RIFABUTIN

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Search structure


Trade Names	MYCOBUTIN RIFABUTIN
Synonyms	Ansamycin LM 427 LM-427 MYCOBUTIN Mycobutin Rifabutin
Status
Molecule Category	UNKNOWN
ATC	J04AB04
UNII	1W306TDA6S
EPA CompTox	DTXSID0033960


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	ATEBXHFBFRCZMA-VXTBVIBXSA-N
Smiles	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C2=NC3(CCN(CC(C)C)CC3)NC2=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)C4=O
InChI	InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C46H62N4O11
Molecular Weight	847.02
AlogP	4.62
Hydrogen Bond Acceptor	14.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	4.0
Polar Surface Area	205.55
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	61.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action	Action	Reference
Bacterial DNA-directed RNA polymerase inhibitor	INHIBITOR	PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	26700-26700	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	15900	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antimycobacterial activity against Mycobacterium avium 1581 at 0.1 mg/mL after 15 days relative to control	Mycobacterium avium	99.0 %
Antimycobacterial activity against Mycobacterium avium 1581 at 0.2 mg/mL after 15 days relative to control	Mycobacterium avium	99.0 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 2 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control	Mycobacterium leprae	96.0 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 0.2 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control	Mycobacterium leprae	84.0 %

Cross References

Resources	Reference
ChEBI	45367
ChEMBL	CHEMBL444633
DrugBank	DB00615
DrugCentral	2376
FDA SRS	1W306TDA6S
KEGG	C07235
PDB	RBT
PharmGKB	PA451249
PubChem	6323490
SureChEMBL	SCHEMBL36043
ZINC	ZINC000169621215

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).