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Chemistry

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Also known as: Rifamycin sv, Rifocin, Rifamicine sv, Rifomycin sv, Rifamicina, Rifamycine
Molecular Formula
C37H47NO12
Molecular Weight
697.8  g/mol
InChI Key
HJYYPODYNSCCOU-ODRIEIDWSA-N
FDA UNII
DU69T8ZZPA

Rifamycin
A group of ANTI-BACTERIAL AGENTS characterized by a chromophoric naphthohydroquinone group spanned by an aliphatic bridge not previously found in other known ANTI-BACTERIAL AGENTS. They have been isolated from fermentation broths of Streptomyces mediterranei.
Rifamycin is a Rifamycin Antibacterial.
1 2D Structure

Rifamycin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
2.1.2 InChI
InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
2.1.3 InChI Key
HJYYPODYNSCCOU-ODRIEIDWSA-N
2.1.4 Canonical SMILES
CC1C=CC=C(C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C
2.1.5 Isomeric SMILES
C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C
2.2 Other Identifiers
2.2.1 UNII
DU69T8ZZPA
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Rifamycins

2. Rifomycin

3. Rifomycins

2.3.2 Depositor-Supplied Synonyms

1. Rifamycin Sv

2. Rifocin

3. Rifamicine Sv

4. Rifomycin Sv

5. Rifamicina

6. Rifamycine

7. Rifamycinum

8. Rifocyn

9. 6998-60-3

10. Cb-01-11

11. Aemcolo

12. Du69t8zzpa

13. M-14

14. Chebi:29673

15. 6998-60-3 (free Acid)

16. 15105-92-7

17. Rifamycin Sv, An Antibiotic Produced By Certain Strains Of Streptomyces Mediterranei, Or The Same Substance Produced By Any Other Means

18. Rifamycine [inn-french]

19. Rifamycinum [inn-latin]

20. Rifamicina [inn-spanish]

21. (7s,9e,11s,12r,13s,14r,15r,16r,17s,18s,19e,21z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl Acetate

22. [(7s,9e,11s,12r,13s,14r,15r,16r,17s,18s,19e,21z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] Acetate

23. Rifomycin

24. Einecs 230-273-3

25. Unii-du69t8zzpa

26. Tuborin

27. Rifamycin-sv

28. Nsc133100

29. Rifamycin [usan:inn:ban:dcf]

30. Rifamycin [inn]

31. Rifamycin (usan/inn)

32. Rifamycin [usan]

33. Rifamycin Sv [mi]

34. Rifamycin [who-dd]

35. Schembl151824

36. Chembl437765

37. Gtpl4570

38. Dtxsid1032014

39. Rifamycin Sv [ep Impurity]

40. Bdbm50391000

41. Lmpk05000005

42. Akos024281286

43. Zinc169633673

44. Db11753

45. 2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2h)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate

46. Rifaximin Impurity C [ep Impurity]

47. D02549

48. Sr-01000872597

49. Sr-01000872597-1

50. (pentahydroxy-methoxy-heptamethyl-dioxo-[?]yl) Acetate

51. Q26270990

52. (2s,12z,14e,16s,17s,18r,19r,20r,21s,22r,23s,24e)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl Acetate

53. (7s,11s,12r,13s,14r,15r,16r,17s,18s,19z,21z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl Acetate

54. (7s,11s,13s,17s,18s,12r,14r,15r,16r)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7 ,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1<4, 7>.0<5,28>]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl Acetate

55. 2,7-(epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,11(2h)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, (2s,16s,17s,18r,19r,20r,21s,22r,23s)-

56. 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2h)-dione 21-acetate

2.4 Create Date
2005-12-16
3 Chemical and Physical Properties
Molecular Weight 697.8 g/mol
Molecular Formula C37H47NO12
XLogP34.9
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Exact Mass697.30982593 g/mol
Monoisotopic Mass697.30982593 g/mol
Topological Polar Surface Area201 Ų
Heavy Atom Count50
Formal Charge0
Complexity1330
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Rifamycin is indicated for the treatment of adult patients with travelers' diarrhea caused by noninvasive strains of _E. coli_. The status of the disease should not be complicated by fever or blood in the stool. To prevent drug-resistant bacteria, it is important to mention that the use of rifamycin for this indication should be only done in cases where the infection is proven or strongly suspected to be caused by bacteria. Travallers' diarrhea is very common problem affecting 20-60% of the travellers and it is defined as an increase in frequency of bowel movements to three or more loose stools per day during a trip abroad. This condition is rarely life threatening but in severe cases it can produce dehydration and sepsis. The most common cause of travellers' diarrhea is a pathogen and from the pathogens identified, bacteria is the most common cause followed by norovirus, rotavirus and similar viruses.


FDA Label


Treatment of acute infectious diarrhoea


Treatment of acute infectious diarrhoea


5 Pharmacology and Biochemistry
5.1 Pharmacology

Rifamycin is known to be effective against Gram-positive and Gram-negative pathogens and mycobacteria. It is very effective against _E. coli_ reporting a MIC90 of 64-128 mcg/ml without showing cross-resistance with other antimicrobial agents. The specific indication of rifamycin is extremely important as ther were previous reports that indicated a high risk factor in the generation of resistant _E. coli_ strains in patients with inflammatory bowel disease. In clinical trials, rifamycin was tested in a randomized clinical trial of travellers' coming from Mexico and Guatemala. In this trial, rifamycin was proven to significantly reduce the symptoms of travellers' diarrhea.


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
RIFAMYCIN
5.3.2 FDA UNII
DU69T8ZZPA
5.3.3 Pharmacological Classes
Rifamycins [CS]; Rifamycin Antibacterial [EPC]
5.4 ATC Code

J04AB03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AA - Antibiotics

A07AA13 - Rifamycin


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AX - Other antibiotics for topical use

D06AX15 - Rifamycin


J - Antiinfectives for systemic use

J04 - Antimycobacterials

J04A - Drugs for treatment of tuberculosis

J04AB - Antibiotics

J04AB03 - Rifamycin


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA16 - Rifamycin


S - Sensory organs

S02 - Otologicals

S02A - Antiinfectives

S02AA - Antiinfectives

S02AA12 - Rifamycin


5.5 Absorption, Distribution and Excretion

Absorption

Rifamycin has a very poor absorption and thus, the generation of an oral modified-release formulation using the technology of the multi-matrix structure was required for the generation of the FDA approved product. This preparation allows the delivery of the active ingredient in the distal small bowel and colon without interfering with the flora in the upper gastrointestinal tract. The multi-matrix is made by a lipophiic matrix surrounded in a hydrophilic matrix which allows for the protection of the active ingredient from dissolution in the intestinal aqueous fluids before it arrives in the cecum. All this matrix is surrounded by a gastro-resistant polymer that only desintegrate in a pH lower than 7. All this administration-customed formulation allows for a bioavailability of <0.1% and the plasma concentrations are reported to be of <2 ng/ml in patients receiving a dose of 400 mg. This confirms that the site of action of rifamycin stays in the small intestine and colon which prevents the need for dose adjustments in special populations as well as systemic drug interactions. The reported Cmax, tmax, AUC and mean residence time after a dosage of 250 mg of rifamycin is 36 mg/L, 5 min, 11.84 mg.h/L and 0.49 h respectively.


Route of Elimination

From the administered dose, 18%, 50% and 21% is recovered in feces during the first 24, 48 and 72h after administration. This will represent about 90% of the administered dose eliminated by the feces while the urinary secretion is negligible.


Volume of Distribution

The reported volume of distribution after measured after a dosage of 250 mg of rifamycin is 101.8 L.


Clearance

The reported clearance when a dose of 250 mg of rifamycin was administered is 23.3 L/h.


5.6 Metabolism/Metabolites

When absorbed, rifamycin is mainly metabolzied in hepatocytes and intestinal microsomes to a 25-deacetyl metabolite.


5.7 Biological Half-Life

The reported half-life when a dose of 250 mg of rifamycin was administered is 3 h.


5.8 Mechanism of Action

Rifamycins, as well as all the other members of this group, present an antibacterial mechanism of action related to the inhibition of RNA synthesis. This mechanism of action is done by the strong binding to the DNA-dependent RNA polymerase of prokaryotes. The inhibition of the RNA synthesis is thought to be related with the initiation phase of the process and to involve stacking interactions between the naphthalene ring and the aromatic moiety in the polymerase. As well, it has been suggested that the presence of zinc atoms in the polymerase allows for the binding of phenolic -OH groups of the naphthalene ring. In eukaryotic cells, the binding is significantly reduced making them at least 100 to 10,000 times less sensitive to the action of rifamycins. The members of the rifamycin family present the same mechanism of action and the structural modifications are usually related to pharmacokinetic properties as well as to the interaction with eukaryotic cells.


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Looking for 6998-60-3 / Rifamycin API manufacturers, exporters & distributors?

Rifamycin manufacturers, exporters & distributors 1

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API | Excipient name

Rifamycin

Synonyms

Rifamycin sv, Rifocin, Rifamicine sv, Rifomycin sv, Rifamicina, Rifamycine

Cas Number

6998-60-3

Unique Ingredient Identifier (UNII)

DU69T8ZZPA

About Rifamycin

A group of ANTI-BACTERIAL AGENTS characterized by a chromophoric naphthohydroquinone group spanned by an aliphatic bridge not previously found in other known ANTI-BACTERIAL AGENTS. They have been isolated from fermentation broths of Streptomyces mediterranei.

Rifamycine Chibret Manufacturers

A Rifamycine Chibret manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Rifamycine Chibret, including repackagers and relabelers. The FDA regulates Rifamycine Chibret manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Rifamycine Chibret API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Rifamycine Chibret manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Rifamycine Chibret Suppliers

A Rifamycine Chibret supplier is an individual or a company that provides Rifamycine Chibret active pharmaceutical ingredient (API) or Rifamycine Chibret finished formulations upon request. The Rifamycine Chibret suppliers may include Rifamycine Chibret API manufacturers, exporters, distributors and traders.

click here to find a list of Rifamycine Chibret suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Rifamycine Chibret USDMF

A Rifamycine Chibret DMF (Drug Master File) is a document detailing the whole manufacturing process of Rifamycine Chibret active pharmaceutical ingredient (API) in detail. Different forms of Rifamycine Chibret DMFs exist exist since differing nations have different regulations, such as Rifamycine Chibret USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Rifamycine Chibret DMF submitted to regulatory agencies in the US is known as a USDMF. Rifamycine Chibret USDMF includes data on Rifamycine Chibret's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Rifamycine Chibret USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Rifamycine Chibret suppliers with USDMF on PharmaCompass.

Rifamycine Chibret NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Rifamycine Chibret as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Rifamycine Chibret API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Rifamycine Chibret as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Rifamycine Chibret and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Rifamycine Chibret NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Rifamycine Chibret suppliers with NDC on PharmaCompass.

Rifamycine Chibret GMP

Rifamycine Chibret Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Rifamycine Chibret GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Rifamycine Chibret GMP manufacturer or Rifamycine Chibret GMP API supplier for your needs.

Rifamycine Chibret CoA

A Rifamycine Chibret CoA (Certificate of Analysis) is a formal document that attests to Rifamycine Chibret's compliance with Rifamycine Chibret specifications and serves as a tool for batch-level quality control.

Rifamycine Chibret CoA mostly includes findings from lab analyses of a specific batch. For each Rifamycine Chibret CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Rifamycine Chibret may be tested according to a variety of international standards, such as European Pharmacopoeia (Rifamycine Chibret EP), Rifamycine Chibret JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Rifamycine Chibret USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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