Rifamycin sodiumProduct ingredient for Rifamycin

Name
Rifamycin sodium
Drug Entry
Rifamycin

Rifamycin is the prime member of the rifamycin family which are represented by drugs that are a product of fermentation from the gram-positive bacterium Amycolatopsis mediterranei, also known as Streptomyces mediterranei. The parent compound of rifamycin was rifamycin B which was originally obtained as a main product in the presence of diethylbarburitic acid. Some small modifications where performed in this inactive compound and with the creation of rifamycin SV there was the first antibiotic used intravenously for the treatment of tuberculosis.2

Rifamycin has had several direct derivative products such as rifamycin SV, rifaximin, rifampin and rifamycin CV. All of the derivatives have slight different physicochemical properties when compared to the parent structure.1

Rifamycin was further developed by Cosmo Technologies Ltd and approved in November 16, 2018 by the FDA as a prescription drug after being granted the designation of Qualified Infectious Disease Product which allowed it to have a status a priority review.10 This drug was also sent for review to the EMA in 2015 by Dr. Falk Pharma Gmbh and it was granted a waiver for the tested conditions.11

Accession Number
DBSALT002065
Structure
Synonyms
Not Available
External IDs
CB-01-11 / CB-0111
UNII
32086GS35Z
CAS Number
14897-39-3
Weight
Average: 719.76
Monoisotopic: 719.29177021
Chemical Formula
C37H46NNaO12
InChI Key
YVOFSHPIJOYKSH-NLYBMVFSSA-M
InChI
InChI=1S/C37H47NO12.Na/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41;/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46);/q;+1/p-1/b11-10+,14-13+,17-12-;/t16-,18+,19+,20+,25-,29-,30+,33+,37-;/m0./s1
IUPAC Name
sodium (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-13-(acetyloxy)-15,17,27,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-2-olate
SMILES
[Na+].CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C2=C(C(O)=C(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C=C2O)C([O-])=C3C
ChemSpider
21248601
ChEMBL
CHEMBL2105680
Predicted Properties
PropertyValueSource
Water Solubility0.00982 mg/mLALOGPS
logP4.37ALOGPS
logP4.17Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)7.09Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area204.14 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity198.35 m3·mol-1Chemaxon
Polarizability71.67 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon