Rifampicin
semisynthetic antibiotic derived from Amycolatopsis rifamycinica (previously known as Amycolatopsis mediterranei and Streptomyces mediterranei). Broad antibacterial activity inhibits DNA-dependent RNA polymerase. Therapy of tuberculosis.
General
Type : Drug, Not A\/B H target, Acetate, Natural, Antibiotic
Chemical_Nomenclature : [(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
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 : 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
Other name(s) : DB01045 || CHEBI:28077 || CHEMBL374478 || rifampin || Rifadin || Rimactane || Rimactan
MW : 822.9
Formula : C43H58N4O12
CAS_number :
PubChem : 135398735
UniChem : JQXXHWHPUNPDRT-WLSIYKJHSA-N
Target
Structures : No structure
Families : Arylacetamide_deacetylase
References (9)
| Title : Epicatechin gallate and epigallocatechin gallate are potent inhibitors of human arylacetamide deacetylase - Yasuda_2021_Drug.Metab.Pharmacokinet_39_100397 |
| Author(s) : Yasuda K , Watanabe K , Fukami T , Nakashima S , Ikushiro SI , Nakajima M , Sakaki T |
| Ref : Drug Metab Pharmacokinet , 39 :100397 , 2021 |
| Abstract : |
| PubMedSearch : Yasuda_2021_Drug.Metab.Pharmacokinet_39_100397 |
| PubMedID: 34171773 |
| Title : Role of human AADAC on hydrolysis of eslicarbazepine acetate and effects of AADAC genetic polymorphisms on hydrolase activity - Hirosawa_2021_Drug.Metab.Dispos__ |
| Author(s) : Hirosawa K , Fukami T , Tashiro K , Sakai Y , Kisui F , Nakano M , Nakajima M |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , : , 2021 |
| Abstract : |
| PubMedSearch : Hirosawa_2021_Drug.Metab.Dispos__ |
| PubMedID: 33446525 |
| Gene_locus related to this paper: human-AADAC |
| Title : Influence of Single Nucleotide Polymorphisms on Rifampin Pharmacokinetics in Tuberculosis Patients - Thomas_2020_Antibiotics.(Basel)_9_307 |
| Author(s) : Thomas L , Sekhar Miraj S , Surulivelrajan M , Varma M , Sanju CSV , Rao M |
| Ref : Antibiotics (Basel) , 9 : , 2020 |
| Abstract : |
| PubMedSearch : Thomas_2020_Antibiotics.(Basel)_9_307 |
| PubMedID: 32521634 |
| Title : A Population Pharmacokinetic Analysis Shows that Arylacetamide Deacetylase (AADAC) Gene Polymorphism and HIV Infection Affect the Exposure of Rifapentine - Francis_2019_Antimicrob.Agents.Chemother_63_e01964 |
| Author(s) : Francis J , Zvada SP , Denti P , Hatherill M , Charalambous S , Mungofa S , Dawson R , Dorman S , Gupte N , Wiesner L , Jindani A , Harrison TS , Olagunju A , Egan D , Owen A , McIlleron HM |
| Ref : Antimicrobial Agents & Chemotherapy , 63 : , 2019 |
| Abstract : |
| PubMedSearch : Francis_2019_Antimicrob.Agents.Chemother_63_e01964 |
| PubMedID: 30670438 |
| Gene_locus related to this paper: human-AADAC |
| Title : Difference in substrate specificity of carboxylesterase and arylacetamide deacetylase between dogs and humans - Yoshida_2018_Eur.J.Pharm.Sci_111_167 |
| Author(s) : Yoshida T , Fukami T , Kurokawa T , Gotoh S , Oda A , Nakajima M |
| Ref : Eur J Pharm Sci , 111 :167 , 2018 |
| Abstract : |
| PubMedSearch : Yoshida_2018_Eur.J.Pharm.Sci_111_167 |
| PubMedID: 28966098 |
| Gene_locus related to this paper: canfa-CESDD1 , canfa-f1p6w8 , canlf-e2r2h2 |
| Title : Isolation and characterization of arylacetamide deacetylase in cynomolgus macaques - Uno_2015_J.Vet.Med.Sci_77_721 |
| Author(s) : Uno Y , Hosokawa M , Imai T |
| Ref : J Vet Med Sci , 77 :721 , 2015 |
| Abstract : |
| PubMedSearch : Uno_2015_J.Vet.Med.Sci_77_721 |
| PubMedID: 25715734 |
| Title : Species differences in tissue distribution and enzyme activities of arylacetamide deacetylase in human, rat, and mouse - Kobayashi_2012_Drug.Metab.Dispos_40_671 |
| Author(s) : Kobayashi Y , Fukami T , Nakajima A , Watanabe A , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 40 :671 , 2012 |
| Abstract : |
| PubMedSearch : Kobayashi_2012_Drug.Metab.Dispos_40_671 |
| PubMedID: 22207054 |
| Gene_locus related to this paper: human-AADAC , mouse-aryla , ratno-aryla |
| Title : A novel polymorphic allele of human arylacetamide deacetylase leads to decreased enzyme activity - Shimizu_2012_Drug.Metab.Dispos_40_1183 |
| Author(s) : Shimizu M , Fukami T , Kobayashi Y , Takamiya M , Aoki Y , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 40 :1183 , 2012 |
| Abstract : |
| PubMedSearch : Shimizu_2012_Drug.Metab.Dispos_40_1183 |
| PubMedID: 22415931 |
| Gene_locus related to this paper: human-AADAC |
| Title : Human arylacetamide deacetylase is responsible for deacetylation of rifamycins: rifampicin, rifabutin, and rifapentine - Nakajima_2011_Biochem.Pharmacol_82_1747 |
| Author(s) : Nakajima A , Fukami T , Kobayashi Y , Watanabe A , Nakajima M , Yokoi T |
| Ref : Biochemical Pharmacology , 82 :1747 , 2011 |
| Abstract : |
| PubMedSearch : Nakajima_2011_Biochem.Pharmacol_82_1747 |
| PubMedID: 21856291 |
| Gene_locus related to this paper: human-AADAC |