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 A4
Genes
HSA1573(CYP2J2) 1576(CYP3A4)
PTR456896(CYP2J2) 463582(CYP3A4)
PPS100976899(CYP3A4) 100984148(CYP2J2)
GGO101148349 101149513
PON100436782 100447634
NLE100589053 100593175
MCC678670(CYP3A4) 693631
MCF102119662(CYP2J2) 102144258(CYP3A4)
CSAB103224719(CYP2J2) 103246766
CATY105584402 105595967
PANU101015175 101026757 116276324 116276330
TGE112621193 112630798
RRO104668045 104673585
RBB108532916 108538168
TFN117072034 117091994
PTEH111522986 111530171 111534893
CJC100397287(CYP2J2) 100404344(CYP3A4)
SBQ101037403 101041470
CSYR103252931 103256114
MMUR105868328 105868331 105882593 105882595 105882596
OGA100948865 100950432 100950736 100951049 100951361
MMU100066(Cyp2j11) 13109(Cyp2j5) 13110(Cyp2j6) 230459(Cyp2j13) 242546(Cyp2j12) 665095(Cyp2j8) 74519(Cyp2j9)
MCAL110292385 110292662 110292766 110293055 110293363 110293364 110306650
MPAH110323111 110323251 110323340 110323372 110323386 110323498
RNO100912642 313373(Cyp2j10) 313375(Cyp2j3) 502969(Cyp2j16) 65210(Cyp2j4)
MCOC116095445 116095729 116095730 116096253 116096254 116096255 116096256
MUN110560670 110560674 110560675 110562464 110562465 110562466 110562514
CGE100764171 100764471 100764768 100765057
PLEU114681971 114681974 114681989 114681994 114689366 114693759 114693760 114693761 114693762 114693764
NGI103730878 103730879 103730880 103737136
HGL101719021 101719368
CCAN109684284
DORD105989978 105990009
DSP122108987 122111431
NCAR124966849
OCU100301544(CYP2J1)
OPI101531357 101531516
TUP102490783 102491196 102491623 102492033 102492447
CFA610195(CYP2J2)
VVP112926087
VLG121499260
AML100482335
UMR103663082
UAH113254606
UAR123795371
ELK111143525
LLV125097704
MPUF101684683
ORO101382939
EJU114212028
ZCA113926705
MLX118020215
FCA101097746
PYU121027220
PBG122480573
PTG102958105
PPAD109266776
AJU106974984
HHV120236077
BTA107132327 510406(CYP2J2) 511936 521656 530929
BOM102283844 102284389
BIU109556228 109556861
BBUB102409898 102410549 102411225 102411786
CHX102184867 102190572 102190840 102191099
OAS101104943 101121563 101121820 768095(CYP2J)
ODA120856578 120857076 120857077 120857078 120857079
CCAD122436913 122436914 122436915 122436916
SSC100524750(CYP2J34) 100524940 100525112 100621407 110261221
CFR102509190 102509309 102511878 102518893
CBAI105064824 105064834 105064844 105064851 105065015
CDK105092804 105092849 105096275 105096288
VPC102524867 102535306 102535561 102535809 102536059 102536560 102543101 102543350
LVE103072875
OOR101287985
DLE111175878
PCAD102995526
PSIU116764420
ECB100067247
EPZ103564165
EAI106833456
MYB102259820
MYD102765527
MMYO118676695
MLF102439141
MNA107531748
PKL118723974 118723975
HAI109371253 109389703 109389708
AJM119042498
PDIC114496360 114496679 114497261 114497336
PHAS123816495 123830867 123831702
MMF118627182
RFQ117026547 117026565 117027269
PALE102885276
PGIG120621913
PVP105303444
RAY107518358
TOD119236796 119236797
SARA101547147 101547409 101547677 101547951 101558147 101558420
LAV100658115 100670142
TMU101350163
DNM101411038 101437056 101438656 101439086 101439781 101440211 101440653 101447575
MDO100031902 100031907 100031914 100031960 100031971 100031975 100031980 100031984
GAS123243734 123245774 123245775 123245776 123247875 123247893
SHR100921692 100921949 100922742 100922989
PCW110212934 110212942 110212976 110212978
OAA100087745
GGA101750603(CYP2J21) 424676(CYP2J23) 424677(CYP2J22) 424729(CYP2J19)
PCOC116235297 116236300 116236311
MGP100547794 104912427 104912428 104912494
CJO107317676 107317691 107317696
NMEL110402810 110402814
APLA101792912 101796247
ACYG106032922 106033102
AFUL116491839 116491861
TGU100224220(CYP2J40) 100230439(CYP2J19A)
LSR110477035 110477061
SCAN103815060 103815209(CYP2J19)
PMOA120503273 120503274
OTC121345089 121345090
PRUF121362071 121362072
GFR102032779 102039653
FAB101811920 101817417
PHI102099263 102112918
PMAJ107208256 107208257
CCAE111932992 111932994
CCW104695151 104695152
ETL114069063
ZAB102067922
FPG101919387
CLV102088854 102089036 102093649 102094339
EGZ104123882 104123941
NNI104009259 104009336
ACUN113483076 113483077
TALA104356817 104369422 116964786 122152520
PADL103913325 103913366
ACHC115349168 115349169
AROW112967651 112976566
NPD112942289 112948473 112948476 112948493
DNE112991483 112991487
ASN102371261 102371780
AMJ102557714(CYP2P10)
CPOO109307018
GGN109305297
PSS102449417 102457302(CYP2J19) 102460777
CMY102936353 102940076(CYP2J19)
CPIC101931915 101938148(CYP2J19) 101939779 103305685
TST117882110
CABI116833772
MRV120370576 120370577 120370720 120370721
ACS100567522
SUND121927978 121927980 121927981
VKO123018898 123019432 123019440 123019512 123025295 123025296 123025297 123025298 123025301
PMUA114598918 114598919 114598920 114598921 114598923 114598924 114598925
ZVI118088450 118088451 118088452 118088453 118088455 118088457
GJA107111277 107114997
STOW125437750 125437751 125437990
DRE100034366(cyp2p8) 100034406(cyp2p7) 393108(cyp2p6) 393592(cyp2p9) 399485(cyp2p10) 797309(cyp2j20)
SRX107737305
SANH107665313
SGH107556152 107556153
CCAR109081729 109112720 109112721 109112722
CAUA113059714 113062930 113062932 113062933 113062936 113063170 113077208
PPRM120493435 120495341
MAMB125271930 125277848 125277849 125277850 125277851 125277854 125277856
AMEX103037239
EEE113568096 113586377
TRU101075700
LCO104930795 104930796
CGOB115007060
ELY117253502 117253503 117253504
PLEP121939575 121939585
SLUC116063278
ECRA117950841
PFLV114560939
PPUG119216714
MSAM119900968 119900969 119900982 119901367
CUD121511981 121511983 121511984 121511985
MZE101469747 101471484 101471776 101472450 101472746 101473039 101473341 101473625 101474137 112429716 112430356 112430410
ONL100699361 100699634 100699898 100700165 100700439 100700441 100700978 100701255 100701799 109194408 109196838 109196840
OAU116315351 116327896 116327898 116331077 116331078 116331079 116331081 116331082 116331187 116331213 120436259 120436353
OLA100302452(cyp2p3) 105353996
OML112138317 112150360 112150361 112150362 118597890
XMA102216555 102216815 102224544 102235118 102238098 102238367
XCO114150919 114150920 114150922
XHE116725631 116725632 116725633 116725634 116725636 116725637 116725638 116725642 116725644
PRET103461257 103463736 103463738 103463739
PFOR103137021 103137022 103137164 103137165
PLAI106949663 106949692 106949693 106949694 106961243 106961249
PMEI106908422 106908423 106917754 106917779 106917780
GAF122838407 122838408 122838409 122838410 122838411
CVG107095777 107099581
CTUL119777086 119790019 119790034
GMU124873252 124873920
NFU107395372 107395373
KMR108230681 108230682 108230683 108230684 108230685
ALIM106517296 106517297 106517298
NWH119421487 119430737
AOCE111563453 111564682 111564718 111564989 111564993 111586280 111586281 111586282
CSEM103383190
POV109625616
SSEN122777824 122777825
LCF108879066 108879067
SDU111232055 111232106
SLAL111653766 111656353
BPEC110173990
SASA106584062
OTW112250281
OMY110521776
OGO124038052
ONE115145370
SALP111971193
SNH120052641
ELS105025359
SFM108923501 108923503 108927875 108934003 108935367 108935464 114909092 114911247 114911248 114911249 114911250 114911251 114911252 114911257 114911278
PKI111834855 111834857 111834858 111834859
AANG118224796 118224797 118224802
PSPA121327058 121330919
ARUT117409945 117409954 117417241 117417316
CMK103185273
RTP109921744
BFO118405297 118407101 118419304 118428418 118428431 118429635 118432366
BBEL109461524 109461651 109461725 109461727 109462264 109465453 109465656 109466367 109467919 109471284 109472128 109472267 109472270 109475266 109477936 109480295 109482013 109482167 109483920 109483935 109483947 109483948 109485002 109487178
SCLV120333811 120334172 120334246 120335033 120342965 120343352
PVM113807691
PJA122242547 122243682 122252347 122252348 122259834 122259836 122260679 122263851
PCHN125027237 125037284 125037285 125037286 125037288 125037553 125040652 125047318 125047985
HAME121853159 121857091 121863598 121874841
PCLA123746738 123751553 123756377 123767033 123767752 123770238 123770240
PTRU123506617 123506674 123514413 123517642
HAZT108665745 108667157 108667158 108674876 108676835
EAF111695177 111696904 111696905 111698334 111704925 111704939 111706377 111709242 111713706 111717082 111717477 111718077
LSM121115047 121119889 121121717
DSV119441628 119457522 119459311 119461188 119461547 119462117
RSAN119374231 119382467 119383506 119383507 119386647 119390617 119397387 119406751
RMP119161891 119166963 119169660 119171404 119173720
VDE111244479
VJA111272117
SDM118180345 118185452 118189454 118190843 118190848 118202040 118203101 118206070
BGT106054489 106054491 106054493 106055467 106057592 106057638 106059997 106059999 106060000 106069709 106070555 106074975 106075280
GAE121374745 121382078
HRF124113283 124118458 124118459 124118462 124123854 124124584 124125095 124140343 124140344 124144343 124144711 124145712 124145752 124147838 124147839 124147840 124152329
HRJ124253755 124261308 124267336 124267348 124270526 124272540 124279341 124281198 124281746 124285163 124290622 124290663 124291032 124291033 124291034
CRG105326330 105329932 105332463 105333819 105333882 117689293 117689294
PMAX117316069 117343471
MMER123535803 123536866 123543547 123556433 123558935
OSN115217140 115217142 115220404 115224293 115227007 115231155 115232209
XEN124445682
 » 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

DBGET integrated database retrieval system