KEGG   ENZYME: 1.14.14.73
Entry
EC 1.14.14.73               Enzyme                                 

Name
albendazole monooxygenase (sulfoxide-forming);
albendazole sulfoxidase (ambiguous);
albendazole hydroxylase (ambiguous);
CYP3A4 (gene name);
CYP2J2 (gene name);
CYP1A2 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
albendazole,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (sulfoxide-forming)
Reaction(IUBMB)
(1) albendazole + [reduced NADPH---hemoprotein reductase] + O2 = albendazole S-oxide + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12068];
(2) fenbendazole + [reduced NADPH---hemoprotein reductase] + O2 = fenbendazole S-oxide + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12069]
Reaction(KEGG)
R12068 R12069
Substrate
albendazole [CPD:C01779];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
fenbendazole [CPD:C21876]
Product
albendazole S-oxide [CPD:C02809];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
fenbendazole S-oxide [CPD:C21882]
Comment
This is one of the activities carried out by some microsomal cytochrome P-450 monooxygenases. A similar conversion is also carried out by a different microsomal enzyme (EC 1.14.13.32, albendazole monooxygenase (flavin-containing)), but it is estimated that cytochrome P-450s are responsible for 70% of the activity.
History
EC 1.14.14.73 created 2018
Orthology
K07418  cytochrome P450 family 2 subfamily J
K17689  cytochrome P450 family 3 subfamily A polypeptide 4
Genes
HSA: 1573(CYP2J2) 1576(CYP3A4)
PTR: 456896(CYP2J2) 463582(CYP3A4)
PPS: 100976899 100984148
GGO: 101148349 101149513
PON: 100436782 100447634
NLE: 100589053 100593175
MCC: 678670(CYP3A4) 693631
MCF: 102119662(CYP2J2) 102144258(CYP3A8)
CSAB: 103224719(CYP2J2) 103246766
RRO: 104668045 104673585
CJC: 100397287(CYP2J2)
SBQ: 101041470
MMU: 100066(Cyp2j11) 13109(Cyp2j5) 13110(Cyp2j6) 230459(Cyp2j13) 242546(Cyp2j12) 665095(Cyp2j8) 74519(Cyp2j9)
RNO: 100912642 313373(Cyp2j10) 313375(Cyp2j3) 502969(Cyp2j16) 65210(Cyp2j4)
CCAN: 109684284
OCU: 100301544(CYP2J1)
CFA: 479740(CYP3A4) 610195(CYP2J2)
VVP: 112926087
AML: 100482335
UMR: 103663082
UAH: 113254606
ORO: 101382939
ELK: 111143525
FCA: 101097746
PTG: 102958105
PPAD: 109266776
AJU: 106974984
BIU: 109556228
OAS: 101121820 768095(CYP2J)
LVE: 103072875
OOR: 101287985
DLE: 111175878
PCAD: 102995526
ECB: 100067247
EPZ: 103564165
EAI: 106833456
MYB: 102259820
MYD: 102765527
MNA: 107531748
HAI: 109389708
PALE: 102885276
RAY: 107518358
TMU: 101350163
SHR: 100921692
OAA: 100087745
GGA: 101750603(CYP2J21) 424676(CYP2J23) 424677(CYP2J22)
CJO: 107317691
APLA: 101792912
ACYG: 106033102
TGU: 100224220(CYP2J40)
SCAN: 103815060 103815209(CYP2J19)
GFR: 102039653
FAB: 101817417
PHI: 102112918
PMAJ: 107208256
CCW: 104695151
FPG: 101919387
FCH: 102056779
EGZ: 104123941
AMJ: 102557714(CYP2P10)
CMY: 102940076(CYP2J19)
PVT: 110075668
PBI: 103061770
TSR: 106539643
DRE: 100034366(cyp2p8) 100034406(cyp2p7) 797309(cyp2j20)
SANH: 107665313
MZE: 112429716
OLA: 100302452(cyp2p3)
BPEC: 110173990
MALB: 109964028
SASA: 106584062
CMK: 103185273
RTP: 109921744
DMN: 117188691
AME: 727290
HST: 105187605
PGC: 109858307
OBO: 105280474
NVI: 100121599(Cyp303a1)
CSOL: 105360113
MDL: 103580958
TCA: 658783(CYP305A1)
DPA: 109543005
ATD: 109595197
BMOR: 101743283(CYP303A1)
BMAN: 114246377
PMAC: 106717103
PRAP: 111003399
API: 100162206
DNX: 107166593
AGS: 114124824
BTAB: 109029996
MYI: 110454048
OBI: 106870255
DFA: DFA_07281(CYP513C1)
 » show all
Reference
1  [PMID:7736906]
  Authors
Moroni P, Buronfosse T, Longin-Sauvageon C, Delatour P, Benoit E
  Title
Chiral sulfoxidation of albendazole by the flavin adenine dinucleotide-containing and cytochrome P450-dependent monooxygenases from rat liver microsomes.
  Journal
Drug Metab Dispos 23:160-5 (1995)
Reference
2  [PMID:10759686]
  Authors
Rawden HC, Kokwaro GO, Ward SA, Edwards G.
  Title
Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes.
  Journal
Br J Clin Pharmacol 49:313-22 (2000)
DOI:10.1046/j.1365-2125.2000.00170.x
Reference
3  [PMID:11137466]
  Authors
Asteinza J, Camacho-Carranza R, Reyes-Reyes RE, Dorado-Gonzalez V V, Espinosa-Aguirre JJ
  Title
Induction of cytochrome P450 enzymes by albendazole treatment in the rat.
  Journal
Environ Toxicol Pharmacol 9:31-37 (2000)
DOI:10.1016/S1382-6689(00)00059-4
Reference
4  [PMID:19923256]
  Authors
Lee CA, Neul D, Clouser-Roche A, Dalvie D, Wester MR, Jiang Y, Jones JP 3rd, Freiwald S, Zientek M, Totah RA.
  Title
Identification of novel substrates for human cytochrome P450 2J2.
  Journal
Drug Metab Dispos 38:347-56 (2010)
DOI:10.1124/dmd.109.030270
  Sequence
[hsa:1573]
Reference
5  [PMID:23959307]
  Authors
Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee DY, Lee SJ, Yea SS, Lee HS, Lee T, Liu KH
  Title
CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems.
  Journal
Antimicrob Agents Chemother 57:5448-56 (2013)
DOI:10.1128/AAC.00843-13
  Sequence
[hsa:1573]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.73
IUBMB Enzyme Nomenclature: 1.14.14.73
ExPASy - ENZYME nomenclature database: 1.14.14.73
BRENDA, the Enzyme Database: 1.14.14.73
CAS: 9059-22-7

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