Drug Details

General Information of the Drug (ID: DR3806)
Name
Rifampicin
Synonyms
Rifampicin; rifampin; Rifadin; Rimactane; Rimactan; Rifamycin AMP; 13292-46-1; Rifaldazine; Rifaprodin; Riforal; Tubocin; Rifa; Rifampicinum; Archidyn; Rifoldin; Rifoldine; Rimactizid; Rifagen; Rimazid; Rifampicin SV; L-5103 Lepetit; R/AMP; Arficin; Benemicin; Doloresum; Eremfat; Fenampicin; Rifadine; Rifaldazin; Rifamor; Rifinah; Rifobac; Rimactazid; Sinerdol; Arzide; Rifcin; Rifam; Dione 21-acetate; Rifampicine [French]; Rifampicina; Rifampicinum [INN-Latin]; Ba 41166/E; Rifampicina [INN-Spanish]; 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV; CCRIS 551; Rifadin I.V.; HSDB 3181; C43H58N4O12; UNII-VJT6J7R4TR; BA-41166E; NSC113926; VJT6J7R4TR; NSC-113926; Rifampicine; Abrifam; Rifamycin, 3-(((4-methyl-1-piperazinyl)imino)methyl)-; RFP; CHEBI:28077; 3-(4-Methylpiperazinyliminomethyl)-rifamycin SV; 8-(4-Methylpiperazinyliminomethyl) rifamycin SV; L-5103; (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; 8-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV; Rifamycin, 3-[[(4-methyl-1-piperazinyl)imino]methyl]-; Rifomycin SV, 8-(N-(4-methyl-1-piperazinyl)formidoyl)-; Rifaldin; DSSTox_CID_1244; DSSTox_RID_76035; DSSTox_GSID_21244; RIF; (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; CAS-13292-46-1; 3-(4-Methylpiperazinyliminomethyl)rifamycin SV; 3-([(4-Methyl-1-piperazinyl)imino]methyl)rifamycin SV; 8-[[(4-Methyl-1-piperazinyl)imino]methyl]rifamycin sv; rifamcin; [1,11,13]trienimino)naphto[2,1-b]furan-21-yl acetate; Rifomycin sv, 8-[N-(4-Methyl-1-piperazinyl)formidoyl]-; Rifamsolin; Rifampicin [INN:BAN:JAN]; Famcin; MFCD00151389; Rimactane (TN); NCGC00094777-01; AZT + Rifampin; Rifampin (USP); (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 acet; (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; [pentahydroxy-methoxy-heptamethyl-[(E)-(4-methylpiperazin-1-yl)iminomethyl]-dioxo-[?]yl] acetate; Rifampicin & EEP; Prestwick_833; EINECS 236-312-0; R-Cin; Rifadin (TN); NSC 113926; Piperine & Rifampicin; Rifampicin & Propolis; Reserpine & Rifampicin; Rifampin [USAN:USP]; Prestwick2_000525; Prestwick3_000525; Spectrum5_002018; 3-[[(4-Methyl-1-piperazinyl)imino]-methyl]rifamycin; Rifampicin (JP17/INN); SCHEMBL23490; BSPBio_000509; L-5103-LEPETIT; 8CI); BPBio1_000561; CHEMBL374478; DTXSID6021244; HMS1569J11; HMS2089F12; HMS2096J11; HMS3713J11; DRG-0109; Rifampicin, >=97.0% (HPLC); Rifampicin, powder, gamma-irradiated; Tox21_111329; Tox21_201385; Tox21_300550; Ba 41166; BDBM50370232; GR-306; NIH-10782; AKOS015951372; Rifampicin - CAS 13292-46-1; Rifampicin, >=97% (HPLC), powder; Tox21_111329_1; BA 411661E; CCG-208267; DB01045; NCGC00022678-03; NCGC00022678-04; NCGC00022678-05; NCGC00022678-06; NCGC00179536-02; NCGC00254537-01; NCGC00258936-01; 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; M880; ST057531; C06688; D00211; J10110; Rifampicin, VETRANAL(TM), analytical standard; AB00383022_07; 292R461; SR-05000002118; 8-[[(4-Methyl-1-piperazinyl)imino[methyl]rifamycin; 8-[[(4-Methylpiperazinyl)imino]methyl]rifamycin sv; SR-05000002118-3; WLN: V1 WQ A&1 E&1 E1UN- AT6N DNTJ D1; 3-[(4-Methyl-1-piperazinyl)iminomethyl]rifamycin SV; Rifampicin, European Pharmacopoeia (EP) Reference Standard; Rifampin, United States Pharmacopeia (USP) Reference Standard; Rifampin, Pharmaceutical Secondary Standard; Certified Reference Material; 4,7>.0<5,28>]triaconta-1(28),2,4,9,1 9,21,25(29),26-octaen-13-yl acetate; Rifampicin, plant cell culture tested, BioReagent, >=97% (HPLC), crystalline; yl]-, (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-; (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; (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; 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-(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; 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); 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<; 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; Rifampicin in combination with actinonin, BB-3497, hydroxylamine hydrochloride, and 1,10-phenanthroline; RMP; 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
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Molecular Type
Small molecule
Disease HIV-associated tuberculosis [ICD-11: 1C60] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C43H58N4O12
PubChem CID
135398735
Canonical SMILES
CC1C=CC=C(C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C=NN5CCN(CC5)C)C
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
InChIKey
JQXXHWHPUNPDRT-WLSIYKJHSA-N
CAS Number
CAS 13292-46-1
ChEBI ID
CHEBI:28077
TTD Drug ID
D0G3DL
DrugBank ID
DB01045
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Allium sativum      Allium sativum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 Garlic extracts or compounds have a good potential as antitubercular(s) drug if given as a supplement to ATT.
          Ferutinin      Ferula sinkiangensisK     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 The combination of 1 with each antitubercular drug led to mutual enhancement of the antimycobacterial activity with isoniazid and ethionamide, while no such effect was observed with rifampin or streptomycin.
          Fosfomycin      Streptomyces fradiae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 In patients with implanted foreign devices, combination therapy was associated with a better long-term outcome.
          Oleanolic acid      Olea europaea     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Vero CVCL_0059 Healthy Chlorocebus sabaeus
                    Experimental
                    Result(s)		 Oleanolic acid and combination displayed either a synergistic interaction or did not show any interaction against two drug-sensitive strains.
Target and Pathway
Target(s) Bacterial RNA polymerase switch region (Bact RNAP-SR)  Molecule Info  [6]
References
Reference 1 Drugs used to treat Parkinson's disease, present status and future directions. CNS Neurol Disord Drug Targets. 2008 Oct;7(4):321-42.
Reference 2 Antitubercular activity of garlic (allium sativum) extract on combination with conventional antitubercular drugs in tubercular lymphadenitis. Indian J Clin Biochem. 1999 Jan;14(1):12-8.
Reference 3 Antimycobacterial activity of ferutinin alone and in combination with antitubercular drugs against a rapidly growing surrogate of Mycobacterium tuberculosis. Nat Prod Res. 2011 Jul;25(12):1142-9.
Reference 4 Combination therapy with rifampicin or fosfomycin in patients with Staphylococcus aureus bloodstream infection at high risk for complications or relapse: results of a large prospective observational cohort. J Antimicrob Chemother. 2020 Aug 1;75(8):2282-2290.
Reference 5 In vitro synergistic interactions of oleanolic acid in combination with isoniazid, rifampicin or ethambutol against Mycobacterium tuberculosis. J Med Microbiol. 2010 May;59(Pt 5):567-572.
Reference 6 Bacillus subtilis tolerance of moderate concentrations of rifampin involves the sigma(B)-dependent general and multiple stress response. J Bacteriol. 2002 Jan;184(2):459-67.
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