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72559-06-9 molecular structure
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(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1^{4,7}.0^{5,31}.0^{26,30}]tritriacontane-28,4'-piperidin]-1,3,5(31),9,19,21,25,29-octaen-13-yl acetate

ChemBase ID: 497
Molecular Formular: C46H62N4O11
Molecular Mass: 847.00468
Monoisotopic Mass: 846.44150882
SMILES and InChIs

SMILES:
C12(CCN(CC1)CC(C)C)N=C1c3c4c(c(c5c3C(=O)[C@@](O/C=C/[C@@H]([C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H](O)[C@H](/C=C/C=C(\C(=O)NC(=C1N2)C4=O)/C)C)C)O)C)OC(=O)C)C)OC)(O5)C)C)O
Canonical SMILES:
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2C4=NC5(NC4=C(C(=O)c2c(c3C)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)CCN(CC5)CC(C)C
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
InChIKey:
ATEBXHFBFRCZMA-VXTBVIBXSA-N

Cite this record

CBID:497 http://www.chembase.cn/molecule-497.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1^{4,7}.0^{5,31}.0^{26,30}]tritriacontane-28,4'-piperidin]-1,3,5(31),9,19,21,25,29-octaen-13-yl acetate
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1^{4,7}.0^{5,31}.0^{26,30}]tritriacontane-28,4'-piperidin]-1(31),2,4,9,19,21,25,29-octaen-13-yl acetate
IUPAC Traditional name
@rifabutin
Brand Name
Ansamycin
Alfacid
Mycobutin
Synonyms
Rifabutinum [Latin]
Rifabutine [French]
Rifabutina [Spanish]
RBT
Antibiotic LM 427
Ansatipine
Ansatipin
Rifabutin
Mycobutin
Ansamycin
LM 427
CAS Number
72559-06-9
PubChem SID
46506468
160963960
PubChem CID
6323490

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1741 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.9468403  H Acceptors 13 
H Donor LogD (pH = 5.5) 2.153332 
LogD (pH = 7.4) 3.853648  Log P 4.1864443 
Molar Refractivity 232.6445 cm3 Polarizability 88.737564 Å3
Polar Surface Area 205.55 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 4.25  LOG S -4.7 
Solubility (Water) 1.70e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Minimally soluble (0.19 mg/mL) expand Show data source
Hydrophobicity(logP)
4.1 expand Show data source
Storage Condition
-20°C expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank - DB00615 external link
Item Information
Drug Groups approved
Description A broad-spectrum antibiotic that is being used as prophylaxis against disseminated Mycobacterium avium complex infection in HIV-positive patients. [PubChem]
Indication For the prevention of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced HIV infection.
Pharmacology Rifabutin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. Because of rapid emergence of resistant bacteria, use is restricted to treatment of mycobacterial infections and a few other indications. Rifabutin is well absorbed when taken orally and is distributed widely in body tissues and fluids, including the CSF. It is metabolized in the liver and eliminated in bile and, to a much lesser extent, in urine, but dose adjustments are unnecessary with renal insufficiency.
Toxicity LD50 = 4.8 g/kg (mouse, male)
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Of the five metabolites that have been identified, 25-O-desacetyl and 31-hydroxy are the most predominant. The former metabolite has an activity equal to the parent drug and contributes up to 10% to the total antimicrobial activity.
Absorption Rifabutin is readily absorbed from the gastrointestinal tract, with an absolute bioavailability averaging 20%.
Half Life 45 (± 17) hours
Protein Binding 85%
Elimination A mass-balance study in three healthy adult volunteers with 14C-labeled rifabutin showed that 53% of the oral dose was excreted in the urine, primarily as metabolites. About 30% of the dose is excreted in the feces.
Clearance * 0.69 +/- 0.32 L/hr/kg
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1741 external link
Research Area: Infection
Biological Activity:
Rifabutin(Mycobutin) is a semisynthetic ansamycin antibiotic with potent antimycobacterial properties. Rifabutin inhibits bacterial DNA-dependent RNA polymerase, thereby suppressing the initiation of RNA formation and leading to inhibition of RNA synthesis and transcription. [1, 2]

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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