Fidaxomicin

Identification

Summary

Fidaxomicin is a macrolide antibiotic used to treat diarrhea associated with Clostridium difficile infection.

Brand Names

Dificid

Generic Name

Fidaxomicin

DrugBank Accession Number

DB08874

Background

Fidaxomicin is a novel macrolide antibiotic used in the treatment of diarrhea caused by Clostridioides (formerly Clostridium) difficile in adult and pediatric patients over the age of 6 months.¹⁰ Fidaxomicin is a naturally-occurring 18-member macrocycle derived from fermentation.⁸ Because fidaxomicin contains an 18-membered lactone ring in its structure, it is referred to as a macrocyclic lactone antibiotic drug.⁶ The antibacterial activity of fidaxomicin is distinct from macrolides and rifamycins, as the bactericidal activity is time-dependent, and not concentration-dependent.⁶ Fidaxomicin was the first macrocyclic lactone antibiotic with activity against C. difficile,⁴ and it displays a narrow spectrum of activity against gram-positive anaerobes.² It mediates its potent bactericidal action on the bacteria by inhibiting the bacterial RNA synthase, thereby disrupting bacterial transcription.⁴ The minimum inhibitory concentration (MIC₉₀) for fidaxomicin is four times less than that of vancomycin, which was the primary drug of choice for C. difficile infection before the approval of fidaxomicin.⁶ Unlike vancomycin, however, fidaxomicin has a negligible effect on normal colonic microflora.⁷

The FDA initially approved fidaxomicin in May 2011 for the treatment of C. difficile-associated diarrhea in adult patients over the age of 18.⁶ Later that year in December, the drug was also approved by the European Medicine Agency.⁶ In June 2012, fidaxomicin was also granted approval by Health Canada.⁴ The approved indication of fidaxomicin was expanded by the FDA in January 2020 to include pediatric patients over the age of 6 months in the treatment population.¹⁰

Type

Small Molecule

Groups

Approved

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Fidaxomicin (DB08874)

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Weight

Average: 1058.05
Monoisotopic: 1056.4252209

Chemical Formula

C₅₂H₇₄Cl₂O₁₈

Synonyms

• Difimicin
• Fidaxomicin
• Fidaxomicina
• Lipiarmicin
• Lipiarmycin
• Lipiarrmycin
• Tiacumicin B

External IDs

• OPT 80
• OPT-80
• PAR 01
• PAR 101
• PAR-101

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Pharmacology

Indication

Fidaxomicin is indicated for the treatment of Clostridioides (formerly Clostridium) difficile-associated diarrhea in adult and pediatric patients 6 months of age and older.¹⁰

Fidaxomicin should only be used in patients with proven or strongly suspected C. difficile infection to reduce the risk of development of drug-resistant bacteria and maximize the therapeutic effectiveness of fidaxomicin and other antimicrobial agents.¹⁰

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Clostridium difficile-associated diarrhea (cdad)		••••••••••••		•••• •••••• •• •• ••••• •••• ••	•••••••• ••••••• ••••••
Treatment of	Clostridium difficile-associated diarrhea (cdad)		••••••••••••	•••••• •••••••••		••••••

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Pharmacodynamics

Fidaxomicin has a narrow-spectrum antibacterial profile, with potent bactericidal activity specifically against C. difficile.⁵ The minimum inhibitory concentration for 90% of organisms for fidaxomicin against C. difficile ranged from 0.0078 to 2 μg/mL in vitro.² The bactericidal activity of fidaxomicin is time-dependent.⁶ Other than C. difficile, fidaxomicin has moderate inhibitory activity against Gram-positive bacteria (S. aureus and Enterococcus spp.) ⁵ and poor activity against normal colonic flora, including anaerobes and enteric Gram-negative bacilli.⁴ Isolates of C. difficile that are resistant to rifamycins or other antimicrobial classes (such as cephalosporins, fluoroquinolones, clindamycin) were not shown to be cross-resistant to fidaxomicin.⁴

Mechanism of action

Clostridium difficile is a Gram-positive bacterium that causes various gastrointestinal complications, such as antibiotic-associated diarrhea. C. difficile infection can be caused by antibiotic therapy, resulting in the disruption of the human gut flora leads to an overgrowth of C. difficile. The consequences of C. difficile infection can be mild to severe and sometimes fatal.⁶

Fidaxomicin gets hydrolyzed to its active metabolite, OP-1118, upon oral administration. Both compounds mediate a bactericidal activity against C. difficile by inhibiting bacterial RNA polymerase at the initiation phase of the transcription cycle.⁴ The RNA polymerase is an essential bacterial enzyme that regulates gene expression, catalyzes nucleic acid interactions, and promotes several bacterial enzymatic reactions critical for bacterial survival.⁴ The core RNA polymerase is composed of a complex of different subunits and contains the active site.⁹ To initiate bacterial transcription, the active site of the core RNA polymerase binds to a promoter-specificity σ initiation factor, which locates and binds to a promoter region of the DNA. The DNA-RNA polymerase interaction promotes subsequent steps of transcription, which involves the separation of DNA strands.¹ Fidaxomicin binds to the DNA template-RNA polymerase complex, thereby preventing the initial separation of DNA strands during transcription and inhibiting messenger RNA synthesis.⁴ The narrow spectrum of antimicrobial activity of fidaxomicin may be explained by the unique target site of fidaxomicin and differing σ subunits of the core structure of RNA polymerase among bacterial species.⁴

Target	Actions	Organism
ARNA polymerase sigma factor	inhibitor	Clostridium difficile (strain 630)

Absorption

Following oral administration of a single dose of 200 mg fidaxomicin in healthy adults, the C_max of fidaxomicin and its main metabolite OP-1118 were 5.20 ± 2.81 ng/mL and 12.0 ± 6.06, respectively. The median T_max of fidaxomicin was 2 hours. The systemic absorption of fidaxomicin following oral administration is minimal.¹⁰

In a food-effect study involving healthy adults in either with a high-fat meal versus under fasting conditions, the C_max of fidaxomicin and OP-1118 were decreased by 21.5% and 33.4%, respectively; however, this effect is deemed to be clinically insignificant as the therapeutic action of fidaxomicin does not depend on drug concentrations in the systemic circulation.¹⁰

Volume of distribution

Fidaxomicin is mainly confined to the gastrointestinal tract when orally administered.¹⁰ There is limited information on the volume of distribution of fidaxomicin.

Protein binding

Since fidaxomicin has minimal systemic absorption following oral administration, there is limited information on the plasma protein binding profile of fidoxamicin.

Metabolism

Following oral administration, fidaxomicin is transformed to its main and pharmacologically active metabolite, OP-1118, via hydrolysis at the isobutyryl ester. As cytochrome enzymes are not involved in the metabolism of fidaxomicin, it is speculated that this biotransformation is mediated by gastric acid or enzymatic activity of intestinal microsomes.^6,10

Hover over products below to view reaction partners

• Fidaxomicin
  • OP-1118

Route of elimination

Following oral administration, fidaxomicin is mainly excreted in feces. More than 92% of the dose was recovered in the faces as either the unchanged parent drug or metabolites in one study consisting of healthy adults receiving single doses of 200 mg and 300 mg of fidaxomicin. In another study of healthy adults, approximately 0.59% fo the oral dose (200 mg) administered was recovered in the urine as the main metabolite, OP-1118.¹⁰

Half-life

Following oral administration of a single dose of 200 mg fidaxomicin in healthy adults, the elimination half-life of fidaxomicin was approximately 11.7 ± 4.80 hours.¹⁰

Clearance

There is limited information on the clearance of fidaxomicin.

Adverse Effects

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Toxicity

In rats, the LD₅₀ of fidaxomicin was approximately 200 mg/kg and the no observed adverse effect level (NOAEL) was determined to be 62.5 mg/kg following administration of a single intravenous dose.⁵

There is limited clinical data on acute overdose in humans.¹⁰

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acenocoumarol	The risk or severity of bleeding can be increased when Fidaxomicin is combined with Acenocoumarol.
Ambroxol	The risk or severity of methemoglobinemia can be increased when Fidaxomicin is combined with Ambroxol.
Articaine	The risk or severity of methemoglobinemia can be increased when Fidaxomicin is combined with Articaine.
BCG vaccine	The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Fidaxomicin.
Benzocaine	The risk or severity of methemoglobinemia can be increased when Fidaxomicin is combined with Benzocaine.

Food Interactions

• Take with or without food. High-fat meal decreases the Cmax of fidaxomicin and its metabolite in a clinically insignificant way.

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dificid	Tablet	200 mg	Oral	Merck Ltd.	2012-06-21	Not applicable
Dificid	Tablet, film coated	200 mg/1	Oral	Merck Sharp & Dohme Llc	2011-05-27	Not applicable
Dificid	Tablet, film coated	200 mg/1	Oral	Avera McKennan Hospital	2015-04-17	2017-05-24
Dificid	Granule, for suspension	200 mg/5mL	Oral	Merck Sharp & Dohme Llc	2020-02-18	Not applicable
Dificlir	Tablet, film coated	200 mg	Oral	Tillotts Pharma Gmb H	2016-09-08	Not applicable

Categories

ATC Codes

A07AA12 — Fidaxomicin

• A07AA — Antibiotics
• A07A — INTESTINAL ANTIINFECTIVES
• A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Alimentary Tract and Metabolism
• Anti-Bacterial Agents
• Anti-Infective Agents
• Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
• Carbohydrates
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 Enzyme Inhibitors
• Intestinal Antiinfectives
• Lactones
• Macrolide Antibacterial
• Macrolides
• Other Macrolides
• P-glycoprotein substrates
• Polyketides

Classification

Not classified

Affected organisms

• Gram-positive Bacteria
• Peptoclostridium difficile

Chemical Identifiers

UNII

Z5N076G8YQ

CAS number

873857-62-6

InChI Key

ZVGNESXIJDCBKN-UUEYKCAUSA-N

InChI

InChI=1S/C52H74Cl2O18/c1-13-30-22-26(6)33(56)18-16-15-17-31(23-66-51-45(65-12)42(61)44(29(9)67-51)69-49(64)35-32(14-2)36(53)39(58)37(54)38(35)57)48(63)68-34(28(8)55)20-19-25(5)21-27(7)43(30)70-50-41(60)40(59)46(52(10,11)72-50)71-47(62)24(3)4/h15-17,19,21-22,24,28-30,33-34,40-46,50-51,55-61H,13-14,18,20,23H2,1-12H3/b16-15+,25-19+,26-22+,27-21+,31-17+/t28-,29-,30+,33+,34+,40-,41+,42+,43+,44-,45+,46+,50-,51-/m1/s1

IUPAC Name

(2R,3S,4S,5S,6R)-6-{[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-12-{[(2R,3S,4R,5S)-3,4-dihydroxy-6,6-dimethyl-5-[(2-methylpropanoyl)oxy]oxan-2-yl]oxy}-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy}-4-hydroxy-5-methoxy-2-methyloxan-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate

SMILES

[H][C@@]1(O[C@@H]2[C@@H](CC)\C=C(C)\[C@@H](O)C\C=C\C=C(CO[C@@H]3O[C@H](C)[C@@H](OC(=O)C4=C(CC)C(Cl)=C(O)C(Cl)=C4O)[C@H](O)[C@@H]3OC)\C(=O)O[C@@H](C\C=C(/C)\C=C2/C)[C@@H](C)O)OC(C)(C)[C@@H](OC(=O)C(C)C)[C@H](O)[C@@H]1O

References

Synthesis Reference

Youe-Kong Shue, Chi-Jen Frank Du, Ming-Hsi Chiou, Mei-Chiao Wu, Yuan-Ting Chen, Franklin W. Okumu, Jonathan James Duffield, "Medium for the Production of Tiacumicin B." U.S. Patent US20100028970, issued February 04, 2010.

US20100028970

General References

1. Artsimovitch I, Seddon J, Sears P: Fidaxomicin is an inhibitor of the initiation of bacterial RNA synthesis. Clin Infect Dis. 2012 Aug;55 Suppl 2:S127-31. doi: 10.1093/cid/cis358. [Article]
2. Crawford T, Huesgen E, Danziger L: Fidaxomicin: a novel macrocyclic antibiotic for the treatment of Clostridium difficile infection. Am J Health Syst Pharm. 2012 Jun 1;69(11):933-43. doi: 10.2146/ajhp110371. [Article]
3. Authors unspecified: Fidaxomicin: Difimicin; Lipiarmycin; OPT 80; OPT-80; PAR 101; PAR-101. Drugs R D. 2010;10(1):37-45. doi: 10.2165/11537730-000000000-00000. [Article]
4. Zhanel GG, Walkty AJ, Karlowsky JA: Fidaxomicin: A novel agent for the treatment of Clostridium difficile infection. Can J Infect Dis Med Microbiol. 2015 Nov-Dec;26(6):305-12. doi: 10.1155/2015/934594. [Article]
5. Weiss K, Allgren RL, Sellers S: Safety analysis of fidaxomicin in comparison with oral vancomycin for Clostridium difficile infections. Clin Infect Dis. 2012 Aug;55 Suppl 2:S110-5. doi: 10.1093/cid/cis390. [Article]
6. Vaishnavi C: Fidaxomicin--the new drug for Clostridium difficile infection. Indian J Med Res. 2015 Apr;141(4):398-407. doi: 10.4103/0971-5916.159251. [Article]
7. Louie TJ, Cannon K, Byrne B, Emery J, Ward L, Eyben M, Krulicki W: Fidaxomicin preserves the intestinal microbiome during and after treatment of Clostridium difficile infection (CDI) and reduces both toxin reexpression and recurrence of CDI. Clin Infect Dis. 2012 Aug;55 Suppl 2:S132-42. doi: 10.1093/cid/cis338. [Article]
8. Shue YK, Sears PS, Shangle S, Walsh RB, Lee C, Gorbach SL, Okumu F, Preston RA: Safety, tolerance, and pharmacokinetic studies of OPT-80 in healthy volunteers following single and multiple oral doses. Antimicrob Agents Chemother. 2008 Apr;52(4):1391-5. doi: 10.1128/AAC.01045-07. Epub 2008 Feb 11. [Article]
9. Mariani R, Maffioli SI: Bacterial RNA polymerase inhibitors: an organized overview of their structure, derivatives, biological activity and current clinical development status. Curr Med Chem. 2009;16(4):430-54. doi: 10.2174/092986709787315559. [Article]
10. FDA Approved Drug Products: DIFICID (fidaxomicin) tablets, for oral use [Link]
11. Santa Cruz Biotechnology, Inc.: Fidaxomicin Safety Data Sheet [Link]

External Links

KEGG Drug

D09394

PubChem Compound

70678896

PubChem Substance

175427128

ChemSpider

8209640

RxNav

1111103

ChEBI

68590

ChEMBL

CHEMBL1255800

PDBe Ligand

FI8

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Fidaxomicin

PDB Entries

6bzo / 6c06 / 6fbv / 7l7b

FDA label

Download (207 KB)

MSDS

Download (143 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Clostridium Difficile	1
4	Completed	Treatment	Clostridium Difficile (C. Difficile) / Diarrhea / Enterocolitis	1
4	Completed	Treatment	Clostridium Difficile Infection (CDI)	2
4	Completed	Treatment	Clostridium Difficile Infection (CDI) / Inflammatory Bowel Diseases (IBD)	1
4	Recruiting	Treatment	Clostridium / Clostridium Difficile (C. Difficile) / Coronavirus Disease 2019 (COVID‑19) / Fidaxomicin / Vancomycin	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Granule, for suspension	Oral	200 mg/5mL
Tablet	Oral	200 mg
Tablet	Oral	200.000 mg
Tablet, film coated	Oral	200 mg/1
Granule	Oral	40 MG/ML
Tablet, film coated	Oral	200 MG

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8859510	Yes	2014-10-14	2028-01-31
US7906489	Yes	2011-03-15	2027-09-04
US7378508	Yes	2008-05-27	2028-01-31
US7863249	Yes	2011-01-04	2028-01-31
US8586551	Yes	2013-11-19	2024-01-15
US9808530	Yes	2017-11-07	2034-11-28

Properties

State

Solid

Experimental Properties

Property	Value	Source
boiling point (°C)	1046.4	MSDS (Santa Cruz Biotechnology)

Predicted Properties

Property	Value	Source
Water Solubility	0.0125 mg/mL	ALOGPS
logP	5.59	ALOGPS
logP	8.56	Chemaxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	5.87	Chemaxon
pKa (Strongest Basic)	-1.4	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	15	Chemaxon
Hydrogen Donor Count	7	Chemaxon
Polar Surface Area	266.66 Å2	Chemaxon
Rotatable Bond Count	15	Chemaxon
Refractivity	269.66 m3·mol-1	Chemaxon
Polarizability	109.15 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.6628
Blood Brain Barrier	-	0.8559
Caco-2 permeable	-	0.6641
P-glycoprotein substrate	Substrate	0.8975
P-glycoprotein inhibitor I	Non-inhibitor	0.5357
P-glycoprotein inhibitor II	Non-inhibitor	0.902
Renal organic cation transporter	Non-inhibitor	0.9112
CYP450 2C9 substrate	Non-substrate	0.8485
CYP450 2D6 substrate	Non-substrate	0.8756
CYP450 3A4 substrate	Substrate	0.6796
CYP450 1A2 substrate	Non-inhibitor	0.7059
CYP450 2C9 inhibitor	Non-inhibitor	0.6775
CYP450 2D6 inhibitor	Non-inhibitor	0.8859
CYP450 2C19 inhibitor	Non-inhibitor	0.6826
CYP450 3A4 inhibitor	Non-inhibitor	0.899
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7301
Ames test	Non AMES toxic	0.7118
Carcinogenicity	Non-carcinogens	0.928
Biodegradation	Not ready biodegradable	0.9721
Rat acute toxicity	2.6789 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9875
hERG inhibition (predictor II)	Non-inhibitor	0.7335

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-4004202930-cb176c6639a74243eebf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014r-5030000019-f082dc4926cdef97b9e2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kb-2007900300-82f8b0ba3bb1d5cd4cf1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-9131000104-ca422151e0b8dfb67c2d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a5d-7669401730-d5f24b39fdcc8c41a3eb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0540-9012300110-8cac8f334bc68f650c2c

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. RNA polymerase sigma factor

Kind

Protein

Organism

Clostridium difficile (strain 630)

Pharmacological action

Yes

Actions

Inhibitor

General Function

Transcription factor activity, sequence-specific dna binding

Specific Function

Sigma factors are initiation factors that promote the attachment of RNA polymerase to specific initiation sites and are then released.Sigma factors are initiation factors that promote the attachmen...

Gene Name

sigA1

Uniprot ID

Q18BX5

Uniprot Name

RNA polymerase sigma factor SigA

Molecular Weight

44426.185 Da

References

1. Venugopal AA, Johnson S: Fidaxomicin: a novel macrocyclic antibiotic approved for treatment of Clostridium difficile infection. Clin Infect Dis. 2012 Feb 15;54(4):568-74. doi: 10.1093/cid/cir830. Epub 2011 Dec 7. [Article]
2. Zhanel GG, Walkty AJ, Karlowsky JA: Fidaxomicin: A novel agent for the treatment of Clostridium difficile infection. Can J Infect Dis Med Microbiol. 2015 Nov-Dec;26(6):305-12. doi: 10.1155/2015/934594. [Article]
3. Artsimovitch I, Seddon J, Sears P: Fidaxomicin is an inhibitor of the initiation of bacterial RNA synthesis. Clin Infect Dis. 2012 Aug;55 Suppl 2:S127-31. doi: 10.1093/cid/cis358. [Article]

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Drug created at May 12, 2013 22:32 / Updated at February 20, 2024 23:54