Details of the Drug

General Information of Drug (ID: DMLE7IO)

Drug Name
Tigecycline
Synonyms
Tigilcycline; Tygacil; Tigecycline [USAN]; GAR 936; GAR-936; TBG-MINO; Tygacil (TN); Tygacil(TM); GAR-936,Tigecycline; Tigecycline (JAN/USAN); WAY-GAR-936; Tygacil, GAR-936, WAY-GAR-936, TBG-MINO, Tigecycline; N-[(5aR,6aS,7S,9Z,10aS)-9-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-1,10a,12-trihydroxy-8,10,11-trioxo-5a,6,6a,7-tetrahydro-5H-tetracen-2-yl]-2-(tert-butylamino)acetamide; (4S,12aS)-4,7-Bis(dimethylamino)-9-{2-[(tert-butyl)amino]acetylamino}-3,10,12,12a-tetrahydroxy-1,11-dioxo-4,5,6,12a,4a,5a-hexahydronaphthacene-2-carboxamide; (4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide; (4S,4aS,5aR,12aS)-9-[(N-tert-butylglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; 9-t-Butylglycylamido minocycline
Indication
Disease Entry ICD 11 Status REF
Skin infection 1F28-1G0Z Approved [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01AA12: Tigecycline
J01AA: Tetracyclines
J01A: TETRACYCLINES
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 585.6
Logarithm of the Partition Coefficient (xlogp) 1.1
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 11
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.8 mL/min/kg [3]
Elimination
22% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 27 - 43 hours [3]
Metabolism
The drug is metabolized via the liver []
Unbound Fraction
The unbound fraction of drug in plasma is 0.2% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 12 L/kg [3]
Water Solubility
The ability of drug to dissolve in water is measured as 295 mg/mL [2]
Chemical Identifiers
Formula
C29H39N5O8
IUPAC Name
(4S,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Canonical SMILES
CC(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
InChI
InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36-37,40,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1
InChIKey
SOVUOXKZCCAWOJ-HJYUBDRYSA-N
Cross-matching ID
PubChem CID
54686904
ChEBI ID
CHEMBL149836
CAS Number
220620-09-7
UNII
70JE2N95KR
DrugBank ID
DB00560
TTD ID
D0G4OD
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2) TTQ8KVI F4NA87_STAAU Binder [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Tigecycline (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mycophenolic acid DMRBMAU Moderate Altered absorption of Tigecycline due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [4]
Porfimer Sodium DM7ZWNY Moderate Increased risk of photosensitivity reactions by the combination of Tigecycline and Porfimer Sodium. Lung cancer [2C25] [5]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Tigecycline due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [4]

References

1 Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110.
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
5 Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]