Synonym
IC 9564; IC9564; IC-9564
IUPAC/Chemical Name
Heptanoic acid, 3-hydroxy-4-((8-(((3beta)-3-hydroxy-28-oxolup-20(29)-en-28-yl)amino)-1-oxooctyl)amino)-6-methyl-, (R-(R*,S*))-
InChi Key
SPZFCKVVHXRLAI-ZGEYYWTRSA-N
InChi Code
InChI=1S/C46H78N2O6/c1-29(2)27-33(34(49)28-39(52)53)48-38(51)15-13-11-10-12-14-26-47-41(54)46-23-18-31(30(3)4)40(46)32-16-17-36-43(7)21-20-37(50)42(5,6)35(43)19-22-45(36,9)44(32,8)24-25-46/h29,31-37,40,49-50H,3,10-28H2,1-2,4-9H3,(H,47,54)(H,48,51)(H,52,53)/t31-,32+,33-,34+,35-,36+,37-,40+,43-,44+,45+,46-/m0/s1
SMILES Code
CC(C)C[C@H](NC(=O)CCCCCCCNC(=O)[C@]12CC[C@H]([C@@H]1[C@H]3CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC2)C(=C)C)[C@H](O)CC(=O)O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
755.14
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.
| 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 |
1. Huang L, Ho P, Lee KH, Chen CH. Synthesis and anti-HIV activity of bi-functional betulinic acid derivatives. Bioorg Med Chem. 2006 Apr 1;14(7):2279-89. doi: 10.1016/j.bmc.2005.11.016. Epub 2005 Nov 28. PMID: 16314103.
2. Holz-Smith SL, Sun IC, Jin L, Matthews TJ, Lee KH, Chen CH. Role of human immunodeficiency virus (HIV) type 1 envelope in the anti-HIV activity of the betulinic acid derivative IC9564. Antimicrob Agents Chemother. 2001 Jan;45(1):60-6. doi: 10.1128/AAC.45.1.60-66.2001. PMID: 11120945; PMCID: PMC90240.
3. Huang L, Lai W, Ho P, Chen CH. Induction of a nonproductive conformational change in gp120 by a small molecule HIV type 1 entry inhibitor. AIDS Res Hum Retroviruses. 2007 Jan;23(1):28-32. doi: 10.1089/aid.2006.0137. PMID: 17263629.
4. Sun IC, Chen CH, Kashiwada Y, Wu JH, Wang HK, Lee KH. Anti-AIDS agents 49. Synthesis, anti-HIV, and anti-fusion activities of IC9564 analogues based on betulinic acid. J Med Chem. 2002 Sep 12;45(19):4271-5. doi: 10.1021/jm020069c. PMID: 12213068.
5. Lai W, Huang L, Ho P, Li Z, Montefiori D, Chen CH. Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2008 Jan;52(1):128-36. doi: 10.1128/AAC.00737-07. Epub 2007 Oct 22. PMID: 17954689; PMCID: PMC2223896.
