tigecycline 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK2,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAPK1,MAPK10,MAPK7,MAPK9,MAPKAPK2,MAPKAPK5,MARK4,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIM2,PLK1,PLK2,PLK3,PLK4,PRKCD,PRKDC,PTK2,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 69
kinase-selectivity-class AXL,CDK4,EIF2AK3,EPHB4,GRK2,MAP2K6,MAPK7,STK33,TEK 9
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 262.24 29.61 68 5919 8047 90614413
Pancreatitis acute 205.76 29.61 78 5909 32037 90590423
Drug resistance 195.23 29.61 74 5913 30375 90592085
Blood fibrinogen decreased 154.98 29.61 31 5956 1139 90621321
Coagulopathy 147.08 29.61 56 5931 23233 90599227
Hypofibrinogenaemia 132.72 29.61 28 5959 1342 90621118
Pancreatitis 122.63 29.61 69 5918 69757 90552703
Thrombocytopenia 100.76 29.61 94 5893 208631 90413829
Dysbiosis 99.54 29.61 23 5964 1679 90620781
Multiple organ dysfunction syndrome 84.73 29.61 54 5933 68282 90554178
Drug ineffective 72.40 29.61 227 5760 1384071 89238389
Systemic inflammatory response syndrome 68.98 29.61 23 5964 6493 90615967
Off label use 66.21 29.61 190 5797 1102062 89520398
Septic shock 65.55 29.61 50 5937 84110 90538350
Multiple-drug resistance 61.21 29.61 22 5965 7754 90614706
Paraspinal abscess 59.50 29.61 11 5976 264 90622196
Sepsis 59.31 29.61 66 5921 179748 90442712
Lipase increased 57.00 29.61 23 5964 11088 90611372
Escherichia infection 55.35 29.61 25 5962 15870 90606590
Klebsiella infection 55.20 29.61 22 5965 10275 90612185
Mitochondrial toxicity 49.84 29.61 11 5976 652 90621808
Mycobacterium abscessus infection 49.64 29.61 12 5975 1063 90621397
Pain 48.24 29.61 5 5982 996336 89626124
Hepatic failure 48.23 29.61 31 5956 39697 90582763
Acinetobacter infection 46.75 29.61 13 5974 1995 90620465
Nausea 46.19 29.61 169 5818 1110147 89512313
Haemodynamic instability 45.81 29.61 20 5967 11719 90610741
Graft versus host disease in gastrointestinal tract 44.50 29.61 15 5972 4373 90618087
Vomiting 44.34 29.61 133 5854 788160 89834300
Nephropathy toxic 44.31 29.61 20 5967 12668 90609792
Coagulation time prolonged 44.25 29.61 12 5975 1678 90620782
Tonsillitis bacterial 44.20 29.61 8 5979 170 90622290
Abscess 42.41 29.61 22 5965 18869 90603591
Morganella infection 42.29 29.61 10 5977 806 90621654
Adjusted calcium decreased 42.22 29.61 8 5979 220 90622240
Deafness 41.51 29.61 23 5964 22491 90599969
Biloma 41.36 29.61 7 5980 99 90622361
Platelet count decreased 41.27 29.61 48 5939 136921 90485539
Arthralgia 40.10 29.61 3 5984 778519 89843941
Blood urea increased 40.08 29.61 25 5962 30388 90592072
Coma hepatic 38.94 29.61 9 5978 657 90621803
Graft versus host disease 38.84 29.61 16 5971 8128 90614332
Blood bilirubin increased 38.69 29.61 28 5959 43442 90579018
Haemostasis 38.06 29.61 8 5979 376 90622084
Globulins decreased 37.54 29.61 8 5979 402 90622058
Renal failure 36.31 29.61 44 5943 130963 90491497
Immunosuppressant drug level increased 35.93 29.61 13 5974 4667 90617793
Headache 35.53 29.61 7 5980 862739 89759721
Bacterial sepsis 35.20 29.61 13 5974 4942 90617518
Hepatotoxicity 35.15 29.61 27 5960 45815 90576645
Graft versus host disease in skin 34.51 29.61 12 5975 3841 90618619
Acute kidney injury 33.90 29.61 69 5918 320318 90302142
Wound haemorrhage 33.88 29.61 11 5976 2856 90619604
Ototoxicity 33.59 29.61 10 5977 1954 90620506
Respiratory failure 33.18 29.61 40 5947 118378 90504082
Enterococcal infection 32.53 29.61 15 5972 9976 90612484
Agranulocytosis 29.91 29.61 22 5965 34980 90587480

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
Coagulopathy 238.02 27.15 105 7956 22057 42591217
Pathogen resistance 225.87 27.15 84 7977 11366 42601908
Drug resistance 214.39 27.15 112 7949 34136 42579138
Off label use 184.28 27.15 383 7678 637952 41975322
Drug ineffective 173.49 27.15 371 7690 629826 41983448
Septic shock 172.81 27.15 141 7920 91531 42521743
Hypofibrinogenaemia 166.50 27.15 44 8017 1923 42611351
Blood fibrinogen decreased 155.69 27.15 40 8021 1563 42611711
Klebsiella infection 106.63 27.15 49 8012 11283 42601991
Enterococcal infection 91.66 27.15 45 8016 11994 42601280
Multiple organ dysfunction syndrome 90.02 27.15 101 7960 96934 42516340
Coagulation time prolonged 83.93 27.15 24 8037 1408 42611866
Treatment failure 83.04 27.15 79 7982 62545 42550729
Ototoxicity 76.49 27.15 25 8036 2300 42610974
Pancreatitis acute 74.62 27.15 57 8004 33507 42579767
Drug reaction with eosinophilia and systemic symptoms 71.37 27.15 61 8000 42014 42571260
Sepsis 67.91 27.15 129 7932 199205 42414069
Mycobacterium chelonae infection 65.72 27.15 19 8042 1159 42612115
Thrombocytopenia 64.63 27.15 123 7938 190156 42423118
Dysbiosis 58.72 27.15 16 8045 785 42612489
Deafness neurosensory 57.78 27.15 23 8038 3723 42609551
Platelet count decreased 56.45 27.15 97 7964 138484 42474790
Nausea 49.71 27.15 176 7885 396623 42216651
Clostridium difficile colitis 49.22 27.15 37 8024 21215 42592059
Blood bilirubin increased 44.36 27.15 47 8014 42205 42571069
Trichosporon infection 42.82 27.15 13 8048 939 42612335
Pancreatitis 41.69 27.15 46 8015 43222 42570052
Liver injury 41.40 27.15 32 8029 19116 42594158
Drug ineffective for unapproved indication 39.26 27.15 46 8015 46117 42567157
Lipase increased 37.69 27.15 24 8037 10542 42602732
Fatigue 37.27 27.15 18 8043 435623 42177651
Gallstone ileus 36.20 27.15 6 8055 22 42613252
Pseudomonas infection 35.27 27.15 27 8034 15896 42597378
Fungaemia 34.06 27.15 15 8046 3121 42610153
Candida infection 33.93 27.15 30 8031 21580 42591694
Activated partial thromboplastin time prolonged 33.12 27.15 26 8035 15877 42597397
Staphylococcal infection 32.82 27.15 38 8023 37605 42575669
Bilirubin conjugated increased 31.78 27.15 15 8046 3662 42609612
Myasthenia gravis crisis 31.52 27.15 10 8051 836 42612438
Acoustic neuroma 31.50 27.15 7 8054 145 42613129
Acinetobacter test positive 31.41 27.15 7 8054 147 42613127
Bacterial infection 31.02 27.15 32 8029 27847 42585427
Fall 30.83 27.15 4 8057 234516 42378758
Pain 30.29 27.15 5 8056 244843 42368431
Dizziness 28.88 27.15 6 8055 249248 42364026
Flavobacterium infection 28.35 27.15 6 8055 98 42613176
Megacolon 28.33 27.15 12 8049 2273 42611001
Product use in unapproved indication 27.56 27.15 87 7974 184369 42428905

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 411.14 24.08 130 12800 17542 110558827
Coagulopathy 410.85 24.08 161 12769 40750 110535619
Drug resistance 345.06 24.08 156 12774 56218 110520151
Blood fibrinogen decreased 314.68 24.08 71 12859 2604 110573765
Off label use 250.20 24.08 542 12388 1499643 109076726
Drug ineffective 240.65 24.08 538 12392 1520002 109056367
Pancreatitis acute 236.29 24.08 123 12807 60151 110516218
Septic shock 233.86 24.08 173 12757 157355 110419014
Hypofibrinogenaemia 222.87 24.08 53 12877 2454 110573915
Dysbiosis 153.32 24.08 38 12892 2094 110574275
Multiple organ dysfunction syndrome 147.17 24.08 130 12800 151580 110424789
Thrombocytopenia 147.10 24.08 192 12738 348693 110227676
Klebsiella infection 143.67 24.08 62 12868 19947 110556422
Coagulation time prolonged 132.12 24.08 36 12894 2881 110573488
Sepsis 126.96 24.08 173 12757 327173 110249196
Platelet count decreased 114.85 24.08 138 12792 230305 110346064
Enterococcal infection 107.75 24.08 51 12879 20315 110556054
Drug reaction with eosinophilia and systemic symptoms 99.42 24.08 80 12850 82015 110494354
Pancreatitis 96.36 24.08 83 12847 93450 110482919
Acinetobacter infection 94.41 24.08 29 12901 3544 110572825
Multiple-drug resistance 85.24 24.08 38 12892 13197 110563172
Lipase increased 84.44 24.08 42 12888 18630 110557739
Pain 82.98 24.08 8 12922 954947 109621422
Mycobacterium chelonae infection 73.14 24.08 23 12907 3037 110573332
Pseudomonas infection 68.71 24.08 42 12888 27811 110548558
Blood bilirubin increased 65.52 24.08 61 12869 75911 110500458
Activated partial thromboplastin time prolonged 63.70 24.08 37 12893 22331 110554038
Clostridium difficile colitis 62.40 24.08 47 12883 43731 110532638
Ototoxicity 58.72 24.08 21 12909 4110 110572259
Blood urea increased 57.04 24.08 49 12881 54908 110521461
Hepatotoxicity 56.79 24.08 52 12878 63348 110513021
Hepatic failure 55.09 24.08 53 12877 68686 110507683
Headache 54.02 24.08 18 12912 882359 109694010
Escherichia infection 51.41 24.08 33 12897 23783 110552586
Treatment failure 49.86 24.08 104 12826 277130 110299239
Paraspinal abscess 48.43 24.08 11 12919 415 110575954
Prothrombin time prolonged 47.69 24.08 28 12902 17233 110559136
Deafness neurosensory 47.56 24.08 23 12907 9596 110566773
Fall 47.54 24.08 7 12923 603475 109972894
Nephropathy toxic 47.12 24.08 33 12897 27445 110548924
Systemic inflammatory response syndrome 46.47 24.08 25 12905 13018 110563351
Arthralgia 45.82 24.08 17 12913 779615 109796754
Mycobacterium abscessus infection 45.72 24.08 14 12916 1692 110574677
Trichosporon infection 44.99 24.08 13 12917 1287 110575082
Drug ineffective for unapproved indication 43.80 24.08 57 12873 102781 110473588
Renal failure 41.90 24.08 86 12844 226488 110349881
Amylase increased 41.84 24.08 23 12907 12496 110563873
Haemodynamic instability 40.44 24.08 28 12902 22860 110553509
Joint swelling 40.32 24.08 3 12927 442842 110133527
Abscess 40.27 24.08 30 12900 27439 110548930
Bacterial sepsis 40.01 24.08 21 12909 10405 110565964
Morganella infection 39.89 24.08 12 12918 1367 110575002
Renal impairment 39.01 24.08 75 12855 188370 110387999
Acute kidney injury 38.88 24.08 162 12768 635268 109941101
Tonsillitis bacterial 37.02 24.08 8 12922 239 110576130
Adjusted calcium decreased 36.71 24.08 8 12922 249 110576120
Product use in unapproved indication 35.54 24.08 124 12806 447253 110129116
Nausea 34.83 24.08 255 12675 1235435 109340934
Cholestasis 34.31 24.08 40 12890 64478 110511891
Drug-induced liver injury 34.21 24.08 55 12875 120012 110456357
Coma hepatic 33.88 24.08 10 12920 1067 110575302
Procalcitonin increased 33.87 24.08 14 12916 4042 110572327
Eosinophilic pneumonia acute 33.58 24.08 11 12919 1654 110574715
Staphylococcal infection 33.32 24.08 41 12889 69903 110506466
Respiratory failure 33.24 24.08 76 12854 215256 110361113
Candida infection 32.89 24.08 34 12896 47975 110528394
Electrocardiogram QT prolonged 32.54 24.08 51 12879 108909 110467460
Fatigue 32.44 24.08 58 12872 1215900 109360469
Immunosuppressant drug level increased 32.34 24.08 19 12911 11705 110564664
Transaminases increased 31.56 24.08 38 12892 63352 110513017
Graft versus host disease in gastrointestinal tract 31.42 24.08 17 12913 8951 110567418
Klebsiella bacteraemia 31.41 24.08 14 12916 4855 110571514
Biloma 31.33 24.08 7 12923 245 110576124
Pneumonia pseudomonal 31.26 24.08 16 12914 7530 110568839
Hepatic function abnormal 31.23 24.08 45 12885 89250 110487119
Peripheral swelling 31.08 24.08 5 12925 404029 110172340
Aspergillus infection 31.06 24.08 25 12905 25591 110550778
Haemostasis 30.57 24.08 8 12922 548 110575821
Acinetobacter test positive 30.27 24.08 7 12923 286 110576083
Mitochondrial toxicity 29.83 24.08 12 12918 3233 110573136
Acoustic neuroma 29.70 24.08 7 12923 311 110576058
Dizziness 29.63 24.08 23 12907 698170 109878199
Flavobacterium infection 29.62 24.08 6 12924 130 110576239
Alopecia 29.24 24.08 4 12926 364749 110211620
Agranulocytosis 29.09 24.08 36 12894 61724 110514645
Thrombin time prolonged 29.04 24.08 7 12923 343 110576026
Stenotrophomonas infection 28.94 24.08 14 12916 5844 110570525
Myasthenia gravis crisis 28.75 24.08 10 12920 1804 110574565
Fungaemia 28.43 24.08 14 12916 6072 110570297
Bilirubin conjugated increased 28.13 24.08 14 12916 6210 110570159
Globulins decreased 28.00 24.08 8 12922 761 110575608
Hepatitis cholestatic 27.59 24.08 20 12910 17546 110558823
Pneumonia klebsiella 27.29 24.08 14 12916 6618 110569751
Hypertriglyceridaemia 26.76 24.08 19 12911 16135 110560234
Depression 26.60 24.08 3 12927 317332 110259037
Megacolon 26.57 24.08 12 12918 4293 110572076
Pain in extremity 26.34 24.08 12 12918 487106 110089263
Deafness 26.06 24.08 23 12907 26686 110549683
Abdominal infection 25.48 24.08 12 12918 4719 110571650
Wound haemorrhage 25.47 24.08 12 12918 4726 110571643
Acute hepatic failure 25.29 24.08 26 12904 36442 110539927
Blood alkaline phosphatase increased 25.17 24.08 36 12894 70899 110505470
Endocarditis 25.14 24.08 17 12913 13354 110563015
Gallstone ileus 24.73 24.08 4 12926 22 110576347
Product dose omission issue 24.70 24.08 4 12926 321778 110254591
Penile oedema 24.47 24.08 6 12924 316 110576053
Geotrichum infection 24.41 24.08 8 12922 1204 110575165
Alanine aminotransferase increased 24.20 24.08 61 12869 183712 110392657

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 D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011500 Protein Synthesis Inhibitors
FDA EPC N0000175938 Tetracycline-class Antibacterial
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:36047 antibacterial drug

Related Drugs by ATC class:

J01AA Tetracyclines 13 drugs

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
10929 IUPHAR_LIGAND_ID
C087533 MESH_SUPPLEMENTAL_RECORD_UI
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 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 70121-1647 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS NDA 22 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 71288-019 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 30 sections
Tigecycline HUMAN PRESCRIPTION DRUG LABEL 1 71288-019 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 30 sections