Details of the Drug

General Information of Drug (ID: DM0D9YJ)

Drug Name

Dirithromycin

Synonyms

Dirithromycine; Dirithromycinum; Diritromicina; Divitross; Dynabac; Noriclan; Valodin; Dirithromycine [French]; Dirithromycinum [Latin]; Diritromicina [Spanish]; LY 237216; AS-E 136; ASE-136; Dynabac (TN); LY-237216; Dirithromycin (USP/INN); Dirithromycin [USAN:BAN:INN]; (9S)-9-deoxo-11-deoxy-9,11-[imino[2-(2-methoxyethoxy)ethylidene]erythromycin

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]
Bronchitis	CA20	Approved	[2]
Mycoplasma pneumoniae pneumonia	N.A.	Approved	[2]
Pars planitis	N.A.	Approved	[2]
Pneumonia	CA40	Approved	[2]
Staphylococcus aureus infection	N.A.	Approved	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

835.1

Logarithm of the Partition Coefficient (xlogp)

4.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 16 - 65 hours (in patients with normal renal function) [3]

Chemical Identifiers

Formula: C42H78N2O14
IUPAC Name: (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Canonical SMILES: CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O
InChI: InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1
InChIKey: WLOHNSSYAXHWNR-DWIOZXRMSA-N

Cross-matching ID

PubChem CID: 6473883
ChEBI ID: CHEBI:474014
CAS Number: 62013-04-1
DrugBank ID: DB00954
TTD ID: D06ZUP
VARIDT ID: DR01366
INTEDE ID: DR0516

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 50S ribosomal RNA (Bact 50S rRNA)	TTUWYEA	NOUNIPROTAC	Binder	[4]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[5]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2	Dirithromycin FDA Label
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Review of macrolides and ketolides: focus on respiratory tract infections. Drugs. 2001;61(4):443-98.
5	Arginine-482 is not essential for transport of antibiotics, primary bile acids and unconjugated sterols by the human breast cancer resistance protein (ABCG2). Biochem J. 2005 Jan 15;385(Pt 2):419-26.
6	Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14.