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CHEBI:28077 - rifampicin
| Formula | C43H58N4O12 |
| Net Charge | 0 |
| Average Mass | 822.953 |
| Monoisotopic Mass | 822.40512 |
| SMILES | CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C)CC5)c(O)c4c3C2=O)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 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Escherichia coli (ncbitaxon:562) | - | PubMed (21988831) |
| Roles Classification |
|---|
| Chemical Role: | Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). |
| Biological Roles: | DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. antiviral agent A substance that destroys or inhibits replication of viruses. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. anti-HBV agent An antiviral agent that destroys or inhibits the replication of the hepatitis B virus. anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus. pregnane X receptor agonist An agonist that selectively binds to and activates a pregnane X receptor. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. leprostatic drug A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions. antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis. EC 2.7.7.6 (RNA polymerase) inhibitor An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. |
| Applications: | antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. vasodilator agent A drug used to cause dilation of the blood vessels. antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism. angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. laxative An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic. antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. hypoglycemic agent A drug which lowers the blood glucose level. antiamoebic agent An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae. cardiovascular drug A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume. antiemetic A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors. neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. antifibrotic agent Any agent which acts to reduce fibrosis. antirheumatic drug A drug used to treat rheumatoid arthritis. leprostatic drug A substance that suppresses Mycobacterium leprae, ameliorates the clinical manifestations of leprosy, and/or reduces the incidence and severity of leprous reactions. anticoagulant An agent that prevents blood clotting. antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. antiparkinson drug A drug used in the treatment of Parkinson's disease. analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. anti-ulcer drug One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| rifampicin (CHEBI:28077) has role Escherichia coli metabolite (CHEBI:76971) |
| rifampicin (CHEBI:28077) has role analgesic (CHEBI:35480) |
| rifampicin (CHEBI:28077) has role angiogenesis inhibitor (CHEBI:48422) |
| rifampicin (CHEBI:28077) has role anti-HBV agent (CHEBI:64951) |
| rifampicin (CHEBI:28077) has role anti-HIV agent (CHEBI:64946) |
| rifampicin (CHEBI:28077) has role anti-ulcer drug (CHEBI:49201) |
| rifampicin (CHEBI:28077) has role antiamoebic agent (CHEBI:171664) |
| rifampicin (CHEBI:28077) has role antibacterial agent (CHEBI:33282) |
| rifampicin (CHEBI:28077) has role anticoagulant (CHEBI:50249) |
| rifampicin (CHEBI:28077) has role antiemetic (CHEBI:50919) |
| rifampicin (CHEBI:28077) has role antifibrotic agent (CHEBI:233423) |
| rifampicin (CHEBI:28077) has role antifungal agent (CHEBI:35718) |
| rifampicin (CHEBI:28077) has role antihypertensive agent (CHEBI:35674) |
| rifampicin (CHEBI:28077) has role antiinfective agent (CHEBI:35441) |
| rifampicin (CHEBI:28077) has role antimicrobial agent (CHEBI:33281) |
| rifampicin (CHEBI:28077) has role antineoplastic agent (CHEBI:35610) |
| rifampicin (CHEBI:28077) has role antiparkinson drug (CHEBI:48407) |
| rifampicin (CHEBI:28077) has role antirheumatic drug (CHEBI:35842) |
| rifampicin (CHEBI:28077) has role antitubercular agent (CHEBI:33231) |
| rifampicin (CHEBI:28077) has role antiviral agent (CHEBI:22587) |
| rifampicin (CHEBI:28077) has role cardiovascular drug (CHEBI:35554) |
| rifampicin (CHEBI:28077) has role DNA synthesis inhibitor (CHEBI:59517) |
| rifampicin (CHEBI:28077) has role EC 2.7.7.6 (RNA polymerase) inhibitor (CHEBI:37416) |
| rifampicin (CHEBI:28077) has role geroprotector (CHEBI:176497) |
| rifampicin (CHEBI:28077) has role hypoglycemic agent (CHEBI:35526) |
| rifampicin (CHEBI:28077) has role immunosuppressive agent (CHEBI:35705) |
| rifampicin (CHEBI:28077) has role laxative (CHEBI:50503) |
| rifampicin (CHEBI:28077) has role leprostatic drug (CHEBI:35816) |
| rifampicin (CHEBI:28077) has role neuroprotective agent (CHEBI:63726) |
| rifampicin (CHEBI:28077) has role pregnane X receptor agonist (CHEBI:77318) |
| rifampicin (CHEBI:28077) has role protein synthesis inhibitor (CHEBI:48001) |
| rifampicin (CHEBI:28077) has role vasodilator agent (CHEBI:35620) |
| rifampicin (CHEBI:28077) is a N-iminopiperazine (CHEBI:46847) |
| rifampicin (CHEBI:28077) is a N-methylpiperazine (CHEBI:46920) |
| rifampicin (CHEBI:28077) is a cyclic ketal (CHEBI:59779) |
| rifampicin (CHEBI:28077) is a hydrazone (CHEBI:38532) |
| rifampicin (CHEBI:28077) is a rifamycins (CHEBI:26580) |
| rifampicin (CHEBI:28077) is a semisynthetic derivative (CHEBI:72588) |
| rifampicin (CHEBI:28077) is tautomer of rifampicin zwitterion (CHEBI:71365) |
| Incoming Relation(s) |
| 2'-hydroxyrifampicin (CHEBI:111544) has functional parent rifampicin (CHEBI:28077) |
| 21-phosphorifampicin (CHEBI:140276) has functional parent rifampicin (CHEBI:28077) |
| rifampicin zwitterion (CHEBI:71365) is tautomer of rifampicin (CHEBI:28077) |
| 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)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate |
| INNs | Source |
|---|---|
| rifampicin | KEGG DRUG |
| rifampicina | DrugBank |
| rifampicine | WHO MedNet |
| rifampicinum | DrugBank |
| Synonyms | Source |
|---|---|
| 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV | ChemIDplus |
| Abrifam | ChEMBL |
| BA 411661E | ChEMBL |
| BA 41166/E | ChEMBL |
| BA-41166/E | ChEMBL |
| BA-41166E | ChEMBL |
| Brand Names | Source |
|---|---|
| Eremfat | ChEMBL |
| Rifa | ChEMBL |
| Rifampin component of rifamate | ChEMBL |
| Rifampin component of rifater | ChEMBL |
| Rimactane | ChEMBL |
| Manual Xrefs | Databases |
|---|---|
| C06688 | KEGG COMPOUND |
| D00211 | KEGG DRUG |
| DB01045 | DrugBank |
| HMDB0015179 | HMDB |
| NL6509961 | Patent |
| RFP | PDBeChem |
| Rifampicin | Wikipedia |
| US3342810 | Patent |
| Registry Numbers | Sources |
|---|---|
| Reaxys:5723476 | Reaxys |
| CAS:13292-46-1 | ChemIDplus |
| CAS:13292-46-1 | KEGG COMPOUND |
| Citations |
|---|