Compound: Arterolane
SMILES: O=C(NCC(N)(C)C)CC1CCC2(OOC3(O2)C4CC5CC(C4)CC3C5)CC1
InChIKey: VXYZBLXGCYNIHP-UHFFFAOYSA-N
Synonyms: Arterolane, 664338-39-0, Glucoamylase, OZ277, Arterolane [INN], trioxolane, RBx11160, OZ 277, OZ-277, RBX-11160, 3N1TN351VB, arterolano, OZ 277;RBx 11160, N-(2-amino-2-methylpropyl)-2-{dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1''-cyclohexane]-4''-yl}acetamide, arterolanum, UNII-3N1TN351VB, OZ277 cpd, ARTEROLANE [WHO-DD], CHEMBL221773, CHEMBL404431, CHEMBL578577, CHEMBL580910, orb1707641, SCHEMBL4547841, CHEMBL1197433, CHEMBL1673202, SCHEMBL10307589, SCHEMBL11379522, SCHEMBL12612733, SCHEMBL13951812, DTXSID50985095, CHEBI:136054, VXYZBLXGCYNIHP-BBMJWGJISA-N, VXYZBLXGCYNIHP-CAGINOIPSA-N, GLXC-15807, RBx 11160, EX-A11058, MFCD18251543, AKOS040741167, AT25294, NCGC00274173-01, DA-71050, HY-10852, MS-26573, CS-0002648, DISPIRO(CYCLOHEXANE-1,3'-(1,2,4)TRIOXOLANE-5',2''-TRICYCLO(3.3.1.13,7)DECANE)-4-ACETAMIDE, N-(2-AMINO-2-METHYLPROPYL)-, CIS-, N-(2-AMINO-2-METHYLPROPYL)-2-((1R,3R,4''S,5R,5'S,7R)-DISPIRO[ADAMANTANE-2,3'-[1,2,4]TRIOXOLANE-5',1''-CYCLOHEXAN]-4''-YL)ACETAMIDE, N-(2-Amino-2-methylpropyl)-2-[(1s,1''s,3''s,4s)-dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.1~3,7~]decan]-4-yl]acetamide, N-(2-amino-2-methylpropyl)-2-[(1s,4s)-dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.1(3,7)]decan]-4-yl]acetamide
Theoretical properties:
molecular_formula: C22H36N2O4
molecular_weight: 392.5 g/mol
exact_mass: 392.26750763 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 28
topological_polar_surface_area: 82.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Arterolane is an oxaspiro compound that is dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.13,7]decane] substituted by a 2-[(2-amino-2-methylpropyl)amino]-2-oxoethyl group at position 4s. Its maleic acid salt is used as an antimalarial drug in combination with piperaquine. It has a role as an antimalarial and an antiplasmodial drug. It is a secondary carboxamide, a trioxolane, an oxaspiro compound, a primary amino compound and a member of adamantanes. It is a conjugate base of an arterolane(1+).
chebi: An oxaspiro compound that is dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.1<small><sup>3,7</small></sup>]decane] substituted by a 2-[(2-amino-2-methylpropyl)amino]-2-oxoethyl group at position 4<i>s</i>. Its maleic acid salt is used as an antimalarial drug in combination with piperaquine.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Arterolane, also known as OZ277 or RBx 11160, is an antimalarial compound marketed by Ranbaxy Laboratories. It was discovered by US and European scientists coordinated by the Medicines for Malaria Venture (MMV). Its molecular structure is uncommon for pharmacological compounds in that it has both an ozonide (trioxolane) group and an adamantane substituent.
Initial results were disappointing, and in 2007 MMV withdrew support, after having invested $20M in the research; Ranbaxy said at the time that it intended to continue developing arterolane in combination with another drug. In 2009, Ranbaxy started a Phase II clinical trial of arterolane in combination with piperaquine, and it was published in 2015.
In 2012, Ranbaxy obtained approval to market an arterolane/piperaquine combination drug in India, under the brand name Synriam. In 2014, the product was also approved in Nigeria, Uganda, Senegal, Cameroon, Guinea, Kenya and Ivory Coast.