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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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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

1.17633594E12
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

1.17633594E12
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: 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)
Sensitization
Sources: Page: p.1
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: 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
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: 6.0
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
In vitro activity against anaerobes of retapamulin, a new topical antibiotic for treatment of skin infections.
2007 Apr
Retapamulin: a semisynthetic pleuromutilin compound for topical treatment of skin infections in adults and children.
2007 Dec
New drugs: retapamulin, bismuth subcitrate potassium, and rotigotine.
2007 Jul-Aug
Gateways to clinical trials.
2007 Jun
Gateways to clinical trials.
2007 May
Altabax approved to treat impetigo.
2007 Oct
[Introduction to cutaneous bacterial infections].
2007 Sep
Current and novel antibiotics against resistant Gram-positive bacteria.
2008
Retapamulin: a review of its use in the management of impetigo and other uncomplicated superficial skin infections.
2008
Retapamulin: a new topical antibiotic for the treatment of uncomplicated skin infections.
2008 Feb
Retapamulin (Altabax)--a new topical antibiotic.
2008 Feb 25
Clones and drones: do variants of Panton-Valentine leukocidin extend the reach of community-associated methicillin-resistant Staphylococcus aureus?
2008 Jan 15
Efficacy and safety of retapamulin ointment as treatment of impetigo: randomized double-blind multicentre placebo-controlled trial.
2008 May
Local antibiotics in dermatology.
2008 May-Jun
In vitro activity of retapamulin against Staphylococcus aureus isolates resistant to fusidic acid and mupirocin.
2008 Oct
Microbiological profile of a new topical antibacterial: retapamulin ointment 1%.
2009 Apr
Allergic contact cermatitis to retapamulin ointment.
2009 Aug
Topical retapamulin in the management of infected traumatic skin lesions.
2009 Feb
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: 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 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 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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