Entry
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
BRITE hierarchy
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)
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
HSA : 1573(CYP2J2) 1576(CYP3A4)
PTR : 456896(CYP2J2) 463582(CYP3A4)
PPS : 100976899(CYP3A4) 100984148(CYP2J2)
PPYG : 129016979 129041698
SSYN : 129458528 129489604
MCC : 678670(CYP3A4) 693631
MCF : 102119662(CYP2J2) 102144258(CYP3A4)
MTHB : 126950475 126962785
CSAB : 103224719(CYP2J2) 103246766
CATY : 105584402 105595967
PANU : 101015175 101026757 116276324 116276330
MLEU : 105534929 105543708
PTEH : 111522986 111530171 111534893
CANG : 105511111 105513064
CJC : 100397287(CYP2J2) 100404344(CYP3A4)
CIMI : 108308036(CYP3A4) 108314910(CYP2J2)
ANAN : 105710194(CYP2J2) 105719456(CYP3A4)
CSYR : 103252931 103256114
MMUR : 105868328 105868331 105882593 105882595 105882596
LCAT : 123631591 123631593 123635586 123635587 123635588
PCOQ : 105806078 105806372 105806374
OGA : 100948865 100950432 100950736 100951049 100951361
MMU : 100066(Cyp2j11) 13109(Cyp2j5) 13110(Cyp2j6) 230459(Cyp2j13) 242546(Cyp2j12) 546837(Cyp2j7) 665095(Cyp2j8) 74519(Cyp2j9)
MCAL : 110292385 110292662 110292766 110293055 110293363 110293364 110306650
MPAH : 110323111 110323251 110323340 110323372 110323386 110323498
RNO : 100912642 313373(Cyp2j10) 313375(Cyp2j3) 502969(Cyp2j16) 65210(Cyp2j4)
MCOC : 116095445 116095729 116095730 116096253 116096254 116096255 116096256
ANU : 117709291 117709292 117709294 117709295 117709296 117709297 117709298 117709299
MUN : 110560670 110560674 110560675 110562464 110562465 110562466 110562514
CGE : 100764171 100764471 100764768 100765057
MAUA : 101830438 101830700 101841191 101841462
PROB : 127224955 127224956 127224957 127224959
PLEU : 114681971 114681974 114681989 114681994 114689366 114693759 114693760 114693761 114693762 114693764
MORG : 121448178 121448207 121448212 121448217 121448239 121448362 121448363 121448623 121448757 121448759 121448836 121448885
MFOT : 126498042 126498043 126498046 126498047 126498076 126498100 126508049
AAMP : 119816658 119816659 119816660 119816661 119816663 119816664 119816666 119816978
NGI : 103730878 103730879 103730880 103737136
DORD : 105989978 105990009
PLOP : 125355228 125355229
TUP : 102490783 102491196 102491623 102492033 102492447
BTA : 107132327 510406(CYP2J30) 511936 521656 530929
BBUB : 102409898 102410549 102410893 102411225 102411786
BBIS : 105002568 105002577 105002593 105002602 105002609
CHX : 102184867 102190572 102190840 102191099
OAS : 101121563 101121820 768095(CYP2J)
BTAX : 128044628 128044629 128045187
ODA : 120856578 120857076 120857077 120857078 120857079
CCAD : 122436913 122436914 122436915 122436916
MBEZ : 129540345 129540908 129540938 129541372 129541501
SSC : 100524750(CYP2J34) 100524940 100525112 100621407 110261221
CFR : 102509190 102509309 102511878 102518893
CBAI : 105064824 105064834 105064844 105064851 105065015
CDK : 105092804 105092849 105096275 105096288
VPC : 102524867 102535306 102535561 102535809 102536059 102536560 102543101 102543350
PDIC : 114496360 114496679 114497261 114497336
PHAS : 123816495 123830867 123831702
HAI : 109371253 109389703 109389708
RFQ : 117026547 117026565 117027269
SARA : 101547147 101547409 101547677 101547951 101558147 101558420
SETR : 126010975 126010977 126010978 126010985 126010986 126011645
ETF : 101644960 101645270 101645590
DNM : 101411038 101437056 101438656 101439086 101439781 101440211 101440653 101447575
MDO : 100031902 100031907 100031914 100031960 100031971 100031975 100031980 100031984
GAS : 123243734 123245774 123245775 123245776 123247875 123247893
SHR : 100921692 100921949 100922209 100922468 100922742 100922989 116419008
AFZ : 127563232 127563233 127563234 127563235 127563236 127563237 127563238
PCW : 110212934 110212942 110212976 110212978
TVP : 118846138 118846140 118846141 118846143 118846144 118846152 118846466 118846467 118846468
GGA : 101750603(CYP2J21) 424676(CYP2J23) 424677(CYP2J22) 424729(CYP2J19)
PCOC : 116235297 116236300 116236311
MGP : 100547794 104912427 104912428 104912494
CJO : 107317676 107317691 107317696
TPAI : 128072441 128072442 128072444 128072445 128072446 128072447
LMUT : 125692983 125693898 125693899
NMEL : 110402810 110402814
APLA : 101792912 101796247
CATA : 118243378 118243450
AFUL : 116491839 116491861
TGU : 100224220(CYP2J40) 100230439(CYP2J19A)
SCAN : 103815060 103815209(CYP2J19)
PMOA : 120503273 120503274
PRUF : 121362071 121362072
PMAJ : 107208256 107208257
CCAE : 111932992 111932994
CBRC : 103615060 103615112
ZLE : 135450762 135450763 135450766
SATI : 136365094 136365095
SHAB : 115611484 115611485 115611814 115611815 115611982
ACUN : 113483076 113483077
TALA : 104356817 104369422 116964786 122152520
ACHC : 115349168 115349169
HALD : 104317809 104317810
AGEN : 126041970 126041971
CSTI : 104561860 104561861
MNB : 103769046 103769625 103776455 103779509 103780917
DPUB : 104301748 104301760 104308782
PCAO : 104041925 104041927
PADL : 103913325 103913366
AFOR : 103905667 103905758
GSTE : 104260318 104260319
CLV : 102088854 102089036 102093649 102094339
PLET : 104623376 104623378
CMAC : 104478964 104484601
CUCA : 104066545 104066584
TEO : 104371533 104377407 104382055
BREG : 104632733 104632734
CPEA : 104385164 104385194
AROW : 112967651 112976566
NPD : 112942289 112948473 112948476 112948493
TGT : 104571164 104571376 104575346 104575680 104575681
SCAM : 104152907 104153320
PSS : 102449417 102457302(CYP2J19) 102460777
CMY : 102936353 102940076(CYP2J19)
CCAY : 125640754 125640755
CPIC : 101931915 101937882 101938148(CYP2J19) 101939779 103305685
MRV : 120370576 120370577 120370720 120370721
ASAO : 132772700 132772701 132772702 132773987
SUND : 121927978 121927980 121927981
VKO : 123018898 123019432 123019440 123019512 123025295 123025296 123025297 123025298 123025301
PMUA : 114598918 114598919 114598920 114598921 114598923 114598924 114598925
PRAF : 128410871 128410872 128410874 128410875 128410876 128410877 128410878 128415691 128415692 128415694 128415695 128415696 128415697 128415703
ZVI : 118088450 118088451 118088452 118088453 118088455 118088457
STOW : 125437750 125437751 125437990
DRE : 100034366(cyp2p8) 100034406(cyp2p7) 393108(cyp2p6) 393592(cyp2p9) 399485(cyp2p10) 797309(cyp2j20)
CCAR : 109081729 109112720 109112721 109112722
CAUA : 113059714 113062932 113062933 113062936 113077208
CGIB : 127939007 127939011 127939012 127944356 127944764 127956825
PTET : 122325384 122325385 122325386
LROH : 127163996 127182750 127182753 127182754 127182755
OMC : 131526777 131526778 131538917
PPRM : 120493435 120495341
MAMB : 125271930 125277848 125277849 125277850 125277851 125277854 125277856
CERY : 137018370 137018936 137018939 137018940 137018941
MANU : 129429259 129429260
AMEX : 103037239 125803022
CMAO : 118815408 118815409
CHAR : 105900861 105900876
ELY : 117253502 117253503 117253504
EFO : 125895935 125895937 125895938
PLEP : 121939575 121939585
MSAM : 119900968 119900969 119900982 119901367
CUD : 121511981 121511983 121511984 121511985
ALAT : 119028085 119028086 119028087 119028088 119028090
MZE : 101469747 101471484 101471776 101472450 101472746 101473039 101473341 101473625 101474137 112429716 112430356 112430410
ONL : 100699361 100699634 100699898 100700165 100700439 100700441 100700978 100701255 100701799 109194408 109196838 109196840
OAU : 116315351 116327896 116327898 116331077 116331078 116331079 116331081 116331082 116331187 116331213 120436259 120436353
OLA : 100302452(cyp2p3) 105353996
OML : 112138317 112150360 112150361 112150362 118597890
CSAI : 133458178 133458179 133458180 133458188
XMA : 102216555 102216815 102224544 102235118 102238098 102238367
XCO : 114150919 114150920 114150922
XHE : 116725631 116725632 116725633 116725634 116725636 116725637 116725638 116725642 116725644
PRET : 103461257 103463736 103463738 103463739
PFOR : 103137021 103137022 103137164 103137165
PLAI : 106949663 106949692 106949693 106949694 106961243 106961249
PMEI : 106908422 106908423 106917754 106917779 106917780
GAF : 122838407 122838408 122838409 122838410 122838411
PPRL : 129377269 129377278 129377282 129377290
CTUL : 119777086 119790019 119790034
KMR : 108230681 108230682 108230683 108230684 108230685
ALIM : 106517296 106517297 106517298
AOCE : 111563453 111564682 111564718 111564989 111564993 111586280 111586281 111586282
MCEP : 125009824 125009825 125009826 125009827 125009828 125009830 125009831 125009832 125009834
SSEN : 122777824 122777825
SLAL : 111653766 111656353
BSPL : 114852938 114853161 114853162 114853163 114854720 114854721 114854722 114854723
STRU : 115157896 115192271
SFM : 108923501 108923503 108927875 108934003 108935367 108935464 114909092 114911247 114911248 114911249 114911250 114911251 114911252 114911257 114911278
PKI : 111834855 111834857 111834858 111834859
AANG : 118224796 118224797 118224802
PSPA : 121327058 121330919
ARUT : 117409945 117409954 117417241 117417316
PSEX : 120514266 120514351 120514536 120514588 120514690 120514765
PMRN : 116942349 116949610
BFO : 118405297 118407101 118419304 118428418 118429635 118432366
BBEL : 109461524 109461651 109461725 109461727 109462264 109465453 109465656 109466367 109467919 109471284 109472128 109472267 109472270 109475266 109477936 109480295 109482013 109482167 109483920 109483935 109483947 109483948 109485002
SCLV : 120333811 120334172 120334246 120343352
LPIC : 129255057 129255413 129259914 129260274 129261294 129263280 129267050 129267667 129272440 129272952 129272957 129273267 129274630 129276166 129276247 129281166 129281317 129281383 129281480 129281481 129281482 129281553 129282251
ARUN : 117287782 117288024 117288160 117288161 117288273 117288601 117289770 117294724 117298615 117299860 117299861 117301387 117303760 117304080 117304753 117304847 117304890 117305170 117307185
PJA : 122242547 122243682 122252347 122252348 122259834 122259836 122260679 122263851
PCHN : 125037284 125037285 125037286 125037288 125037553 125040652 125047318 125047985
HAME : 121853159 121857091 121874841
PCLA : 123746738 123751553 123756377 123767033 123767752 123770238 123770240
CQD : 128685195 128686126 128686746 128693801 128694775 128697090 128703751 128704994
PTRU : 123506617 123506674
ESN : 126984741 126987539 126992673
MNZ : 135202400 135214473 135220037 135223714
MRJ : 136828209 136834865 136847066 136848421 136848600 136855122
HAZT : 108665745 108667157 108667158 108674876 108676835
EAF : 111695177 111696904 111696905 111698334 111704925 111704939 111706377 111709242 111713706 111717082 111717477 111718077
LSM : 121115047 121119889 121121717
TCF : 131880430 131880431 131881008 131883247 131884276 131893305
PPOI : 119091992 119095707 119101079 119101087 119101104 119101111 119101120 119101130 119104411 119109569
DSV : 119441628 119457522 119461188 119461547 119462117
RSAN : 119374231 119383506 119383507 119386647 119390617 119397387 119406751
RMP : 119166963 119169660 119171404 119173720
ABRU : 129957692 129964081 129964121 129968576 129968577 129972410 129972618 129973475 129973840 129980922
UDV : 129220639 129220886 129229762 129233369 129234350
SDM : 118180345 118189454 118190843 118190848 118202040 118203101 118206070
LPOL : 106459164 106475453
PMEO : 129583244 129584069 129586991 129587294 129588909 129588911 129590632 129591781 129596265 129598004 129599617 129599629 129599630 129600908 129600978 129600979 129600986
PVUL : 126809973 126810313 126811410 126811411 126811412 126811413 126811418 126825321 126832216
BGT : 106054491 106054493 106055467 106057592 106057638 106059997 106060000 106070555 106074975
HRF : 124113283 124118458 124118459 124140343 124140344 124144343 124144711 124147838 124147839 124147840 124152329
HRJ : 124261308 124267336 124267348 124279341 124281198 124281746 124290622 124290663 124291032 124291033 124291034
CRG : 105329932 105332463 117689293
CANU : 128155298 128176608 128181027 128188649
CVN : 111108895 111110523 111110669 111122683 111123229 111128037 111132556
OED : 125650159 125650617 125651484 125651530 125652691 125652692 125652694 125652695 125654191 125656391 125681271 125683308 130046407 130054718
PMAX : 117316069 117343471
MMER : 123543547 123558935
RPHI : 132718487 132725871 132732507 132737309 132749504
DPOL : 127856874 127856875 127866967 127866970 127872507
MAEA : 128209932 128232792 128233722
OSN : 115217140 115217142 115220404 115224293 115227007 115232209
LLON : 135489098 135494781 135498002 135500702 135503101
» show all
Taxonomy
Reference
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
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
Reference
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
Reference
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
Sequence
Reference
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
Sequence
Other DBs
LinkDB
All DBs