| ID Source | ID |
|---|---|
| PubMed CID | 65914 |
| CHEMBL ID | 454095 |
| CHEMBL ID | 87602 |
| SCHEMBL ID | 635373 |
| MeSH ID | M0173591 |
| Synonym |
|---|
| brn 3657541 |
| abecarnilum [inn-latin] |
| isopropyl 6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylate |
| isopropyl 6-(benzyloxy)-4-(methoxymethyl)-9h-pyrido(3,4-b)indole-3-carboxylate |
| zk 112119 |
| abecarnil [inn] |
| 9h-pyrido(3,4-b)indole-3-carboxylic acid, 1-(methoxymethyl)-6-(phenylmethoxy)-, 1-methylethyl ester |
| sh-524 |
| zk-112119 |
| 111841-85-1 |
| D02594 |
| abecarnil (inn) |
| PDSP2_001738 |
| PDSP2_001758 |
| PDSP1_001775 |
| abecarnil |
| PDSP1_001755 |
| bdbm50244033 |
| isopropyl 6-(benzyloxy)-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate |
| propan-2-yl 4-(methoxymethyl)-6-phenylmethoxy-9h-pyrido[3,4-b]indole-3-carboxylate |
| CHEMBL454095 , |
| bdbm50065238 |
| 6-benzyloxy-4-methoxymethyl-9h-beta-carboline-3-carboxylic acid isopropyl ester(abecarnil) |
| 6-benzyloxy-4-methoxymethyl-9h-beta-carboline-3-carboxylic acid isopropyl ester |
| chembl87602 |
| abecarnilum |
| izm1pnj3jl , |
| unii-izm1pnj3jl |
| SCHEMBL635373 |
| 9h-pyrido(3,4-b)indole-3-carboxylic acid, 4-(methoxymethyl)-6-(phenylmethoxy)-, 1-methylethyl ester |
| abecarnil [who-dd] |
| abecarnil [mart.] |
| abecarnil [mi] |
| RLFKILXOLJVUNF-UHFFFAOYSA-N |
| 6-benzyloxy-4-methoxymethyl-9h-pyrido[3,4-b]indole-3-carboxylic acid-(1-methyl-ethyl)-ester |
| 6-benzyloxy-4-methoxymethyl-9h-pyrido[3,4-b]indole-3-carboxylic acid-1-methylethyl-ester |
| 6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester |
| DTXSID40149745 |
| HY-105115 |
| Q4666461 |
| CS-0025044 |
Abecarnil (ABC) is a beta-carboline that acts as an agonist at benzodiazepine (BZD) receptors. It has potent anxiolytic activity but no muscle relaxant side effects in rodents.
Oral treatment with abecarnil (0.5-10 mg/kg) showed a potent anticonflict activity in the water-lick test in rats. Treatment with abECarnil prevented the severe signs of HPNS occurring between 51 and 91 ATA.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Oral treatment with abecarnil (0.5-10 mg/kg) showed a potent anticonflict activity in the water-lick test in rats." | ( Pharmacological characterization of the novel anxiolytic beta-carboline abecarnil in rodents and primates. Akai, T; Kuno, S; Mizuta, E; Nakada, Y; Ozawa, M; Sugimachi, K; Yabuuchi, F; Yamaguchi, M, 1994) | 0.84 |
| "Treatment with abecarnil prevented the severe signs of HPNS occurring between 51 and 91 ATA." | ( Interactions of the beta carboline abecarnil with the high pressure neurological syndrome in a primate model. Halsey, MJ; Jordan, CJ; MacLean, CJ; Mehta, RL; Meldrum, BS; Passingham, S; Pearce, PC; Pearson, J; Ward, EM, 1992) | 0.9 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Development of novel antiepileptic drugs (AEDs) requires determining the margin between the desired anticonvulsant effect and undesired adverse effects (AE) (therapeutic index)." | ( Kindling increases the sensitivity of rats to adverse effects of certain antiepileptic drugs. Hönack, D; Löscher, W, 1995) | 0.29 |
| " Safety and tolerability were evaluated by changes in vital signs, incidence and severity of adverse reactions and biochemical and haematological screening." | ( Human studies on abecarnil a new beta-carboline anxiolytic: safety, tolerability and preliminary pharmacological profile. Dorow, R; Duka, T; Fichte, K; Krause, W; McDonald, S; Schütt, B, 1993) | 0.63 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The terminal half-life of the unchanged drug in plasma was relatively similar in all species (0." | ( Pharmacokinetics of the anxiolytic beta-carboline derivative abecarnil in the mouse, rat, rabbit, dog, cynomolgus monkey and baboon. Studies on species differences. Krause, W; Mengel, H, 1990) | 0.52 |
| " Pharmacokinetic parameters were obtained with use of model-independent and model-dependent methods." | ( Pharmacokinetics of abecarnil in patients with renal insufficiency. Frye, RF; Hayes, PE; Karara, AH; Matzke, GR; Rault, RM; Robinson, WT; Weaver, ML, 1996) | 0.62 |
Abecarnil was rapidly and nearly completely absorbed after an oral dose of 10 mg; bioavailability was 40%. The bioavailability of abecarnill was 20-30% in all the species investigated.
Abecarnil (isopropyl-6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylate) was tested in healthy male subjects. Abrupt discontinuation at either dosage range causes definite rebound symptoms within the first week after withdrawal.
| Excerpt | Relevance | Reference |
|---|---|---|
| "1 mg/kg and oral dosing of 10 mg/kg using 14C-labeled drug and HPLC with fluorescence detection for measurement of the unchanged drug." | ( Placental transfer of the anxiolytic beta-carboline abecarnil in rabbit. Krause, W; Mechelke, B, 1992) | 0.53 |
| " Abecarnil (isopropyl-6-benzyloxy-4-methoxymethyl-beta-carboline-3-carboxylate), a beta-carboline with high affinity for benzodiazepine receptors, was tested in healthy male subjects; single doses of abecarnil were given in five dosage levels (1 mg, 5 mg, 10 mg, 20 mg, 40 mg) and in a multiple dose study in four dosage levels (15 mg, 30 mg, 60 mg, 90 mg day-1) for 7 days." | ( Human studies on abecarnil a new beta-carboline anxiolytic: safety, tolerability and preliminary pharmacological profile. Dorow, R; Duka, T; Fichte, K; Krause, W; McDonald, S; Schütt, B, 1993) | 1.54 |
| " Abrupt discontinuation of abecarnil at either dosage range causes definite rebound symptoms within the first week after withdrawal." | ( Double-blind, placebo-controlled trial of two doses of abecarnil for geriatric anxiety. Bystritsky, A; Small, GW, 1997) | 0.84 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Gamma-aminobutyric acid receptor subunit alpha-1 | Homo sapiens (human) | Kd | 0.0010 | 0.0001 | 0.0102 | 0.0760 | AID343089 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Homo sapiens (human) | Kd | 0.0084 | 0.0005 | 0.1283 | 0.8260 | AID343090 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1079941 | Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source] | |||
| AID71266 | Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-6-beta-3-gamma-2 | 2000 | Journal of medicinal chemistry, Jan-13, Volume: 43, Issue:1 | Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach. |
| AID343090 | Binding affinity to GABAA alpha-5-beta-2-gamma-2 receptor | 2008 | Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13 | Selective influence on contextual memory: physiochemical properties associated with selectivity of benzodiazepine ligands at GABAA receptors containing the alpha5 subunit. |
| AID1079947 | Comments (NB not yet translated). [column 'COMMENTAIRES' in source] | |||
| AID72927 | Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-1-beta-3-gamma-2 | 2000 | Journal of medicinal chemistry, Jan-13, Volume: 43, Issue:1 | Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach. |
| AID1079934 | Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source] | |||
| AID219953 | Binding affinity measured using LtK- cell membranes expressing GABA alpha-3-beta-3-gamma-2 receptor | 1998 | Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14 | Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) |
| AID1079938 | Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source] | |||
| AID1079944 | Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source] | |||
| AID73244 | Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-3-beta-3-gamma-2 | 2000 | Journal of medicinal chemistry, Jan-13, Volume: 43, Issue:1 | Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach. |
| AID219791 | Binding affinity measured using LtK- cell membranes expressing GABA alpha-1-beta-3-gamma-2 receptor | 1998 | Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14 | Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) |
| AID73089 | Binding affinity to human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-2-beta-3-gamma-2 | 2000 | Journal of medicinal chemistry, Jan-13, Volume: 43, Issue:1 | Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach. |
| AID1079940 | Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source] | |||
| AID1079932 | Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source] | |||
| AID73529 | Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyric acid A receptor alpha-5-beta-3-gamma-2 | 1998 | Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14 | Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) |
| AID1079948 | Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source] | |||
| AID1079945 | Animal toxicity known. [column 'TOXIC' in source] | |||
| AID343089 | Binding affinity to GABAA alpha-1-beta-2-gamma-2 receptor | 2008 | Journal of medicinal chemistry, Jul-10, Volume: 51, Issue:13 | Selective influence on contextual memory: physiochemical properties associated with selectivity of benzodiazepine ligands at GABAA receptors containing the alpha5 subunit. |
| AID1079933 | Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is | |||
| AID1079936 | Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source] | |||
| AID1079931 | Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source] | |||
| AID1079939 | Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source] | |||
| AID1079946 | Presence of at least one case with successful reintroduction. [column 'REINT' in source] | |||
| AID1079949 | Proposed mechanism(s) of liver damage. [column 'MEC' in source] | |||
| AID1079942 | Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source] | |||
| AID71267 | Binding affinity measured using LtK- cell membranes expressing Gamma-aminobutyric acid A receptor alpha-6-beta-3-gamma-2 | 1998 | Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14 | Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) |
| AID219938 | Binding affinity measured using LtK- cell membranes expressing GABA alpha-2-beta-3-gamma-2 receptor | 1998 | Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14 | Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) |
| AID1079943 | Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source] | |||
| AID73523 | Binding affinity for human recombinant gamma-aminobutyric-acid (GABA) A receptor alpha-5-beta-3-gamma-2 | 2000 | Journal of medicinal chemistry, Jan-13, Volume: 43, Issue:1 | Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach. |
| AID1079935 | Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source] | |||
| AID1079937 | Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source] | |||
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (1.10) | 18.7374 |
| 1990's | 73 (80.22) | 18.2507 |
| 2000's | 15 (16.48) | 29.6817 |
| 2010's | 2 (2.20) | 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] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (29.40) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 12 (12.50%) | 5.53% |
| Reviews | 13 (13.54%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 71 (73.96%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||