rifampicin

Ligand id: 2765

Name: rifampicin

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 220.15
Molecular weight 822.41
XLogP 1.96
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

References
1. Blumberg B, Sabbagh W, Juguilon H, Bolado J, van Meter CM, Ong ES, Evans RM. (1998)
SXR, a novel steroid and xenobiotic-sensing nuclear receptor.
Genes Dev.12 (20): 3195-205. [PMID:9784494]
2. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P. (2012)
Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.
J. Med. Chem.55 (10): 4740-63. [PMID:22541068]
3. Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA. (1998)
The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions.
J. Clin. Invest.102 (5): 1016-23. [PMID:9727070]
4. Liu X, Huang J, Sun Y, Zhan K, Zhang Z, Hong M. (2013)
Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2.
Drug Metab. Dispos.41 (3): 602-7. [PMID:23255551]
5. Treiber A, Schneiter R, Häusler S, Stieger B. (2007)
Bosentan is a substrate of human OATP1B1 and OATP1B3: inhibition of hepatic uptake as the common mechanism of its interactions with cyclosporin A, rifampicin, and sildenafil.
Drug Metab. Dispos.35 (8): 1400-7. [PMID:17496208]
6. Vavricka SR, Van Montfoort J, Ha HR, Meier PJ, Fattinger K. (2002)
Interactions of rifamycin SV and rifampicin with organic anion uptake systems of human liver.
Hepatology36 (1): 164-72. [PMID:12085361]