Vancomycin

Vancomycin
Clinical data
Pronunciation	/væŋkəˈmaɪsɪn/
Trade names	Vancocin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604038
License data	EU EMA: by INN; US DailyMed: Vancomycin; US FDA: Vancomycin;
Pregnancy; category	AU: B2;
Routes of; administration	Intravenous, oral
Drug class	Glycopeptide antibiotic
ATC code	A07AA09 (WHO) J01XA01 (WHO) S01AA28 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	Negligible (oral)
Metabolism	Excreted unchanged
Elimination half-life	4 h to 11 h (adults, normal renal function); 6 d to 10 d (adults, impaired renal function)
Excretion	urine (IV), feces (oral)
Identifiers
	IUPAC name (1S,2R,18R,19R,22S,25R,28R,40S)- 48- {[(2S,3R,4S,5S,6R)- 3- {[(2S,4S,5S,6S)- 4- amino- 5- hydroxy- 4,6- dimethyloxan- 2- yl]oxy}- 4,5- dihydroxy- 6- (hydroxymethyl)oxan- 2- yl]oxy}- 22- (carbamoylmethyl)- 5,15- dichloro- 2,18,32,35,37- pentahydroxy- 19- [(2R)- 4- methyl- 2- (methylamino)pentanamido]- 20,23,26,42,44- pentaoxo- 7,13- dioxa- 21,24,27,41,43- pentaazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta- 3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49- pentadecaene- 40- carboxylic acid;
CAS Number	1404-90-6 ;
PubChem CID	14969;
PubChem SID	46505261;
DrugBank	DB00512 ;
ChemSpider	14253 ;
UNII	6Q205EH1VU;
KEGG	D00212 ; as HCl: D00926 ;
ChEBI	CHEBI:28001 ;
ChEMBL	ChEMBL262777 ;
CompTox Dashboard (EPA)	DTXSID0042664 ;
ECHA InfoCard	100.014.338
Chemical and physical data
Formula	C66H75Cl2N9O24
Molar mass	1449.27 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2Oc3c4cc5cc3Oc6ccc(cc6Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7c8ccc(c(c8)-c9c(cc(cc9O)O)[C@H](NC(=O)[C@H]([C@@H](c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)CO)O)O)(C)N)O;
	InChI InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1 ; Key:MYPYJXKWCTUITO-LYRMYLQWSA-N ;
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Vancomycin is a glycopeptide antibiotic medication used to treat certain bacterial infections. It is administered intravenously (injection into a vein) to treat complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also taken orally (by mouth) to treat Clostridioides difficile infections. When taken orally, it is poorly absorbed.

Common side effects include pain in the area of injection and allergic reactions. Occasionally, hearing loss, low blood pressure, or bone marrow suppression occur. Safety in pregnancy is not clear, but no evidence of harm has been found, and it is likely safe for use when breastfeeding. It is a type of glycopeptide antibiotic and works by blocking the construction of a cell wall.

Vancomycin was approved for medical use in the United States in 1958. It is on the World Health Organization's List of Essential Medicines. The WHO classifies vancomycin as critically important for human medicine. It is available as a generic medication. Vancomycin is made by the soil bacterium Amycolatopsis orientalis.