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Rifampicin(CAS No. 13292-46-1)

Rifampicin C43H58N4O12 (cas 13292-46-1) Molecular Structure

13292-46-1 Structure

Identification and Related Records

【Name】
Rifampicin
【CAS Registry number】
13292-46-1
【Synonyms】
3-[[(4-methyl-1-piperazinyl)imino]methyl]-rifamycin
3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV
5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(N-(4-methyl-1-piperazinyl)formimidoyl)-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione 21-acetate
8-(4-Methylpiperazinyliminomethyl) rifamycin SV
【EINECS(EC#)】
236-312-0
【Molecular Formula】
C43H58N4O12 (Products with the same molecular formula)
【Molecular Weight】
822.95
【Inchi】
InChI=1/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
【Canonical SMILES】
CC1C=CC=C(C(=O)NC2=C(C3=C(C(=C4C(=C3C(=O)C2=CNN5CCN(CC5)C)C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C
【Isomers smiles】
C[C@H]1/C=C/C=C(\C(=O)NC\2=C(C3=C(C(=C4C(=C3C(=O)/C2=C/NN5CCN(CC5)C)C(=
O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)
OC(=O)C)C)OC)C)C)O)O)/C
【MOL File】
13292-46-1.mol

Chemical and Physical Properties

【Appearance】
Red to orange crystalline solid
【Density】
1.34 g/cm3
【Melting Point】
183℃ (dec.)
【Boiling Point】
1004.42 °C at 760 mmHg
【Vapour】
0mmHg at 25°C
【Refractive Index】
1.613
【Flash Point】
561.253 °C
【Solubilities】
slightly soluble
【Color/Form】
Red to orange platelets from acetone
Red-brown crystalline powder
【Stability】
Stable under normal shipping and handling conditions.
【HS Code】
29419000
【Storage temp】
2-8°C
【Spectral properties】
Max absorption (pH 7.38): 237 nm (Epsilon= 33,200); 255 nm (Epsilon= 32,100); 334 nm (Epsilon= 27,000); 475 nm (Epsilon= 15,400)
【Computed Properties】
Molecular Weight:822.94022 [g/mol]
Molecular Formula:C43H58N4O12
XLogP3-AA:4
H-Bond Donor:6
H-Bond Acceptor:15
Rotatable Bond Count:5
Tautomer Count:1000
Exact Mass:822.405123
MonoIsotopic Mass:822.405123
Topological Polar Surface Area:217
Heavy Atom Count:59
Formal Charge:0
Complexity:1750
Isotope Atom Count:0
Defined Atom Stereocenter Count:9
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:4
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/37/38
【Safety Statements 】
S26;S36
【Safety】

Hazard Codes:?HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-36/38
?R22:Harmful if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S37/39:Wear suitable gloves and eye/face protection.

【Formulations/Preparations】
Oral: Capsules: 150 mg, Rifadin (Aventis), Rifampin Capsules (Eon); 300 mg, Rifadin (Aventis), Rifampin Capsules (Eon), Rimacetane (with parabens) (Sandoz). Parenteral: For Injection: 600 mg Rifadin IV (with sodium formaldehyde sulfoxylate) (Aventis), Rifampin for Injection (Bedford).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl rifampin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

?Rifampicin , its cas register number is 13292-46-1. It also can be called Rifampin ; Rimactane ; Rifadin ; Rimactan ; and 3-[[(4-methyl-1-piperazinyl)imino]methyl]-rifamycin . It?is a bactericidal antibiotic drug of the rifamycin group, and is a semisynthetic compound derived from Amycolatopsis rifamycinica.?There are various types of rifamycins from which this is derived, but this particular form is by far the most clinically effective. It inhibits DNA-dependent RNA polymerase in bacterial cells by binding its beta-subunit, thus preventing transcription to RNA and subsequent translation to proteins.

【Octanol/Water Partition Coefficient】
log Kow = 4.24 /Estimated/
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Rifamycin sv ... is converted to 8-carboxaldehyde derivative, known ? as 3-formylrifamycin sv, and this is condensed with 1-amino-4-methylpiperazine in schiff base reaction to yield rifampin.
Rifamycin SV + dimethylformamide + N-methyl-piperazine (Vilsmeier reaction/diazotisation/reduction/imine formation)
Semisynthetic antibiotic obtained by reacting 3-formylrifamycin SV with 1-amino-4-methylpiperazine in tetrahydrofuran.
【Usage】

Semisynthetic antibiotic. Antibacerial (tuberculostatic)

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances obtained from various species of microorganisms that are, alone or in combination with other agents, of use in treating various forms of tuberculosis; most of these agents are merely bacteriostatic, induce resistance in the organisms, and may be toxic.
- Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
- Substances that suppress Mycobacterium leprae, ameliorate the clinical manifestations of leprosy, and/or reduce the incidence and severity of leprous reactions.
- Compounds that inhibit cell production of DNA or RNA.
【Therapeutic Uses】
Antibiotics, Antitubercular; Enzyme Inhibitors; Leprostatic Agents; Nucleic Acid Synthesis Inhibitors
Rifampin is indicated in combination with other antituberculosis medications in the treatment of all forms of tuberculosis, including tuberculous meningitis. /Included in US product labeling/
Rifampin is indicated in the treatment of close contacts of patients with proved or suspected infection caused by Neisseria meningitidis. These contacts include other household members, children in nurseries, persons in day care centers, and closed populations, such as military recruits. Health care providers who have intimate exposure (e.g., mouth-to-mouth resuscitation) with index cases also should receive prophylactic therapy. /Included in US product labeling/
Rifampin is used in the treatment of close contacts of patients with proved or suspected infections caused by Hemophilus influenza type b if at least one of the contacts is 4 years of age or younger. A close contact is defined as one who has spent 4 or more hours per day for five of the seven most recent days with the index case. /NOT included in US product labeling/
Rifampin is used in combination with other agents in the treatment of leprosy (Hansen's disease). /NOT included in US labeling/
Rifampin is used in combination with other agents in the treatment of certain atypical (nontuberculous) mycobacterial infections, such as those caused by Mycobacterium avium complex (MAC). /NOT included in US product labeling/
Rifampin, administered concurrently with other antistaphylococcal agents, also may be used in the treatment of serious infections caused by Staphylococcus species (including methicillin- and multiresistant strains). /NOT included in US product labeling/
【Biomedical Effects and Toxicity】
Rifampin is distributed throughout the body and is present in effective concentrations in many organs and body fluids, including the CSF. This is perhaps best exemplified by the fact that the drug may impart an orange-red color to the urine, feces, saliva, sputum, tears, and sweat ... .
Up to 30% of a dose of the drug is excreted in the urine and 60% to 65% in the feces; less than half of this may be unaltered antibiotic.
The oral administration of rifampin produces peak concentrations in plasma in 2 to 4 hours; after ingestion of 600 mg this value is about 7 ug/mL, but there is considerable variability
Following absorption from the gastrointestinal tract, rifampin is eliminated rapidly in the bile, and an enterohepatic circulation ensues.
Rifampin was rapidly absorbed with mean peak serum levels of 5.9 mug/mL & 5.5 mug/mL, 2 hr and 1 hr after administration on days 1 and 8. Total urinary excretion was greater on day 8 than day 1, reflecting well known enzyme inducing activity of this drug. [EMERSON AM ET AL; J ANTIMICROB CHEMOTHER 4: 523 (1978)] PubMed Abstract
In a single-dose study in healthy fasting males, the extent of absorption (as measured by area under the plasma concentration-time curve) of isoniazid, rifampin, or pyrazinamide in dosages of 250, 6O0, or 1500 mg, respectively, was similar whether the drugs were administered individually as capsules (rifampin) and tablets (isoniazid and pyrazinamide) or as a fixed combination containing isoniazid 50 mg, rifampin 120 mg, and pyrazinamide 300 mg per tablet.
... A bioassay was developed and used to examine levels of rifampin in the posterior tibial nerve and serum of 8 patients (ages 17-70 yr), 6 of whom had inactive leprosy, who received an oral dose of 600 mg rifampin. Within 8 to 12 hr after ingestion of rifampin, the drug was detected in concn ranging from 0.52 to 4.1 mcg/mL in serum and in concn ranging from 0.6 to 6.3 ng/mg in posterior tibial nerve fiber tissue. [Guebre-Xabier M, et al; Antimicrob Agents Chemother 39: 1866-70 (1995)] PubMed Abstract
The effects of time and method of admin of rifampin with respect to feeding were evaluated in five mature horses. There was a significant (P less than or equal to 0.05) delay in time of maximum serum concn and an apparent but not significant incr in oral absorption when rifampin was given as a top dressing on grain as compared with admin in corn syrup 2 hr before or 2 hr after feeding. Although there were no differences between admin before or after feeding, admin 2 hr prior to feeding was selected as the method of choice for future experiments. The effects of age on rifampin disposition were subsequently examined using this method of admin in six, l wk old foals. Rifampin (10 mg/kg) was given at incr age from 1 through 10 wk and the pharmacokinetic disposition parameters compared. There were significant differences in the slope of the elimination phase (beta) and area under the curve (AUC ) at 1 wk through 6 wk compared with 10 wk or with values in the five mature horses. [Burrows GE, et al; J Vet Pharmacol Ther 15 (2): 124-32 (1992)] PubMed Abstract
Comparison of the transcutaneous absorption of rifaximin (L/105; I) and rifampin (rifampicin; II) in rats is described. Rifaximin was practically not absorbed after topical, cutaneous application. On the contrary, under the same exptl /situation/ II was well absorbed. Results indicate that I may be useful for topical applications of skin infections.
Rifampicin (rifampin; I) serum and urine levels, as well as serum bilirubin, were followed during and after parenteral I admin to 11 adult patients. Patients were admin doses of either 300, 450, or 600 mg diluted to 500 mL as a continuous iv infusion over a period of 3 hr. Patients had normal liver and renal function. Also, patients had not received I previously or any enzyme inducing drug or antibiotic within the last 4 wk or 5 days respectively. Iv and oral serum levels were similar. Incr doses gave incr peaks and areas under the curve, while half-life remained practically unchanged. Serum bilirubin levels followed the same patterns as seen with oral I. Urinary excretion incr with larger dosages from 10% to almost 20% of an admin dose. A 600 mg dose of I administered by iv drip over a 3 hr period exhibits an overall pharmacokinetic pattern similar to that seen following the same oral dose.

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