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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:29506
CAS Number: 205110-48-1
UNII: J0086219X6
DrugBank ID: DB06419
TTD ID: D0D7TD
INTEDE ID: DR0292

Repurposed Drugs (RPD)

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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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A5 (CYP3A5)_{Main DME}	DEIBDNY	CP3A5_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.