrome 152.16 24.85 121 9375 120125 79614767
Klebsiella infection 150.09 24.85 60 9436 15660 79719232
Sepsis 114.17 24.85 150 9346 269278 79465614
Off label use 106.17 24.85 290 9206 906925 78827967
Pancreatitis 104.19 24.85 77 9419 68498 79666394
Blood fibrinogen decreased 91.87 24.85 25 9471 1954 79732938
Acinetobacter infection 87.85 24.85 26 9470 2751 79732141
Enterococcal infection 87.65 24.85 41 9455 15619 79719273
Drug reaction with eosinophilia and systemic symptoms 73.45 24.85 61 9435 64183 79670709
Pain 59.74 24.85 7 9489 703795 79031097
Mycobacterium chelonae infection 56.47 24.85 18 9478 2438 79732454
Treatment failure 55.81 24.85 84 9412 170402 79564490
Multiple-drug resistance 55.36 24.85 25 9471 8783 79726109
Hepatotoxicity 51.01 24.85 45 9451 51307 79683585
Blood urea increased 48.95 24.85 43 9453 48747 79686145
Clostridium difficile colitis 48.43 24.85 36 9460 32247 79702645
Trichosporon infection 48.03 24.85 13 9483 995 79733897
Ototoxicity 47.58 24.85 17 9479 3257 79731635
Hepatic failure 46.11 24.85 46 9450 61166 79673726
Product use in unapproved indication 43.98 24.85 94 9402 250265 79484627
Pseudomonas infection 42.29 24.85 28 9468 20875 79714017
Morganella infection 42.06 24.85 12 9484 1115 79733777
Deafness neurosensory 41.52 24.85 19 9477 6879 79728013
Haemodynamic instability 39.38 24.85 25 9471 17357 79717535
Nephropathy toxic 38.07 24.85 26 9470 20393 79714499
Adjusted calcium decreased 37.62 24.85 8 9488 217 79734675
Fall 36.40 24.85 7 9489 487622 79247270
Renal failure 35.90 24.85 76 9420 200892 79534000
Staphylococcal infection 35.31 24.85 39 9457 58256 79676636
Headache 35.18 24.85 17 9479 653755 79081137
Pneumonia pseudomonal 34.70 24.85 16 9480 5895 79728997
Biloma 34.50 24.85 7 9489 150 79734742
Klebsiella bacteraemia 34.05 24.85 13 9483 2997 79731895
Activated partial thromboplastin time prolonged 33.58 24.85 21 9475 14207 79720685
Myasthenia gravis crisis 33.39 24.85 10 9486 1101 79733791
Coma hepatic 33.37 24.85 10 9486 1103 79733789
Lipase increased 33.17 24.85 22 9474 16444 79718448
Candida infection 33.07 24.85 31 9465 38183 79696709
Haemostasis 33.00 24.85 8 9488 394 79734498
Platelet count decreased 32.91 24.85 72 9424 194592 79540300
Dysbiosis 32.48 24.85 10 9486 1209 79733683
Fungaemia 31.96 24.85 14 9482 4577 79730315
Globulins decreased 31.74 24.85 8 9488 463 79734429
Electrocardiogram QT prolonged 31.64 24.85 46 9450 90340 79644552
Hepatitis cholestatic 31.57 24.85 20 9476 13832 79721060
Flavobacterium infection 31.17 24.85 6 9490 97 79734795
Hypertriglyceridaemia 30.56 24.85 19 9477 12721 79722171
Arthralgia 30.55 24.85 15 9481 571788 79163104
Aspergillus infection 30.16 24.85 22 9474 19139 79715753
Endocarditis 28.49 24.85 17 9479 10580 79724312
Immunosuppressant drug level increased 28.29 24.85 16 9480 9011 79725881
Mycobacterium abscessus infection 28.27 24.85 9 9487 1213 79733679
Fatigue 28.25 24.85 42 9454 929685 78805207
Acute kidney injury 27.92 24.85 129 9367 519275 79215617
Pneumonia klebsiella 27.56 24.85 13 9483 5041 79729851
Systemic inflammatory response syndrome 27.25 24.85 17 9479 11448 79723444
Procalcitonin increased 27.04 24.85 11 9485 2995 79731897
Escherichia infection 26.81 24.85 20 9476 17997 79716895
Wound haemorrhage 26.75 24.85 12 9484 4149 79730743
Geotrichum infection 25.93 24.85 8 9488 973 79733919
Acinetobacter test positive 25.57 24.85 6 9490 257 79734635
Drug ineffective for unapproved indication 25.52 24.85 31 9465 51207 79683685
Liver abscess 25.33 24.85 13 9483 6041 79728851
Cholestasis 25.10 24.85 31 9465 52078 79682814
Blood bilirubin increased 25.08 24.85 35 9461 66197 79668695
Eosinophilic pneumonia acute 25.05 24.85 8 9488 1090 79733802
Abdominal infection 25.04 24.85 11 9485 3618 79731274
Acinetobacter bacteraemia 25.00 24.85 6 9490 283 79734609

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 0008-4990 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
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 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 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