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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H47NO4S
Molecular Weight 517.7657
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RETAPAMULIN

SMILES

C=C[C@]1(C)C[C@]([H])([C@]2(C)[C@]([H])(C)CC[C@]3(CCC(=O)[C@@]23[H])[C@@]([H])(C)[C@]1([H])O)OC(=O)CS[C@]4([H])C[C@@]5([H])CC[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

HIDE SMILES / InChI

Molecular Formula C30H47NO4S
Molecular Weight 517.7657
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
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

Curator's Comment:: Now a part of GlaxoSmithKline.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ALTABAX

Approved Use

ALTABAX 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 Date

1176336000000
Curative
ALTABAX

Approved Use

ALTABAX 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 Date

1176336000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
unhealthy
Disc. AE: Skin irritation, Sensitization...
AEs leading to
discontinuation/dose reduction:
Skin irritation (severe)
Sensitization
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
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:
unhealthy
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
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
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
weak [IC50 >99 uM]
weak [IC50 >99 uM]
weak [IC50 >99 uM]
weak [IC50 >99 uM]
weak [IC50 >99 uM]
weak [IC50 >99 uM]
weak [IC50 >99 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci.
2006 Jul
Gateways to clinical trials.
2006 Oct
Retapamulin ointment twice daily for 5 days vs oral cephalexin twice daily for 10 days for empiric treatment of secondarily infected traumatic lesions of the skin.
2006 Sep-Oct
Topical retapamulin ointment, 1%, versus sodium fusidate ointment, 2%, for impetigo: a randomized, observer-blinded, noninferiority study.
2007
Gateways to clinical trials.
2007 Jun
Gateways to clinical trials.
2007 May
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: a review of its use in the management of impetigo and other uncomplicated superficial skin infections.
2008
A primer on topical antibiotics for the skin and eyes.
2008 Apr
Local antibiotics in dermatology.
2008 May-Jun
Retapamulin for impetigo and other infections.
2008 Oct
In vitro activity of retapamulin against Staphylococcus aureus isolates resistant to fusidic acid and mupirocin.
2008 Oct
Gateways to clinical trials.
2008 Sep
Microbiological profile of a new topical antibacterial: retapamulin ointment 1%.
2009 Apr
Lost in translation: differences in antimicrobial indication approval policies between the United States and Europe.
2009 Jul
Agents for the decolonization of methicillin-resistant Staphylococcus aureus.
2009 Mar
[Pediatric dermatology. New aspects of bacterial skin infections in children].
2009 Mar
Mutilins derivatives: from veterinary to human-used antibiotics.
2009 Oct
Daptomycin: a novel lipopeptide antibiotic against Gram-positive pathogens.
2010
The pleuromutilin antibiotics: a new class for human use.
2010 Feb
Retapamulin.
2010 Jan
Retapamulin: what is the role of this topical antimicrobial in the treatment of bacterial infections in atopic dermatitis?
2010 Jan
Retapamulin: an emerging antimicrobial allergen.
2010 May-Jun
Retapamulin: an antibacterial with a novel mode of action in an age of emerging resistance to Staphylococcus aureus.
2010 Oct
Patents

Patents

Sample Use Guides

A thin layer of retapamulin (Altabax) should be applied to the affected area (up to 100 cm2 in total
Route of Administration: Topical
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 Fri Jun 25 22:13:34 UTC 2021
Edited
by admin
on Fri Jun 25 22:13:34 UTC 2021
Record UNII
4MG6O8991R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RETAPAMULIN
EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
RETAPAMULIN [INN]
Common Name English
RETAPAMULIN [MI]
Common Name English
ALTABAX
Brand Name English
RETAPAMULIN [EMA EPAR]
Common Name English
SB 275833
Common Name English
RETAPAMULIN [MART.]
Common Name English
(3AS,4R,5S,6S,8R,9R,9AR,10R)-6-ETHENYL-5-HYDROXY-4,6,9,10-TETRAMETHYL-1-OXODECAHYDRO-3A,9-PROPANO-3AH-CYCLOPENTA(8)ANNULEN-8-YL (((1R,3S,5S)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL)SULFANYL)ACETATE
Common Name English
SB-275833
Code English
RETAPAMULIN [ORANGE BOOK]
Common Name English
RETAPAMULIN [USAN]
Common Name English
RETAPAMULIN [VANDF]
Common Name English
RETAPAMULIN [WHO-DD]
Common Name English
ALTARGO
Brand Name English
ACETIC ACID, (((3-EXO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL)THIO)-, (3AS,4R,5S,6S,8R,9R,9AR,10R)-6-ETHENYLDECAHYDRO-5-HYDROXY-4,6,9,10-TETRAMETHYL-1-OXO-3A,9-PROPANO-3AH-CYCLOPENTACYCLOOCTEN-8-YL ESTER
Common Name English
NSC-759885
Code English
Classification Tree Code System Code
WHO-ATC D06AX13
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
WHO-VATC QD06AX13
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
NDF-RT N0000175434
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
NDF-RT N0000175433
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
NCI_THESAURUS C258
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
EMA ASSESSMENT REPORTS ALTARGO(AUTHORIZED IMPETIGO)
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
Code System Code Type Description
FDA UNII
4MG6O8991R
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
WIKIPEDIA
RETAPAMULIN
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
INN
8494
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
CAS
224452-66-8
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
DRUG BANK
DB01256
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
MESH
C508887
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
EVMPD
SUB25391
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
RXCUI
642274
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M9551
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C61924
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
ChEMBL
CHEMBL409542
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
DRUG CENTRAL
2371
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
LACTMED
Retapamulin
Created by admin on Fri Jun 25 22:13:34 UTC 2021 , Edited by admin on Fri Jun 25 22:13:34 UTC 2021
PRIMARY
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