Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01220)
Name
Lonafarnib
Synonyms    Click to Show/Hide the Synonyms of This API
Lonafarnib; 193275-84-2; Sarasar; Sch66336; Sch 66336; Sch-66336; UNII-IOW153004F; Lonafarnib (SCH66336); CHEMBL298734; IOW153004F; (R)-4-(2-(4-(3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)piperidin-1-yl)-2-oxoethyl)piperidine-1-carboxamide; 1-Piperidinecarboxamide, 4-(2-(4-((11R)-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-yl)-1-piperidinyl)-2-oxoethyl)-; 1-PIPERIDINECARBOXAMIDE, 4-[2-[4-[(11R)-3,10-DIBROMO-8-CHLORO-6,11-DIHYDRO-5H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN-11-YL]-1-PIPERIDINYL]-2-OXOETHYL]-; 4-(2-{4-[(11R)-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide; SMR004701448; 193275-86-4; Lonafarnib (USAN/INN); Lonafarnib [USAN:INN]; C27H31Br2ClN4O2; lonafarnibum; Zokinvy; 4-(2-(4-(8-Chloro-3,10-dibromo-6,11-dihydro-5H-benzo-(5,6)-cyclohepta(1,2-b)-pyridin-11(R)-yl)-1-piperidinyl)-2-oxo-ethyl)-1-piperidinecarboxamide; SCH-066336; 4-[2-[4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-piperidinyl]-2-oxoethyl]-1-piperidinecarboxamide; 1o5m; (non-labelled)Lonafarnib-d9; SCHEMBL19032; Sarasar; ; ; SCH 66336; (+)-4-(2-(4-(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-yl)-piperidin-1-yl))-2-oxoethyl)-piperidine-1-carboxamide; cc-590; MLS006010423; MLS006011106; GTPL8024; Lonafarnib, >=98% (HPLC); BDBM14459; CHEBI:47097; DTXSID90172927; BCP07027; EX-A1630; ZINC3950115; NSC719467; s2797; AKOS005145760; CCG-270312; CS-0792; DB06448; NSC-719467; SB16694; NCGC00346707-01; 1-Piperidinecarboxamide, 4-(2-(4-((11R-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-yl)-1-piperidinyl)-2-oxoethyl)-; AC-32661; AS-56182; HY-15136; SW220034-1; Y0240; Lestaurtinib/CEP-701/KT-5555/SPM-924; A12328; D04768; S-7680; W-5338; 117735-EP2295426A1; 117735-EP2295427A1; 117735-EP2298768A1; J-514232; Q3258910; (+)-4-[2-[4-(8-Chloro-3,10-dibromo-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(R)-yl)-1-piperidin-yl]-2-oxo-ethyl]-1-piperidinecarboxamide; (+)-4[2-[4-(8-Chloro-3,11-dihydro-5H-benzo[5,6] cyclohepta[1,2-b]-pyridin-11(R)-yl-1-piperidinyl]-2-oxo-ethyl]-1-piperidinecarboxamide; 4-(2-{4-[(2R)-6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide; 4-[2-[4-[(11R)-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[1,2]cyclohepta[2,4-b]pyridin-11-yl]piperidin-1-yl]-2-oxoethyl]piperidine-1-carboxamide; 4-[2-[4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5h-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-Piperidinyl]-2-oxoethyl]-1-Piperidi necarboxamide
Clinical Status
Approved
PubChem CID
148195
Formula
C27H31Br2ClN4O2
Canonical SMILES
C1CN(CCC1CC(=O)N2CCC(CC2)[C@@H]3C4=C(CCC5=C3N=CC(=C5)Br)C=C(C=C4Br)Cl)C(=O)N
InChI
1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1
InChIKey
DHMTURDWPRKSOA-RUZDIDTESA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=148195"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 638.8 Topological Polar Surface Area 79.5
XlogP 4.8 Complexity 790
Heavy Atom Count 36 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Lonafarnib 50 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Croscarmellose Sodium; Magnesium Stearate; Poloxamer 188; Povidone; Silicon Dioxide; Gelatin; Titanium Dioxide; Yellow Iron Oxide; Red Iron Oxide; Ammonia Solution; Black Iron Oxide; Butyl Alcohol; Dehydrated Alcohol; Isopropyl Alcohol; Potassium Hydroxide; Propylene Glycol; Purified Water; Shellac
                   Dosage Form Capsule
                   Company Eiger Biopharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [1]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [3]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Lonafarnib 75 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Croscarmellose Sodium; Magnesium Stearate; Poloxamer 188; Povidone; Silicon Dioxide; Gelatin; Titanium Dioxide; Yellow Iron Oxide; Red Iron Oxide; Ammonia Solution; Black Iron Oxide; Butyl Alcohol; Dehydrated Alcohol; Isopropyl Alcohol; Potassium Hydroxide; Propylene Glycol; Purified Water; Shellac
                   Dosage Form Capsule
                   Company Eiger Biopharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [1]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [3]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
2 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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