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Chemistry

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Also known as: Tiacumicin b, Dificid, Dificlir, Lipiarmycin, Opt-80, 873857-62-6
Molecular Formula
C52H74Cl2O18
Molecular Weight
1058.0  g/mol
InChI Key
ZVGNESXIJDCBKN-UUEYKCAUSA-N
FDA UNII
Z5N076G8YQ

Fidaxomicin
A narrow-spectrum macrolide antibacterial agent that is used in the treatment of diarrhea associated with CLOSTRIDIUM DIFFICILE INFECTION.
Fidaxomicin is a Macrolide Antibacterial.
1 2D Structure

Fidaxomicin

2 Identification
2.1 Computed Descriptors
2.1.1 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-methylpropanoyloxy)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
2.1.2 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
2.1.3 InChI Key
ZVGNESXIJDCBKN-UUEYKCAUSA-N
2.1.4 Canonical SMILES
CCC1C=C(C(CC=CC=C(C(=O)OC(CC=C(C=C(C1OC2C(C(C(C(O2)(C)C)OC(=O)C(C)C)O)O)C)C)C(C)O)COC3C(C(C(C(O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)C
2.1.5 Isomeric SMILES
CC[C@H]1/C=C(/[C@H](C/C=C/C=C(/C(=O)O[C@@H](C/C=C(/C=C(/[C@@H]1O[C@H]2[C@H]([C@H]([C@@H](C(O2)(C)C)OC(=O)C(C)C)O)O)\C)\C)[C@@H](C)O)\CO[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)\C
2.2 Other Identifiers
2.2.1 UNII
Z5N076G8YQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dificid

2. Lipiarmycin

3. Lipiarmycin A3

4. Lipiarmycin A4

5. Lipiarmycin B

6. Lipiarmycin B3

7. Lipiarmycin B4

8. Par 101

9. Par-101

10. Par101

11. Tiacumicin B

12. Tiacumicin C

2.3.2 Depositor-Supplied Synonyms

1. Tiacumicin B

2. Dificid

3. Dificlir

4. Lipiarmycin

5. Opt-80

6. 873857-62-6

7. Par-101

8. Clostomicin B1

9. Lipiarmicin

10. Difimicin

11. Z5n076g8yq

12. Lipiarmycin A3

13. R-tiacumicin B

14. Lipiarmycin A 3

15. Fidaxomicin [usan]

16. Fidaxomicin [usan:inn]

17. Unii-z5n076g8yq

18. Lipiarrmycin

19. Par 01

20. Clostomycin B1

21. Fidaxomicin (dificid)

22. Brn 5228707

23. Fidaxomicin [mi]

24. Fidaxomicin [inn]

25. Fidaxomicin [jan]

26. Fidaxomicin [vandf]

27. Fidaxomicin [who-dd]

28. Chembl1255800

29. Schembl10000818

30. Fidaxomicin, >=98% (hplc)

31. Gtpl10909

32. Fidaxomicin [orange Book]

33. Dtxsid901016415

34. Fi8

35. Mfcd27976367

36. Db08874

37. F1216

38. Opt-80;par-101;clostomicin B1;tiacumicin B

39. Q5446672

40. (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

41. [(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-methylpropanoyloxy)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

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 1058.0 g/mol
Molecular Formula C52H74Cl2O18
XLogP36.4
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count18
Rotatable Bond Count15
Exact Mass1056.4252209 g/mol
Monoisotopic Mass1056.4252209 g/mol
Topological Polar Surface Area267 Ų
Heavy Atom Count72
Formal Charge0
Complexity1970
Isotope Atom Count0
Defined Atom Stereocenter Count14
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count5
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDificid
PubMed HealthFidaxomicin (By mouth)
Drug ClassesAntibiotic
Drug LabelDIFICID (fidaxomicin) is a macrolide antibacterial drug for oral administration. Its CAS chemical name is Oxacyclooctadeca-3,5,9,13,15-pentaen-2-one, 3-[[[6-deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl--D-mannopyranosyl]oxy]meth...
Active IngredientFidaxomicin
Dosage FormTablet
RouteOral
Strength200mg
Market StatusPrescription
CompanyCubist Pharms

2 of 2  
Drug NameDificid
PubMed HealthFidaxomicin (By mouth)
Drug ClassesAntibiotic
Drug LabelDIFICID (fidaxomicin) is a macrolide antibacterial drug for oral administration. Its CAS chemical name is Oxacyclooctadeca-3,5,9,13,15-pentaen-2-one, 3-[[[6-deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl--D-mannopyranosyl]oxy]meth...
Active IngredientFidaxomicin
Dosage FormTablet
RouteOral
Strength200mg
Market StatusPrescription
CompanyCubist Pharms

4.2 Drug 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. 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.


FDA Label


Dificlir film-coated tablets is indicated for the treatment of Clostridioides difficile infections (CDI) also known as C. difficile-associated diarrhoea (CDAD) in adult and paediatric patients with a body weight of at least 12. 5 kg.

Consideration should be given to official guidelines on the appropriate use of antibacterial agents.

Dificlir granules for oral suspension is indicated for the treatment of Clostridioides difficile infections (CDI) also known as C. difficile-associated diarrhoea (CDAD) in adults and paediatric patients from birth to < 18 years of age.

Consideration should be given to official guidelines on the appropriate use of antibacterial agents.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Fidaxomicin has a narrow-spectrum antibacterial profile, with potent bactericidal activity specifically against C. difficile. The minimum inhibitory concentration for 90% of organisms for fidaxomicin against _C. difficile_ ranged from 0.0078 to 2 g/mL _in vitro_. The bactericidal activity of fidaxomicin is time-dependent. Other than _C. difficile_, fidaxomicin has moderate inhibitory activity against Gram-positive bacteria (_S. aureus_ and _Enterococcus spp._) and poor activity against normal colonic flora, including anaerobes and enteric Gram-negative bacilli. 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.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FIDAXOMICIN
5.3.2 FDA UNII
Z5N076G8YQ
5.3.3 Pharmacological Classes
Macrolides [CS]; Macrolide Antibacterial [EPC]
5.4 ATC Code

A07AA12


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AA - Antibiotics

A07AA12 - Fidaxomicin


5.5 Absorption, Distribution and Excretion

Absorption

Following oral administration of a single dose of 200 mg fidaxomicin in healthy adults, the Cmax of fidaxomicin and its main metabolite OP-1118 were 5.20 2.81 ng/mL and 12.0 6.06, respectively. The median Tmax of fidaxomicin was 2 hours. The systemic absorption of fidaxomicin following oral administration is minimal. In a food-effect study involving healthy adults in either with a high-fat meal versus under fasting conditions, the Cmax 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.


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.


Volume of Distribution

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


Clearance

There is limited information on the clearance of fidaxomicin.


5.6 Metabolism/Metabolites

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.


5.7 Biological 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.


5.8 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. 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. 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. The core RNA polymerase is composed of a complex of different subunits and contains the active site. To initiate bacterial transcription, the active site of the core RNA polymerase binds to a promoter-specificity 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. Fidaxomicin binds to the DNA template-RNA polymerase complex, thereby preventing the initial separation of DNA strands during transcription and inhibiting messenger RNA synthesis. The narrow spectrum of antimicrobial activity of fidaxomicin may be explained by the unique target site of fidaxomicin and differing subunits of the core structure of RNA polymerase among bacterial species.


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US Patents

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01

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26th North American ISSX
Not Confirmed

CUBIST PHARMS LLC

Switzerland
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FIDAXOMICIN

US Patent Number : 7906489*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-09-04

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02

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26th North American ISSX
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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 7906489

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code : U-2741

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-03-04

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03

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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 7863249*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2028-01-31

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04

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26th North American ISSX
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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
Not Confirmed

FIDAXOMICIN

US Patent Number : 8859510

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code : U-2741

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-07-31

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05

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CUBIST PHARMS LLC

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FIDAXOMICIN

US Patent Number : 9808530*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 213138

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2034-11-28

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06

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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 7378508*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2028-01-31

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07

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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 8859510

Drug Substance Claim :

Drug Product Claim :

Application Number : 213138

Patent Use Code : U-2741

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-07-31

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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 7906489

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code : U-319

Delist Requested :

Patent Use Description : TREATMENT OF MICROBIAL...

Patent Expiration Date : 2027-03-04

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26th North American ISSX
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CUBIST PHARMS LLC

Switzerland
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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 8859510*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 201699

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2028-01-31

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26th North American ISSX
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CUBIST PHARMS LLC

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26th North American ISSX
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FIDAXOMICIN

US Patent Number : 8586551*PED

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Application Number : 201699

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Patent Expiration Date : 2024-01-15

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