Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H47NO4S |
Molecular Weight | 517.763 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C(=O)CC[C@]13CC[C@@H](C)[C@@]2(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CS[C@H]4C[C@@H]5CC[C@H](C4)N5C
InChI
InChIKey=STZYTFJPGGDRJD-NHUWBDDWSA-N
InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22-,24-,26+,27+,28-,29+,30+/m1/s1
Molecular Formula | C30H47NO4S |
Molecular Weight | 517.763 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Retapamulin is a topical antibiotic which was approved by FDA (Altabax brand name) for the treatment of impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. Retapamulin exerts its antibacterial action by binding to 50S subunit of the bacterial ribosome.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11377180
Curator's Comment: Now a part of GlaxoSmithKline.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364096 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ALTABAX Approved UseALTABAX is indicated for use in adults and pediatric patients aged 9 months and older for the topical treatment of impetigo (up to 100 cm2 in total area in adults or 2% total body surface area in pediatric patients aged 9 months or older) due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. Launch Date2007 |
|||
Curative | ALTABAX Approved UseALTABAX is indicated for use in adults and pediatric patients aged 9 months and older for the topical treatment of impetigo (up to 100 cm2 in total area in adults or 2% total body surface area in pediatric patients aged 9 months or older) due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. Launch Date2007 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.5 ng/mL |
1 % 1 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered: |
RETAPAMULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
49.6 ng × h/mL |
1 % 1 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered: |
RETAPAMULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6% |
1 % 1 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered: |
RETAPAMULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes Sources: Page: p.1 |
Disc. AE: Skin irritation, Sensitization... AEs leading to discontinuation/dose reduction: Skin irritation (severe) Sources: Page: p.1Sensitization |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Sensitization | Disc. AE | 1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes Sources: Page: p.1 |
Skin irritation | severe Disc. AE |
1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
weak [IC50 1.1 uM] | unlikely (co-administration study) Comment: retapamulin inhibited CYP3A4 isoenzyme activity, IC50 ranged from 1.1 uM with midazolam to 6.2 uM with nifedipine; I/Ki ratios are less than 0.1 for all CYP P450 isoenzymes and no clinically relevant DDI are anticipated when retapamulin is coadministered with other drugs metabolized by CYPs Page: 6.0 |
||
Page: 5, 6 |
weak [IC50 28.2 uM] | unlikely (co-administration study) Comment: in vitro inhibitor of digoxin transport by P-gp with a calculated IC50 value of 28.2 uM; it is unlikely that retapamulin will inhibit P-gp mediated transport of co-administered drugs Page: 5, 6 |
||
Page: 6.0 |
weak [IC50 >99 uM] | |||
Page: 6.0 |
weak [IC50 >99 uM] | |||
Page: 6.0 |
weak [IC50 >99 uM] | |||
Page: 6.0 |
weak [IC50 >99 uM] | |||
Page: 6.0 |
weak [IC50 >99 uM] | |||
Page: 6.0 |
weak [IC50 >99 uM] | |||
Page: 6.0 |
weak [IC50 >99 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 5.0 |
major | yes (co-administration study) Comment: coadministration with ketaconazole increased retapamulin Cmax by 80% and AUC by 77% Page: 5.0 |
||
Page: 5.0 |
minor | |||
Page: 5.0 |
minor | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
Page: 5.0 |
yes | |||
Page: 6.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Molecule of the month. Retapamulin. | 2006 Dec |
|
Topical retapamulin ointment (1%, wt/wt) twice daily for 5 days versus oral cephalexin twice daily for 10 days in the treatment of secondarily infected dermatitis: results of a randomized controlled trial. | 2006 Dec |
|
Gateways to clinical trials. | 2006 Oct |
|
New drugs: retapamulin, bismuth subcitrate potassium, and rotigotine. | 2007 Jul-Aug |
|
Gateways to clinical trials. | 2007 Jun |
|
Altabax approved to treat impetigo. | 2007 Oct |
|
Altabax (retapamulin ointment), 1%. | 2007 Sep-Oct |
|
Spotlight on retapamulin in impetigo and other uncomplicated superficial skin infections. | 2008 |
|
Retapamulin for impetigo and other infections. | 2008 Oct |
|
Gateways to clinical trials. | 2008 Sep |
|
Microbiological profile of a new topical antibacterial: retapamulin ointment 1%. | 2009 Apr |
|
Agents for the decolonization of methicillin-resistant Staphylococcus aureus. | 2009 Mar |
|
[Pediatric dermatology. New aspects of bacterial skin infections in children]. | 2009 Mar |
Patents
Sample Use Guides
A thin layer of retapamulin (Altabax) should be applied to the affected area (up to 100 cm2 in total
area in adults or 2% total body surface area in pediatric patients aged 9 months or older) twice
daily for 5 days.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21947094
In vitro activity of retapamulin was determinde against methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant S. aureus (MRSA), and linezolid and methicillin-resistant S. aureus (LR-MRSA). MSSA and MRSA isolates were susceptible to retapamulin, with an MIC90 of 0.094 mg/L and 0.125 mg/L respectively, but retapamulin MICs for the 18 LR-MRSA strains were over 32 mg/L in all cases.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:45:10 GMT 2023
by
admin
on
Fri Dec 15 15:45:10 GMT 2023
|
Record UNII |
4MG6O8991R
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
D06AX13
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
||
|
WHO-VATC |
QD06AX13
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
||
|
NDF-RT |
N0000175434
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
||
|
NDF-RT |
N0000175433
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
||
|
NCI_THESAURUS |
C258
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
ALTARGO(AUTHORIZED IMPETIGO)
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
4MG6O8991R
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
RETAPAMULIN
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
DTXSID00870265
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
8494
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
224452-66-8
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
DB01256
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
C508887
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
SUB25391
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
642274
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | RxNorm | ||
|
100000089366
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
m9551
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | Merck Index | ||
|
PP-62
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
759885
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
C61924
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
4MG6O8991R
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
CHEMBL409542
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
2371
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY | |||
|
Retapamulin
Created by
admin on Fri Dec 15 15:45:10 GMT 2023 , Edited by admin on Fri Dec 15 15:45:10 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE |
|
||
|
TARGET ORGANISM->INHIBITOR |
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
TARGET ORGANISM->INHIBITOR |
|
||
|
BINDER->LIGAND |
BINDING
|
||
|
TRANSPORTER -> SUBSTRATE |
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT |
|
||
|
METABOLITE -> PARENT |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|