Vancomycin

Vancomycin

Clinical data
Pronunciation	/væŋkəˈmaɪsᵻn/
Trade names	Vancocin
AHFS/Drugs.com	Monograph
MedlinePlus	a604038
License data	US FDA: Vancocin
Pregnancy category	AU: B2 B (PO) / C (IV)(US)
Routes of administration	IV, by mouth
ATC code	A07AA09 (WHO) J01XA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Negligible (oral)
Metabolism	Excreted unchanged
Biological half-life	4 h to 11 h (adults) 6 d to 10 d (adults, impaired renal function)
Excretion	Renal
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 Y
PubChem CID	14969
DrugBank	DB00512 Y
ChemSpider	14253 Y
UNII	6Q205EH1VU
KEGG	D00212 Y
ChEBI	CHEBI:28001 Y
ChEMBL	CHEMBL262777 Y
ECHA InfoCard	100.014.338
Chemical and physical data
Formula	C66H75Cl2N9O24
Molar mass	1449.3 g.mol−1
3D model (Jmol)	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 Y Key:MYPYJXKWCTUITO-LYRMYLQWSA-N Y

Vancomycin is an antibiotic used to treat a number of bacterial infections. It is recommended intravenously as a first-line treatment for complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant S. aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also recommended by mouth as a treatment for severe Clostridium difficile colitis. When taken by mouth it is very 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 first sold in 1954. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world of an intravenous dose is about US$1.70 to 6.00. In the United States, the pills are more expensive than the intravenous solution. The intravenous solution may be safely taken by mouth for the treatment of C. difficile colitis to reduce costs. Vancomycin is made by the soil bacterium Amycolatopsis orientalis.