Norvancomycin (NVCM; A-51568A; N-Demethylvancomycin) hydrochloride is a macrocyclic antibiotic of the glycopeptide class that is widely used in the treatment of endocarditis, osteomyelitis, pneumonia, sepsis or soft tissue infections caused by Staphylococcus (including Methicillin-resistant strains and multidrug-resistant microbial strains). Norvancomycin is widely used in China to treat bacterial infections of Gram-positive cocci and bacilli, especially infections of methicillin-resistant Staphylococcus aureus and methicillin-resistant Staphylococcus epidermidis. Norvancomycin shows pharmacological properties and antibac-terial activities similar to those of vancomycin, which exhibits significant inhibitory activity against Gram-positive cocciandbacilli, especially to methicillin-resistant Staphylococcus aureus (MRSA)andmethicillin-resistant Staphylococcusepidermidis (MRSE).Dueto its potential clinical application, norvancomycin was commercially developed by the North China Pharmaceutical Company and has been widely used in China to treat endocarditis, osteomy-elitis, and other severe infections caused by S. aureus (includingmethicillin-resistant strains) for 3 decades.

Physicochemical Properties

Molecular Formula	C65H74CL3N9O24
Molecular Weight	1471.7
Exact Mass	1469.391
CAS #	213997-73-0
Related CAS #	213997-73-0
PubChem CID	92044444
Appearance	Typically exists as solid at room temperature
Hydrogen Bond Donor Count	20
Hydrogen Bond Acceptor Count	26
Rotatable Bond Count	12
Heavy Atom Count	101
Complexity	2940
Defined Atom Stereocenter Count	18
SMILES	ClC1C=C2C=CC=1OC1=CC3[C@H](C(N[C@H]4C(N[C@H](C(N[C@H](C(=O)O)C5C=C(C=C(C=5C5=C(C=CC4=C5)O)O)O)=O)[C@@H]2O)=O)=O)NC([C@H](CC(N)=O)NC([C@@H]([C@@H](C2C=CC(=C(C=2)Cl)OC(C=3)=C1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1C[C@@](C)([C@@H]([C@H](C)O1)O)N)O)NC([C@@H](CC(C)C)N)=O)=O)=O.Cl
InChi Key	LLWFHCJFZGXUAT-UMXPSMRGSA-N
InChi Code	InChI=1S/C65H73Cl2N9O24.ClH/c1-22(2)11-33(68)57(87)75-48-50(82)25-6-9-37(31(66)13-25)96-39-15-27-16-40(54(39)100-64-55(53(85)52(84)41(21-77)98-64)99-43-20-65(4,70)56(86)23(3)95-43)97-38-10-7-26(14-32(38)67)51(83)49-62(92)74-47(63(93)94)30-17-28(78)18-36(80)44(30)29-12-24(5-8-35(29)79)45(59(89)76-49)73-60(90)46(27)72-58(88)34(19-42(69)81)71-61(48)91;/h5-10,12-18,22-23,33-34,41,43,45-53,55-56,64,77-80,82-86H,11,19-21,68,70H2,1-4H3,(H2,69,81)(H,71,91)(H,72,88)(H,73,90)(H,74,92)(H,75,87)(H,76,89)(H,93,94);1H/t23-,33+,34-,41+,43-,45+,46+,47-,48+,49-,50+,51+,52+,53-,55+,56+,64-,65-;/m0./s1
Chemical 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-19-[[(2R)-2-amino-4-methylpentanoyl]amino]-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[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(39),35,37,46,49-pentadecaene-40-carboxylic acid;hydrochloride
Synonyms	Norvancomycin hydrochloride; A-51568A; A 51568A; A51568A; N-Demethylvancomycin; Desmethyl-vancomycin hydrochloride
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

The Journal of Antibiotics,70,p158–165(2017);Journal of Chromatography B, 1072, 1, 2018, 199-204.

Solubility Data

Solubility (In Vitro)

H2O : ≥ ~100 mg/mL (~67.95 mM) DMSO : ≥ ~100 mg/mL (~67.95 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (1.70 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (1.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (1.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (1.70 mM) Solubility in Formulation 5: 100 mg/mL (67.95 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	0.6795 mL	3.3974 mL	6.7949 mL
	5 mM	0.1359 mL	0.6795 mL	1.3590 mL
	10 mM	0.0679 mL	0.3397 mL	0.6795 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.