Vancomycin HCl
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MedKoo CAT#: 318971

CAS#: 1404-93-9

Description: Vancomycin is an antibiotic used to treat a number of bacterial infections. Vancomycin acts by inhibiting proper cell wall synthesis in gram-positive bacteria. Due to the different mechanism by which gram-negative bacteria produce their cell walls and the various factors related to entering the outer membrane of gram-negative organisms, vancomycin is not active against gram-negative bacteria (except some nongonococcal species of Neisseria). The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Under normal circumstances, this is a five-point interaction.


Price and Availability

Size
Price

200mg
USD 250
2g
USD 950
Size
Price

500mg
USD 450
Size
Price

1g
USD 650

Vancomycin HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318971
Name: Vancomycin HCl
CAS#: 1404-93-9
Chemical Formula: C66H76Cl3N9O24
Exact Mass:
Molecular Weight: 1485.723
Elemental Analysis: C, 53.36; H, 5.16; Cl, 7.16; N, 8.48; O, 25.84


Related CAS #: 1404-93-9 (HCl)   123409-00-7 (HCl hydrate)   1404-90-6 (free base)  

Synonym: Vancomycin HCl; Vanco-saar; Vancocin; Vancocin HCl; Vancocine.

IUPAC/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}- 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 hydrochloride

InChi Key: LCTORFDMHNKUSG-XTTLPDOESA-N

InChi Code: InChI=1S/C66H75Cl2N9O24.ClH/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);1H/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-;/m0./s1

SMILES Code: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O.Cl


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in water

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
CAS#1404-93-9 (Vancomycin HCl salt)
CAS#123409-00-7 (Vancomycin HCl hydrate);
CAS#1404-90-6 (Vancomycin free base).


References

1: Bhongsatiern JJ, Stockmann C, Yu T, Constance JE, Moorthy G, Spigarelli MG, Desai PB, Sherwin CM. Renal function descriptors in neonates: Which creatinine-based formula best describes vancomycin clearance? J Clin Pharmacol. 2015 Sep 28. doi: 10.1002/jcph.650. [Epub ahead of print] Review. PubMed PMID: 26412385.

2: Javorska L, Krcmova LK, Solichova D, Solich P, Kaska M. Modern methods for vancomycin determination in biological fluids by methods based on high-performance liquid chromatography - A review. J Sep Sci. 2015 Sep 9. doi: 10.1002/jssc.201500600. [Epub ahead of print] Review. PubMed PMID: 26351070.

3: O'Driscoll T, Crank CW. Vancomycin-resistant enterococcal infections: epidemiology, clinical manifestations, and optimal management. Infect Drug Resist. 2015 Jul 24;8:217-30. doi: 10.2147/IDR.S54125. eCollection 2015. Review. PubMed PMID: 26244026; PubMed Central PMCID: PMC4521680.

4: Hanrahan T, Whitehouse T, Lipman J, Roberts JA. Vancomycin-associated nephrotoxicity: A meta-analysis of administration by continuous versus intermittent infusion. Int J Antimicrob Agents. 2015 Sep;46(3):249-53. doi: 10.1016/j.ijantimicag.2015.04.013. Epub 2015 Jun 7. Review. PubMed PMID: 26141230.

5: Spagnolo AM, Orlando P, Panatto D, Amicizia D, Perdelli F, Cristina ML. Staphylococcus aureus with reduced susceptibility to vancomycin in healthcare settings. J Prev Med Hyg. 2014 Dec;55(4):137-44. Review. PubMed PMID: 26137787.

6: Martínková J. [Current view of vancomycin in the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infections]. Klin Mikrobiol Infekc Lek. 2015 Mar;21(1):16-23. Review. Czech. PubMed PMID: 26098489.

7: Chunhui C, Xiaogang X. Genetic characteristics of vancomycin resistance gene cluster in Enterococcus spp. Yi Chuan. 2015 May;37(5):452-7. doi: 10.16288/j.yczz.14-420. Review. PubMed PMID: 25998433.

8: Tsoulas C, Nathwani D. Review of meta-analyses of vancomycin compared with new treatments for Gram-positive skin and soft-tissue infections: Are we any clearer? Int J Antimicrob Agents. 2015 Jul;46(1):1-7. doi: 10.1016/j.ijantimicag.2015.03.011. Epub 2015 Apr 30. Review. PubMed PMID: 25982913.

9: Bruniera FR, Ferreira FM, Saviolli LR, Bacci MR, Feder D, da Luz Gonçalves Pedreira M, Sorgini Peterlini MA, Azzalis LA, Campos Junqueira VB, Fonseca FL. The use of vancomycin with its therapeutic and adverse effects: a review. Eur Rev Med Pharmacol Sci. 2015 Feb;19(4):694-700. Review. PubMed PMID: 25753888.

10: Reardon J, Lau TT, Ensom MH. Vancomycin loading doses: a systematic review. Ann Pharmacother. 2015 May;49(5):557-65. doi: 10.1177/1060028015571163. Epub 2015 Feb 23. Review. PubMed PMID: 25712445.

11: Barber KE, King ST, Stover KR, Pogue JM. Therapeutic options for vancomycin-resistant enterococcal bacteremia. Expert Rev Anti Infect Ther. 2015 Mar;13(3):363-77. doi: 10.1586/14787210.2015.1001839. Review. PubMed PMID: 25661903.

12: Holmes NE, Tong SY, Davis JS, Hal SJ. Treatment of methicillin-resistant Staphylococcus aureus: vancomycin and beyond. Semin Respir Crit Care Med. 2015 Feb;36(1):17-30. doi: 10.1055/s-0034-1397040. Epub 2015 Feb 2. Review. PubMed PMID: 25643268.

13: Kang DG, Holekamp TF, Wagner SC, Lehman RA Jr. Intrasite vancomycin powder for the prevention of surgical site infection in spine surgery: a systematic literature review. Spine J. 2015 Apr 1;15(4):762-70. doi: 10.1016/j.spinee.2015.01.030. Epub 2015 Jan 28. Review. PubMed PMID: 25637469.

14: Mutters NT, Werner G, Tacconelli E, Mischnik A. [Treatment options for serious infections caused by vancomycin-resistant enterococci]. Dtsch Med Wochenschr. 2015 Jan;140(1):42-5. doi: 10.1055/s-0040-100428. Epub 2015 Jan 12. Review. German. PubMed PMID: 25580973.

15: Bakhsheshian J, Dahdaleh NS, Lam SK, Savage JW, Smith ZA. The use of vancomycin powder in modern spine surgery: systematic review and meta-analysis of the clinical evidence. World Neurosurg. 2015 May;83(5):816-23. doi: 10.1016/j.wneu.2014.12.033. Epub 2014 Dec 19. Review. PubMed PMID: 25535069.

16: Chuang YC, Wang JT, Lin HY, Chang SC. Daptomycin versus linezolid for treatment of vancomycin-resistant enterococcal bacteremia: systematic review and meta-analysis. BMC Infect Dis. 2014 Dec 13;14:687. doi: 10.1186/s12879-014-0687-9. Review. PubMed PMID: 25495779; PubMed Central PMCID: PMC4269951.

17: Rubinstein E, Keynan Y. Vancomycin revisited - 60 years later. Front Public Health. 2014 Oct 31;2:217. doi: 10.3389/fpubh.2014.00217. eCollection 2014. Review. PubMed PMID: 25401098; PubMed Central PMCID: PMC4215627.

18: Kacířová I, Grundmann M. [Therapeutic monitoring of vancomycin in routine clinical practice]. Vnitr Lek. 2014 Oct;60(10):846-51. Review. Czech. PubMed PMID: 25382007.

19: Wang Y, Zou Y, Xie J, Wang T, Zheng X, He H, Dong W, Xing J, Dong Y. Linezolid versus vancomycin for the treatment of suspected methicillin-resistant Staphylococcus aureus nosocomial pneumonia: a systematic review employing meta-analysis. Eur J Clin Pharmacol. 2015 Jan;71(1):107-15. doi: 10.1007/s00228-014-1775-x. Epub 2014 Oct 30. Review. PubMed PMID: 25355172.

20: Patel R, Gallagher JC. Vancomycin-resistant enterococcal bacteremia pharmacotherapy. Ann Pharmacother. 2015 Jan;49(1):69-85. doi: 10.1177/1060028014556879. Epub 2014 Oct 28. Review. PubMed PMID: 25352037.