rifampicin (CHEBI:28077)

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CHEBI:28077 - rifampicin

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ChEBI Name	rifampicin

ChEBI ID	CHEBI:28077

Definition	A member of the class of rifamycins that is a a semisynthetic antibiotic derived from Amycolatopsis rifamycinica (previously known as Amycolatopsis mediterranei and Streptomyces mediterranei).

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45308, CHEBI:8858, CHEBI:26577

Supplier Information	ChemicalBook:CB8130110, eMolecules:30512639, eMolecules:511318, Selleckchem:Medroxyprogesterone-acetate, ZINC000005029557

Download	Molfile XML SDF

more structures >>

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M END): 25 ms

reading 117 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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117 atoms created

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Wikipedia	License
Medroxyprogesterone acetate (MPA), also known as depot medroxyprogesterone acetate (DMPA) in injectable form and sold under the brand name Depo-Provera among others, is a hormonal medication of the progestin type. It is used as a method of birth control and as a part of menopausal hormone therapy. It is also used to treat endometriosis, abnormal uterine bleeding, paraphilia, and certain types of cancer. The medication is available both alone and in combination with an estrogen. It is taken by mouth, used under the tongue, or by injection into a muscle or fat. Common side effects include menstrual disturbances such as absence of periods, abdominal pain, and headaches. More serious side effects include bone loss, blood clots, allergic reactions, and liver problems. Use is not recommended during pregnancy as it may harm the baby. MPA is an artificial progestogen, and as such activates the progesterone receptor, the biological target of progesterone. It also has androgenic activity and weak glucocorticoid activity. Due to its progestogenic activity, MPA decreases the body's release of gonadotropins and can suppress sex hormone levels. It works as a form of birth control by preventing ovulation . MPA was discovered in 1956 and was introduced for medical use in the United States in 1959. It is on the World Health Organization's List of Essential Medicines. MPA is the most widely used progestin in menopausal hormone therapy and in progestogen-only birth control. DMPA is approved for use as a form of long-acting birth control in more than 100 countries. In 2022, it was the 276th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.
Read full article at Wikipedia

Formula

C43H58N4O12

Net Charge

Average Mass

822.94020

Monoisotopic Mass

822.40512

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

SMILES

CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(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)c(\C=N\N1CCN(C)CC1)c(O)c4c3C2=O

Metabolite of Species	Details
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	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. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. 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. protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein. pregnane X receptor agonist An agonist that selectively binds to and activates a pregnane X receptor.

Application(s):	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. antiamoebic agent An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae. neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	rifampicin (CHEBI:28077) has role Escherichia coli metabolite (CHEBI:76971) rifampicin (CHEBI:28077) has role angiogenesis inhibitor (CHEBI:48422) rifampicin (CHEBI:28077) has role antiamoebic agent (CHEBI:171664) rifampicin (CHEBI:28077) has role antineoplastic agent (CHEBI:35610) rifampicin (CHEBI:28077) has role antitubercular agent (CHEBI:33231) 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 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) 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	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[23.3.1.1^4,7.0^5,28]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate

INNs	Sources
rifampicin	KEGG DRUG
rifampicina	DrugBank
rifampicinum	DrugBank

Synonyms	Sources
3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV	ChemIDplus
RFP	DrugBank
rifamcin	ChEBI
Rifampicin	KEGG COMPOUND
Rifampin	KEGG COMPOUND

Manual Xrefs	Databases
C06688	KEGG COMPOUND
D00211	KEGG DRUG
DB01045	DrugBank
HMDB0015179	HMDB
NL6509961	Patent
RFP	PDBeChem
Rifampicin	Wikipedia
US3342810	Patent
View more database links

Registry Numbers	Types	Sources
13292-46-1	CAS Registry Number	KEGG COMPOUND
13292-46-1	CAS Registry Number	ChemIDplus
5723476	Reaxys Registry Number	Reaxys

Citations	Types	Sources
11600355	PubMed citation	Europe PMC
14665784	PubMed citation	Europe PMC
14670633	PubMed citation	Europe PMC
15331348	PubMed citation	Europe PMC
15383168	PubMed citation	Europe PMC
15705662	PubMed citation	Europe PMC
16159084	PubMed citation	Europe PMC
16515773	PubMed citation	Europe PMC
17828712	PubMed citation	Europe PMC
18332862	PubMed citation	Europe PMC
19386087	PubMed citation	Europe PMC
19458074	PubMed citation	Europe PMC
19723399	PubMed citation	Europe PMC
24718527	PubMed citation	Europe PMC
25720500	PubMed citation	Europe PMC
26725427	PubMed citation	Europe PMC
26819743	PubMed citation	Europe PMC
27082586	PubMed citation	Europe PMC
27143080	PubMed citation	Europe PMC
27182275	PubMed citation	Europe PMC
27242224	PubMed citation	Europe PMC
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Last Modified

28 October 2021

CHEBI:28077 - rifampicin

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