Details of the Drug

General Information of Drug (ID: DMIGX84)

Drug Name
Cethromycin
Synonyms
Restanza; Cethromycin [USAN]; ABT 773; A-195773; ABT-773; Abbott-195773; A-195773.0; Cethromycin (USAN/INN); (1R,2R,4R,6R,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(E)-3-quinolin-3-ylprop-2-enoxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone; (1R,2R,4R,6S,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(E)-3-quinolin-3-ylprop-2-enoxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone; (1S,2R,5R,7R,8R,9R,11R,13R,14R)-2-Ethyl-1,5,7,9,11,13-Hexamethyl-9-[3-(3-quinolyl)-2(E)-propenyloxy]-8-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyloxy]-3,17-dioxa-15-azabicyclo[12.3.0]hepta; (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyl-3a,7,9,11,13,15 hexamethyl-11-((3-(quinolin-3-yl)prop-2-enyl)oxy)-10-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)octahydro-2H-oxacyclotetradecino(4,3-d)oxazole-2,6,8,14(1H,7H,9H)-tetrone; (3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyl-3a,7,9,11,13,15-hexamethyl-11-((3-(quinolin-3-yl)prop-2-enyl)oxy)-10-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)octahydro-2H-oxacyclotetradecino(4,3-d)oxazole-2,6,8,14(1H,7H,9H)-tetrone
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Phase 3 [1]
Pneumonia CA40 Phase 3 [1]
Affected Organisms
Bacteria
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 765.9
Logarithm of the Partition Coefficient (xlogp) 5.4
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 0.902 +/- 0.469 mgh/L [2]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 0.181 +/- 0.084 mg/L [2]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2.01 +/- 1.30 h [2]
Clearance
The clearance of drug is 63 L/h [2]
Elimination
Cethromycin is primarily excreted by the biliary route, with 87.2% of an initial dose recovered in feces and only 7.0% in urine [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 5.66 +/- 0.77 hours (after a single oral dose of 150 mg) [2]
Metabolism
The drug is metabolized via the liver [3]
Vd
The volume of distribution (Vd) of drug is 1433 +/- 843 L [2]
Chemical Identifiers
Formula
C42H59N3O10
IUPAC Name
(1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-1,5,7,9,11,13-hexamethyl-9-[(E)-3-quinolin-3-ylprop-2-enoxy]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
Canonical SMILES
CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC/C=C/C4=CC5=CC=CC=C5N=C4)C)C)NC(=O)O2)C
InChI
InChI=1S/C42H59N3O10/c1-11-32-42(8)36(44-40(50)55-42)25(4)33(46)23(2)21-41(7,51-18-14-15-28-20-29-16-12-13-17-30(29)43-22-28)37(26(5)34(47)27(6)38(49)53-32)54-39-35(48)31(45(9)10)19-24(3)52-39/h12-17,20,22-27,31-32,35-37,39,48H,11,18-19,21H2,1-10H3,(H,44,50)/b15-14+/t23-,24-,25+,26+,27-,31+,32-,35-,36-,37-,39+,41-,42-/m1/s1
InChIKey
PENDGIOBPJLVBT-ONLVEXIXSA-N
Cross-matching ID
PubChem CID
447451
ChEBI ID
CHEMBL29506
CAS Number
205110-48-1
UNII
J0086219X6
DrugBank ID
DB06419
TTD ID
D0D7TD
INTEDE ID
DR0292
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA 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
Bacterial 23S ribosomal RNA (Bact 23S rRNA) TTLFGBV NOUNIPROTAC Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A5 (CYP3A5)
Main DME 		DEIBDNY CP3A5_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
2 Steady-state plasma and intrapulmonary pharmacokinetics and pharmacodynamics of cethromycin. Antimicrob Agents Chemother. 2004 Sep;48(9):3508-15. doi: 10.1128/AAC.48.9.3508-3515.2004.
3 Human Disposition and Metabolism of Orally Administered (14C)ABT-773
4 CYP3A5 genotype has a dose-dependent effect on ABT-773 plasma levels. Clin Pharmacol Ther. 2004 Jun;75(6):516-28.