Details of the Drug

General Information of Drug (ID: DMEH3O7)

Drug Name

Rifamycin

Synonyms

Rifamycin SV; Rifamycin SV MMX; Rifamycin sodium; CB-01-11; Rifamycin (oral controlled-release, gastrointestinal-specific); Rifamycin (oral controlled-release, gastrointestinal-specific), Cosmo/Dr Falk/Santarus

Indication

Disease Entry	ICD 11	Status	REF
Diarrhea	ME05.1	Approved	[1]
Infectious disease	1A00-CA43.1	Phase 3	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

697.8

Logarithm of the Partition Coefficient (xlogp)

4.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The clearance of drug is 23.3 L/h [3]
Elimination: From the administered dose, 18%, 50% and 21% is recovered in feces during the first 24, 48 and 72h after administration [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 3 hours [3]
Metabolism: The drug is metabolized via the hepatocytes and intestinal microsomes to a 25-deacetyl metabolite [3]
Vd: The volume of distribution (Vd) of drug is 101.8 L [3]

Chemical Identifiers

Formula: C37H47NO12
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
Canonical 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
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
InChIKey: HJYYPODYNSCCOU-ODRIEIDWSA-N

Cross-matching ID

PubChem CID: 6324616
ChEBI ID: CHEBI:29673
CAS Number: 6998-60-3
DrugBank ID: DB11753
TTD ID: D0FX2Q
VARIDT ID: DR00614
ACDINA ID: D01389

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial RNA polymerase sigma factor SigA (Bact sigA)	TTR6YA2	SIGA_STAA8	Modulator	[4]
Mycobacterium RNA polymerase (MycB RNAP)	TT79JGK	RPOA_MYCTU ; RPOB_MYCTU ; RPOC_MYCTU ; RPOZ_MYCTU	Inhibitor	[1]
Staphylococcus Plastid RNA polymerase beta (Stap-coc rpoB)	TTS31JH	RPOB_STAA8	Modulator	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
C-reactive protein (CRP)	OT0RFT8F	CRP_HUMAN	Gene/Protein Processing	[5]
Glutathione S-transferase A1 (GSTA1)	OTA7K5XA	GSTA1_HUMAN	Gene/Protein Processing	[6]
Glutathione S-transferase Mu 1 (GSTM1)	OTSBF2MO	GSTM1_HUMAN	Gene/Protein Processing	[6]
Solute carrier organic anion transporter family member 1B1 (SLCO1B1)	OTNEN8QK	SO1B1_HUMAN	Gene/Protein Processing	[7]
Solute carrier organic anion transporter family member 1B3 (SLCO1B3)	OTOM3BUH	SO1B3_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Ascorbic acid	E00579	54670067	Acidulant; Antioxidant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Glyceryl distearate	E00681	101269	Lubricant
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
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⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Rifamycin 194mg tablet	194mg	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Rifamycin action on RNA polymerase in antibiotic-tolerant Mycobacterium tuberculosis results in differentially detectable populations.Proc Natl Acad Sci U S A. 2017 Jun 13;114(24):E4832-E4840.
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4570).
3	Systemic absorption of rifamycin SV MMX administered as modified-release tablets in healthy volunteers. Antimicrob Agents Chemother. 2011 May;55(5):2122-8. doi: 10.1128/AAC.01504-10. Epub 2011 Mar 14.
4	NCBI report
5	Multiple intra-articular treatment of rheumatoid arthritis: a randomized prospective study comparing rifamycin SV with pefloxacin. J Int Med Res. 1992 Feb;20(1):27-39. doi: 10.1177/030006059202000104.
6	The influence of picolines on glutathione transferase activity and subunit composition in human liver derived Hep G2 cells. Biochem Pharmacol. 1994 Nov 16;48(10):1976-8.
7	Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1. Drug Metab Dispos. 2005 Apr;33(4):537-46.
8	Neonicotinoid pesticides poorly interact with human drug transporters. J Biochem Mol Toxicol. 2019 Oct;33(10):e22379. doi: 10.1002/jbt.22379. Epub 2019 Jul 31.