dmp 323 profile

(4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one : A 1,3-diazepanone ring with two 4-(hydroxymethyl)benzyl groups as substituents at positions N-1 and N-4, two benzyl groups at C-4 and C-7, and two hydroxy groups at C-5 and C-6 respectively. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	72404
CHEMBL ID	21145
CHEBI ID	42082
SCHEMBL ID	2770886
MeSH ID	M0227660

Synonym
(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis({[4-(hydroxymethyl)phenyl]methyl})-1,3-diazepan-2-one
bdbm150
xm-323
(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[[4-(hydroxymethyl)phenyl]methyl]-1,3-diazepan-2-one
dmp 323
[4r-(4.alpha.,5.alpha.,6.beta.,7.beta.)]-hexahydro-5,6-dihydroxy-1,3-bis[(4-hydroxymethyl)phenyl]methyl]-4,7-bis(phenylmethyl)-2h-1,3-diazepin-2-one
dmp-323
xm323
dmp323
151867-81-1
[4-r-(-4-alpha,5-alpha,6-beta,7-beta)]-hexahydro-5,6-bis(hydroxy)-[1,3-bis([4-hydroxymethyl-phenyl]methyl)-4,7-bis(phen ylmethyl)]-2h-1,3-diazepinone
[4-r-(-4-alpha,5-alpha,6-beta,7-beta)]-hexahydro-5,6-bis(hydroxy)-[1,3-bis([4-hydroxymethyl-phenyl]methyl)-4,7-bis(phenylmethyl)]-2h-1,3-diazepinone
(4s,5r,6r,7s)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[[4-(hydroxymethyl)phenyl]methyl]-1,3-diazepan-2-one
dmp323(inhibitor of dupont merck)
1QBS
1MEU
1MET
1MES ,
2h-1,3-diazepin-2-one, hexahydro-5,6-dihydroxy-1,3-bis((4-(hydroxymethyl)phenyl)methyl)-4,7-bis(phenylmethyl)-, (4alpha,5alpha,6beta,7beta)-
chebi:42082 ,
CHEMBL21145
(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one
unii-kxn3869xb2
kxn3869xb2 ,
jcr 424
SCHEMBL2770886
DTXSID40164892
jcr-424
[4-r-(-4-alpha,5-alpha,6-beta,7-beta)]-hexahydro-5,6-bis(hydroxy)-[1,3-bis([4-hydroxymethyl-phenyl]methyl)-4,7-bis(phen
ylmethyl)]-2h-1,3-diazepinone
Q27120453
XCVGQMUMMDXKCY-WZJLIZBTSA-N ,
(4r-(4a,5a,6b,7b))-hexahydro-5,6-dihydroxy-1,3-bis((4-(hydroxymethyl)phenyl)methyl)-4,7-bis(phenylmethyl)-2h-1,3-diazepin-2-one
2h-1,3-diazepin-2-one, hexahydro-5,6-dihydroxy-1,3-bis((4-(hydroxymethyl)phenyl)methyl)-4,7-bis(phenylmethyl)-, (4r-(4.alpha.,5.alpha.,6.beta.,7.beta.))-
(4r,5s,6s,7r)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis(4-(hydroxymethyl)benzyl)-1,3-diazepan-2-one
AKOS040745751

Excerpt	Reference	Relevance
"DMP 323 proved to be a P-gp substrate in competition studies with P-gp inhibitor ritonavir and H17 as a representative of another class of non-peptidic HIV-1 protease inhibitors."	( P-glycoprotein effects of cyclic urea HIV protease inhibitor DMP 323 in competitional absorption studies. Gyémánt, N; Hilgeroth, A; Molnár, J; Richter, M, 2006)	1.3
"DMP 323 is a symmetrically substituted cyclic urea compound with demonstrated activity against human immunodeficiency virus (HIV) in vitro. "	( Pharmacokinetics of HIV protease inhibitor DMP 323 in rats and dogs. Burcham, DL; Grubb, MF; Huang, SM; Quon, CY; Saxton, PL; Wong, YN, )	1.84
"DMP 323 is a potent inhibitor of the protease of human immunodeficiency virus (HIV), with antiviral activity against both HIV type 1 and HIV type 2. "	( Potency and selectivity of inhibition of human immunodeficiency virus protease by a small nonpeptide cyclic urea, DMP 323. Cawood, PG; Erickson-Viitanen, S; Klabe, RM; Meek, JL; O'Neal, PL, 1994)	1.94

Excerpt	Reference	Relevance
"DMP 323 has been measured in rat and dog plasma via liquid-liquid extraction and HPLC."	( Pharmacokinetics of HIV protease inhibitor DMP 323 in rats and dogs. Burcham, DL; Grubb, MF; Huang, SM; Quon, CY; Saxton, PL; Wong, YN, )	1.12

Excerpt	Reference	Relevance
" Absolute bioavailability of DMP 323 from oral doses ranged from 15 to 27% in rats and from 37 to 38% in dogs."	( Pharmacokinetics of HIV protease inhibitor DMP 323 in rats and dogs. Burcham, DL; Grubb, MF; Huang, SM; Quon, CY; Saxton, PL; Wong, YN, )	0.69
" The small size probably contributes to the observed good oral bioavailability in animals."	( Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas. Aldrich, PE; Bacheler, LT; Chang, CH; Confalone, PN; Daneker, WF; DeLucca, GV; Emmett, G; Eyermann, CJ; Han, Q; Hodge, CN; Holler, ER; Jadhav, PK; Klabe, RM; Kornhauser, DM; Lam, PY; Li, L; Li, R; Markwalder, JA; McHugh, RJ; Rayner, MM; Ru, Y; Seitz, SP; Sharpe, TR; Shum, L; Winslow, DL, 1996)	0.29
" Using this approach several very potent (IC90 11 nM) and orally bioavailable (F% 93-100%) compounds were discovered (21, 22)."	( Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues. Bacheler, LT; Cordova, B; De Lucca, GV; Erickson-Viitanen, S; Garber, S; Kim, UT; Klabe, RM; Ko, SS; Lam, GN; Liang, J; Logue, KA; Trainor, GL; Wright, MR, 1998)	0.3
" The ultimate success of DMP 850 and DMP 851 in clinical trials might depend on achieving or exceeding the oral bioavailability seen in dog."	( Design and selection of DMP 850 and DMP 851: the next generation of cyclic urea HIV protease inhibitors. Anderson, PS; Bacheler, LT; Chang, CH; Cordova, B; Erickson-Viitanen, S; Garber, S; Johnson, BL; Klabe, RM; Ko, SS; Lam, PY; Li, R; Reid, C; Rodgers, JD; Ru, Y; Seitz, SP; Trainor, GL; Wang, H; Wright, MR, 1998)	0.3
"Cyclic ureas form a perspective class of non-peptidic HIV-1 protease inhibitors with major bioavailability problems."	( P-glycoprotein effects of cyclic urea HIV protease inhibitor DMP 323 in competitional absorption studies. Gyémánt, N; Hilgeroth, A; Molnár, J; Richter, M, 2006)	0.58

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-HIV agent	An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
diazepanone
ureas
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.2735	0.0004	0.2735	0.8000	AID977610
Chain B, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.2735	0.0004	0.2735	0.8000	AID977610
Chain A, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.2735	0.0004	0.2735	0.8000	AID977610
Chain B, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.2735	0.0004	0.2735	0.8000	AID977610
Chain A, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.2735	0.0004	0.2735	0.8000	AID977610
Chain B, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.2735	0.0004	0.2735	0.8000	AID977610
Chain A, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.0003	0.0003	0.0003	0.0003	AID977610
Chain B, HIV-1 PROTEASE	Human immunodeficiency virus 1	Ki	0.0003	0.0003	0.0003	0.0003	AID977610
Gag-Pol polyprotein	Human immunodeficiency virus type 1 (BRU ISOLATE)	Ki	0.0003	0.0000	0.0828	3.3000	AID1795214
Gag-Pol polyprotein	Human immunodeficiency virus type 1 (NEW YORK-5 ISOLATE)	Ki	0.0010	0.0000	0.1220	3.1000	AID1795299
Protease	Human immunodeficiency virus 1	IC50 (µMol)	0.0625	0.0001	0.2248	7.3200	AID162189; AID199081
Protease	Human immunodeficiency virus 1	Ki	0.0003	0.0000	0.0443	3.1000	AID160270; AID160292; AID160316; AID160455; AID160473; AID160474; AID160475; AID161876; AID162710; AID163483; AID163487; AID82912
Protease	Human immunodeficiency virus 1	Ki	0.0003	0.0000	0.0284	1.1000	AID711570
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Protease	Human immunodeficiency virus 1	Kd	0.0038	0.0001	0.0412	0.5770	AID162706
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thromboxane-A synthase	Rattus norvegicus (Norway rat)	IC90 (µMol)	0.1146	0.0104	0.0703	0.1250	AID210277
Protease	Human immunodeficiency virus 1	IC90 (µMol)	0.1048	0.0020	0.6784	7.3000	AID105206; AID210277
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (53)

Assay ID	Title	Year	Journal	Article
AID235097	Resistance of constructed mutant 84V virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus).	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID711570	Inhibition of HIV-1 protease	2011	Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8	Synopsis of some recent tactical application of bioisosteres in drug design.
AID160767	Association rate constant for the interaction between inhibitor and HIV-1 protease	2002	Journal of medicinal chemistry, Dec-05, Volume: 45, Issue:25	Relationships between structure and interaction kinetics for HIV-1 protease inhibitors.
AID160475	Inhibitory activity against HIV-1 Protease	1996	Journal of medicinal chemistry, Jan-19, Volume: 39, Issue:2	A novel, picomolar inhibitor of human immunodeficiency virus type 1 protease.
AID82611	Antiviral activity against mutant virus HIV-1 mutant (84V/82F) strain	1998	Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13	Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID162710	Affinity against HIV protease	1997	Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25	Nonsymmetrically substituted cyclic urea HIV protease inhibitors.
AID160316	Binding affinity to inhibit the purified wild-type HIV-1 Protease	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID162696	Percent Inhibition against HIV-1 protease at 10 uM; nd= not determined.	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Cyclic HIV-1 protease inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities.
AID161876	Inhibitory activity against HIV-1 protease	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID163483	Binding affinity for HIV-1 protease enzyme was measured by using fluorescent peptide substrate	1998	Journal of medicinal chemistry, Apr-23, Volume: 41, Issue:9	Nonpeptide cyclic cyanoguanidines as HIV-1 protease inhibitors: synthesis, structure-activity relationships, and X-ray crystal structure studies.
AID210277	Inhibition of HIV RNA synthesis in T-cell line	1997	Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25	Nonsymmetrically substituted cyclic urea HIV protease inhibitors.
AID82610	Antiviral activity against mutant virus HIV-1 mutant (84V) strain	1998	Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13	Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID18152	Bioavailability in rat	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID711531	Antiviral activity against HIV-1	2011	Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8	Synopsis of some recent tactical application of bioisosteres in drug design.
AID235094	Resistance of constructed mutant 48V/90M virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus)	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID19831	Partition coefficient (logP) (HPLC)	1997	Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25	Nonsymmetrically substituted cyclic urea HIV protease inhibitors.
AID230790	Ability to increase whole-cell antiviral efficacy through better translation defined as the ratio between IC90 and Ki	1996	Journal of medicinal chemistry, May-24, Volume: 39, Issue:11	Preparation and structure-activity relationship of novel P1/P1'-substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors.
AID227243	Whole cell antiviral activity.	1998	Bioorganic & medicinal chemistry letters, Apr-07, Volume: 8, Issue:7	The synthesis and evaluation of cyclic ureas as HIV protease inhibitors: modifications of the P1/P1' residues.
AID162189	Inhibition concentration against HIV-1 protease	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Cyclic HIV-1 protease inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities.
AID13696	Bioavailability as maximal plasma concentration in dogs	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID104226	Antiviral potency evaluated by measuring accumulation of viral RNA transcripts 3 days after infection of MT-2 cells with HIV-1 RF	1998	Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13	Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID82912	HIV protease inhibition.	1998	Bioorganic & medicinal chemistry letters, Apr-07, Volume: 8, Issue:7	The synthesis and evaluation of cyclic ureas as HIV protease inhibitors: modifications of the P1/P1' residues.
AID160270	Binding affinity against HIV-1 protease	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Cyclic HIV-1 protease inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities.
AID235093	Resistance of constructed mutant 461/47V/50V virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus).	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID160766	Dissociation rate constant for the interaction between inhibitor and HIV-1 protease	2002	Journal of medicinal chemistry, Dec-05, Volume: 45, Issue:25	Relationships between structure and interaction kinetics for HIV-1 protease inhibitors.
AID160473	Inhibitory activity against HIV protease	1996	Journal of medicinal chemistry, May-24, Volume: 39, Issue:11	Preparation and structure-activity relationship of novel P1/P1'-substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors.
AID82612	Antiviral activity against ritonavir virus (HIV-1 mutated at 46I/63P/71V/82F/84V and resistant to ritonavir)	1998	Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13	Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID105206	Inhibitory concentration against accumulation of viral p24 antigen following infection of MT-4 cells	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID160292	Inhibition of HIV-1 protease	1999	Journal of medicinal chemistry, Jan-28, Volume: 42, Issue:2	Three-dimensional quantitative structure-activity relationship study on cyclic urea derivatives as HIV-1 protease inhibitors: application of comparative molecular field analysis.
AID104228	Inhibition of viral infection in HIV-1 (RF)-infected MT-2 cells with an oligonucleotide-based sandwich hybridization assay.	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID210298	The concentration required to inhibit HIV-1 RNA synthesis by 90%. Viral RNA quantified by a sandwich hybridization assay	1996	Journal of medicinal chemistry, Oct-11, Volume: 39, Issue:21	HIV protease inhibitory bis-benzamide cyclic ureas: a quantitative structure-activity relationship analysis.
AID104232	The antiviral potency (IC90) was assessed by measuring their effect on the accumulation of viral RNA transcripts on HIV-1 RF infected MT-2 cells	1998	Journal of medicinal chemistry, Apr-23, Volume: 41, Issue:9	Nonpeptide cyclic cyanoguanidines as HIV-1 protease inhibitors: synthesis, structure-activity relationships, and X-ray crystal structure studies.
AID13698	Bioavailability as maximal plasma concentration in rats	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID163487	Inhibitory activity against HIV-1 protease	1996	Journal of medicinal chemistry, Oct-11, Volume: 39, Issue:21	HIV protease inhibitory bis-benzamide cyclic ureas: a quantitative structure-activity relationship analysis.
AID235095	Resistance of constructed mutant 82A virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus).	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID199081	Inhibition of virion associated RT activity relative to untreated, infected control in cord blood mononuclear cells (CBMC) infected with HIV -1 TC354 strain	2000	Journal of medicinal chemistry, Sep-21, Volume: 43, Issue:19	Synthesis, stability, antiviral activity, and protease-bound structures of substrate-mimicking constrained macrocyclic inhibitors of HIV-1 protease.
AID104225	Antiviral potency was assessed by measuring the effect on accumulation of viral RNA transcripts 3 days after infection of MT-2 cells with HIV-1 RF	1996	Journal of medicinal chemistry, May-24, Volume: 39, Issue:11	Preparation and structure-activity relationship of novel P1/P1'-substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors.
AID235098	Resistance of constructed mutant ABT538 virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus)	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID235096	Resistance of constructed mutant 82F virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus).	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID235099	Resistance of constructed mutant MK639 virus was calculated as (IC90 for a mutant virus / IC90 of wt HXB2 virus).	1997	Journal of medicinal chemistry, Jan-17, Volume: 40, Issue:2	Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
AID160474	Inhibitory activity against HIV protease	1998	Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13	Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID105327	In vitro effective concentration against MT-4 cell line	1996	Journal of medicinal chemistry, Jan-19, Volume: 39, Issue:2	A novel, picomolar inhibitor of human immunodeficiency virus type 1 protease.
AID162706	Equilibrium constant for the interaction between inhibitor and HIV-1 Protease	2002	Journal of medicinal chemistry, Dec-05, Volume: 45, Issue:25	Relationships between structure and interaction kinetics for HIV-1 protease inhibitors.
AID18151	Bioavailability in dog	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID160455	Inhibition constant against HIV-1 Protease	2002	Journal of medicinal chemistry, Dec-05, Volume: 45, Issue:25	Relationships between structure and interaction kinetics for HIV-1 protease inhibitors.
AID82609	Antiviral activity against indinavir virus (HIV-1 mutated at 10R/63P/71V/82F/84V and resistant to indinavir)	1998	Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13	Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
AID1811	Experimentally measured binding affinity data derived from PDB	1997	Biochemistry, Feb-18, Volume: 36, Issue:7	Molecular basis of HIV-1 protease drug resistance: structural analysis of mutant proteases complexed with cyclic urea inhibitors.
AID977610	Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB	1997	Biochemistry, Feb-18, Volume: 36, Issue:7	Molecular basis of HIV-1 protease drug resistance: structural analysis of mutant proteases complexed with cyclic urea inhibitors.
AID977610	Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID1811	Experimentally measured binding affinity data derived from PDB	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID1795299	Protease Inhibition Assay from Article 10.1021/jm960728j: \\Cyclic HIV-1 protease inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities.\\	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Cyclic HIV-1 protease inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities.
AID1795214	Protease Inhibition Assay from Article 10.1021/jm9602571: \\Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.\\	1996	Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18	Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas.
AID1799449	Protease Inhibtion Assay from Article 10.1016/s1074-5521(98)90117-x: \\Design and selection of DMP 850 and DMP 851: the next generation of cyclic urea HIV protease inhibitors.\\	1998	Chemistry & biology, Oct, Volume: 5, Issue:10	Design and selection of DMP 850 and DMP 851: the next generation of cyclic urea HIV protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	27 (67.50)	18.2507
2000's	10 (25.00)	29.6817
2010's	3 (7.50)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.44%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	40 (97.56%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.06	1	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
carbamates [no description available]	2.01	1	amino-acid anion
phenol [no description available]	2.06	1	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	5.81	29	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	2.06	1	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
celecoxib [no description available]	2.06	1	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.06	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	2.06	1	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
nimesulide nimesulide: structure. nimesulide : An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.	2.06	1	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
pd 153035 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline: structure given in first source. PD-153035 : A member of the class of quinazolines carrying a 3-bromophenylamino substituent at position 4 and two methoxy substituents at positions 6 and 7.	2.06	1	aromatic amine; aromatic ether; bromobenzenes; quinazolines; secondary amino compound	EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist
trifluperidol Trifluperidol: A butyrophenone with general properties similar to those of HALOPERIDOL. It is used in the treatment of PSYCHOSES including MANIA and SCHIZOPHRENIA. (From Martindale, The Extra Pharmacopoeia, 30th ed, p621)	2.06	1	aromatic ketone
venlafaxine venlafaxine : A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-methoxyphenyl group.	2.06	1	cyclohexanols; monomethoxybenzene; tertiary alcohol; tertiary amino compound	adrenergic uptake inhibitor; analgesic; antidepressant; dopamine uptake inhibitor; environmental contaminant; serotonin uptake inhibitor; xenobiotic
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.06	1	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	1.99	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.01	1	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
mannitol [no description available]	1.99	1	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	1.98	1	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
nifenalol nifenalol: adrenergic beta-blocker with good antiarrhythmic properties; also tends to lower blood pressure & provide protection against angina; minor descriptor (75-86); on-line & INDEX MEDICUS search ETHANOLAMINES (75-86); RN given refers to parent cpd without isomeric designation	2.06	1	C-nitro compound
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	1.99	1	indazole
2'-deoxyadenosine triphosphate 2'-deoxyadenosine triphosphate: RN given refers to unlabeled parent cpd	2.06	1	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.01	1	chromium group element atom	micronutrient
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.06	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
kynostatin 272 kynostatin 272: structure given in first source; contains allophenylnorstatine as a transition-state mimic	1.99	1	peptide
nelfinavir Nelfinavir: A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.. nelfinavir : An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.	2.41	2	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor
thymidine 5'-triphosphate thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.	2.06	1	pyrimidine 2'-deoxyribonucleoside 5'-triphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
amprenavir [no description available]	3.25	6	carbamate ester; sulfonamide; tetrahydrofuryl ester	antiviral drug; HIV protease inhibitor
2'-deoxycytidine 5'-triphosphate 2'-deoxycytidine 5'-triphosphate: RN given refers to unlabeled parent cpd	2.06	1	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
5,6,7,8-tetrahydro-1-naphthol 5,6,7,8-tetrahydro-1-naphthol : 1-naphthol hydrogenated at C-5, -6, -7 and -8.	2.06	1	tetralins
estrone 3-methyl ether estrone 3-methyl ether: RN given refers to cpd with unspecified isomeric designation; structure	2.06	1
hexacarbonyltungsten hexacarbonyltungsten: C6-O6-W	2.01	1
sc 58125 1-((4-methylsulfonyl)phenyl)-3-trifluoromethyl-5-(4-fluorophenyl)pyrazole: a COX-2 inhibitor	2.06	1	organofluorine compound; pyrazoles; sulfone	antineoplastic agent; cyclooxygenase 2 inhibitor
bmy 45778 BMY 45778: structure given in first source; partial prostacyclin agonist	2.06	1	bisoxazole	partial prostacyclin agonist
exp7711 EXP7711: to search, use E#P7711(nm); angiotensin II receptor antagonist; structure given in first source	2.06	1
bmy 42393 BMY 42393: partial prostacyclin agonist	2.06	1
mk 996 MK 996: an AT1-selective angiotensin II receptor antagonist; structure given in first source	2.06	1
ezetimibe Ezetimibe: An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.. ezetimibe : A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).	2.06	1	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
dmp 450 DMP 450: structure in first source	10.18	15
l 158809 L 158809: RN & structure given in first source; angiotensin receptor antagonist	2.06	1
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	3.38	7	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
xv 638 XV638 : A member of the class of diazepanones that is 1,3-diazepane which is substituted by a 3-(1,3-thiazol-2-ylcarbamoyl)benzyl group at positions 1 and 3, oxo group at position 2, hydroxy groups at positions 5S and 6S, and benzyl groups at positions 4R and 7R. It is a potent HIV-1 protease inhibitor.	3.09	5	1,3-thiazoles; benzamides; diazepanone; diol; secondary alcohol; secondary carboxamide; ureas	HIV protease inhibitor
saquinavir Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.	3.09	5	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
a 76928 A 76928: a diol with C2-symmetry	1.99	1
xk 263 [no description available]	2.91	4
dmp 850 DMP 850: structure in first source	1.99	1
telaprevir [no description available]	2.06	1	cyclopentapyrrole; cyclopropanes; oligopeptide; pyrazines	antiviral drug; hepatitis C protease inhibitor; peptidomimetic
chaetomellic acid a chaetomellic acid A: structure given in first source; an inhibitor of farnesyl-protein transferase	2.06	1
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	1.98	1
ophiocordin azepinostatin: isolated from Fusarium merismoides; structure in first source; RN assigned by CAS - 63590-19-2 (ophiocordin; azepinostatin is not the same as ophiocordin)	2.06	1
upf 596 UPF 596: structure in first source	2.06	1
iloprost Iloprost: An eicosanoid, derived from the cyclooxygenase pathway of arachidonic acid metabolism. It is a stable and synthetic analog of EPOPROSTENOL, but with a longer half-life than the parent compound. Its actions are similar to prostacyclin. Iloprost produces vasodilation and inhibits platelet aggregation.. iloprost : A carbobicyclic compound that is prostaglandin I2 in which the endocyclic oxygen is replaced by a methylene group and in which the (1E,3S)-3-hydroxyoct-1-en-1-yl side chain is replaced by a (3R)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl group. A synthetic analogue of prostacyclin, it is used as the trometamol salt (generally by intravenous infusion) for the treatment of peripheral vascular disease and pulmonary hypertension.	2.06	1	carbobicyclic compound; monocarboxylic acid; secondary alcohol	platelet aggregation inhibitor; vasodilator agent
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	3.39	7	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
u 75875 U 75875: structure given in first source	2.01	1
way 133537 [no description available]	2.06	1
dpc 423 [no description available]	2.06	1
snap 6201 [no description available]	2.06	1
deoxyguanosine triphosphate [no description available]	2.06	1	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-triphosphate	Arabidopsis thaliana metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.06	1	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor

Condition	Indicated	Relationship Strength	Studies	Trials
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	0	1.99	1	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	0	2.4	2	0

dmp 323

Description

Cross-References

Synonyms (36)

Research Excerpts

Overview

Effects

Bioavailability

Roles (2)

Drug Classes (2)

Protein Targets (13)

Inhibition Measurements

Activation Measurements

Other Measurements

Bioassays (53)

Research

Studies (40)

Market Indicators

Research Demand Index: 15.62

Study Types

dmp 323

Description

Cross-References

Synonyms (36)

Research Excerpts

Overview

Effects

Bioavailability

Roles (2)

Drug Classes (2)

Protein Targets (13)

Inhibition Measurements

Activation Measurements

Other Measurements

Bioassays (53)

Research

Studies (40)

Market Indicators

Research Demand Index: 15.62

Study Types

Related Drugs (57)

Related Conditions (2)