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

General Information of Drug (ID: DR1252)
Drug Name
Pentamidine isethionate
Synonyms
Pentamidine (isethionate); Pentamidine diisethionate; Pentamidine isethionate salt; Pentamidine isothionate; Pentaminide isetionate; USAF XR-10; V2P3K60DA2; 1,5-Bis(p-amidinophenoxy)pentane bis(2-hydroxyethanesulfonate salt); 140-64-7; 4,4'-(Pentamethylenedioxy)dibenzamidine bis(2-hydroxyethanesulfonate); 4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide bis(2-hydroxyethanesulfonate); CCRIS 1660; CHEBI:7977; MFCD00079213; UNII-V2P3K60DA2; PENTAMIDINE ISETHIONATE; Nebupent (as isethionate); Pentacarinat (as isethionate); Pentam 300 (as isethionate); Pentamide; Pentamidin; Pentamidina; Pentamidina [DCIT]; Pentamidine [INN:BAN:DCF]; Pentamidine mesylate; Pentamidinum; Pentamidinum [INN-Latin]; pentamidine; 100-33-4; 4,4'-(Pentamethylenedioxy)dibenzamidine; 4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide; 4,4'-Diamidinodiphenoxypentane; CCRIS 3825; UNII-673LC5J4LQ; p,p'-(Pentamethylenedioxy)dibenzamidine
Indication Pneumocystis pneumonia [ICD11: CA40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 592.7 Topological Polar Surface Area 284
Heavy Atom Count 39 Rotatable Bond Count 14
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
8813
ChEBI ID
CHEBI:7977
CAS Number
140-64-7
TTD Drug ID
D05EAM
Formula
C23H36N4O10S2
Canonical SMILES
C1=CC(=CC=C1C(=N)N)OCCCCCOC2=CC=C(C=C2)C(=N)N.C(CS(=O)(=O)O)O.C(CS(=O)(=O)O)O
InChI
1S/C19H24N4O2.2C2H6O4S/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23;2*3-1-2-7(4,5)6/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23);2*3H,1-2H2,(H,4,5,6)
InChIKey
YBVNFKZSMZGRAD-UHFFFAOYSA-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
Pentamidine Amidoxime DM001191
5480203
Oxidation - N-Hydroxylation 1 [3] , [4]
Pentamidine isethionate DM003075
8813
Unclear 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001972 Pentamidine isethionate Pentamidine Amidoxime Oxidation - N-Hydroxylation CYP3A5 ... [3], [4]
MR001973 Pentamidine isethionate Pentamidine isethionate Unclear Unclear [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Lauric acid omega-hydroxylase (CYP4A11) DME0029 Homo sapiens
CP4AB_HUMAN
1.14.15.3
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 8  DME(s)
References
1 Pentamidine Isethionate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. doi: 10.1007/s00228-003-0636-9.
3 Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42.
4 Value of preemptive CYP2C19 genotyping in allogeneic stem cell transplant patients considered for pentamidine administration. Clin Transplant. 2011 May-Jun;25(3):E271-5.

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