Novobiocin

Not to be confused with the siderophore antibiotic albomycin.
Novobiocin
Space-filling model of the novobiocin molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		intravenous
ATCvet code
Pharmacokinetic data
Bioavailabilitynegligible oral bioavailability
Metabolismexcreted unchanged
Elimination half-life6 hours
Excretionrenal
Identifiers
  • 4-Hydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl)benzamido]-8-methylcoumarin-7-yl 3-O-carbamoyl-5,5-di-C-methyl-α-L-lyxofuranoside
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.589 Edit this at Wikidata
Chemical and physical data
FormulaC31H36N2O11
Molar mass612.632 g·mol−1
3D model (JSmol)
Melting point152 to 156 °C (306 to 313 °F) (dec.)
  • CC(C)=CCc1c(O)ccc(c1)C(=O)NC=2C(=O)Oc3c(C2O)ccc(c3C)O[C@@H]4OC(C)(C)[C@H](OC)[C@H]([C@H]4O)OC(=O)N
  • InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1 checkY
  • Key:YJQPYGGHQPGBLI-KGSXXDOSSA-N checkY
  (verify)

Novobiocin, also known as albamycin, is an aminocoumarin antibiotic that is produced by the actinomycete Streptomyces niveus, which has recently been identified as a subjective synonym for S. spheroides[1] a member of the class Actinomycetia. Other aminocoumarin antibiotics include clorobiocin and coumermycin A1.[2] Novobiocin was first reported in the mid-1950s (then called streptonivicin).[3][4]

  1. ^ Lanoot B, Vancanneyt M, Cleenwerck I, Wang L, Li W, Liu Z, Swings J (May 2002). "The search for synonyms among streptomycetes by using SDS-PAGE of whole-cell proteins. Emendation of the species Streptomyces aurantiacus, Streptomyces cacaoi subsp. cacaoi, Streptomyces caeruleus and Streptomyces violaceus". International Journal of Systematic and Evolutionary Microbiology. 52 (Pt 3): 823–9. doi:10.1099/00207713-52-3-823. PMID 12054245.
  2. ^ da Silva Eustáquio A (2004). Biosynthesis of aminocoumarin antibiotics in Streptomyces: Generation of structural analogues by genetic engineering and insights into the regulation of antibiotic production (Ph.D. thesis). Universität Tübingen.
  3. ^ Hoeksema H, Johnson JL, Hinman JW (December 1955). "Structural studies on streptonivicin, a new antibiotic". Journal of the American Chemical Society. 77 (24): 6710–6711. doi:10.1021/ja01629a129.
  4. ^ Smith CG, Dietz A, Sokolski WT, Savage GM (February 1956). "Streptonivicin, a new antibiotic. I. Discovery and biologic studies". Antibiotics & Chemotherapy. 6 (2): 135–142. PMID 24543916.