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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H47NO12
Molecular Weight 697.77
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFAMYCIN

SMILES

C[C@@]1([H])/C(/[H])=C(\[H])/C(/[H])=C(/C)\C(=Nc2cc(c3c(c(c(C)c4c3C(=O)[C@@](C)(O/C(/[H])=C(\[H])/[C@@]([H])([C@@]([H])(C)[C@]([H])([C@]([H])(C)[C@@]([H])([C@]([H])(C)[C@@]1([H])O)O)OC(=O)C)OC)O4)O)c2O)O)O

InChI

InChIKey=HJYYPODYNSCCOU-ODRIEIDWSA-N
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

HIDE SMILES / InChI
Rifamycin SV is a derivative of antibiotic rifamycin B (the natural fermentation product of S. mediterranei broths). The primary target of rifampicin on whole bacteria is the synthesis of RNA. Rifamycin belongs to the ansamycin class of antibacterial drugs and acts by inhibiting the beta subunit of the bacterial DNA-dependent RNA polymerase, blocking one of the steps in DNA transcription. This results in inhibition of bacterial synthesis and consequently growth of bacteria. Rifampicin exhibits bactericidal activity on Gram-positive and Gram-negative bacteria and on mycobacteria. Rifamycin SV MMX® (AEMCOLO), a non-absorbable rifamycin antibiotic formulated using the multi-matrix system, was designed to exhibit its pharmacological action on the distal small intestine and colon. AEMCOLO is indicated for the treatment of travelers’ diarrhea (TD) caused by non-invasive strains of Escherichia coli in adults.

Originator

Sources: Sensi P., Margalith P., Timbal M.T. Farmaco (Ed. Sci.) 1959;14:146 | Sensi P., Greco, A.M., Ballotta, R. Antimicrob. Ag. Chemother. 1959;60:262-70
Curator's Comment:: Rifamycin family of antibiotics originally isolated from the fermentation broths of S. mediterranei. https://www.ncbi.nlm.nih.gov/pubmed/4562808

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AEMCOLO

Approved Use

AEMCOLO is a rifamycin antibacterial indicated for the treatment of travelers’ diarrhea caused by noninvasive strains of Escherichia coli in adults

Launch Date

1.54223994E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
36025 ng/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.72 ng/mL
388 mg 2 times / day multiple, oral
dose: 388 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11865.21 ng × h/mL
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.04 h
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
388 mg 2 times / day multiple, oral
dose: 388 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 199
Sources:
Other AEs: Constipation...
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 420
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 420
Sources:
Other AEs: Headache, Dyspepsia...
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 619
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 619
Sources:
Disc. AE: Abdominal pain, Pyrexia...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (0.5%)
Pyrexia (0.3%)
Sources:
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Other AEs: Abdominal distension, Arthralgia...
Other AEs:
Abdominal distension (0.5%)
Arthralgia (0.5%)
Muscle spasms (1%)
Fatigue (1%)
Bronchitis (1%)
Nasopharyngitis (0.5%)
Parasitic gastroenteritis (1%)
Pharyngitis (0.5%)
Urinary tract infection (1%)
Dysmenorrhea (1.5%)
Dysuria (1%)
Dizziness (0.5%)
Conjunctivitis (1%)
Sources:
400 mg 2 times / day multiple, oral
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Constipation 3.5%
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 199
Sources:
Headache 3.3%
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 420
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 420
Sources:
Dyspepsia <2%
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 420
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 420
Sources:
Pyrexia 0.3%
Disc. AE
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 619
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 619
Sources:
Abdominal pain 0.5%
Disc. AE
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
unhealthy, 36.2 years (range: 18 - 87 years)
n = 619
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 619
Sources:
Abdominal distension 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Arthralgia 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Dizziness 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Nasopharyngitis 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Pharyngitis 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Bronchitis 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Conjunctivitis 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Dysuria 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Fatigue 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Muscle spasms 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Parasitic gastroenteritis 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Urinary tract infection 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Dysmenorrhea 1.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
Sources:
Diarrhea 1%
Disc. AE
400 mg 2 times / day multiple, oral
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
yes [EC50 11.1 uM]
yes [IC50 34.4 uM]
yes [IC50 6.5 uM]
yes [Ki 2 uM]
yes
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
yes
unlikely
Comment: Co-administration of rifamycin SV MMX with P-gp inhibitors is not expected to result in a clinically relevant increase in the systemic exposure of rifamycin SV based on the following: i) poor drug solubility; ii) wide safety margin in relation to systemic exposures observed with i.v. rifamycin SV, iii) limited 3-day treatment duration; and iv) colonic release (P-gp levels lower in colon and distal to site of most oral drugs’ absorption (i.e., duodenum and jejunum).
Page: 192.0
PubMed

PubMed

TitleDatePubMed
Potentiation of rifampicin, rifampicin analogs, and tetracycline against animal cells by amphotericin B and polymyxin B.
1973 Jun
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.
1988 Feb
Multiple intra-articular treatment of rheumatoid arthritis: a randomized prospective study comparing rifamycin SV with pefloxacin.
1992 Feb
Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1.
2005 Apr
Antibacterial activities of dendritic amphiphiles against nontuberculous mycobacteria.
2012 Mar
Patents

Sample Use Guides

The recommended dosage of AEMCOLO (rifamycin) delayed-release tablets is 388 mg (two tablets) orally twice daily for three days
Route of Administration: Oral
Rifamycin SV demonstrated similar antimicrobial activity levels against the Enterobacteriaceae, with MIC₅₀ values ranging from 32 to 128 μg/ml for all but one strain (an enterotoxigenic Escherichia coli at >512 μg/ml). For non-Enterobacteriaceae strains, MIC₅₀ values ranged from 2 to 8 μg/ml, with the exception of Campylobacter spp., for which all strains had MIC values of >512 μg/ml. Rifamycin SV also demonstrated excellent activity (MIC₅₀ of ≤ 0.03 μg/ml) against most C. difficile strains (including one hypervirulent NAP1 strain), and this activity was even superior to the potency observed for vancomycin, metronidazole, and rifaximin.
Name Type Language
RIFAMYCIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
M-14
Code English
RIFAMYCIN [WHO-DD]
Common Name English
RIFAMYCIN SV
MI  
Common Name English
RIFAMICINE SV
Common Name English
RIFAXIMIN IMPURITY C [EP]
Common Name English
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
Common Name English
RIFAMYCIN SV [EP]
Common Name English
RIFAMYCIN [USAN]
Common Name English
RIFAMYCIN SV, AN ANTIBIOTIC PRODUCED BY CERTAIN STRAINS OF STREPTOMYCES MEDITERRANEI, OR THE SAME SUBSTANCE PRODUCED BY ANY OTHER MEANS
Common Name English
RIFAMYCIN [INN]
Common Name English
RIFAMYCIN SV [MI]
Common Name English
RIFOMYCIN SV
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB03
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-ATC S01AA16
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-VATC QJ54AB03
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-ATC J04AB03
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
NCI_THESAURUS C280
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-ATC S02AA12
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-VATC QS01AA16
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-VATC QS02AA12
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
Code System Code Type Description
EVMPD
SUB10310MIG
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
WIKIPEDIA
Rifamycin
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
NCI_THESAURUS
C29406
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
DRUG CENTRAL
4817
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
DRUG BANK
DB11753
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
MESH
C023808
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
230-273-3
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
EPA CompTox
6998-60-3
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
RXCUI
35616
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M9613
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY Merck Index
PUBCHEM
6324616
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
CAS
6998-60-3
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
LACTMED
Rifamycin
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
FDA UNII
DU69T8ZZPA
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL437765
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
INN
2293
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY