BI 224436

Chemical compound
  • none
Legal statusLegal status
  • Investigational
Pharmacokinetic dataElimination half-life7 hrs (simulated)[1]Identifiers
  • (2S)-[4-(2,3-Dihydropyrano[4,3,2-de]quinolin-7-yl)-2-methyl-3-quinolinyl] [(2-methyl-2-propanyl)oxy]acetic acid
CAS Number
  • 1155419-89-8
PubChem CID
  • 66561902
ChemSpider
  • 32698770
UNII
  • 99A996378Y
CompTox Dashboard (EPA)
  • DTXSID601029847 Edit this at Wikidata
Chemical and physical dataFormulaC27H26N2O4Molar mass442.515 g·mol−13D model (JSmol)
  • Interactive image
  • CC1=NC2=CC=CC=C2C(=C1[C@@H](C(=O)O)OC(C)(C)C)C3=C4C5=C(C=C3)OCCC5=CC=N4
InChI
  • InChI=1S/C27H26N2O4/c1-15-21(25(26(30)31)33-27(2,3)4)23(17-7-5-6-8-19(17)29-15)18-9-10-20-22-16(12-14-32-20)11-13-28-24(18)22/h5-11,13,25H,12,14H2,1-4H3,(H,30,31)/t25-/m0/s1
  • Key:MIXIIJCBELCMCZ-VWLOTQADSA-N

BI 224436 was an investigational new drug under development for the treatment of HIV infection. BI 224436 is the first non-catalytic site integrase inhibitor (NCINI). It inhibits HIV replication via binding to a conserved allosteric pocket of the HIV integrase enzyme. This makes the drug distinct in its mechanism of action compared to raltegravir and elvitegravir, which bind at the catalytic site.[2] In October 2011, Gilead Sciences purchased exclusive rights to develop BI 224436 and several related compounds under investigation in Boehringer Ingelheim’s noncatalytic site integrase inhibitor program.[3][4]

Clinical trials were abandoned in advance of Phase 1.[5]

References

  1. ^ Brown A, McSharry J, Kulawy R (17 September 2011). Pharmacodynamics of BI 224436 for HIV-1 in an in vitro hollow fiber infection model system. 51st Interscience conference on antimicrobial agents and chemotherapy. Chicago. pp. 17–20.
  2. ^ Fenwick C, Bethell R, Cordingley M, Edwards P, Quinson AM, Robinson P, Simoneau B, Yoakim C (17 September 2011). Levin J (ed.). BI 224436, a non-catalytic site integrase inhibitor, is a potent inhibitor of the replication of treatment-naïve and raltegravir-resistant clinical isolates of HIV-1. 51st Interscience Conference on Antimicrobials and Chemotherapy. Chicago: ICAAC.
  3. ^ "Gilead Negotiates Worldwide License to BI's Early Clinical Stage HIV Program". Genetic Engineering and Biotechnology News. 6 October 2011. Archived from the original on 23 January 2013.
  4. ^ Highleyman L (7 October 2011). "ICAAC: New Integrase Inhibitor BI 224436 Active against Raltegravir-Resistant HIV". HIVandHepatitis.com.
  5. ^ Clinical trial number NCT01276990 for "Safety and Pharmacokinetics of Multiple Rising Oral Doses of BI 224436 in Healthy Male Volunteers." at ClinicalTrials.gov
  • v
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Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)
Capsid inhibitorsEntry/fusion inhibitors
(Discovery and development)Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))Maturation inhibitorsProtease Inhibitors (PI)
(Discovery and development)
1st generation
2nd generation
Reverse-transcriptase
inhibitors (RTIs)
Nucleoside and
nucleotide (NRTI)
Non-nucleoside (NNRTI)
(Discovery and development)
1st generation
2nd generation
Combined formulations
Pharmacokinetic boostersExperimental agents
Uncoating inhibitors
Transcription inhibitors
  • Tat antagonists
Translation inhibitors
BNAbs
Other
Failed agents
°DHHS recommended initial regimen options. ◊Formerly or rarely used agent.


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