A 77003

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

MedKoo CAT#: 571186

CAS#: 134878-17-4

Description: A 77003 is an antiretroviral agent and HIV-1 protease inhibitor. A77003 impairs HIV-1 protease-mediated Gag processing, interferes with the assembly and maturation of the virus, and leads to an irreversible loss of the infectivity of the virus.


Price and Availability

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A 77003 is not in stock, 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#: 571186
Name: A 77003
CAS#: 134878-17-4
Chemical Formula: C42H56N10O6
Exact Mass: 796.4384
Molecular Weight: 796.97
Elemental Analysis: C, 63.30; H, 7.08; N, 17.58; O, 12.04


Synonym: A 77003; A-77003; A77003; Abbott 77003

IUPAC/Chemical Name: L-Altritol, 1,2,5,6-tetradeoxy-2,5-bis(((2S)-3-methyl-2-(((methyl(2-pyrimidinylmethyl)amino)carbonyl)amino)-1-oxobutyl)amino)-1,6-diphenyl-

InChi Key: RMABAXSUFAXYMQ-ZXLHJDKKSA-N

InChi Code: InChI=1S/C42H56N10O6/c1-27(2)35(49-41(57)51(5)25-33-43-19-13-20-44-33)39(55)47-31(23-29-15-9-7-10-16-29)37(53)38(54)32(24-30-17-11-8-12-18-30)48-40(56)36(28(3)4)50-42(58)52(6)26-34-45-21-14-22-46-34/h7-22,27-28,31-32,35-38,53-54H,23-26H2,1-6H3,(H,47,55)(H,48,56)(H,49,57)(H,50,58)/t31-,32-,35-,36-,37-,38+/m0/s1

SMILES Code: O[C@@H]([C@H]([C@@H](NC([C@@H](NC(N(C)CC1=NC=CC=N1)=O)C(C)C)=O)CC2=CC=CC=C2)O)[C@@H](NC([C@@H](NC(N(C)CC3=NC=CC=N3)=O)C(C)C)=O)CC4=CC=CC=C4


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

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: Bilello JA, Bilello PA, Kort JJ, Dudley MN, Leonard J, Drusano GL. Efficacy of constant infusion of A-77003, an inhibitor of the human immunodeficiency virus type 1 (HIV-1) protease, in limiting acute HIV-1 infection in vitro. Antimicrob Agents Chemother. 1995 Nov;39(11):2523-7. PubMed PMID: 8585738; PubMed Central PMCID: PMC162977.

2: Drusano GL, Prichard M, Bilello PA, Bilello JA. Modeling combinations of antiretroviral agents in vitro with integration of pharmacokinetics: guidance in regimen choice for clinical trial evaluation. Antimicrob Agents Chemother. 1996 May;40(5):1143-7. PubMed PMID: 8723455; PubMed Central PMCID: PMC163280.

3: Ho DD, Toyoshima T, Mo H, Kempf DJ, Norbeck D, Chen CM, Wideburg NE, Burt SK, Erickson JW, Singh MK. Characterization of human immunodeficiency virus type 1 variants with increased resistance to a C2-symmetric protease inhibitor. J Virol. 1994 Mar;68(3):2016-20. PubMed PMID: 8107264; PubMed Central PMCID: PMC236669.

4: Rose RE, Gong YF, Greytok JA, Bechtold CM, Terry BJ, Robinson BS, Alam M, Colonno RJ, Lin PF. Human immunodeficiency virus type 1 viral background plays a major role in development of resistance to protease inhibitors. Proc Natl Acad Sci U S A. 1996 Feb 20;93(4):1648-53. PubMed PMID: 8643685; PubMed Central PMCID: PMC39996.

5: Borman AM, Paulous S, Clavel F. Resistance of human immunodeficiency virus type 1 to protease inhibitors: selection of resistance mutations in the presence and absence of the drug. J Gen Virol. 1996 Mar;77 ( Pt 3):419-26. PubMed PMID: 8601776.

6: Kageyama S, Hoekzema DT, Murakawa Y, Kojima E, Shirasaka T, Kempf DJ, Norbeck DW, Erickson J, Mitsuya H. A C2 symmetry-based HIV protease inhibitor, A77003, irreversibly inhibits infectivity of HIV-1 in vitro. AIDS Res Hum Retroviruses. 1994 Jun;10(6):735-43. PubMed PMID: 8074936.

7: Baldwin ET, Bhat TN, Liu B, Pattabiraman N, Erickson JW. Structural basis of drug resistance for the V82A mutant of HIV-1 proteinase. Nat Struct Biol. 1995 Mar;2(3):244-9. PubMed PMID: 7773792.

8: Mo H, Markowitz M, Majer P, Burt SK, Gulnik SV, Suvorov LI, Erickson JW, Ho DD. Design, synthesis, and resistance patterns of MP-134 and MP-167, two novel inhibitors of HIV type 1 protease. AIDS Res Hum Retroviruses. 1996 Jan 1;12(1):55-61. PubMed PMID: 8825619.

9: Gulnik SV, Suvorov LI, Liu B, Yu B, Anderson B, Mitsuya H, Erickson JW. Kinetic characterization and cross-resistance patterns of HIV-1 protease mutants selected under drug pressure. Biochemistry. 1995 Jul 25;34(29):9282-7. PubMed PMID: 7626598.

10: Kaplan AH, Michael SF, Wehbie RS, Knigge MF, Paul DA, Everitt L, Kempf DJ, Norbeck DW, Erickson JW, Swanstrom R. Selection of multiple human immunodeficiency virus type 1 variants that encode viral proteases with decreased sensitivity to an inhibitor of the viral protease. Proc Natl Acad Sci U S A. 1994 Jun 7;91(12):5597-601. PubMed PMID: 8202533; PubMed Central PMCID: PMC44043.

11: Tisdale M, Myers RE, Maschera B, Parry NR, Oliver NM, Blair ED. Cross-resistance analysis of human immunodeficiency virus type 1 variants individually selected for resistance to five different protease inhibitors. Antimicrob Agents Chemother. 1995 Aug;39(8):1704-10. PubMed PMID: 7486905; PubMed Central PMCID: PMC162812.

12: Patick AK, Rose R, Greytok J, Bechtold CM, Hermsmeier MA, Chen PT, Barrish JC, Zahler R, Colonno RJ, Lin PF. Characterization of a human immunodeficiency virus type 1 variant with reduced sensitivity to an aminodiol protease inhibitor. J Virol. 1995 Apr;69(4):2148-52. PubMed PMID: 7884862; PubMed Central PMCID: PMC188882.

13: Kempf DJ, Marsh KC, Paul DA, Knigge MF, Norbeck DW, Kohlbrenner WE, Codacovi L, Vasavanonda S, Bryant P, Wang XC, et al. Antiviral and pharmacokinetic properties of C2 symmetric inhibitors of the human immunodeficiency virus type 1 protease. Antimicrob Agents Chemother. 1991 Nov;35(11):2209-14. PubMed PMID: 1803993; PubMed Central PMCID: PMC245361.

14: Withers-Ward ES, Amado RG, Koka PS, Jamieson BD, Kaplan AH, Chen IS, Zack JA. Transient renewal of thymopoiesis in HIV-infected human thymic implants following antiviral therapy. Nat Med. 1997 Oct;3(10):1102-9. PubMed PMID: 9334721.

15: Erickson J, Kempf D. Structure-based design of symmetric inhibitors of HIV-1 protease. Arch Virol Suppl. 1994;9:19-29. Review. PubMed PMID: 8032250.

16: Kedes DH, Ganem D. Sensitivity of Kaposi's sarcoma-associated herpesvirus replication to antiviral drugs. Implications for potential therapy. J Clin Invest. 1997 May 1;99(9):2082-6. PubMed PMID: 9151779; PubMed Central PMCID: PMC508037.

17: Powell DJ, Bur D, Wlodawer A, Gustchina A, Payne SL, Dunn BM, Kay J. Expression, characterisation and mutagenesis of the aspartic proteinase from equine infectious anaemia virus. Eur J Biochem. 1996 Oct 15;241(2):664-74. Erratum in: Eur J Biochem 1997 May 15;246(1):258. PubMed PMID: 8917470.

18: Kaplan AH, Zack JA, Knigge M, Paul DA, Kempf DJ, Norbeck DW, Swanstrom R. Partial inhibition of the human immunodeficiency virus type 1 protease results in aberrant virus assembly and the formation of noninfectious particles. J Virol. 1993 Jul;67(7):4050-5. PubMed PMID: 8510215; PubMed Central PMCID: PMC237772.

19: Reedijk M, Boucher CA, van Bommel T, Ho DD, Tzeng TB, Sereni D, Veyssier P, Jurriaans S, Granneman R, Hsu A, et al. Safety, pharmacokinetics, and antiviral activity of A77003, a C2 symmetry-based human immunodeficiency virus protease inhibitor. Antimicrob Agents Chemother. 1995 Jul;39(7):1559-64. PubMed PMID: 7492104; PubMed Central PMCID: PMC162781.

20: Frecer V, Miertus S, Tossi A, Romeo D. Rational design of inhibitors for drug-resistant HIV-1 aspartic protease mutants. Drug Des Discov. 1998 Oct;15(4):211-31. PubMed PMID: 10546067.