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Rifamycin

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Also known as M-14RifamicinaRifamicine svRifamycineRifomycinRifomycin svrifamycin SVRifamycin SVdRIFAMYCIN SV SODIUM

Summary

Rifamycin (CHEMBL437765) is an approved small-molecule antimicrobial agent (ATC S02AA12) targeting SLCO1A2, SLCO1B1, and SLCO1B3; indicated across 5 conditions including eye infectious disorder and tuberculosis.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: S02AA12 (+4 more)
  • Targets: 4 (SLCO1A2, SLCO1B1, SLCO1B3…)
  • Indications: 5 conditions
  • Clinical trials: 5
  • Chemistry: 697.8 Da · C37H47NO12

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL437765
NameRifamycin
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID6324616
ChEBICHEBI:29673
ATCS02AA12, A07AA13, J04AB03, D06AX15, S01AA16
Molecular formulaC37H47NO12
Molecular weight697.8
InChIKeyHJYYPODYNSCCOU-ODRIEIDWSA-N

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

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

ChEBI definition: A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.

Pharmacological roles (ChEBI): antimicrobial agent, antitubercular agent.

Other ChEBI roles (chemical / environmental): bacterial metabolite.

Also known as: M-14, Rifamicina, Rifamicine sv, Rifamycin, Rifamycine, Rifomycin, Rifomycin sv, rifamycin, rifamycin SV, Rifamycin SV, Rifamycin SVd, RIFAMYCIN

Parent form; salt/anhydrous children: CHEMBL2105680

Patent coverage: 1,221 distinct patent families (2,798 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 2,075 (74%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
SLCO1A2OATP1A2Inhibition4.960.2%P46721
SLCO1B1OATP1B1Inhibition5.70%Q9Y6L6
SLCO1B3OATP1B3Inhibition0%Q9NPD5
SLCO2B1OATP2B1Inhibition0%O94956

Broader ChEMBL bioactivity targets: 12 (assay-derived). Sample: Solute carrier organic anion transporter family member 1B1, Solute carrier organic anion transporter family member 1B3, Solute carrier organic anion transporter family member 1A2, Solute carrier organic anion transporter family member 2B1, Solute carrier organic anion transporter family member 1A1, Solute carrier organic anion transporter family member 1A4, Thromboxane A2 receptor, Bile salt export pump, Muscarinic acetylcholine receptor M1, Prostaglandin G/H synthase 1.

Bioactivity

ChEMBL activities: 12 potent at pChembl ≥ 5 of 17 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
SLCO1B16.64IC50230nMCHEMBL_ACT_11000850
SLCO1B15.7Ki2000nMCHEMBL_ACT_11002855
SLCO1B35.52Ki3000nMCHEMBL_ACT_11003101
SLCO2B15.52Ki3000nMCHEMBL_ACT_11003102
O701275.51IC503100nMCHEMBL_ACT_15449951
O701275.42Ki3800nMCHEMBL_ACT_11002871
ABCB115.2IC506300nMCHEMBL_ACT_15460419
P467205.18Ki6600nMCHEMBL_ACT_11003219
O359135.14Ki7300nMCHEMBL_ACT_11003245
ADRA1A5.09AC508131nMCHEMBL_ACT_25208621
TBXA2R5.06AC508767nMCHEMBL_ACT_25211194
ABCB115.02IC509500nMCHEMBL_ACT_18051960

Target pathways

Aggregated over 4 target gene(s): SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1.

Top Reactome pathways

20 total, by targets touching each:

PathwayTargetsGenes
Transport of small molecules4SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Transport of vitamins, nucleosides, and related molecules4SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
SLC-mediated transmembrane transport4SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Organic anion transport by SLCO transporters4SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
Metabolism3SLCO1A2, SLCO1B1, SLCO1B3
Recycling of bile acids and salts3SLCO1A2, SLCO1B1, SLCO1B3
Heme degradation3SLCO1B1, SLCO1B3, SLCO2B1
Bile acid and bile salt metabolism3SLCO1A2, SLCO1B1, SLCO1B3
Metabolism of lipids3SLCO1A2, SLCO1B1, SLCO1B3
Metabolism of steroids3SLCO1A2, SLCO1B1, SLCO1B3
Drug ADME3SLCO1A2, SLCO1B1, SLCO1B3
Atorvastatin ADME3SLCO1B1, SLCO1B3, SLCO2B1
Disease2SLCO1B1, SLCO1B3
Metabolism of porphyrins2SLCO1B1, SLCO1B3
SLC transporter disorders2SLCO1B1, SLCO1B3
Disorders of transmembrane transporters2SLCO1B1, SLCO1B3
Defective SLCO1B3 causes hyperbilirubinemia, Rotor type (HBLRR)1SLCO1B3
Defective SLCO1B1 causes hyperbilirubinemia, Rotor type (HBLRR)1SLCO1B1
Aspirin ADME1SLCO2B1
Ciprofloxacin ADME1SLCO1A2

Dominant GO biological processes

GO termTargets
xenobiotic metabolic process4
monoatomic ion transport4
obsolete organic anion transport4
bile acid and bile salt transport4
sodium-independent organic anion transport4
transmembrane transport4
lipid transport3
heme catabolic process3
prostaglandin transport2
obsolete organic cation transport1
thyroid hormone transport1
transport across blood-brain barrier1

Indications & clinical

Indications

5 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
eye infectious disorder4MONDO:0043885EFO:1001888
tuberculosis4MONDO:0018076MONDO:0018076
diarrheal disease3MONDO:0001673HP:0002014
irritable bowel syndrome2MONDO:0005052EFO:0000555
dysentery2MONDO:0001517EFO:1001869

Clinical trials

Total trials: 5.

Phase distribution

PhaseTrials
PHASE32
PHASE41
PHASE21
Not specified1

Top trials by phase / activity

NCTPhaseStatusTitle
NCT04349579PHASE4UNKNOWNEvaluation of the Effects of Irrigation of the Extraction Socket With Rifamycine
NCT01208922PHASE3COMPLETEDRifamycin SV-MMX® Tablets Versus Ciprofloxacin Capsules in Acute Traveller’s Diarrhoea
NCT05575518PHASE3UNKNOWNA Pragmatic Trial With Optimized Dose of Rifampicin and Moxifloxacin for the Treatment of Drug Susceptible Pulmonary Tuberculosis
NCT04026984PHASE2UNKNOWNEvaluate Safety and Efficacy of Rifamycin SV MMX in the Treatment of Traveler’s Diarrhea in Children Age 6 to 11 Years
NCT03528915Not specifiedCOMPLETEDPrevalence of Conjunctivitis and Indentification of Risk Factors With and Without Prophylactic Antibiotic Treatment in Neonates

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

308 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DigoxinChEMBL + PubChemPhase 4 (approved)SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
PravastatinChEMBL + PubChemPhase 4 (approved)SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
RIFAMPINChEMBL + PubChemPhase 4 (approved)SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
RitonavirChEMBL + PubChemPhase 4 (approved)SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
VerapamilChEMBL + PubChemPhase 4 (approved)SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
GlycyrrhizinChEMBL + PubChemPhase 2 (approved)SLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
DexamethasonePubChemApprovedSLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
ErythromycinPubChemApprovedSLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
MethotrexatePubChemApprovedSLCO1A2, SLCO1B1, SLCO1B3, SLCO2B1
ATAZANAVIRChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
ATORVASTATINChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
CLARITHROMYCINChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
CYCLOSPORINEChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
ERLOTINIBChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
GEMFIBROZILChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
INDOMETHACINChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
LovastatinChEMBL + PubChemPhase 4 (approved)SLCO1A2, SLCO1B1, SLCO2B1
OLMESARTAN MEDOXOMILChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
PACLITAXELChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
TELMISARTANChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
VINBLASTINEChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
VINCRISTINEChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
ELTROMBOPAGChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
SULFASALAZINEChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3, SLCO2B1
SILYBIN AChEMBLPhase 3SLCO1B1, SLCO1B3, SLCO2B1
GENISTEINChEMBL + PubChemPhase 2 (approved)SLCO1B1, SLCO1B3, SLCO2B1
SILICRISTINChEMBLPhase 2SLCO1B1, SLCO1B3, SLCO2B1
AcyclovirPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
AllopurinolPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
AmantadinePubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
aminohippuric acidPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
AmitriptylinePubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
AtenololPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
chenodiolPubChemApprovedSLCO1A2, SLCO1B1, SLCO1B3
Cholic AcidPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
EzetimibePubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
MetforminPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
PhenytoinPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
SildenafilPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
theophyllinePubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
ValacyclovirPubChemApprovedSLCO1B1, SLCO1B3, SLCO2B1
CANDESARTAN CILEXETILChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3
DOXORUBICINChEMBL + PubChemPhase 4 (approved)SLCO1B3, SLCO2B1
ETOPOSIDEChEMBL + PubChemPhase 4 (approved)SLCO1B3, SLCO2B1
GLYBURIDEChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO2B1
HYDROXYZINE PAMOATEChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3
MITOXANTRONEChEMBL + PubChemPhase 4 (approved)SLCO1B3, SLCO2B1
SIMVASTATINChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO2B1
TANNIC ACIDChEMBL + PubChemPhase 4 (approved)SLCO1B1, SLCO1B3
BETA CAROTENEChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
CARBENOXOLONEChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
DICLOXACILLINChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
ERYTHROMYCIN ESTOLATEChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
ERYTHROMYCIN ETHYLSUCCINATEChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
LOSARTANChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
MOMETASONE FUROATEChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
NONOXYNOL 9ChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
TELITHROMYCINChEMBLPhase 4 (approved)SLCO1B1, SLCO1B3
ADMILPARANTChEMBLPhase 3SLCO1B1, SLCO1B3
ALISPORIVIRChEMBLPhase 3SLCO1B1, SLCO1B3

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot