Dirithromycin
Pharmaceutical drug
title: "Dirithromycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["macrolide-antibiotics", "prodrugs", "fourteen-membered-rings", "tetrols", "lactones", "tetrahydropyrans", "methoxy-compounds"] description: "Pharmaceutical drug" topic_path: "general/macrolide-antibiotics" source: "https://en.wikipedia.org/wiki/Dirithromycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Pharmaceutical drug ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| Verifiedfields | changed |
| verifiedrevid | 460794200 |
| IUPAC_name | (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-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| image | Dirithromycin.svg |
| image_class | skin-invert-image |
| width | 280 |
| tradename | Dynabac |
| Drugs.com | |
| MedlinePlus | a604026 |
| licence_US | Clarithromycin |
| pregnancy_AU | |
| pregnancy_US | |
| pregnancy_category | B |
| legal_AU | |
| legal_UK | |
| legal_US | |
| routes_of_administration | Oral |
| bioavailability | 10% |
| protein_bound | 15 to 30% |
| metabolism | Hyrolized to erythromycyclamine in 1.5 hours |
| CAS_number_Ref | |
| CAS_number | 62013-04-1 |
| ATC_prefix | J01 |
| ATC_suffix | FA13 |
| PubChem | 6917067 |
| DrugBank_Ref | |
| DrugBank | DB00954 |
| ChemSpiderID_Ref | |
| ChemSpiderID | 5292341 |
| UNII_Ref | |
| UNII | 1801D76STL |
| ChEBI_Ref | |
| ChEBI | 474014 |
| KEGG_Ref | |
| KEGG | D03865 |
| ChEMBL_Ref | |
| ChEMBL | 3039471 |
| C | 42 |
| smiles | O=C4OC@@HCC |
| StdInChI_Ref | |
| StdInChI | 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 |
| StdInChIKey_Ref | |
| StdInChIKey | WLOHNSSYAXHWNR-NXPDYKKBSA-N |
| melting_point | 186 |
| melting_high | 189 |
| melting_notes | (dec.) |
| :: |
| Verifiedfields = changed | verifiedrevid = 460794200 | IUPAC_name = (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-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one | image = Dirithromycin.svg | image_class = skin-invert-image | width = 280
| tradename = Dynabac | Drugs.com = | MedlinePlus = a604026 | licence_US = Clarithromycin | pregnancy_AU = | pregnancy_US = | pregnancy_category = B | legal_AU = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Oral
| bioavailability = 10% | protein_bound = 15 to 30% | metabolism = Hyrolized to erythromycyclamine in 1.5 hours | elimination_half-life = | excretion =
| CAS_number_Ref = | CAS_number = 62013-04-1 | ATC_prefix = J01 | ATC_suffix = FA13 | ATC_supplemental = | PubChem = 6917067 | DrugBank_Ref = | DrugBank = DB00954 | ChemSpiderID_Ref = | ChemSpiderID = 5292341 | UNII_Ref = | UNII = 1801D76STL | ChEBI_Ref = | ChEBI = 474014 | KEGG_Ref = | KEGG = D03865 | ChEMBL_Ref = | ChEMBL = 3039471
| C=42 | H=78 | N=2 | O=14 | smiles = O=C4OC@@HCC | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = WLOHNSSYAXHWNR-NXPDYKKBSA-N | melting_point = 186 | melting_high = 189 | melting_notes = (dec.) Dirithromycin is a macrolide glycopeptide antibiotic.
Dirithromycin (Dynabac) is a more lipid-soluble prodrug derivative of 9S-erythromycyclamine prepared by condensation of the latter with 2-(2-methoxyethoxy)acetaldehyde. The 9N, 11O-oxazine ring thus formed is a hemi-aminal that is unstable under both acidic and alkaline aqueous conditions and undergoes spontaneous hydrolysis to form erythromycyclamine. Erythromycyclamine is a semisynthetic derivative of erythromycin in which the 9-ketogroup of the erythronolide ring has been converted to an amino group. Erythromycyclamine retains the antibacterial properties of erythromycin oral administration. The prodrug, dirithromycin, is provided as enteric coated tablets to protect it from acid catalyzed hydrolysis in the stomach. Orally administered dirithromycin is absorbed rapidly into the plasma, largely from the small intestine. Spontaneous hydrolysis to erythromycyclamine occurs in the plasma. Oral bioavailability is estimated to be about 10%, but food does not affect absorption of the prodrug.
Discontinuation
Dirithromycin is no longer available in the United States. Since the production of dirithromycin is discontinued in the U.S., National Institutes of Health recommend that people taking dirithromycin should consult their physicians to discuss switching to another treatment. However, dirithromycin is still available in many European countries.
References
References
- (April 1999). "Review and comparison of advanced-generation macrolides clarithromycin and dirithromycin". Pharmacotherapy.
- (May 2025). "Dynabac Drug Details". U.S. [[Food and Drug Administration]].
- (January 1, 2006). "Dirithromycin". U.S. [[National Library of Medicine]].
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