Novobiocin

Novobiocin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	intravenous
ATCvet code	QJ01XX95 (WHO) ;
Pharmacokinetic data
Bioavailability	negligible oral bioavailability
Metabolism	excreted unchanged
Elimination half-life	6 hours
Excretion	renal
Identifiers
	IUPAC name 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	303-81-1 ;
PubChem CID	9346;
DrugBank	DB01051 ;
ChemSpider	10226117 ;
UNII	17EC19951N;
KEGG	C05080 ;
ChEMBL	ChEMBL36506 ;
CompTox Dashboard (EPA)	DTXSID3041083 ;
ECHA InfoCard	100.005.589
Chemical and physical data
Formula	C31H36N2O11
Molar mass	612.632 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	152 to 156 °C (306 to 313 °F) (dec.)
	SMILES 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 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 ; Key:YJQPYGGHQPGBLI-KGSXXDOSSA-N ;
	(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]

^ 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.
^ 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.
^ 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. Bibcode:1955JAChS..77R6710H. doi:10.1021/ja01629a129.
^ 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.

[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.

[E-2] 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. Bibcode:1955JAChS..77R6710H. 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.

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