U 75875

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

MedKoo CAT#: 526517

CAS#: 112190-24-6

Description: U 75875 is a protease inhibitor.


Price and Availability

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U 75875 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526517
Name: U 75875
CAS#: 112190-24-6
Chemical Formula: C44H59N7O7
Exact Mass: 797.4476
Molecular Weight: 797.998
Elemental Analysis: C, 66.23; H, 7.45; N, 12.29; O, 14.03


Synonym: U75875, U-75875, U 75875, Pnu-75875, Pnu 75875, Pnu75875

IUPAC/Chemical Name: (2S,3S)-N-(4-(L-histidyl)-3-(5-amino-6-cyclohexyl-3,4-dihydroxy-2-isopropylhexanoyl)-5-(2-(naphthalen-1-yloxy)acetyl)pyridin-2-yl)-2-amino-3-methylpentanamide

InChi Key: OOIVLUMWJYOBRV-ZZDUJIROSA-N

InChi Code: InChI=1S/C44H59N7O7/c1-5-25(4)38(47)44(57)51-43-37(41(55)35(24(2)3)42(56)40(54)31(45)18-26-12-7-6-8-13-26)36(39(53)32(46)19-28-20-48-23-50-28)30(21-49-43)33(52)22-58-34-17-11-15-27-14-9-10-16-29(27)34/h9-11,14-17,20-21,23-26,31-32,35,38,40,42,54,56H,5-8,12-13,18-19,22,45-47H2,1-4H3,(H,48,50)(H,49,51,57)/t25-,31?,32-,35?,38-,40?,42?/m0/s1

SMILES Code: N[C@@H]([C@@H](C)CC)C(NC1=NC=C(C(COC2=C3C=CC=CC3=CC=C2)=O)C(C([C@H](CC4=CNC=N4)N)=O)=C1C(C(C(C)C)C(O)C(O)C(N)CC5CCCCC5)=O)=O


Technical Data

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).

Harmonized System Code:
293490


References

1: Pagano PJ, Chong KT. In vitro inhibition of human immunodeficiency virus type 1 by a combination of delavirdine (U-90152) with protease inhibitor U-75875 or interferon-alpha. J Infect Dis. 1995 Jan;171(1):61-7. PubMed PMID: 7528253.

2: Peterson PK, Gekker G, Hu S, Chao CC. Anti-human immunodeficiency virus type 1 activities of U-90152 and U-75875 in human brain cell cultures. Antimicrob Agents Chemother. 1994 Oct;38(10):2465-8. PubMed PMID: 7530933; PubMed Central PMCID: PMC284764.

3: Martin LN, Soike KF, Murphey-Corb M, Bohm RP, Roberts ED, Kakuk TJ, Thaisrivongs S, Vidmar TJ, Ruwart MJ, Davio SR, et al. Effects of U-75875, a peptidomimetic inhibitor of retroviral proteases, on simian immunodeficiency virus infection in rhesus monkeys. Antimicrob Agents Chemother. 1994 Jun;38(6):1277-83. PubMed PMID: 7522427; PubMed Central PMCID: PMC188198.

4: Perno CF, Bergamini A, Pesce CD, Milanese G, Capozzi M, Aquaro S, Thaisrivongs S, Tarpley WG, Zon G, D'Agostini C, et al. Inhibition of the protease of human immunodeficiency virus blocks replication and infectivity of the virus in chronically infected macrophages. J Infect Dis. 1993 Nov;168(5):1148-56. PubMed PMID: 8228348.

5: Ashorn P, McQuade TJ, Thaisrivongs S, Tomasselli AG, Tarpley WG, Moss B. An inhibitor of the protease blocks maturation of human and simian immunodeficiency viruses and spread of infection. Proc Natl Acad Sci U S A. 1990 Oct;87(19):7472-6. PubMed PMID: 2217178; PubMed Central PMCID: PMC54769.

6: Thanki N, Rao JK, Foundling SI, Howe WJ, Moon JB, Hui JO, Tomasselli AG, Heinrikson RL, Thaisrivongs S, Wlodawer A. Crystal structure of a complex of HIV-1 protease with a dihydroxyethylene-containing inhibitor: comparisons with molecular modeling. Protein Sci. 1992 Aug;1(8):1061-72. PubMed PMID: 1304383; PubMed Central PMCID: PMC2142164.

7: Aquaro S, Balestra E, Panti S, Cenci A, Serra F, Francesconi M, Abdelahad D, Caliò R, Perno CF. [Correlation between HIV-inhibiting drug activity in human macrophages and clinical outcome]. Clin Ter. 1998 Jan-Feb;149(921):37-41. Italian. PubMed PMID: 9621487.

8: Kuhn LA, Swanson CA, Pique ME, Tainer JA, Getzoff ED. Atomic and residue hydrophilicity in the context of folded protein structures. Proteins. 1995 Dec;23(4):536-47. PubMed PMID: 8749849.

9: Bergamini A, Bolacchi F, Bongiovanni B, Colizzi V, Cappelli G, Uccella I, Cepparulo M, Capozzi M, Mancino G, Rocchi G. Human immunodeficiency virus type 1 infection modulates the interleukin (IL)-1beta and IL-6 responses of human macrophages to CD40 ligand stimulation. J Infect Dis. 2000 Sep;182(3):776-84. Epub 2000 Aug 17. PubMed PMID: 10950771.

10: Tomasselli AG, Heinrikson RL. Targeting the HIV-protease in AIDS therapy: a current clinical perspective. Biochim Biophys Acta. 2000 Mar 7;1477(1-2):189-214. Review. PubMed PMID: 10708858.

11: Mestres J, Rohrer DC, Maggiora GM. A molecular field-based similarity approach to pharmacophoric pattern recognition. J Mol Graph Model. 1997 Apr;15(2):114-21, 103-6. PubMed PMID: 9385558.

12: Blom NS, Sygusch J. High resolution fast quantitative docking using Fourier domain correlation techniques. Proteins. 1997 Apr;27(4):493-506. PubMed PMID: 9141130.

13: Verkhivker GM. Empirical free energy calculations of human immunodeficiency virus type 1 protease crystallographic complexes. II. Knowledge-based ligand-protein interaction potentials applied to thermodynamic analysis of hydrophobic mutations. Pac Symp Biocomput. 1996:638-52. PubMed PMID: 9390264.

14: Thaisrivongs S, Tomasselli AG, Moon JB, Hui J, McQuade TJ, Turner SR, Strohbach JW, Howe WJ, Tarpley WG, Heinrikson RL. Inhibitors of the protease from human immunodeficiency virus: design and modeling of a compound containing a dihydroxyethylene isostere insert with high binding affinity and effective antiviral activity. J Med Chem. 1991 Aug;34(8):2344-56. PubMed PMID: 1875334.

15: Sandak B, Nussinov R, Wolfson HJ. A method for biomolecular structural recognition and docking allowing conformational flexibility. J Comput Biol. 1998 Winter;5(4):631-54. PubMed PMID: 10072081.

16: Bergamini A, Faggioli E, Bolacchi F, Gessani S, Cappannoli L, Uccella I, Demin F, Capozzi M, Cicconi R, Placido R, Vendetti S, Colizzi GM, Rocchi G. Enhanced production of tumor necrosis factor-alpha and interleukin-6 due to prolonged response to lipopolysaccharide in human macrophages infected in vitro with human immunodeficiency virus type 1. J Infect Dis. 1999 Apr;179(4):832-42. PubMed PMID: 10068578.

17: Verkhivker GM, Rejto PA. A mean field model of ligand-protein interactions: implications for the structural assessment of human immunodeficiency virus type 1 protease complexes and receptor-specific binding. Proc Natl Acad Sci U S A. 1996 Jan 9;93(1):60-4. PubMed PMID: 8552675; PubMed Central PMCID: PMC40178.

18: Babé LM, Craik CS. Constitutive production of nonenveloped human immunodeficiency virus type 1 particles by a mammalian cell line and effects of a protease inhibitor on particle maturation. Antimicrob Agents Chemother. 1994 Oct;38(10):2430-9. PubMed PMID: 7840583; PubMed Central PMCID: PMC284757.

19: Mulichak AM, Hui JO, Tomasselli AG, Heinrikson RL, Curry KA, Tomich CS, Thaisrivongs S, Sawyer TK, Watenpaugh KD. The crystallographic structure of the protease from human immunodeficiency virus type 2 with two synthetic peptidic transition state analog inhibitors. J Biol Chem. 1993 Jun 25;268(18):13103-9. PubMed PMID: 8514751.