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]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01FA13: Dirithromycin
J01FA: Macrolides
J01F: MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
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) 12
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 16
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
UNII
1801D76STL
DrugBank ID
DB00954
TTD ID
D06ZUP
VARIDT ID
DR01366
INTEDE ID
DR0516
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 50S ribosomal RNA (Bact 50S rRNA) TTUWYEA NOUNIPROTAC Binder [4]

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

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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.