Cosalane

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H584356

CAS#: 154212-56-3

Description: Cosalane is active against a variety of HIV-1 strains and HIV-2. The compound inhibits the binding of gp120 to CD4 cells and of the postbinding events that lead to fusion of the virus with the cell membrane.


Chemical Structure

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Cosalane
CAS# 154212-56-3

Theoretical Analysis

Hodoodo Cat#: H584356
Name: Cosalane
CAS#: 154212-56-3
Chemical Formula: C45H60Cl2O6
Exact Mass: 766.38
Molecular Weight: 767.869
Elemental Analysis: C, 70.39; H, 7.88; Cl, 9.23; O, 12.50

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Cosalane; NSC 658586; NSC-658586

IUPAC/Chemical Name: Benzoic acid, 3,3'-(4-(3beta,5alpha)-cholestan-3-yl-1-butenylidene)bis(5-chloro-6-hydroxy-

InChi Key: VOJOOGPALCATLT-ZFQBPCNVSA-N

InChi Code: InChI=1S/C45H60Cl2O6/c1-25(2)8-6-9-26(3)35-14-15-36-32-13-12-30-20-27(16-18-44(30,4)37(32)17-19-45(35,36)5)10-7-11-31(28-21-33(42(50)51)40(48)38(46)23-28)29-22-34(43(52)53)41(49)39(47)24-29/h11,21-27,30,32,35-37,48-49H,6-10,12-20H2,1-5H3,(H,50,51)(H,52,53)/t26-,27+,30+,32+,35-,36+,37+,44+,45-/m1/s1

SMILES Code: CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](CC/C=C(C5=CC(C(O)=O)=C(O)C(Cl)=C5)\C6=CC(C(O)=O)=C(O)C(Cl)=C6)CC[C@]4(C)[C@@]3([H])CC[C@]12C

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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 767.87 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:
In vitro protocol:
In vivo protocol:

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1: Casimiro-Garcia A, De Clercq E, Pannecouque C, Witvrouw M, Loftus TL, Turpin JA, Buckheit RW Jr, Fanwick PE, Cushman M. Synthesis and anti-HIV activity of cosalane analogues incorporating two dichlorodisalicylmethane pharmacophore fragments. Bioorg Med Chem. 2001 Nov;9(11):2827-41. PubMed PMID: 11597463.

2: Zhan P, Li Z, Liu X. Cosalane and its analogues: a unique class of anti-HIV agents. Mini Rev Med Chem. 2010 Sep;10(10):966-76. Review. PubMed PMID: 20540707.

3: Golebiewski WM, Keyes RF, Cushman M. Exploration of the effects of linker chain modifications on anti-HIV activities in a series of cosalane analogues. Bioorg Med Chem. 1996 Oct;4(10):1637-48. PubMed PMID: 8931933.

4: Kuchimanchi KR, Gandhi MD, Sheta RR, Johnston TP, Santhosh KC, Cushman M, Mitra AK. Intestinal absorption and biodistribution of cosalane and its amino acid conjugates: novel anti-HIV agents. Int J Pharm. 2002 Jan 14;231(2):197-211. PubMed PMID: 11755272.

5: Santhosh KC, De Clercq E, Pannecouque C, Witvrouw M, Loftus TL, Turpin JA, Buckheit RW, Cushman M. Anti-HIV activity of a series of cosalane amino acid conjugates. Bioorg Med Chem Lett. 2000 Nov 20;10(22):2505-8. PubMed PMID: 11086716.

6: Udata C, Patel J, Pal D, Hejchman E, Cushman M, Mitra AK. Enhanced transport of a novel anti-HIV agent--cosalane and its congeners across human intestinal epithelial (Caco-2) cell monolayers. Int J Pharm. 2003 Jan 2;250(1):157-68. PubMed PMID: 12480282.

7: Cushman M, Golebiewski WM, McMahon JB, Buckheit RW Jr, Clanton DJ, Weislow O, Haugwitz RD, Bader JP, Graham L, Rice WG. Design, synthesis, and biological evaluation of cosalane, a novel anti-HIV agent which inhibits multiple features of virus reproduction. J Med Chem. 1994 Sep 16;37(19):3040-50. PubMed PMID: 7932526.

8: Venkatesh S, Li J, Xu Y, Vishnuvajjala R, Anderson BD. Intrinsic solubility estimation and pH-solubility behavior of cosalane (NSC 658586), an extremely hydrophobic diprotic acid. Pharm Res. 1996 Oct;13(10):1453-9. PubMed PMID: 8899834.

9: Choo V. Anti-HIV activity of cosalane. Lancet. 1993 Sep 18;342(8873):733. PubMed PMID: 8103830.

10: Casimiro-Garcia A, De Clercq E, Pannecouque C, Witvrouw M, Stup TL, Turpin JA, Buckheit RW Jr, Cushman M. Synthesis and anti-HIV activity of cosalane analogues incorporating nitrogen in the linker chain. Bioorg Med Chem. 2000 Jan;8(1):191-200. PubMed PMID: 10968278.

11: Paul GC, De Clercq E, Pannecouque C, Witvrouw M, Loftus TL, Turpin JA, Buckheit RW Jr, Cushman M. Identification of optimal anion spacing for anti-HIV activity in a series of cosalane tetracarboxylates. Bioorg Med Chem Lett. 2000 Sep 18;10(18):2149-52. PubMed PMID: 10999491.

12: Howard OM, Dong HF, Oppenheim JJ, Insaf S, Santhosh KC, Paul G, Cushman M. Inhibition of RANTES/CCR1-mediated chemotaxis by cosalane and related compounds. Bioorg Med Chem Lett. 2001 Jan 8;11(1):59-62. PubMed PMID: 11140734.

13: Keyes RF, Golebiewski WM, Cushman M. Correlation of anti-HIV potency with lipophilicity in a series of cosalane analogs having normal alkenyl and phosphodiester chains as cholestane replacements. J Med Chem. 1996 Jan 19;39(2):508-14. PubMed PMID: 8558520.

14: Cushman M, Golebiewski WM, Graham L, Turpin JA, Rice WG, Fliakas-Boltz V, Buckheit RW Jr. Synthesis and biological evaluation of certain alkenyldiarylmethanes as anti-HIV-1 agents which act as non-nucleoside reverse transcriptase inhibitors. J Med Chem. 1996 Aug 2;39(16):3217-27. PubMed PMID: 8759644.

15: Cushman M, Insaf S, Paul G, Ruell JA, De Clercq E, Schols D, Pannecouque C, Witvrouw M, Schaeffer CA, Turpin JA, Williamson K, Rice WG. Extension of the polyanionic cosalane pharmacophore as a strategy for increasing anti-HIV potency. J Med Chem. 1999 May 20;42(10):1767-77. PubMed PMID: 10346929.

16: Santhosh KC, Paul GC, De Clercq E, Pannecouque C, Witvrouw M, Loftus TL, Turpin JA, Buckheit RW Jr, Cushman M. Correlation of anti-HIV activity with anion spacing in a series of cosalane analogues with extended polycarboxylate pharmacophores. J Med Chem. 2001 Mar 1;44(5):703-14. PubMed PMID: 11262081.

17: Cushman M, Insaf S, Ruell JA, Schaeffer CA, Rice WG. Synthesis of a cosalane analog with an extended polyanionic pharmacophore conferring enhanced potency as an anti-HIV agent. Bioorg Med Chem Lett. 1998 Apr 7;8(7):833-6. PubMed PMID: 9871550.

18: Cushman M, Golebiewski WM, Pommier Y, Mazumder A, Reymen D, De Clercq E, Graham L, Rice WG. Cosalane analogues with enhanced potencies as inhibitors of HIV-1 protease and integrase. J Med Chem. 1995 Feb 3;38(3):443-52. PubMed PMID: 7853337.

19: Gabriel JL, Mitchell WM. Functional design of potential inhibitors of human immunodeficiency virus (HIV) binding to CD4+ target cells: a molecular model of gp120 predicts ligand binding. Drug Des Discov. 1996 Oct;14(2):103-14. PubMed PMID: 9010617.

20: Udata C, Mitra AK, Badr MZ. Disposition of cosalane, a novel anti-HIV agent, in isolated perfused rat livers. Drug Metab Dispos. 1999 Aug;27(8):947-50. PubMed PMID: 10421624.