Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1603)
Drug Name
LS-172108
Synonyms
Tirilazad; Tirilazad (INN); LS-172108; PNU 74006F; RBKASMJPSJDQKY-RBFSKHHSSA-N; SCHEMBL483318; Tirilazad [INN:BAN]; Tirilazadum; Tirilazadum [INN-Latin]; U 74006; YD064E883I; ZINC43133316; tirilazad of tirilazad; 110101-66-1; 21-[4-(2,6-Di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16-methylpregna-1,4,9(11)-triene-3,20-dione; AC1L2XOZ; C38H52N6O2; CHEBI:135853; CHEMBL1630578; D08606; DB13050; Pregna-1,4,9(11)-triene-3,20-dione, 21-(4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)erazinyl)-16-methyl-, (16alpha)-; S048; UNII-YD064E883I
Indication Cerebral stroke [ICD11: 8B11] Phase 1/2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 624.9 Topological Polar Surface Area 72.9
Heavy Atom Count 46 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
104903
ChEBI ID
CHEBI:135853
CAS Number
110101-66-1
Formula
C38H52N6O2
Canonical SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1C(=O)CN5CCN(CC5)C6=NC(=NC(=C6)N7CCCC7)N8CCCC8)C)C
InChI
1S/C38H52N6O2/c1-26-22-31-29-9-8-27-23-28(45)10-12-37(27,2)30(29)11-13-38(31,3)35(26)32(46)25-41-18-20-43(21-19-41)34-24-33(42-14-4-5-15-42)39-36(40-34)44-16-6-7-17-44/h10-12,23-24,26,29,31,35H,4-9,13-22,25H2,1-3H3/t26-,29-,31+,35-,37+,38+/m1/s1
InChIKey
RBKASMJPSJDQKY-RBFSKHHSSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
(6S,8S,10R,13S,14S,16R,17S)-17-[2-[4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)piperazin-1-yl]acetyl]-6-hydroxy-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one DM005751
9852390
Oxidation - Hydrolyzationn 1 [2]
17-[2-[4-(2,6-Dipyrrolidin-1-ylpyrimidin-4-yl)piperazin-1-yl]acetyl]-6-hydroxy-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one DM005752
77315328
Oxidation - Hydrolyzationn 1 [2]
17-[2-[4-[2-(3-Hydroxypyrrolidin-1-yl)-6-pyrrolidin-1-ylpyrimidin-4-yl]piperazin-1-yl]acetyl]-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one DM005753
154699585
Oxidation - Hydrolyzationn 1 [2]
17-[2-[4-[6-(3-Hydroxypyrrolidin-1-yl)-2-pyrrolidin-1-ylpyrimidin-4-yl]piperazin-1-yl]acetyl]-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one DM005754
154699747
Oxidation - Hydrolyzationn 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006136 LS-172108 (6S,8S,10R,13S,14S,16R,17S)-17-[2-[4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)piperazin-1-yl]acetyl]-6-hydroxy-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Oxidation - Hydrolyzationn CYP3A4 [2]
MR006137 LS-172108 17-[2-[4-(2,6-Dipyrrolidin-1-ylpyrimidin-4-yl)piperazin-1-yl]acetyl]-6-hydroxy-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Oxidation - Hydrolyzationn CYP3A4 [2]
MR006138 LS-172108 17-[2-[4-[2-(3-Hydroxypyrrolidin-1-yl)-6-pyrrolidin-1-ylpyrimidin-4-yl]piperazin-1-yl]acetyl]-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Oxidation - Hydrolyzationn CYP3A4 [2]
MR006139 LS-172108 17-[2-[4-[6-(3-Hydroxypyrrolidin-1-yl)-2-pyrrolidin-1-ylpyrimidin-4-yl]piperazin-1-yl]acetyl]-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Oxidation - Hydrolyzationn CYP3A4 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Tirilazad mesylate in acute ischemic stroke: A systematic review. Tirilazad International Steering Committee. Stroke. 2000 Sep;31(9):2257-65.;
2 Biotransformation of tirilazad in human: 1. Cytochrome P450 3A-mediated hydroxylation of tirilazad mesylate in human liver microsomes. J Pharmacol Exp Ther. 1996 May;277(2):982-90.

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