(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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

• ChemBase ID: 134128
• Molecular Formular: C43H58N4O12
• Molecular Mass: 822.94022
• Monoisotopic Mass: 822.40512332
• SMILES: Cc1c(c2c3c4c1O[C@@](C4=O)(O/C=C\[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C\C=C(/C(=O)Nc(c2O)c(c3O)/C=N/N1CCN(CC1)C)\C)C)O)C)O)C)OC(=O)C)C)OC)C)O
• Canonical SMILES: CO[C@H]1/C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C)c(c(c2c(c3C)O)O)NC(=O)/C(=C\C=C/[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)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-YOPQJBRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate; (7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
• IUPAC Traditional name: (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate; (7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
• Synonyms: Rifampicin; 3-(4-Methylpiperazinyliminomethyl)rifamycin SV; Rifampin; Rifamycin AMP; 3-(4-甲基-1-哌嗪基亚胺甲基)利福霉素SV; 利米定; 甲哌利福霉素; 利福平

Database IDs

• CAS Number: 13292-46-1
• EC Number: 236-312-0
• MDL Number: MFCD00151389
• Beilstein Number: 5723476
• PubChem SID: 24899383; 24888155; 24899391; 24899363; 162228405; 24870383
• PubChem CID: 24871024

CALCULATED PROPERTIES

• Acid pKa: 6.8984513
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 1.6852435
• LogD (pH = 7.4): 2.7622907
• Log P: 2.7698967
• Molar Refractivity: 225.5828 cm^3
• Polarizability: 86.47999 Å^3
• Polar Surface Area: 220.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble100 mg/mL; H2O: soluble1.3 mg/mL (pH 4.3); H2O: soluble2.5 mg/mL at 25 °C (pH 7.3)
• Apperance: crystalline; faint-orange to red-brown powder; powder

Safety Information

• RTECS: VJ7000000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97% (HPLC); ≥97.0% (HPLC)
• Grade: Biotechnology Performance Certified; VETRANAL™, analytical standard
• Suitability: plant cell culture tested
• Impurities: endotoxin, tested
• Sterility: γ-irradiated
• Empirical Formula (Hill Notation): C43H58N4O12

DETAILS

Sigma Aldrich - R5777

Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - R7382

Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Application
Rifampicin, a rifamycin, is active against mycobacteria. Rifamycin, is also an inhibitor of chloroplast RNA polymerase and may be used to study chloroplast-level DNA transcription in plants.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - R3501

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Rifampicin inhibits the assembly of DNA and protein into mature virus particles. It inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase, which results in cell death1.
Application
Rifampicin is used to treat Tuberculosis and Tuberculosis-related mycobacterial infections1. It is widely used as an antipruritic agent in the autoimmune cholestatic liver disease, primary biliary cirrhosis (PBC). It has been shown to cause hepatitis2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - R8883

Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Reconstitution
在小瓶中直接用甲醇制备储存液 (25mg/mL)。
Application
Rifampicin is used as an inhibitor of transcription initiation, blocking initiation of RNA synthesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 83907

Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Application
Rifampicin is used as a selective cytochrome P4503A4 inducer. Studies have shown that rifampicin inhibits African Swine Fever Virus replication in tissue culture 1 and inhibits the induction of tyrosine aminotransferase by cortisol in rat hepatoma cells grown in culture 2.

Sigma Aldrich - 46713

Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC