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Drug

D1084 | rifampicin

Molecular Formula C43H58N4O12
Molecular Weight 822.9
Structure
State solid
Clearance * 0.19 +/- 0.06 L/hr/kg [300 mg IV] * 0.14 +/- 0.03 L/hr/kg [600 mg IV]
Route of elimination Less than 30% of the dose is excreted in the urine as rifampin or metabolites.
Protein binding 0.89
Half life 3.35 (+/- 0.66) hours
Absorption Well absorbed from gastrointestinal tract.

J

J04AM07 Rifampicin, ethambutol and isoniazid


[J04AM] Combinations of drugs for treatment of tuberculosis


[J04A] DRUGS FOR TREATMENT OF TUBERCULOSIS


[J04] ANTIMYCOBACTERIALS


[J] Antiinfectives for systemic use

J04AM06 Rifampicin, pyrazinamide, ethambutol and isoniazid


[J04AM] Combinations of drugs for treatment of tuberculosis


[J04A] DRUGS FOR TREATMENT OF TUBERCULOSIS


[J04] ANTIMYCOBACTERIALS


[J] Antiinfectives for systemic use

J04AM05 Rifampicin, pyrazinamide and isoniazid


[J04AM] Combinations of drugs for treatment of tuberculosis


[J04A] DRUGS FOR TREATMENT OF TUBERCULOSIS


[J04] ANTIMYCOBACTERIALS


[J] Antiinfectives for systemic use

J04AM02 Rifampicin and isoniazid


[J04AM] Combinations of drugs for treatment of tuberculosis


[J04A] DRUGS FOR TREATMENT OF TUBERCULOSIS


[J04] ANTIMYCOBACTERIALS


[J] Antiinfectives for systemic use

J04AB02 Rifampicin


[J04AB] Antibiotics


[J04A] DRUGS FOR TREATMENT OF TUBERCULOSIS


[J04] ANTIMYCOBACTERIALS


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 25.06±6.38 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 15.45 human HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 6.15±2.20 rat hepatocytes MMP assay decrease IC50 163
MEMBRANE POTENTIAL > 800 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 124.1 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
SWELLING > 800 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 124.1 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
Cytochrome c > 200 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 58 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (98.28%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (87.93%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (87.93%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (86.21%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 subcutaneous 621mg/kg (621mg/kg) Japanese Journal of Antibiotics. Vol. 23, Pg. 242, 1970.
mouse LD50 intraperitoneal 416mg/kg (416mg/kg) Chemotherapia. Vol. 12, Pg. 155, 1967.
mouse LD50 intravenous 260mg/kg (260mg/kg) Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970.
rat LD50 oral 1570mg/kg (1570mg/kg) Japanese Journal of Antibiotics. Vol. 23, Pg. 257, 1970.
women TDLo oral 744mg/kg/9W-I (744mg/kg) American Journal of Kidney Diseases. Vol. 31, Pg. 108, 1998.
man TDLo oral 13mg/kg/2D (13mg/kg) sense organs and special senses: other: eye British Medical Journal. Vol. 1, Pg. 199, 1976.
rat LD50 intraperitoneal 511mg/kg (511mg/kg) Japanese Journal of Antibiotics. Vol. 23, Pg. 257, 1970.
man TDLo oral 814mg/kg/15W- (814mg/kg) American Journal of Kidney Diseases. Vol. 32, Pg. 533, 1998.
rat LD50 subcutaneous 534mg/kg (534mg/kg) Japanese Journal of Antibiotics. Vol. 23, Pg. 242, 1970.
women TDLo oral 504mg/kg/42D- (504mg/kg) American Journal of Medicine. Vol. 87, Pg. 459, 1989.
mouse LD50 oral 500mg/kg (500mg/kg) Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles. Vol. 269, Pg. 2147, 1969.
guinea pig LD50 intraperitoneal 639mg/kg (639mg/kg) Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970.
rabbit LD50 oral 2120mg/kg (2120mg/kg) Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970.
man LDLo oral 857mg/kg (857mg/kg) JAMA, Journal of the American Medical Association. Vol. 240, Pg. 2283, 1978.
women TDLo oral 315mg/kg/5W-I (315mg/kg) skin and appendages (skin): "dermatitis, other: after systemic exposure" Journal of the American Academy of Dermatology. Vol. 17, Pg. 303, 1987.
human TDLo oral 180mg/kg (180mg/kg) British Medical Journal. Vol. 2, Pg. 1189, 1977.


  • (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-8-[[(4-methylpiperazin-1-yl)imino]methyl]-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca (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-8-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl ac (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-8-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acet
    (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-8-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate (2S,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-8-{[(4-methylpiperazin-1-yl)imino]methyl}-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate (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-26-{(E)-[(4-methylpiperazin-1-yl)imino] methyl}-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
    (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-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1(4,7).0(5,28)]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate 13292-46-1 2,11,13]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-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-, 21-acetate
    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-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-, 21-acetate 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-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-, 21-acetate ( 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-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-, 21-acetate (8CI)
    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-8-[(E)-[(4-methyl-1-piperazinyl)imino]meth 26-[(1E)-2-(4-methylpiperazinyl)-2-azavinyl](7S,11S,13S,17S,18S,12R,14R,15R,16 R)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-d ioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1< 292R461
    3-(((4-Methyl-1-piperazinyl)imino)-methyl)rifamycin 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV 3-(4-Methylpiperazinyliminomethyl)-rifamycin SV
    3-(4-Methylpiperazinyliminomethyl)rifamycin SV 3-([(4-Methyl-1-piperazinyl)imino]methyl)rifamycin SV 3-[(4-Methyl-1-piperazinyl)iminomethyl]rifamycin SV
    3-[[(4-Methyl-1-piperazinyl)imino]-methyl]rifamycin 4,7>.0<5,28>]triaconta-1(28),2,4,9,1 9,21,25(29),26-octaen-13-yl acetate 5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione 21-acetate
    5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-beta)furan-1,11(2H)-dione 21-acetate 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-, 21-acetate 8-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV
    8-(4-Methylpiperazinyliminomethyl) rifamycin SV 8-[[(4-Methyl-1-piperazinyl)imino[methyl]rifamycin 8-[[(4-Methyl-1-piperazinyl)imino]methyl]rifamycin sv
    8-[[(4-Methylpiperazinyl)imino]methyl]rifamycin sv 8CI) AB00383022_07
    AB1009526 AKOS015951372 AZT + Rifampin
    Abrifam Archidyn Arficin
    Arzide BA-411661E BA-41166E
    BDBM50370232 BPBio1_000561 BSPBio_000509
    Ba 41166 Ba 41166/E Benemicin
    Benemycin C06688 C43H58N4O12
    CAS-13292-46-1 CCG-208267 CCRIS 551
    CHEBI:28077 CHEMBL374478 Certified Reference Material
    D00211 DB01045 DRG-0109
    DSSTox_CID_1244 DSSTox_GSID_21244 DSSTox_RID_76035
    DTXSID6021244 Dione 21-acetate Dipicin
    Doloresum EINECS 236-312-0 Eremfat
    Famcin Fenampicin GR-306
    HMS1569J11 HMS2089F12 HMS2096J11
    HMS3713J11 HSDB 3181 J10110
    JQXXHWHPUNPDRT-WLSIYKJHSA-N L-5103 L-5103 Lepetit
    L-5103-LEPETIT LS-7689 M880
    MFCD00151389 NCGC00022678-03 NCGC00022678-04
    NCGC00022678-05 NCGC00022678-06 NCGC00094777-01
    NCGC00179536-02 NCGC00254537-01 NCGC00258936-01
    NIH-10782 NSC 113926 NSC-113926
    NSC113926 Piperine & Rifampicin Prestwick2_000525
    Prestwick3_000525 Prestwick_833 R-Cin
    R/AMP RFP RIF
    RMP Reserpine & Rifampicin Rifa
    Rifadin Rifadin (TN) Rifadin I.V
    Rifadin I.V. Rifadine Rifagen
    Rifaldazin Rifaldazine Rifaldin
    Rifam Rifamicin AMP Rifamor
    Rifampicin Rifampicin & EEP Rifampicin & Propolis
    Rifampicin (JP17/INN) Rifampicin SV Rifampicin [INN:BAN:JAN]
    Rifampicin, >=97% (HPLC), powder Rifampicin, >=97.0% (HPLC) Rifampicin, European Pharmacopoeia (EP) Reference Standard
    Rifampicin, VETRANAL(TM), analytical standard Rifampicin, plant cell culture tested, BioReagent, >=97% (HPLC), crystalline Rifampicin, powder, gamma-irradiated
    Rifampicina Rifampicina [INN-Spanish] Rifampicine
    Rifampicine [French] Rifampicinum Rifampicinum [INN-Latin]
    Rifampin (USP) Rifampin [USAN:USP] Rifampin [USAN]
    Rifampin, Pharmaceutical Secondary Standard Rifampin, United States Pharmacopeia (USP) Reference Standard Rifamsolin
    Rifamycin AMP Rifamycin, 3-(((4-methyl-1-piperazinyl)imino)methyl)- Rifamycin, 3-[[(4-methyl-1-piperazinyl)imino]methyl]-
    Rifaprodin Rifater Rifcin
    Rifinah Rifobac Rifoldin
    Rifoldine Rifomycin SV, 8-(N-(4-methyl-1-piperazinyl)formidoyl)- Rifomycin sv, 8-[N-(4-Methyl-1-piperazinyl)formidoyl]-
    Riforal Rimactan Rimactane
    Rimactane (TN) Rimactazid Rimactizid
    Rimazid Rimycin SCHEMBL23490
    SR-05000002118 SR-05000002118-3 ST057531
    Sinerdol Spectrum5_002018 Stereoisomer of 5,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-he@ptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione 21-acetate;
    Tox21_111329 Tox21_111329_1 Tox21_201385
    Tox21_300550 Tubocin UNII-VJT6J7R4TR
    VJT6J7R4TR WLN: V1 WQ A&1 E&1 E1UN- AT6N DNTJ D1 [1,11,13]trienimino)naphto[2,1-b]furan-21-yl acetate
    [pentahydroxy-methoxy-heptamethyl-[(E)-(4-methylpiperazin-1-yl)iminomethyl]-dioxo-[?]yl] acetate rifamcin rifampin
    yl]-, (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-

    DrugBank DB01045
    CAS Number 13292-46-1, 38776-75-9, 6998-60-3
    PubChem Compound 135398735
    KEGG Compound ID C06688
    KEGG Drug D00211
    ChEBI 28077