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 antibiotics. 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

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: 1790.56411
Molecular Weight: 1989.09
Elemental Analysis: C, 51.93; H, 5.22; Cl, 5.35; N, 7.04; O, 27.35; P, 3.11

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2.0g USD 14950.0 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 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1989.09 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

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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.

Additional Information

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