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Rifamycin

Rifamycin structure

CAS No:
6998-60-3
Formula:
C37H47NO12
Chemical Name:
Rifamycin
Synonyms:
Rifamycin;Rifomycin SV;2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione,5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-,21-acetate;2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan,rifamycin deriv.;Rifamycin SV;Rifocin;Rifomycin;[2S-(2R*,12Z,14E,16R*,17R*,18S*,19S*,20S*,21R*,22S*,23R*,24E)]-21-(Acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione;NSC 133100;(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-21-(Acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione;2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione,21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-,(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-;Riphogal;Rifogal;Rifamicine SV;Rifampin SV;Rifocine;Rifamycin SV MMX;1404-54-2
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

ChEBI: A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.

Rifamycin is a nonabsorbable rifampin-like antibacterial agent that is used as treatment of travelers’ diarrhea. Rifamycin has minimal oral absorption and has not been implicated in causing liver test abnormalities or clinically apparent liver injury.

Rifamycin Basic Attributes

Molecular Weight：

697.77

Exact Mass：

697.77

EC Number：

230-273-3

DSSTox ID：

DTXSID1032014

HScode：

2941903000

Characteristics

PSA：

201

XLogP3：

4.89210

Density：

1.2275 (rough estimate)

Melting Point：

300 °C

Toxicity：

LD50 in mice (mg/kg): 550 i.v.; 625 i.p.; 2120 orally (Bergamini, Fowst)

Specific rotation：

D20 -4° (methanol)

Toxicity

Hepatotoxicity：

In prelicensure controlled trials in patients with traveler’s diarrhea, rates of serum ALT elevations were similar in subjects treated with rifamycin compared to placebo or comparator agent (ciprofloxacin) and no participants developed clinically apparent liver injury. Since its approval, there have been no published reports of hepatotoxicity attributed to rifamycin. Because of its minimal absorption rifamycin is considered unlikely to cause liver injury.

Drug Information

LiverTox Summary：

Drug Classes：

Antiinfective Agents

Rifamycin Use and Manufacturing

Used in the synthesis of rifampicin

Computed Properties

Molecular Weight:697.8
XLogP3:4.9
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:3
Exact Mass:697.30982593
Monoisotopic Mass:697.30982593
Topological Polar Surface Area:201
Heavy Atom Count:50
Complexity:1330
Undefined Atom Stereocenter Count:9
Undefined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 6998-60-3

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