Oritavancin diphosphate
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MedKoo CAT#: 317101

CAS#: 192564-14-0 (diphosphate)

Description: Oritavancin, also known as LY333328, is a novel semisynthetic glycopeptide antibiotic. On August 6, 2014, the FDA approved oritavancin for treatment of skin infections. Oritavancin possesses potent and rapid bactericidal activity in vitro against a broad spectrum of both resistant and susceptible Gram-positive bacteria, including Staphylococcus aureus, MRSA, enterococci, and streptococci. Oritavancin was more active than either metronidazole or vancomycin against strains of Clostridium difficile tested. Oritavancin has potential use as a therapy for exposure to Bacillus anthracis, the Gram-positive bacterium that causes anthrax, having demonstrated efficacy in a mouse model both before and after exposure to the bacterium. The 4'-chlorobiphenylmethyl group disrupts the cell membrane of Gram-positive bacteria. It also acts by inhibition of transglycosylation and inhibition of transpeptidation.


Chemical Structure

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Oritavancin diphosphate
CAS# 192564-14-0 (diphosphate)

Theoretical Analysis

MedKoo Cat#: 317101
Name: Oritavancin diphosphate
CAS#: 192564-14-0 (diphosphate)
Chemical Formula: C86H103Cl3N10O34P2
Exact Mass: 1,790.56
Molecular Weight: 1,989.090
Elemental Analysis: C, 51.93; H, 5.22; Cl, 5.35; N, 7.04; O, 27.35; P, 3.11

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3850 Ready to ship
2g USD 6450 2 Weeks
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Related CAS #: 192564-14-0 (diphosphate)   171099-57-3 (free base)    

Synonym: LY333328; LY-333328; LY 333328; Oritavancin; Oritavancin diphosphate; brand name: Orbactiv.

IUPAC/Chemical Name: (4R)-22-O-(3-Amino-2,3,6-trideoxy-3-C-methyl-α-L-arabinohexopyranosyl)-N3-(p-(p-chlorophenyl)benzyl)vancomycin diphosphate

InChi Key: PWTROOMOPLCZHB-BHYQHFGMSA-N

InChi Code: InChI=1S/C86H97Cl3N10O26.2H3O4P/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114;2*1-5(2,3)4/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117);2*(H3,1,2,3,4)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-;;/m0../s1

SMILES Code: C[C@H]1[C@H](O)[C@@](C)(N)C[C@H](O[C@H]2[C@H]3C(N[C@H](C(O)=O)C4=CC(O)=CC(O)=C4C5=C(O)C=CC([C@@H](NC([C@H]6C7=CC(OC8=C(Cl)C=C2C=C8)=C(O[C@H]9[C@H](O[C@H]%10C[C@](C)(NCC%11=CC=C(C%12=CC=C(Cl)C=C%12)C=C%11)[C@@H](O)[C@H](C)O%10)[C@@H](O)[C@H](O)[C@@H](CO)O9)C(OC%13=C(Cl)C=C([C@@H](O)[C@@H](NC([C@H](NC)CC(C)C)=O)C(N[C@@H](CC(N)=O)C(N6)=O)=O)C=C%13)=C7)=O)C(N3)=O)=C5)=O)O1.O=P(O)(O)O.O=P(O)(O)O

Appearance: 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 DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

HS Tariff Code: 2934.99.9001

More Info: Related CAS# 192564-14-0 (Oritavancin diphosphate salt); 171099-57-3 (Oritavancin) Oritavancin free base theoretical analysis. Chemical Formula: C86H97Cl3N10O26 Exact Mass: 1790.56411 Molecular Weight: 1793.11600 Elemental Analysis: C, 57.61; H, 5.45; Cl, 5.93; N, 7.81; O, 23.20

Biological target: Oritavancin diphosphate (LY333328 diphosphate) is a semisynthetic glycopeptide antibiotic.
In vitro activity: Oritavancin demonstrates in vitro activity against most Gram-positive and anaerobic bacteria (Table 1). Its spectrum of activity is similar to that of vancomycin and teicoplanin, but is distinguished by its activity against vancomycin-resistant organisms. In addition to the target organisms, oritavancin has in vitro activity against other Gram-positive organisms, including modest activity against species intrinsically resistant to glycopeptides (Lactobacillus, Leuconostoc, and Pediococcus spp.). Oritavancin does not have activity against Gram-negative organisms. Reference: Core Evid. 2015 Feb 11;10:39-47. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334198/
In vivo activity: In a murine neutropenic thigh model study, oritavancin was found to be effective in the treatment of complicated skin infections due to S. aureus. It was also found that using oritavancin in a higher but less frequent dose was more effective than using multiple small doses. Reference: Reference: Core Evid. 2015 Feb 11;10:39-47. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334198/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 40.0 20.10

Preparing Stock Solutions

The following data is based on the product molecular weight 1,989.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kmeid J, Kanafani ZA. Oritavancin for the treatment of acute bacterial skin and skin structure infections: an evidence-based review. Core Evid. 2015 Feb 11;10:39-47. doi: 10.2147/CE.S51284. PMID: 25709561; PMCID: PMC4334198.
In vitro protocol: 1. Kmeid J, Kanafani ZA. Oritavancin for the treatment of acute bacterial skin and skin structure infections: an evidence-based review. Core Evid. 2015 Feb 11;10:39-47. doi: 10.2147/CE.S51284. PMID: 25709561; PMCID: PMC4334198.
In vivo protocol: 1. Kmeid J, Kanafani ZA. Oritavancin for the treatment of acute bacterial skin and skin structure infections: an evidence-based review. Core Evid. 2015 Feb 11;10:39-47. doi: 10.2147/CE.S51284. PMID: 25709561; PMCID: PMC4334198.

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1: Kmeid J, Kanafani ZA. Oritavancin for the treatment of acute bacterial skin and skin structure infections: an evidence-based review. Core Evid. 2015 Feb 11;10:39-47. doi: 10.2147/CE.S51284. eCollection 2015. Review. PubMed PMID: 25709561; PubMed Central PMCID: PMC4334198.

2: Das B, Sarkar C, Schachter J. Oritavancin - a new semisynthetic lipoglycopeptide agent to tackle the challenge of resistant gram positive pathogens. Pak J Pharm Sci. 2013 Sep;26(5):1045-55. Review. PubMed PMID: 24035967.

3: Karaoui LR, El-Lababidi R, Chahine EB. Oritavancin: an investigational lipoglycopeptide antibiotic. Am J Health Syst Pharm. 2013 Jan 1;70(1):23-33. doi: 10.2146/ajhp110572. Review. PubMed PMID: 23261897.

4: Bouza E, Burillo A. Oritavancin: a novel lipoglycopeptide active against Gram-positive pathogens including multiresistant strains. Int J Antimicrob Agents. 2010 Nov;36(5):401-7. doi: 10.1016/j.ijantimicag.2010.06.048. Epub 2010 Aug 21. Review. PubMed PMID: 20729040.

5: Zhanel GG, Calic D, Schweizer F, Zelenitsky S, Adam H, Lagacé-Wiens PR, Rubinstein E, Gin AS, Hoban DJ, Karlowsky JA. New lipoglycopeptides: a comparative review of dalbavancin, oritavancin and telavancin. Drugs. 2010 May 7;70(7):859-86. doi: 10.2165/11534440-000000000-00000. Review. Erratum in: Drugs. 2011 Mar 26;71(5):526. PubMed PMID: 20426497.

6: Guskey MT, Tsuji BT. A comparative review of the lipoglycopeptides: oritavancin, dalbavancin, and telavancin. Pharmacotherapy. 2010 Jan;30(1):80-94. doi: 10.1592/phco.30.1.80. Review. PubMed PMID: 20030476.

7: Anderson DL. Oritavancin for skin infections. Drugs Today (Barc). 2008 Aug;44(8):563-75. doi: 10.1358/dot.2008.44.8.1250078. Review. PubMed PMID: 18846268.

8: Crandon J, Nicolau DP. Oritavancin: a potential weapon in the battle against serious Gram-positive pathogens. Future Microbiol. 2008 Jun;3(3):251-63. doi: 10.2217/17460913.3.3.251. Review. PubMed PMID: 18505390.

9: Poulakou G, Giamarellou H. Oritavancin: a new promising agent in the treatment of infections due to Gram-positive pathogens. Expert Opin Investig Drugs. 2008 Feb;17(2):225-43. doi: 10.1517/13543784.17.2.225. Review. PubMed PMID: 18230056.

10: Ward KE, Mersfelder TL, LaPlante KL. Oritavancin--an investigational glycopeptide antibiotic. Expert Opin Investig Drugs. 2006 Apr;15(4):417-29. Review. PubMed PMID: 16548791.