Details of the Drug

General Information of Drug (ID: DMVMIK2)

Drug Name
Roxithromycin
Synonyms
Assoral; Overall; RXM; Rossitrol; Roxithromycine; Roxithromycinum; Roxitromicina; Rulid; Rulide; Surlid; Roxithromycine [French]; Roxithromycinum [Latin]; Roxitromicina [Spanish]; RC2952; RU 28965; RU 965; Biaxsig (TN); Coroxin (TN); RU-28965; RU-965; Roxar (TN); Roximycin (TN); Roxithromycin & Tumor Necrosis Factor; Roxo (TN); Rulide (TN); Surlid (TN); Tirabicin (TN); Roxithromycin [USAN:INN:JAN]; Roxl-150 (TN); Roxithromycin (JP15/USAN/INN); Erythromycin 9-(-O-[2-methoxyethoxy]methyloxime);Erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime); Erythromycin, 9-(O-((2-methoxyethoxy)methyl)oxime); 9-(O-((2-Methoxyethoxy)methyl)oxime)erythromycin; 9-[O-(2-methoxyethoxymethyl)-oxime] of erythromycin
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Withdrawn from market [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01FA06: Roxithromycin
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 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 837
Logarithm of the Partition Coefficient (xlogp) 3.1
Rotatable Bond Count (rotbonds) 13
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 17
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
Elimination
12% 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 12 hours [3]
Metabolism
The drug is metabolized via the hepatic []
Water Solubility
The ability of drug to dissolve in water is measured as 0.1 mg/mL [2]
Chemical Identifiers
Formula
C41H76N2O15
IUPAC Name
(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
Canonical SMILES
CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/OCOCCOC)/[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
InChI
InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
InChIKey
RXZBMPWDPOLZGW-XMRMVWPWSA-N
Cross-matching ID
PubChem CID
6915744
ChEBI ID
CHEMBL1214185
CAS Number
80214-83-1
UNII
21KOF230FA
DrugBank ID
DB00778
TTD ID
D0Y4FL
VARIDT ID
DR00708
INTEDE ID
DR1448
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

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 Inhibitor [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Integrin beta-4 (ITGB4) OT28UK84 ITB4_HUMAN Gene/Protein Processing [7]
Laminin subunit gamma-2 (LAMC2) OTJMTM72 LAMC2_HUMAN Gene/Protein Processing [7]
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Gene/Protein Processing [8]
Tumor necrosis factor ligand superfamily member 6 (FASLG) OTZARCHH TNFL6_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1465).
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Molecular insights into 14-membered macrolides using the MM-PBSA method. J Chem Inf Model. 2009 Jun;49(6):1558-67.
5 Differences in assessment of macrolide interaction with human MDR1 (ABCB1, P-gp) using rhodamine-123 efflux, ATPase activity and cellular accumulation assays. Eur J Pharm Sci. 2010 Sep 11;41(1):86-95.
6 Hepatic veno-occlusive disease associated with immunosuppressive cyclophosphamide dosing and roxithromycin. Ann Pharmacother. 2006 Apr;40(4):767-70.
7 Effects of eight antibacterial agents on cell survival and expression of epithelial-cell- or cell-adhesion-related genes in human gingival epithelial cells. J Periodontal Res. 2004 Feb;39(1):50-8. doi: 10.1111/j.1600-0765.2004.00704.x.
8 Liver toxicity of macrolide antibiotics in zebrafish. Toxicology. 2020 Aug;441:152501. doi: 10.1016/j.tox.2020.152501. Epub 2020 May 23.
9 Roxithromycin promotes lymphocyte apoptosis in Dermatophagoides-sensitive asthma patients. Eur J Pharmacol. 2003 Aug 8;474(2-3):273-81. doi: 10.1016/s0014-2999(03)01998-8.