RETAPAMULIN

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022055s002lbl.pdf

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
70S ribosome 16 Target ID: CHEMBL2364096 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022055s002lbl.pdf	Inhibitor 8228

Conditions

Condition	Modality	Targets	Highest Phase	Product
Impetigo due to Staphylococcus aureus 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022055s002lbl.pdf	Curative		Approved 8360	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
Impetigo due to Streptococcus pyogenes 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022055s002lbl.pdf	Curative		Approved 8360	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

C_max

Value	Dose	Co-administered	Analyte	Population
3.5 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/18416589/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/18416589/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% REVIEW https://pubmed.ncbi.nlm.nih.gov/18416589/	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf Page: p.1	Disc. AE: Skin irritation, Sensitization... AEs leading to discontinuation/dose reduction: Skin irritation (severe) Sensitization Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf Page: p.1

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: impetigo due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022055s004lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709 inhibitor 1579	substrate 1010 inhibitor 1752	substrate 1193 inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2A6 704 CYP2B6 799 CYP2C8 901 CYP2C19 1463 P-gp 1437	CYP3A5 391 CYP1A2 1032 CYP2C19 985 CYP2C8 688 P-gp 1527

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0
P-gp 1626	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5, 6
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]
CYP2C8 955	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	weak [IC50 >99 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1709	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	major	yes (co-administration study) Comment: coadministration with ketaconazole increased retapamulin Cmax by 80% and AUC by 77% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0
CYP2C8 688	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	minor
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	minor
CYP1A2 1032	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	no
CYP2C19 985	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	no
CYP2C9 1010	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	no
CYP3A5 391	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 5.0	yes
P-gp 1527	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022055s000_ClinPharmR.pdf Page: 6.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0039HR	https://www.aablocks.com/goods/Goods/detail?id=AA0039HR
AEchem Scientific Corp., USA	AE1-017412	http://www.aechemsc.com/info_products/AE1-017412.php
AK Scientific, Inc. (AKSCI)	66719	http://www.aksci.com/item_detail.php?cat=66719
Aaron Chemicals	AR003A9J	http://www.aaronchem.com/224452-66-8
AbMole Bioscience	M2974	http://www.abmole.com/products/retapamulin.html
Achemtek	0102-014536	http://www.achemtek.com/224452-66-8
Ambeed	A195059	https://www.ambeed.com/products/224452-66-8.html
ApexBio Technology	B2019	http://www.apexbt.com/retapamulin.html
AstaTech, Inc.	36342	http://www.astatechinc.com/CPSResult.php?CRNO=36615
Aurora Fine Chemicals LLC	A13.110.966	http://online.aurorafinechemicals.com/info?ID=A13.110.966
Aurora Fine Chemicals LLC	A24.091.139	http://online.aurorafinechemicals.com/info?ID=A24.091.139
Aurum Pharmatech LLC	MP-0763	http://www.Aurumpharmatech.com/Product/ProductDetails/MP_0763
BLD Pharm	BD223980	http://www.bldpharm.com/products/224452-66-8.html
Boerchem	BC677692	http://www.boerchem.com/?product_39573.html
CSNpharm	CSN12909	https://www.csnpharm.com/products/retapamulin.html
Chem Scene	CS-0618	http://www.chemscene.com/224452-66-8.html
ChemMol	44009997	http://www.chemmol.com/chemmol/44009997.html
ChemMol	99062376	http://www.chemmol.com/chemmol/99062376.html
Chemspace	CSSB00020618600	https://chem-space.com/CSSB00020618600
Chemspace	CSSB00020629312	https://chem-space.com/CSSB00020629312
Combi-Blocks	QB-7392	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-7392
Glentham Life Sciences	GA4340	http://www.glentham.com/products/product/GA4340/
Hairui	HR34097	http://www.hairuichem.com/en/product/224452-66-8.html
Lab Network	LN02127170	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02127170
Matrix Scientific	98144	https://www.matrixscientific.com/098144.html
MedChem Express	HY-17010	https://www.medchemexpress.com/Retapamulin.html
MolPort	MolPort-006-167-754	https://www.molport.com/shop/molecule-link/MolPort-006-167-754
MolPort	MolPort-023-220-081	https://www.molport.com/shop/molecule-link/MolPort-023-220-081
MuseChem	A000673	https://www.musechem.com/product/A000673.html
OChem	25925	http://www.ocheminc.com/index.php?act=psearch&pid=452R668
Oakwood	361956	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=150814&ExtHyperLink=1
Renno Tech	RL02708	http://www.rennotech.com/product_show.asp?id=2957
Selleck Chemicals	S4056	http://www.selleckchem.com/products/retapamulin.html
Sigma-Aldrich	CDS023386_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/cds023386?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
TripleBond	CR0022	http://www.triplebond-canada.com/prod/1562/
Yuhao Chemical	LX2351	http://www.chemyuhao.com/224452-66-8.html
abcr GmbH	AB450172	http://www.abcr.com/shop/en/AB450172
eNovation Chemicals	D320205	https://www.enovationchem.com/ProductDetails.asp?ProductID=D320205
iChemical	EBD3585	http://www.ichemical.com/products/224452-66-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Molecule of the month. Retapamulin.	2006 Dec	17299606
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	17097398
Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci.	2006 Jul	16801451
Gateways to clinical trials.	2006 Oct	17136234
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	16957433
Topical retapamulin ointment, 1%, versus sodium fusidate ointment, 2%, for impetigo: a randomized, observer-blinded, noninferiority study.	2007	17911992
In vitro activity against anaerobes of retapamulin, a new topical antibiotic for treatment of skin infections.	2007 Apr	17350985
Retapamulin: a semisynthetic pleuromutilin compound for topical treatment of skin infections in adults and children.	2007 Dec	18041900
New drugs: retapamulin, bismuth subcitrate potassium, and rotigotine.	2007 Jul-Aug	17616504
Gateways to clinical trials.	2007 Jun	17805439
Gateways to clinical trials.	2007 May	17609744
Altabax approved to treat impetigo.	2007 Oct	17901782
[Introduction to cutaneous bacterial infections].	2007 Sep	18093493
Altabax (retapamulin ointment), 1%.	2007 Sep-Oct	17786102
Current and novel antibiotics against resistant Gram-positive bacteria.	2008	21694878
Spotlight on retapamulin in impetigo and other uncomplicated superficial skin infections.	2008	18973410
Retapamulin: a review of its use in the management of impetigo and other uncomplicated superficial skin infections.	2008	18416589
A primer on topical antibiotics for the skin and eyes.	2008 Apr	18459527
Retapamulin: a new topical antibiotic for the treatment of uncomplicated skin infections.	2008 Feb	18389088
Retapamulin (Altabax)--a new topical antibiotic.	2008 Feb 25	18292714
Clones and drones: do variants of Panton-Valentine leukocidin extend the reach of community-associated methicillin-resistant Staphylococcus aureus?	2008 Jan 15	18177251
Drug treatments for skin disease introduced in 2007.	2008 Mar	18373042
Efficacy and safety of retapamulin ointment as treatment of impetigo: randomized double-blind multicentre placebo-controlled trial.	2008 May	18341664
Local antibiotics in dermatology.	2008 May-Jun	18564249
Retapamulin for impetigo and other infections.	2008 Oct	18832258
In vitro activity of retapamulin against Staphylococcus aureus isolates resistant to fusidic acid and mupirocin.	2008 Oct	18567573
Gateways to clinical trials.	2008 Sep	18985183
Microbiological profile of a new topical antibacterial: retapamulin ointment 1%.	2009 Apr	19344241
Allergic contact cermatitis to retapamulin ointment.	2009 Aug	19706058
Topical retapamulin in the management of infected traumatic skin lesions.	2009 Feb	19436611
Lost in translation: differences in antimicrobial indication approval policies between the United States and Europe.	2009 Jul	19695409
Allergic contact dermatitis from retapamulin ointment.	2009 Jul-Aug	19804700
Agents for the decolonization of methicillin-resistant Staphylococcus aureus.	2009 Mar	19249946
[Pediatric dermatology. New aspects of bacterial skin infections in children].	2009 Mar	19238341
Mutilins derivatives: from veterinary to human-used antibiotics.	2009 Oct	19929813
Daptomycin: a novel lipopeptide antibiotic against Gram-positive pathogens.	2010	21694898
The pleuromutilin antibiotics: a new class for human use.	2010 Feb	20112168
Retapamulin.	2010 Jan	20078606
Retapamulin: what is the role of this topical antimicrobial in the treatment of bacterial infections in atopic dermatitis?	2010 Jan	20066388
Retapamulin: a novel topical antibiotic.	2010 Jan-Feb	20061745
Retapamulin: an emerging antimicrobial allergen.	2010 May-Jun	20487660
Retapamulin: an antibacterial with a novel mode of action in an age of emerging resistance to Staphylococcus aureus.	2010 Oct	20941943

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Wed Jul 05 23:13:47 UTC 2023` Edited by `admin` on `Wed Jul 05 23:13:47 UTC 2023`
Record UNII	4MG6O8991R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RETAPAMULIN

Official Name

English

retapamulin [INN]

Common Name

English

RETAPAMULIN [MI]

Common Name

English

ALTABAX

Brand Name

English

RETAPAMULIN [EMA EPAR]

Common Name

English

SB275833

Code

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

ALTARGO

Brand Name

English

Retapamulin [WHO-DD]

Common 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