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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H58N4O12
Molecular Weight 822.9402
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RIFAMPIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(O)C(\C=N\N5CCN(C)CC5)=C(NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C(O)=C4C(O)=C3C

InChI

InChIKey=JQXXHWHPUNPDRT-WLSIYKJHSA-N
InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1

HIDE SMILES / InChI

Molecular Formula C43H58N4O12
Molecular Weight 822.9402
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Rifampin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. It is FDA approved for the treatment of tuberculosis, meningococcal carrier state. Healthy subjects who received rifampin 600 mg once daily concomitantly with saquinavir 1000 mg/ritonavir 100 mg twice daily (ritonavir-boosted saquinavir) developed severe hepatocellular toxicity. Rifampin has been reported to substantially decrease the plasma concentrations of the following antiviral drugs: atazanavir, darunavir, fosamprenavir, saquinavir, and tipranavir. These antiviral drugs must not be co-administered with rifampin. Common adverse reactions include heartburn, epigastric distress, anorexia, nausea, vomiting, jaundice, flatulence, cramps.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
18.5 µM [Ki]
30.2 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RIFADIN
Curative
RIFADIN

Cmax

ValueDoseCo-administeredAnalytePopulation
21.6 mg/L
20 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
25.1 mg/L
25 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
33.1 mg/L
30 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
35.2 mg/L
35 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
7.4 mg/L
10 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
3.3 mg/L
10 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
6.3 mg/L
10 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
325 μg × h/mL
600 mg single, oral
RIFAMPIN plasma
Homo sapiens
113 mg × h/L
20 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
135 mg × h/L
25 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
190 mg × h/L
30 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
235 mg × h/L
35 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens
26.3 mg × h/L
10 mg/kg 1 times / day steady-state, oral
RIFAMPIN serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
17.3 h
600 mg single, oral
25-DESACETYLRIFAMPIN plasma
Homo sapiens
16.3 h
600 mg single, oral
RIFAMPIN plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Tuberculosis: 10 mg/kg, in a single daily administration, not to exceed 600 mg/day, oral or intravenous. It is recommended that oral rifampin be administered once daily, either 1 hour before or 2 hours after a meal with a full glass of water. Meningococcal Carriers: it is recommended that 600 mg rifampin be administered twice daily for two days.
Route of Administration: Other
In Vitro Use Guide
By the absolute concentration method, the MIC50 and MIC90 of rifampicin were 0.5-1 mg/L
Substance Class Chemical
Record UNII
VJT6J7R4TR
Record Status Validated (UNII)
Record Version