Ferroptosis-centered Drug Response Information
General Information of the Drug (ID: ferrodrug0067)
| Name |
Rifampicin
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| Synonyms |
Rifampicin; rifampin; Rifadin; Rimactan; Rimactane; Rifamycin AMP; 13292-46-1; Rifaldazine; Rifaprodin; Rifoldin; Rifa; Rifampicinum; Riforal; Tubocin; L-5103 Lepetit; R/AMP; Archidyn; Rifadine; Rifaldin; Rifoldine; Rimactizid; Abrifam; Eremfat; Rifagen; Rimazid; Rifampicin SV; Arficin; Benemicin; Doloresum; Fenampicin; Rifaldazin; Rifamor; Rifobac; Sinerdol; Arzide; Rifcin; Rifam; Dione 21-acetate; Rifinah; Rimactazid; Ba 41166/E; Rifampicine [French]; Rifampicina; Rifapiam; Rifampicinum [INN-Latin]; Rifampicina [INN-Spanish]; BA-41166E; 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV; CCRIS 551; Rifadin I.V.; NSC-113926; HSDB 3181; Rifamycin, 3-(((4-methyl-1-piperazinyl)imino)methyl)-; L-5103; NSC113926; VJT6J7R4TR; Rifampicine; L-5103-LEPETIT; RFP; CHEBI:28077; 3-(4-Methylpiperazinyliminomethyl)-rifamycin SV; 8-(4-Methylpiperazinyliminomethyl) rifamycin SV; NIH-10782; 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)-; Rifampin [USAN:USP]; C43H58N4O12; UNII-VJT6J7R4TR; (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; [(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)iminomethyl]-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; Famcin; NSC 113926; (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; 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; Rifampin [USAN]; 3-(4-Methylpiperazinyliminomethyl)rifamycin SV; 3-([(4-Methyl-1-piperazinyl)imino]methyl)rifamycin SV; 8-[[(4-Methyl-1-piperazinyl)imino]methyl]rifamycin sv; DTXSID6021244; rifamcin; 3-(((4-METHYL-1-PIPERAZINYL)IMINO)METHYL)RIFAMYCIN; Rifomycin sv, 8-[N-(4-Methyl-1-piperazinyl)formidoyl]-; Rifamsolin; Rifampicin [INN:BAN:JAN]; DRG-0109; Rimactane (TN); 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-{(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; 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; Rifampicin & EEP; Prestwick_833; EINECS 236-312-0; R-Cin; Rifadin (TN); Piperine & Rifampicin; Rifampicin & Propolis; Reserpine & Rifampicin; RIFAMPIN [HSDB]; RIFAMPIN [MI]; RIFAMPICIN [INN]; RIFAMPICIN [JAN]; RIFAMPIN [VANDF]; Prestwick2_000525; Prestwick3_000525; Spectrum5_002018; RIFAMPICIN [IARC]; 3-[[(4-Methyl-1-piperazinyl)imino]-methyl]rifamycin; Rifampicin (JP17/INN); RIFAMPICIN [MART.]; RIFAMYCIN AMP [MI]; RIFAMPICIN [WHO-DD]; RIFAMPICIN [WHO-IP]; SCHEMBL23490; BSPBio_000509; RIFAMPIN [ORANGE BOOK]; 8CI); BPBio1_000561; CHEMBL374478; RIFAMPICIN [EP IMPURITY]; RIFAMPIN [USP MONOGRAPH]; RIFATER COMPONENT RIFAMPIN; RIFAMPICIN [EP MONOGRAPH]; RIFAMATE COMPONENT RIFAMPIN; HMS1569J11; HMS2089F12; HMS2096J11; HMS3713J11; Rifampicin, >=97.0% (HPLC); RIFAMPICINUM [WHO-IP LATIN]; Rifampicin, powder, gamma-irradiated; RIFAMPIN COMPONENT OF RIFATER; Ba 41166; BDBM50370232; GR-306; RIFAMPIN COMPONENT OF RIFAMATE; AKOS015951372; Rifampicin - CAS 13292-46-1; Rifampicin, >=97% (HPLC), powder; BA 411661E; BA-41166/E; CCG-208267; DB01045; NCGC00022678-03; NCGC00022678-04; NCGC00022678-05; NCGC00022678-06; 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; C06688; D00211; Rifampicin, VETRANAL(TM), analytical standard; AB00383022_07; 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; 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 (; 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; 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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| Structure |
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3D MOL
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| Formula |
C43H58N4O12
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| 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-26-[(E)-(4-methylpiperazin-1-yl)iminomethyl]-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
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| 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
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| InChI |
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
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| InChIKey |
JQXXHWHPUNPDRT-WLSIYKJHSA-N
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| PubChem CID | |||||
Full List of Ferroptosis Target Related to This Drug
Unspecific Target
| In total 2 item(s) under this Target | |||||
| Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target | [1] | ||||
| Responsed Disease | Injury of intra-abdominal organs | ICD-11: NB91 | |||
| Responsed Regulator | Heat shock cognate 71 kDa protein (HSPA8) | Suppressor | |||
| Pathway Response | Fatty acid metabolism | hsa01212 | |||
| Autophagy | hsa04140 | ||||
| Cell Process | Cell ferroptosis | ||||
| Cell autophagy | |||||
| In Vitro Model | Hep-G2 cells | Hepatoblastoma | Homo sapiens | CVCL_0027 | |
| AML12 cells | Normal | Mus musculus | CVCL_0140 | ||
| In Vivo Model |
Male C57BL/6 mice (8-10 weeks old and weighing 20-25 g) were purchased from Hunan Experimental Animal Center (Changsha, China). All animals were housed in a 12/12h light/dark cycle and given free access to water and food. All experimental procedures were conducted in accordance with the institutional guidelines for animal care. After a minimum of 7 days of acclimation, the mice were randomly divided into five groups. DILI model group was given rifampicin (350 mg/kg) that was dissolved in saline by gavage daily for 14 days, and the same volume of saline was given as the control. Meanwhile, the other three groups were given the same volume of rifampicin to establish drug liver injury model, and treated with different compounds in the second week as follows: ferrostatin 1 (0.6 mg/kg) was injected into the tail vein every day after 2 h of rifampicin administration; geldanamycin (HSP90 inhibitor) (0.75 mg/kg) was intraperitoneally injected 2 h after rifampicin daily; 3-methyladenine (autophagy inhibitor) (15 mg/kg) was injected into tail vein 2 h after rifampicin every day. After 2 weeks of administration, serum was collected, and then mice were sacrificed by cervical dislocation. After that, liver tissue was taken for different treatments and used for reserve.
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| Response regulation | Inhibition of HSPA8 by rifampicin contributes to ferroptosis via enhancing autophagy. The present study highlights the crucial roles of the HSPA8 and autophagy in ferroptotic cell death driving by rifampicin, particularly illumines multiple promising regulatory nodes for therapeutic interventions in diseases involving anti-tuberculosis drug-induced liver injury (AT-DILI). | ||||
| Experiment 2 Reporting the Ferroptosis-centered Drug Act on This Target | [2] | ||||
| Responsed Disease | Acute kidney failure | ICD-11: GB60 | |||
| Pathway Response | Fatty acid metabolism | hsa01212 | |||
| Ferroptosis | hsa04216 | ||||
| Cell Process | Cell ferroptosis | ||||
| In Vitro Model | CHO-S/H9C2 cells | Normal | Cricetulus griseus | CVCL_A0TS | |
| NRK-49F cells | Normal | Rattus norvegicus | CVCL_2144 | ||
| HK-2 cells | Normal | Homo sapiens | CVCL_0302 | ||
| C2C12 cells | Normal | Mus musculus | CVCL_0188 | ||
| MDA-MB-231 cells | Breast adenocarcinoma | Homo sapiens | CVCL_0062 | ||
| NRK-52E cells | Normal | Rattus norvegicus | CVCL_0468 | ||
| LLC-PK1 cells | Normal | Sus scrofa | CVCL_0391 | ||
| PANC-1 cells | Pancreatic ductal adenocarcinoma | Homo sapiens | CVCL_0480 | ||
| HT22 cells | Normal | Mus musculus | CVCL_0321 | ||
| hUPECs (Human urine-derived podocyte-like epithelial cells) | |||||
| In Vivo Model |
C57BL/6N male mice (CLEA Japan), aged 8-9 weeks, were used. AKI was induced by intraperitoneal injection of cisplatin solution (16 or 17 mg/kg as indicated; Nichi-Iko Pharmaceutical). Mice were orally treated with water only, promethazine (20 mg/kg in water), or rifampicin (20 mg/kg in 0.5% methylcellulose) every 12 hours for 4 days starting 30 minutes before the cisplatin injection, or orally treated with promethazine (20 mg/kg) in the following groups: (1) no promethazine, (2) pretreatment 30 minutes before cisplatin injection, (3) treatment from 30 minutes before injection to 24 hours after injection, (4) treatment from 24 to 96 hours after injection, and (5) treatment every 12 hours from 30 minutes before injection to 96 hours after injection.
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| Response regulation | The study identified eight drugs and hormones that showed antiferroptotic activity, including omeprazole, indole-3-carbinol, rifampicin, promethazine, carvedilol, propranolol, estradiol, and triiodothyronine. Moreover, in mice, the drugs ameliorated acute kidney injury and liver injury, with suppression of tissue lipid peroxidation and decreased cell death. | ||||
References